# Electronic Supplementary Material (ESI) for New Journal of Chemistry.
# This journal is © The Royal Society of Chemistry and the Centre National de la Recherche Scientifique 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_20151204-xiayi-zzw
_database_code_depnum_ccdc_archive 'CCDC 1441152'
_audit_update_record             
;
2017-06-07 deposited with the CCDC.
2017-07-05 downloaded from the CCDC.
;
_audit_creation_date             2017-06-07
_audit_creation_method           
;
Olex2 1.2-alpha
(compiled 2017.06.06 svn.r3414 for OlexSys, GUI svn.r5353)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C15 H13 F3 N4 O3'
_chemical_formula_sum            'C15 H13 F3 N4 O3'
_chemical_formula_weight         354.29
_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           15
_space_group_name_H-M_alt        'C 1 2/c 1'
_space_group_name_Hall           '-C 2yc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z-1/2'

_cell_length_a                   35.076(3)
_cell_length_b                   10.0258(6)
_cell_length_c                   8.8087(5)
_cell_angle_alpha                90
_cell_angle_beta                 94.027(6)
_cell_angle_gamma                90
_cell_volume                     3090.1(4)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    2216
_cell_measurement_temperature    293(2)
_cell_measurement_theta_min      4.3380
_cell_measurement_theta_max      28.7480
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.132
_exptl_absorpt_correction_T_min  0.72307
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.41k (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_oxdiff_exptl_absorpt_empirical_full_min 0.737
_oxdiff_exptl_absorpt_empirical_full_max 1.433
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_exptl_crystal_colour            Colorless
_exptl_crystal_density_diffrn    1.523
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       Block
_exptl_crystal_F_000             1456
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.2
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0143
_diffrn_reflns_av_unetI/netI     0.0261
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       41
_diffrn_reflns_limit_h_min       -43
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       6
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            5809
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.361
_diffrn_reflns_theta_min         3.462
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean 16.0892
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'SuperNova (Mo) X-ray Source'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'micro-focus sealed X-ray tube'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2479
_reflns_number_total             3153
_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       ?
_computing_data_collection       ?
_computing_data_reduction        ?
_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    'XS (Sheldrick, 2008)'
_refine_diff_density_max         0.351
_refine_diff_density_min         -0.390
_refine_diff_density_rms         0.048
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.070
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     240
_refine_ls_number_reflns         3153
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0693
_refine_ls_R_factor_gt           0.0545
_refine_ls_restrained_S_all      1.070
_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)+(0.0586P)²+4.5816P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1397
_refine_ls_wR_factor_ref         0.1516
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H,H) groups
 At 1.5 times of:
  All O(H) groups
2. Others
 Sof(F1)=Sof(F2)=Sof(F3)=1-FVAR(1)
 Sof(F1')=Sof(F2')=Sof(F3')=FVAR(1)
3.a Secondary CH2 refined with riding coordinates:
 C3(H3A,H3B), C2(H2A,H2B), C1(H1C,H1D)
3.b Aromatic/amide H refined with riding coordinates:
 C11(H11), C10(H10), C12(H12), C13(H13)
3.c X=CH2 refined with riding coordinates:
 N1(H1A,H1B)
3.d Idealised tetrahedral OH refined as rotating group:
 O3(H3)
;
_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
O2 O 0.70615(5) 0.41500(16) 1.20410(17) 0.0426(4) Uani 1 1 d . . . . .
O1 O 0.68948(5) 0.12857(16) 1.28264(16) 0.0440(4) Uani 1 1 d . . . . .
O3 O 0.72503(5) 0.70544(18) 1.2143(2) 0.0504(5) Uani 1 1 d . . . . .
H3 H 0.7484 0.7030 1.2292 0.076 Uiso 1 1 calc GR . . . .
N2 N 0.64840(5) 0.13936(18) 0.89847(19) 0.0356(4) Uani 1 1 d . . . . .
N1 N 0.68832(6) -0.03228(18) 1.1008(2) 0.0411(5) Uani 1 1 d . . . . .
H1A H 0.6997 -0.0901 1.1600 0.049 Uiso 1 1 calc R . . . .
H1B H 0.6816 -0.0528 1.0080 0.049 Uiso 1 1 calc R . . . .
N4 N 0.65560(5) 0.30926(18) 1.05529(18) 0.0332(4) Uani 1 1 d . . . . .
N3 N 0.63800(5) 0.36099(19) 0.9262(2) 0.0390(4) Uani 1 1 d . . . . .
C4 C 0.68117(6) 0.0878(2) 1.1523(2) 0.0335(5) Uani 1 1 d . . . . .
C5 C 0.66167(6) 0.1779(2) 1.0361(2) 0.0314(5) Uani 1 1 d . . . . .
C6 C 0.63419(6) 0.2548(2) 0.8361(2) 0.0356(5) Uani 1 1 d . . . . .
C3 C 0.66668(7) 0.3976(2) 1.1846(2) 0.0385(5) Uani 1 1 d . . . . .
H3A H 0.6546 0.4838 1.1677 0.046 Uiso 1 1 calc R . . . .
H3B H 0.6575 0.3600 1.2767 0.046 Uiso 1 1 calc R . . . .
C2 C 0.72315(7) 0.4868(3) 1.0854(3) 0.0460(6) Uani 1 1 d . . . . .
H2A H 0.7149 0.4467 0.9884 0.055 Uiso 1 1 calc R . . . .
H2B H 0.7507 0.4771 1.0992 0.055 Uiso 1 1 calc R . . . .
C9 C 0.58628(6) 0.2570(2) 0.4028(2) 0.0409(5) Uani 1 1 d . . . . .
C8 C 0.60385(7) 0.2607(3) 0.5553(3) 0.0436(6) Uani 1 1 d . . . . .
C7 C 0.61715(7) 0.2613(2) 0.6831(3) 0.0415(5) Uani 1 1 d . . . . .
C1 C 0.71369(8) 0.6319(3) 1.0791(3) 0.0498(6) Uani 1 1 d . . . . .
H1C H 0.7259 0.6714 0.9944 0.060 Uiso 1 1 calc R . . . .
H1D H 0.6863 0.6414 1.0586 0.060 Uiso 1 1 calc R . . . .
C14 C 0.54821(7) 0.2453(3) 0.1168(3) 0.0460(6) Uani 1 1 d . . . . .
C11 C 0.57094(8) 0.3721(3) 0.3351(3) 0.0497(6) Uani 1 1 d . . . . .
H11 H 0.5735 0.4534 0.3857 0.060 Uiso 1 1 calc R . . . .
C10 C 0.58377(8) 0.1370(3) 0.3234(3) 0.0531(7) Uani 1 1 d . . . . .
H10 H 0.5952 0.0606 0.3658 0.064 Uiso 1 1 calc R . . . .
C12 C 0.55188(8) 0.3658(3) 0.1923(3) 0.0526(7) Uani 1 1 d . . . . .
H12 H 0.5415 0.4427 0.1471 0.063 Uiso 1 1 calc R . . . .
C13 C 0.56439(8) 0.1313(3) 0.1815(3) 0.0564(7) Uani 1 1 d . . . . .
H13 H 0.5622 0.0507 0.1295 0.068 Uiso 1 1 calc R . . . .
C15 C 0.52622(8) 0.2369(3) -0.0351(3) 0.0575(7) Uani 1 1 d . . . . .
F1' F 0.5220(5) 0.1176(15) -0.0890(18) 0.075(5) Uiso 0.144(5) 1 d . . P A 1
F2' F 0.5433(3) 0.3036(12) -0.1361(12) 0.041(3) Uiso 0.144(5) 1 d . . P A 1
F3' F 0.4955(3) 0.2906(15) -0.0438(14) 0.054(4) Uiso 0.144(5) 1 d . . P A 1
F1 F 0.49531(8) 0.1667(4) -0.0310(3) 0.1124(15) Uani 0.856(5) 1 d . . P A 2
F2 F 0.54494(8) 0.1800(6) -0.1378(3) 0.143(2) Uani 0.856(5) 1 d . . P A 2
F3 F 0.51416(18) 0.3529(3) -0.0868(4) 0.173(3) Uani 0.856(5) 1 d . . P A 2


_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
O2 C3 1.394(3) . ?
O2 C2 1.434(3) . ?
O1 C4 1.234(2) . ?
O3 H3 0.8200 . ?
O3 C1 1.433(3) . ?
N2 C5 1.325(3) . ?
N2 C6 1.361(3) . ?
N1 H1A 0.8600 . ?
N1 H1B 0.8600 . ?
N1 C4 1.317(3) . ?
N4 N3 1.358(2) . ?
N4 C5 1.346(3) . ?
N4 C3 1.473(3) . ?
N3 C6 1.329(3) . ?
C4 C5 1.495(3) . ?
C6 C7 1.437(3) . ?
C3 H3A 0.9700 . ?
C3 H3B 0.9700 . ?
C2 H2A 0.9700 . ?
C2 H2B 0.9700 . ?
C2 C1 1.492(4) . ?
C9 C8 1.439(3) . ?
C9 C11 1.390(3) . ?
C9 C10 1.391(4) . ?
C8 C7 1.188(3) . ?
C1 H1C 0.9700 . ?
C1 H1D 0.9700 . ?
C14 C12 1.380(4) . ?
C14 C13 1.381(4) . ?
C14 C15 1.499(3) . ?
C11 H11 0.9300 . ?
C11 C12 1.384(3) . ?
C10 H10 0.9300 . ?
C10 C13 1.381(3) . ?
C12 H12 0.9300 . ?
C13 H13 0.9300 . ?
C15 F1' 1.291(15) . ?
C15 F2' 1.294(11) . ?
C15 F3' 1.201(12) . ?
C15 F1 1.295(4) . ?
C15 F2 1.288(4) . ?
C15 F3 1.309(4) . ?

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
C3 O2 C2 115.65(17) . . ?
C1 O3 H3 109.5 . . ?
C5 N2 C6 102.48(18) . . ?
H1A N1 H1B 120.0 . . ?
C4 N1 H1A 120.0 . . ?
C4 N1 H1B 120.0 . . ?
N3 N4 C3 119.82(18) . . ?
C5 N4 N3 109.55(16) . . ?
C5 N4 C3 130.53(17) . . ?
C6 N3 N4 102.41(17) . . ?
O1 C4 N1 125.8(2) . . ?
O1 C4 C5 120.27(19) . . ?
N1 C4 C5 113.94(18) . . ?
N2 C5 N4 110.61(18) . . ?
N2 C5 C4 124.37(19) . . ?
N4 C5 C4 125.01(18) . . ?
N2 C6 C7 122.3(2) . . ?
N3 C6 N2 114.94(18) . . ?
N3 C6 C7 122.8(2) . . ?
O2 C3 N4 112.11(17) . . ?
O2 C3 H3A 109.2 . . ?
O2 C3 H3B 109.2 . . ?
N4 C3 H3A 109.2 . . ?
N4 C3 H3B 109.2 . . ?
H3A C3 H3B 107.9 . . ?
O2 C2 H2A 108.6 . . ?
O2 C2 H2B 108.6 . . ?
O2 C2 C1 114.5(2) . . ?
H2A C2 H2B 107.6 . . ?
C1 C2 H2A 108.6 . . ?
C1 C2 H2B 108.6 . . ?
C11 C9 C8 120.4(2) . . ?
C11 C9 C10 119.5(2) . . ?
C10 C9 C8 120.0(2) . . ?
C7 C8 C9 177.5(3) . . ?
C8 C7 C6 176.7(3) . . ?
O3 C1 C2 115.0(2) . . ?
O3 C1 H1C 108.5 . . ?
O3 C1 H1D 108.5 . . ?
C2 C1 H1C 108.5 . . ?
C2 C1 H1D 108.5 . . ?
H1C C1 H1D 107.5 . . ?
C12 C14 C13 120.2(2) . . ?
C12 C14 C15 120.3(2) . . ?
C13 C14 C15 119.5(2) . . ?
C9 C11 H11 120.0 . . ?
C12 C11 C9 119.9(2) . . ?
C12 C11 H11 120.0 . . ?
C9 C10 H10 120.0 . . ?
C13 C10 C9 120.0(2) . . ?
C13 C10 H10 120.0 . . ?
C14 C12 C11 120.1(2) . . ?
C14 C12 H12 120.0 . . ?
C11 C12 H12 120.0 . . ?
C14 C13 C10 120.1(3) . . ?
C14 C13 H13 120.0 . . ?
C10 C13 H13 120.0 . . ?
F1' C15 C14 114.8(7) . . ?
F1' C15 F2' 105.8(9) . . ?
F2' C15 C14 110.5(5) . . ?
F3' C15 C14 115.7(6) . . ?
F3' C15 F1' 108.3(10) . . ?
F3' C15 F2' 100.3(8) . . ?
F1 C15 C14 112.6(2) . . ?
F1 C15 F3 104.0(4) . . ?
F2 C15 C14 113.4(2) . . ?
F2 C15 F1 104.4(3) . . ?
F2 C15 F3 108.5(4) . . ?
F3 C15 C14 113.2(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
O2 C2 C1 O3 59.6(3) . . . . ?
O1 C4 C5 N2 -173.2(2) . . . . ?
O1 C4 C5 N4 7.8(3) . . . . ?
N1 C4 C5 N2 7.6(3) . . . . ?
N1 C4 C5 N4 -171.4(2) . . . . ?
N4 N3 C6 N2 -0.5(3) . . . . ?
N4 N3 C6 C7 -179.1(2) . . . . ?
N3 N4 C5 N2 -0.5(2) . . . . ?
N3 N4 C5 C4 178.58(19) . . . . ?
N3 N4 C3 O2 -108.7(2) . . . . ?
C5 N2 C6 N3 0.2(3) . . . . ?
C5 N2 C6 C7 178.8(2) . . . . ?
C5 N4 N3 C6 0.6(2) . . . . ?
C5 N4 C3 O2 67.4(3) . . . . ?
C6 N2 C5 N4 0.2(2) . . . . ?
C6 N2 C5 C4 -178.9(2) . . . . ?
C3 O2 C2 C1 70.2(3) . . . . ?
C3 N4 N3 C6 177.41(18) . . . . ?
C3 N4 C5 N2 -176.9(2) . . . . ?
C3 N4 C5 C4 2.2(4) . . . . ?
C2 O2 C3 N4 67.2(2) . . . . ?
C9 C11 C12 C14 -0.2(4) . . . . ?
C9 C10 C13 C14 1.5(4) . . . . ?
C8 C9 C11 C12 -175.7(2) . . . . ?
C8 C9 C10 C13 175.1(2) . . . . ?
C11 C9 C10 C13 -3.4(4) . . . . ?
C10 C9 C11 C12 2.8(4) . . . . ?
C12 C14 C13 C10 1.1(4) . . . . ?
C12 C14 C15 F1' -174.6(10) . . . . ?
C12 C14 C15 F2' 65.9(7) . . . . ?
C12 C14 C15 F3' -47.3(9) . . . . ?
C12 C14 C15 F1 -113.5(4) . . . . ?
C12 C14 C15 F2 128.2(4) . . . . ?
C12 C14 C15 F3 4.1(5) . . . . ?
C13 C14 C12 C11 -1.7(4) . . . . ?
C13 C14 C15 F1' 4.7(10) . . . . ?
C13 C14 C15 F2' -114.9(7) . . . . ?
C13 C14 C15 F3' 132.0(9) . . . . ?
C13 C14 C15 F1 65.8(4) . . . . ?
C13 C14 C15 F2 -52.5(5) . . . . ?
C13 C14 C15 F3 -176.6(4) . . . . ?
C15 C14 C12 C11 177.5(3) . . . . ?
C15 C14 C13 C10 -178.1(3) . . . . ?

_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_cmm5
_database_code_depnum_ccdc_archive 'CCDC 1441261'
_audit_update_record             
;
2017-06-14 deposited with the CCDC.
2017-07-05 downloaded from the CCDC.
;
_audit_creation_date             2017-06-14
_audit_creation_method           
;
Olex2 1.2-alpha
(compiled 2017.06.06 svn.r3414 for OlexSys, GUI svn.r5353)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C15 H16 N4 O4'
_chemical_formula_sum            'C15 H16 N4 O4'
_chemical_formula_weight         316.32
_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                   17.5680(9)
_cell_length_b                   9.9977(5)
_cell_length_c                   8.8328(5)
_cell_angle_alpha                90
_cell_angle_beta                 104.264(6)
_cell_angle_gamma                90
_cell_volume                     1503.55(15)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    1475
_cell_measurement_temperature    294(2)
_cell_measurement_theta_min      4.1170
_cell_measurement_theta_max      26.0770
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.104
_exptl_absorpt_correction_T_min  0.79740
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.41k (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_oxdiff_exptl_absorpt_empirical_full_min 0.641
_oxdiff_exptl_absorpt_empirical_full_max 1.295
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            Colorless
_exptl_crystal_density_diffrn    1.397
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       Block
_exptl_crystal_F_000             664
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.08
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0229
_diffrn_reflns_av_unetI/netI     0.0426
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            6130
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        26.000
_diffrn_reflns_theta_max         26.370
_diffrn_reflns_theta_min         3.557
_diffrn_ambient_temperature      294(2)
_diffrn_detector_area_resol_mean 16.0892
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'SuperNova, Single source at offset, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'micro-focus sealed X-ray tube'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2071
_reflns_number_total             3071
_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       ?
_computing_data_collection       ?
_computing_data_reduction        ?
_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    'SIR2004 (Burla et al., 2007)'
_refine_diff_density_max         0.226
_refine_diff_density_min         -0.181
_refine_diff_density_rms         0.044
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.052
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     218
_refine_ls_number_reflns         3071
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0803
_refine_ls_R_factor_gt           0.0518
_refine_ls_restrained_S_all      1.052
_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)+(0.0603P)²+0.2474P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1228
_refine_ls_wR_factor_ref         0.1418
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2.a Secondary CH2 refined with riding coordinates:
 C15(H15A,H15B), C14(H14A,H14B)
2.b Aromatic/amide H refined with riding coordinates:
 C5(H5), C4(H4C), C6(H6), C3(H3)
2.c X=CH2 refined with riding coordinates:
 N4(H4A,H4B)
2.d Idealised Me refined as rotating group:
 C1(H1A,H1B,H1C)
2.e Idealised tetrahedral OH refined as rotating group:
 O4(H4)
;
_atom_sites_solution_hydrogens   mixed
_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
O3 O 0.41225(9) 0.33598(14) 0.23942(17) 0.0437(4) Uani 1 1 d . . . . .
O2 O 0.37602(9) 0.62388(15) 0.14131(16) 0.0465(4) Uani 1 1 d . . . . .
O4 O 0.44777(9) 0.04424(16) 0.25213(19) 0.0528(4) Uani 1 1 d . . . . .
H4 H 0.4957 0.0451 0.2674 0.079 Uiso 1 1 calc GR . . . .
N3 N 0.30821(10) 0.44025(17) 0.32282(18) 0.0357(4) Uani 1 1 d . . . . .
N1 N 0.28990(10) 0.60814(17) 0.46893(19) 0.0391(4) Uani 1 1 d . . . . .
N2 N 0.27151(10) 0.38598(18) 0.4267(2) 0.0408(4) Uani 1 1 d . . . . .
N4 N 0.37169(11) 0.78393(17) 0.3209(2) 0.0453(5) Uani 1 1 d . . . . .
H4A H 0.3946 0.8428 0.2766 0.054 Uiso 1 1 calc R . . . .
H4B H 0.3575 0.8039 0.4046 0.054 Uiso 1 1 calc R . . . .
O1 O 0.06028(11) 0.4732(2) 1.2559(2) 0.0700(6) Uani 1 1 d . . . . .
C12 C 0.35825(12) 0.6631(2) 0.2605(2) 0.0370(5) Uani 1 1 d . . . . .
C11 C 0.31901(11) 0.5718(2) 0.3505(2) 0.0344(5) Uani 1 1 d . . . . .
C10 C 0.26152(12) 0.4912(2) 0.5114(2) 0.0374(5) Uani 1 1 d . . . . .
C13 C 0.33144(14) 0.3531(2) 0.2069(3) 0.0395(5) Uani 1 1 d . . . . .
C7 C 0.16578(12) 0.4784(2) 0.8850(2) 0.0424(5) Uani 1 1 d . . . . .
C9 C 0.22559(13) 0.4817(2) 0.6401(3) 0.0441(5) Uani 1 1 d . . . . .
C8 C 0.19892(13) 0.4788(2) 0.7513(3) 0.0457(6) Uani 1 1 d . . . . .
C5 C 0.13206(13) 0.3630(2) 0.9285(3) 0.0483(6) Uani 1 1 d . . . . .
H5 H 0.1325 0.2840 0.8732 0.058 Uiso 1 1 calc R . . . .
C15 C 0.42537(14) 0.1178(2) 0.3723(3) 0.0511(6) Uani 1 1 d . . . . .
H15A H 0.4500 0.0773 0.4721 0.061 Uiso 1 1 calc R . . . .
H15B H 0.3690 0.1099 0.3575 0.061 Uiso 1 1 calc R . . . .
C4 C 0.09811(14) 0.3656(3) 1.0528(3) 0.0535(6) Uani 1 1 d . . . . .
H4C H 0.0756 0.2881 1.0807 0.064 Uiso 1 1 calc R . . . .
C2 C 0.09692(13) 0.4819(3) 1.1372(3) 0.0497(6) Uani 1 1 d . . . . .
C14 C 0.44640(14) 0.2632(2) 0.3792(3) 0.0478(6) Uani 1 1 d . . . . .
H14A H 0.4298 0.3039 0.4654 0.057 Uiso 1 1 calc R . . . .
H14B H 0.5031 0.2713 0.4009 0.057 Uiso 1 1 calc R . . . .
C6 C 0.16656(14) 0.5928(3) 0.9725(3) 0.0521(6) Uani 1 1 d . . . . .
H6 H 0.1903 0.6697 0.9465 0.063 Uiso 1 1 calc R . . . .
C3 C 0.13250(14) 0.5956(3) 1.0987(3) 0.0540(6) Uani 1 1 d . . . . .
H3 H 0.1337 0.6735 1.1568 0.065 Uiso 1 1 calc R . . . .
C1 C 0.05491(19) 0.5912(4) 1.3424(3) 0.0827(10) Uani 1 1 d . . . . .
H1A H 0.0333 0.6623 1.2719 0.124 Uiso 1 1 calc GR . . . .
H1B H 0.1063 0.6161 1.4022 0.124 Uiso 1 1 calc GR . . . .
H1C H 0.0215 0.5748 1.4117 0.124 Uiso 1 1 calc GR . . . .
H13A H 0.3015(11) 0.270(2) 0.213(2) 0.038(6) Uiso 1 1 d . . . . .
H13B H 0.3144(12) 0.397(2) 0.107(3) 0.039(6) Uiso 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
O3 C13 1.388(3) . ?
O3 C14 1.431(3) . ?
O2 C12 1.233(2) . ?
O4 H4 0.8200 . ?
O4 C15 1.424(3) . ?
N3 N2 1.358(2) . ?
N3 C11 1.343(3) . ?
N3 C13 1.476(3) . ?
N1 C11 1.323(2) . ?
N1 C10 1.359(3) . ?
N2 C10 1.328(3) . ?
N4 H4A 0.8600 . ?
N4 H4B 0.8600 . ?
N4 C12 1.318(3) . ?
O1 C2 1.361(3) . ?
O1 C1 1.421(3) . ?
C12 C11 1.487(3) . ?
C10 C9 1.432(3) . ?
C13 H13A 0.99(2) . ?
C13 H13B 0.97(2) . ?
C7 C8 1.440(3) . ?
C7 C5 1.393(3) . ?
C7 C6 1.379(3) . ?
C9 C8 1.189(3) . ?
C5 H5 0.9300 . ?
C5 C4 1.372(3) . ?
C15 H15A 0.9700 . ?
C15 H15B 0.9700 . ?
C15 C14 1.497(3) . ?
C4 H4C 0.9300 . ?
C4 C2 1.384(3) . ?
C2 C3 1.380(3) . ?
C14 H14A 0.9700 . ?
C14 H14B 0.9700 . ?
C6 H6 0.9300 . ?
C6 C3 1.389(3) . ?
C3 H3 0.9300 . ?
C1 H1A 0.9600 . ?
C1 H1B 0.9600 . ?
C1 H1C 0.9600 . ?

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
C13 O3 C14 115.55(17) . . ?
C15 O4 H4 109.5 . . ?
N2 N3 C13 119.42(17) . . ?
C11 N3 N2 109.73(16) . . ?
C11 N3 C13 130.81(17) . . ?
C11 N1 C10 102.84(17) . . ?
C10 N2 N3 102.41(16) . . ?
H4A N4 H4B 120.0 . . ?
C12 N4 H4A 120.0 . . ?
C12 N4 H4B 120.0 . . ?
C2 O1 C1 117.9(2) . . ?
O2 C12 N4 125.40(19) . . ?
O2 C12 C11 120.64(18) . . ?
N4 C12 C11 113.96(17) . . ?
N3 C11 C12 124.53(17) . . ?
N1 C11 N3 110.36(18) . . ?
N1 C11 C12 125.11(19) . . ?
N1 C10 C9 122.7(2) . . ?
N2 C10 N1 114.65(17) . . ?
N2 C10 C9 122.68(19) . . ?
O3 C13 N3 111.89(17) . . ?
O3 C13 H13A 114.7(11) . . ?
O3 C13 H13B 108.4(12) . . ?
N3 C13 H13A 102.5(12) . . ?
N3 C13 H13B 106.9(12) . . ?
H13A C13 H13B 112.2(17) . . ?
C5 C7 C8 121.0(2) . . ?
C6 C7 C8 120.4(2) . . ?
C6 C7 C5 118.6(2) . . ?
C8 C9 C10 176.3(3) . . ?
C9 C8 C7 178.6(3) . . ?
C7 C5 H5 119.9 . . ?
C4 C5 C7 120.2(2) . . ?
C4 C5 H5 119.9 . . ?
O4 C15 H15A 108.5 . . ?
O4 C15 H15B 108.5 . . ?
O4 C15 C14 114.88(19) . . ?
H15A C15 H15B 107.5 . . ?
C14 C15 H15A 108.5 . . ?
C14 C15 H15B 108.5 . . ?
C5 C4 H4C 119.5 . . ?
C5 C4 C2 120.9(2) . . ?
C2 C4 H4C 119.5 . . ?
O1 C2 C4 115.7(2) . . ?
O1 C2 C3 124.8(2) . . ?
C3 C2 C4 119.4(2) . . ?
O3 C14 C15 114.33(19) . . ?
O3 C14 H14A 108.7 . . ?
O3 C14 H14B 108.7 . . ?
C15 C14 H14A 108.7 . . ?
C15 C14 H14B 108.7 . . ?
H14A C14 H14B 107.6 . . ?
C7 C6 H6 119.4 . . ?
C7 C6 C3 121.3(2) . . ?
C3 C6 H6 119.4 . . ?
C2 C3 C6 119.5(2) . . ?
C2 C3 H3 120.3 . . ?
C6 C3 H3 120.3 . . ?
O1 C1 H1A 109.5 . . ?
O1 C1 H1B 109.5 . . ?
O1 C1 H1C 109.5 . . ?
H1A C1 H1B 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O2 C12 C11 N3 8.0(3) . . . . ?
O2 C12 C11 N1 -172.07(19) . . . . ?
O4 C15 C14 O3 59.5(3) . . . . ?
N3 N2 C10 N1 -0.5(2) . . . . ?
N3 N2 C10 C9 -178.86(18) . . . . ?
N2 N3 C11 N1 -0.7(2) . . . . ?
N2 N3 C11 C12 179.26(18) . . . . ?
N2 N3 C13 O3 -108.7(2) . . . . ?
N4 C12 C11 N3 -171.41(19) . . . . ?
N4 C12 C11 N1 8.5(3) . . . . ?
O1 C2 C3 C6 -178.6(2) . . . . ?
C11 N3 N2 C10 0.7(2) . . . . ?
C11 N3 C13 O3 69.0(3) . . . . ?
C11 N1 C10 N2 0.1(2) . . . . ?
C11 N1 C10 C9 178.47(19) . . . . ?
C10 N1 C11 N3 0.4(2) . . . . ?
C10 N1 C11 C12 -179.57(19) . . . . ?
C13 O3 C14 C15 68.9(2) . . . . ?
C13 N3 N2 C10 178.83(17) . . . . ?
C13 N3 C11 N1 -178.57(18) . . . . ?
C13 N3 C11 C12 1.4(3) . . . . ?
C7 C5 C4 C2 -0.2(4) . . . . ?
C7 C6 C3 C2 -0.2(4) . . . . ?
C8 C7 C5 C4 -177.6(2) . . . . ?
C8 C7 C6 C3 177.8(2) . . . . ?
C5 C7 C6 C3 -2.0(3) . . . . ?
C5 C4 C2 O1 178.7(2) . . . . ?
C5 C4 C2 C3 -2.0(4) . . . . ?
C4 C2 C3 C6 2.2(4) . . . . ?
C14 O3 C13 N3 66.8(2) . . . . ?
C6 C7 C5 C4 2.2(3) . . . . ?
C1 O1 C2 C4 -177.7(2) . . . . ?
C1 O1 C2 C3 3.1(4) . . . . ?

_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_20170623-xiayi-zzw-1
_database_code_depnum_ccdc_archive 'CCDC 1441262'
_audit_update_record             
;
2017-06-26 deposited with the CCDC.
2017-07-05 downloaded from the CCDC.
;
_audit_creation_date             2017-06-24
_audit_creation_method           
;
Olex2 1.2-alpha
(compiled 2017.06.06 svn.r3414 for OlexSys, GUI svn.r5353)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C14 H14 N4 O3'
_chemical_formula_sum            'C14 H14 N4 O3'
_chemical_formula_weight         286.29
_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           61
_space_group_name_H-M_alt        'P b c a'
_space_group_name_Hall           '-P 2ac 2ab'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'x, -y-1/2, z-1/2'
'-x-1/2, y-1/2, z'

_cell_length_a                   11.4857(7)
_cell_length_b                   6.9956(4)
_cell_length_c                   33.950(3)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2727.8(3)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    2452
_cell_measurement_temperature    175(2)
_cell_measurement_theta_max      28.6860
_cell_measurement_theta_min      3.7190
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.101
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.84069
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.41k (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            Colorless
_exptl_crystal_density_diffrn    1.394
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       Block
_exptl_crystal_F_000             1200
_exptl_crystal_size_max          0.5
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.15
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0226
_diffrn_reflns_av_unetI/netI     0.0302
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       42
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            7406
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.372
_diffrn_reflns_theta_min         3.462
_diffrn_ambient_temperature      175(2)
_diffrn_detector_area_resol_mean 16.0892
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'SuperNova, Single source at offset, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'micro-focus sealed X-ray tube'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2304
_reflns_number_total             2788
_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       ?
_computing_data_collection       ?
_computing_data_reduction        ?
_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         0.367
_refine_diff_density_min         -0.228
_refine_diff_density_rms         0.052
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.165
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     199
_refine_ls_number_reflns         2788
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0596
_refine_ls_R_factor_gt           0.0487
_refine_ls_restrained_S_all      1.165
_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)+(0.0399P)²+3.3858P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1321
_refine_ls_wR_factor_ref         0.1368
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H,H) groups
 At 1.5 times of:
  All O(H) groups
2.a Secondary CH2 refined with riding coordinates:
 C00H(H00E,H00H), C00I(H00I,H00J)
2.b Aromatic/amide H refined with riding coordinates:
 C00F(H00F), C00G(H00G), C00J(H00K), C00K(H00L), C00L(H00M)
2.c X=CH2 refined with riding coordinates:
 N007(H00A,H00B)
2.d Idealised tetrahedral OH refined as rotating group:
 O003(H003)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_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
O001 O 0.53618(14) 0.7574(2) 0.43971(4) 0.0230(4) Uani 1 1 d . . . . .
O002 O 0.31239(15) 0.6646(3) 0.49955(5) 0.0313(4) Uani 1 1 d . . . . .
O003 O 0.60085(16) 1.1466(3) 0.43430(6) 0.0336(5) Uani 1 1 d . . . . .
H003 H 0.6425 1.1817 0.4525 0.050 Uiso 1 1 calc GR . . . .
N004 N 0.18523(16) 0.5810(3) 0.40452(5) 0.0205(4) Uani 1 1 d . . . . .
N005 N 0.37243(16) 0.5754(3) 0.41802(5) 0.0189(4) Uani 1 1 d . . . . .
N006 N 0.36571(16) 0.5385(3) 0.37876(5) 0.0203(4) Uani 1 1 d . . . . .
N007 N 0.12201(17) 0.6535(3) 0.48162(6) 0.0257(5) Uani 1 1 d . . . . .
H00A H 0.0970 0.6790 0.5049 0.031 Uiso 1 1 calc R . . . .
H00B H 0.0734 0.6356 0.4627 0.031 Uiso 1 1 calc R . . . .
C008 C 0.2515(2) 0.5433(3) 0.37213(6) 0.0186(5) Uani 1 1 d . . . . .
C009 C 0.26412(19) 0.5998(3) 0.43273(6) 0.0182(5) Uani 1 1 d . . . . .
C00A C 0.2044(2) 0.5081(3) 0.33355(7) 0.0223(5) Uani 1 1 d . . . . .
C00B C 0.1391(2) 0.4371(3) 0.26062(6) 0.0202(5) Uani 1 1 d . . . . .
C00C C 0.2351(2) 0.6418(3) 0.47488(6) 0.0215(5) Uani 1 1 d . . . . .
C00D C 0.4876(2) 0.5748(3) 0.43670(7) 0.0222(5) Uani 1 1 d . . . . .
C00E C 0.1710(2) 0.4748(3) 0.30112(7) 0.0209(5) Uani 1 1 d . . . . .
C00F C 0.2184(2) 0.3477(3) 0.23578(7) 0.0243(5) Uani 1 1 d . . . . .
H00F H 0.2905 0.3090 0.2454 0.029 Uiso 1 1 calc R . . . .
C00G C 0.0318(2) 0.4963(3) 0.24589(7) 0.0246(5) Uani 1 1 d . . . . .
H00G H -0.0217 0.5557 0.2624 0.030 Uiso 1 1 calc R . . . .
C00H C 0.5743(2) 0.8411(3) 0.40319(6) 0.0219(5) Uani 1 1 d . . . . .
H00E H 0.5082 0.8916 0.3888 0.026 Uiso 1 1 calc R . . . .
H00H H 0.6121 0.7453 0.3870 0.026 Uiso 1 1 calc R . . . .
C00I C 0.6583(2) 0.9991(4) 0.41274(7) 0.0271(5) Uani 1 1 d . . . . .
H00I H 0.7223 0.9487 0.4282 0.033 Uiso 1 1 calc R . . . .
H00J H 0.6901 1.0513 0.3885 0.033 Uiso 1 1 calc R . . . .
C00J C 0.1901(2) 0.3159(4) 0.19651(7) 0.0287(6) Uani 1 1 d . . . . .
H00K H 0.2429 0.2548 0.1800 0.034 Uiso 1 1 calc R . . . .
C00K C 0.0834(2) 0.3752(4) 0.18193(7) 0.0327(6) Uani 1 1 d . . . . .
H00L H 0.0646 0.3535 0.1557 0.039 Uiso 1 1 calc R . . . .
C00L C 0.0049(2) 0.4664(4) 0.20638(7) 0.0311(6) Uani 1 1 d . . . . .
H00M H -0.0662 0.5079 0.1964 0.037 Uiso 1 1 calc R . . . .
H00C H 0.479(2) 0.528(3) 0.4634(7) 0.018(6) Uiso 1 1 d . . . . .
H00D H 0.533(2) 0.486(4) 0.4202(7) 0.022(6) Uiso 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
O001 C00D 1.398(3) . ?
O001 C00H 1.440(3) . ?
O002 C00C 1.231(3) . ?
O003 H003 0.8200 . ?
O003 C00I 1.427(3) . ?
N004 C008 1.363(3) . ?
N004 C009 1.325(3) . ?
N005 N006 1.360(2) . ?
N005 C009 1.351(3) . ?
N005 C00D 1.467(3) . ?
N006 C008 1.331(3) . ?
N007 H00A 0.8600 . ?
N007 H00B 0.8600 . ?
N007 C00C 1.322(3) . ?
C008 C00A 1.438(3) . ?
C009 C00C 1.498(3) . ?
C00A C00E 1.189(3) . ?
C00B C00E 1.447(3) . ?
C00B C00F 1.390(3) . ?
C00B C00G 1.394(3) . ?
C00D H00C 0.97(2) . ?
C00D H00D 0.99(3) . ?
C00F H00F 0.9300 . ?
C00F C00J 1.390(3) . ?
C00G H00G 0.9300 . ?
C00G C00L 1.392(3) . ?
C00H H00E 0.9700 . ?
C00H H00H 0.9700 . ?
C00H C00I 1.502(3) . ?
C00I H00I 0.9700 . ?
C00I H00J 0.9700 . ?
C00J H00K 0.9300 . ?
C00J C00K 1.385(4) . ?
C00K H00L 0.9300 . ?
C00K C00L 1.382(4) . ?
C00L H00M 0.9300 . ?

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
C00D O001 C00H 115.48(17) . . ?
C00I O003 H003 109.5 . . ?
C009 N004 C008 102.74(18) . . ?
N006 N005 C00D 118.31(18) . . ?
C009 N005 N006 109.51(17) . . ?
C009 N005 C00D 132.13(18) . . ?
C008 N006 N005 102.53(17) . . ?
H00A N007 H00B 120.0 . . ?
C00C N007 H00A 120.0 . . ?
C00C N007 H00B 120.0 . . ?
N004 C008 C00A 123.9(2) . . ?
N006 C008 N004 114.74(19) . . ?
N006 C008 C00A 121.3(2) . . ?
N004 C009 N005 110.49(18) . . ?
N004 C009 C00C 123.9(2) . . ?
N005 C009 C00C 125.6(2) . . ?
C00E C00A C008 176.5(3) . . ?
C00F C00B C00E 119.5(2) . . ?
C00F C00B C00G 119.7(2) . . ?
C00G C00B C00E 120.7(2) . . ?
O002 C00C N007 125.6(2) . . ?
O002 C00C C009 121.0(2) . . ?
N007 C00C C009 113.3(2) . . ?
O001 C00D N005 112.89(19) . . ?
O001 C00D H00C 106.4(14) . . ?
O001 C00D H00D 113.7(15) . . ?
N005 C00D H00C 108.1(14) . . ?
N005 C00D H00D 103.8(15) . . ?
H00C C00D H00D 112(2) . . ?
C00A C00E C00B 175.7(2) . . ?
C00B C00F H00F 120.0 . . ?
C00B C00F C00J 120.0(2) . . ?
C00J C00F H00F 120.0 . . ?
C00B C00G H00G 120.1 . . ?
C00L C00G C00B 119.8(2) . . ?
C00L C00G H00G 120.1 . . ?
O001 C00H H00E 110.1 . . ?
O001 C00H H00H 110.1 . . ?
O001 C00H C00I 107.99(18) . . ?
H00E C00H H00H 108.4 . . ?
C00I C00H H00E 110.1 . . ?
C00I C00H H00H 110.1 . . ?
O003 C00I C00H 110.2(2) . . ?
O003 C00I H00I 109.6 . . ?
O003 C00I H00J 109.6 . . ?
C00H C00I H00I 109.6 . . ?
C00H C00I H00J 109.6 . . ?
H00I C00I H00J 108.1 . . ?
C00F C00J H00K 119.9 . . ?
C00K C00J C00F 120.1(2) . . ?
C00K C00J H00K 119.9 . . ?
C00J C00K H00L 120.0 . . ?
C00L C00K C00J 120.1(2) . . ?
C00L C00K H00L 120.0 . . ?
C00G C00L H00M 119.9 . . ?
C00K C00L C00G 120.2(2) . . ?
C00K C00L H00M 119.9 . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.304
_oxdiff_exptl_absorpt_empirical_full_min 0.755
