# Electronic Supplementary Material (ESI) for ChemComm.
# This journal is © The Royal Society of Chemistry 2018

####################################################################### 
# 
# 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_luolong0422_2
_database_code_depnum_ccdc_archive 'CCDC 1811053'
_audit_update_record             
;
2017-12-13 deposited with the CCDC.
2018-01-29 downloaded from the CCDC.
;
_audit_creation_date             2014-04-23
_audit_creation_method           
;
Olex2 1.2
(compiled 2014.03.20 svn.r2914 for OlexSys, GUI svn.r4816)
;
_chemical_name_common            ?
_chemical_name_systematic        
;
 ? 
;
_chemical_formula_moiety         'C14 H16 O4'
_chemical_formula_sum            'C14 H16 O4'
_chemical_formula_weight         248.27
_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'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/n 1'
_space_group_name_Hall           '-P 2yn'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 'x, y, z'
2 '-x+1/2, y+1/2, -z+1/2'
3 '-x, -y, -z'
4 'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   13.2065(13)
_cell_length_b                   6.4912(5)
_cell_length_c                   14.9358(16)
_cell_angle_alpha                90.00
_cell_angle_beta                 110.261(11)
_cell_angle_gamma                90.00
_cell_volume                     1201.16(19)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    1370
_cell_measurement_temperature    292.9(5)
_cell_measurement_theta_max      25.8670
_cell_measurement_theta_min      4.0380
_exptl_absorpt_coefficient_mu    0.100
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.40001
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_density_diffrn    1.373
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             528
_exptl_crystal_size_max          0.31
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.05
_exptl_special_details           
;
 ? 
;
_diffrn_reflns_av_R_equivalents  0.0402
_diffrn_reflns_av_unetI/netI     0.0598
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       4
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            5484
_diffrn_reflns_theta_full        25.50
_diffrn_reflns_theta_max         28.56
_diffrn_reflns_theta_min         3.29
_diffrn_ambient_temperature      292.9(5)
_diffrn_detector_area_resol_mean 16.0733
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.891
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      0.0504411000
_diffrn_orient_matrix_UB_12      -0.0242115000
_diffrn_orient_matrix_UB_13      0.0353365000
_diffrn_orient_matrix_UB_21      -0.0063808000
_diffrn_orient_matrix_UB_22      0.0836147000
_diffrn_orient_matrix_UB_23      0.0282202000
_diffrn_orient_matrix_UB_31      -0.0263065000
_diffrn_orient_matrix_UB_32      -0.0660140000
_diffrn_orient_matrix_UB_33      0.0227751000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'SuperNova (Mo) X-ray Source'
_diffrn_standards_decay_%        ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_number         ?
_reflns_number_gt                1516
_reflns_number_total             2726
_reflns_odcompleteness_completeness 99.74
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_reflns_threshold_expression     >2sigma(I)
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2008)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_refine_diff_density_max         0.410
_refine_diff_density_min         -0.232
_refine_diff_density_rms         0.047
_refine_ls_extinction_coef       0.007(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.090
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     165
_refine_ls_number_reflns         2726
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1094
_refine_ls_R_factor_gt           0.0690
_refine_ls_restrained_S_all      1.090
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0840P)²+0.2225P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1882
_refine_ls_wR_factor_ref         0.2245
_refine_special_details          
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C6(H6), C8(H8), C15(H15)
2.b Secondary CH2 refined with riding coordinates:
 C4(H4A,H4B), C7(H7A,H7B), C9(H9A,H9B), C13(H13A,H13B)
2.c Aromatic/amide H refined with riding coordinates:
 C2(H2), C11(H11)
2.d Idealised Me refined as rotating group:
 C14(H14A,H14B,H14C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_calc_flag
_atom_site_disorder_assembly
_atom_site_disorder_group
_atom_site_refinement_flags_posn
O1 O 0.68605(18) 0.4812(3) 0.02770(16) 0.0625(6) Uani 1 d . . .
O2 O 1.1201(2) 0.6380(4) -0.26092(19) 0.0759(8) Uani 1 d . . .
O3 O 1.1348(2) 0.9634(4) -0.19400(18) 0.0749(8) Uani 1 d . . .
O4 O 0.6207(2) 0.7516(4) -0.0780(2) 0.0887(9) Uani 1 d . . .
C1 C 1.0511(3) 0.8573(4) -0.1791(2) 0.0531(8) Uani 1 d . . .
C2 C 0.9833(2) 0.9238(4) -0.1340(2) 0.0501(7) Uani 1 d . . .
H2 H 0.9892 1.0557 -0.1084 0.060 Uiso 1 calc . . R
C3 C 0.9045(2) 0.7855(4) -0.12776(19) 0.0455(7) Uani 1 d . . .
C4 C 0.8237(2) 0.8443(4) -0.0817(2) 0.0493(7) Uani 1 d . . .
H4A H 0.7546 0.8713 -0.1311 0.059 Uiso 1 calc . . R
H4B H 0.8473 0.9702 -0.0455 0.059 Uiso 1 calc . . R
C6 C 0.7042(3) 0.6830(5) 0.0045(2) 0.0634(9) Uani 1 d . . .
H6 H 0.7111 0.7753 0.0582 0.076 Uiso 1 calc . . R
C7 C 0.7139(3) 0.3540(5) -0.0375(3) 0.0716(10) Uani 1 d . . .
H7A H 0.6538 0.3434 -0.0973 0.086 Uiso 1 calc . . R
H7B H 0.7327 0.2167 -0.0114 0.086 Uiso 1 calc . . R
C8 C 0.8105(2) 0.4554(4) -0.0534(2) 0.0501(7) Uani 1 d . . .
H8 H 0.8763 0.3861 -0.0128 0.060 Uiso 1 calc . . R
C9 C 0.8092(2) 0.4520(4) -0.1557(2) 0.0500(7) Uani 1 d . . .
H9A H 0.8198 0.3119 -0.1732 0.060 Uiso 1 calc . . R
H9B H 0.7393 0.4986 -0.1983 0.060 Uiso 1 calc . . R
C10 C 0.8963(2) 0.5884(4) -0.16711(18) 0.0443(7) Uani 1 d . . .
C11 C 0.9665(2) 0.5259(4) -0.2135(2) 0.0526(8) Uani 1 d . . .
H11 H 0.9615 0.3951 -0.2402 0.063 Uiso 1 calc . . R
C12 C 1.0428(3) 0.6632(5) -0.2185(2) 0.0542(8) Uani 1 d . . .
C13 C 1.1845(3) 0.8192(6) -0.2374(3) 0.0816(12) Uani 1 d . . .
H13A H 1.2562 0.7854 -0.1938 0.098 Uiso 1 calc . . R
H13B H 1.1914 0.8784 -0.2946 0.098 Uiso 1 calc . . R
C14 C 0.5162(4) 0.7481(10) -0.0688(5) 0.152(3) Uani 1 d . . .
H14A H 0.4667 0.8276 -0.1193 0.229 Uiso 1 calc . . GR
H14B H 0.5210 0.8060 -0.0083 0.229 Uiso 1 calc . . GR
H14C H 0.4911 0.6085 -0.0726 0.229 Uiso 1 calc . . GR
C15 C 0.8095(2) 0.6754(4) -0.01513(19) 0.0511(8) Uani 1 d . . .
H15 H 0.8691 0.6871 0.0460 0.061 Uiso 1 calc . . R


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes) 
 are estimated using the full covariance matrix.  The cell esds are taken 
 into account individually in the estimation of esds in distances, angles 
 and torsion angles; correlations between esds in cell parameters are only 
 used when they are defined by crystal symmetry.  An approximate (isotropic) 
 treatment of cell esds is used for estimating esds involving l.s. planes. 
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C6 1.397(4) . ?
O1 C7 1.419(4) . ?
O2 C12 1.384(4) . ?
O2 C13 1.423(4) . ?
O3 C1 1.383(4) . ?
O3 C13 1.422(4) . ?
O4 C6 1.411(4) . ?
O4 C14 1.433(4) . ?
C1 C2 1.364(4) . ?
C1 C12 1.378(4) . ?
C2 H2 0.9300 . ?
C2 C3 1.402(4) . ?
C3 C4 1.505(4) . ?
C3 C10 1.396(4) . ?
C4 H4A 0.9700 . ?
C4 H4B 0.9700 . ?
C4 C15 1.535(4) . ?
C6 H6 0.9800 . ?
C6 C15 1.519(4) . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C7 C8 1.526(4) . ?
C8 H8 0.9800 . ?
C8 C9 1.522(4) . ?
C8 C15 1.540(4) . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C9 C10 1.508(4) . ?
C10 C11 1.397(4) . ?
C11 H11 0.9300 . ?
C11 C12 1.367(4) . ?
C13 H13A 0.9700 . ?
C13 H13B 0.9700 . ?
C14 H14A 0.9600 . ?
C14 H14B 0.9600 . ?
C14 H14C 0.9600 . ?
C15 H15 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
C6 O1 C7 105.5(2) . . ?
C12 O2 C13 105.2(2) . . ?
C1 O3 C13 105.4(3) . . ?
C6 O4 C14 113.5(3) . . ?
C2 C1 O3 128.2(3) . . ?
C2 C1 C12 122.1(3) . . ?
C12 C1 O3 109.7(3) . . ?
C1 C2 H2 121.3 . . ?
C1 C2 C3 117.4(3) . . ?
C3 C2 H2 121.3 . . ?
C2 C3 C4 121.9(2) . . ?
C10 C3 C2 120.6(3) . . ?
C10 C3 C4 117.5(2) . . ?
C3 C4 H4A 109.1 . . ?
C3 C4 H4B 109.1 . . ?
C3 C4 C15 112.3(2) . . ?
H4A C4 H4B 107.9 . . ?
C15 C4 H4A 109.1 . . ?
C15 C4 H4B 109.1 . . ?
O1 C6 O4 111.3(3) . . ?
O1 C6 H6 110.2 . . ?
O1 C6 C15 105.4(2) . . ?
O4 C6 H6 110.2 . . ?
O4 C6 C15 109.4(2) . . ?
C15 C6 H6 110.2 . . ?
O1 C7 H7A 110.4 . . ?
O1 C7 H7B 110.4 . . ?
O1 C7 C8 106.6(3) . . ?
H7A C7 H7B 108.6 . . ?
C8 C7 H7A 110.4 . . ?
C8 C7 H7B 110.4 . . ?
C7 C8 H8 108.4 . . ?
C7 C8 C15 103.2(2) . . ?
C9 C8 C7 115.5(3) . . ?
C9 C8 H8 108.4 . . ?
C9 C8 C15 112.8(2) . . ?
C15 C8 H8 108.4 . . ?
C8 C9 H9A 109.4 . . ?
C8 C9 H9B 109.4 . . ?
H9A C9 H9B 108.0 . . ?
C10 C9 C8 111.1(2) . . ?
C10 C9 H9A 109.4 . . ?
C10 C9 H9B 109.4 . . ?
C3 C10 C9 116.2(2) . . ?
C3 C10 C11 120.5(3) . . ?
C11 C10 C9 123.3(2) . . ?
C10 C11 H11 121.1 . . ?
C12 C11 C10 117.8(3) . . ?
C12 C11 H11 121.1 . . ?
C1 C12 O2 109.9(3) . . ?
C11 C12 O2 128.4(3) . . ?
C11 C12 C1 121.6(3) . . ?
O2 C13 H13A 109.9 . . ?
O2 C13 H13B 109.9 . . ?
O3 C13 O2 109.0(3) . . ?
O3 C13 H13A 109.9 . . ?
O3 C13 H13B 109.9 . . ?
H13A C13 H13B 108.3 . . ?
O4 C14 H14A 109.5 . . ?
O4 C14 H14B 109.5 . . ?
O4 C14 H14C 109.5 . . ?
H14A C14 H14B 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C4 C15 C8 113.8(2) . . ?
C4 C15 H15 108.1 . . ?
C6 C15 C4 115.3(2) . . ?
C6 C15 C8 103.2(2) . . ?
C6 C15 H15 108.1 . . ?
C8 C15 H15 108.1 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O1 C6 C15 C4 154.6(2) . . . . ?
O1 C6 C15 C8 29.9(3) . . . . ?
O1 C7 C8 C9 -139.6(3) . . . . ?
O1 C7 C8 C15 -16.1(3) . . . . ?
O3 C1 C2 C3 -179.8(3) . . . . ?
O3 C1 C12 O2 -0.6(4) . . . . ?
O3 C1 C12 C11 179.8(3) . . . . ?
O4 C6 C15 C4 34.9(4) . . . . ?
O4 C6 C15 C8 -89.8(3) . . . . ?
C1 O3 C13 O2 8.7(4) . . . . ?
C1 C2 C3 C4 -178.4(2) . . . . ?
C1 C2 C3 C10 -0.4(4) . . . . ?
C2 C1 C12 O2 179.0(3) . . . . ?
C2 C1 C12 C11 -0.7(5) . . . . ?
C2 C3 C4 C15 -135.5(3) . . . . ?
C2 C3 C10 C9 179.6(2) . . . . ?
C2 C3 C10 C11 -0.1(4) . . . . ?
C3 C4 C15 C6 -158.1(2) . . . . ?
C3 C4 C15 C8 -39.1(3) . . . . ?
C3 C10 C11 C12 0.3(4) . . . . ?
C4 C3 C10 C9 -2.3(3) . . . . ?
C4 C3 C10 C11 178.0(3) . . . . ?
C6 O1 C7 C8 36.3(4) . . . . ?
C7 O1 C6 O4 76.9(3) . . . . ?
C7 O1 C6 C15 -41.6(3) . . . . ?
C7 C8 C9 C10 169.6(3) . . . . ?
C7 C8 C15 C4 -133.5(3) . . . . ?
C7 C8 C15 C6 -7.9(3) . . . . ?
C8 C9 C10 C3 -47.3(3) . . . . ?
C8 C9 C10 C11 132.4(3) . . . . ?
C9 C8 C15 C4 -8.3(4) . . . . ?
C9 C8 C15 C6 117.4(3) . . . . ?
C9 C10 C11 C12 -179.5(3) . . . . ?
C10 C3 C4 C15 46.4(3) . . . . ?
C10 C11 C12 O2 -179.5(3) . . . . ?
C10 C11 C12 C1 0.1(5) . . . . ?
C12 O2 C13 O3 -9.0(4) . . . . ?
C12 C1 C2 C3 0.8(4) . . . . ?
C13 O2 C12 C1 5.9(4) . . . . ?
C13 O2 C12 C11 -174.5(3) . . . . ?
C13 O3 C1 C2 175.5(3) . . . . ?
C13 O3 C1 C12 -5.0(4) . . . . ?
C14 O4 C6 O1 59.3(5) . . . . ?
C14 O4 C6 C15 175.3(4) . . . . ?
C15 C8 C9 C10 51.3(3) . . . . ?

####################################################################### 
# 
# 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_xiaojian1222
_database_code_depnum_ccdc_archive 'CCDC 1811055'
_audit_update_record             
;
2017-12-13 deposited with the CCDC.
2018-01-29 downloaded from the CCDC.
;
_audit_creation_date             2016-01-11
_audit_creation_method           
;
Olex2 1.2
(compiled 2015.09.30 svn.r3233 for OlexSys, GUI svn.r5103)
;
_chemical_name_common            ?
_chemical_name_systematic        
;
 ? 
;
_chemical_formula_moiety         'C13 H15 F O2'
_chemical_formula_sum            'C13 H15 F O2'
_chemical_formula_weight         222.25
_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'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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_id
_space_group_symop_operation_xyz
1 'x, y, z'
2 '-x, -y, -z'

_cell_length_a                   7.4670(16)
_cell_length_b                   8.1131(16)
_cell_length_c                   10.193(2)
_cell_angle_alpha                107.549(19)
_cell_angle_beta                 90.344(18)
_cell_angle_gamma                106.555(18)
_cell_volume                     561.5(2)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    833
_cell_measurement_temperature    273.77(10)
_cell_measurement_theta_max      23.5300
_cell_measurement_theta_min      4.2090
_exptl_absorpt_coefficient_mu    0.098
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.88765
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.314
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             236
_exptl_crystal_size_max          0.21
_exptl_crystal_size_mid          0.17
_exptl_crystal_size_min          0.15
_exptl_special_details           
;
 ? 
;
_diffrn_reflns_av_R_equivalents  0.0237
_diffrn_reflns_av_unetI/netI     0.0519
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            3562
_diffrn_reflns_theta_full        26.02
_diffrn_reflns_theta_max         26.02
_diffrn_reflns_theta_min         3.33
_diffrn_ambient_environment      air
_diffrn_ambient_temperature      273.77(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.0733
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega  -45.00   41.00   2.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -       20.7416  -57.0000   30.0000 43

#__ type_ start__ end____ width___ exp.time_
  2 omega  -10.00   24.00   2.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      -17.3041  -99.0000  -60.0000 17

#__ type_ start__ end____ width___ exp.time_
  3 omega  -12.00   22.00   2.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      -17.3041  -99.0000   60.0000 17

#__ type_ start__ end____ width___ exp.time_
  4 omega  -47.00   41.00   2.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -       20.7416  -57.0000  150.0000 44

#__ type_ start__ end____ width___ exp.time_
  5 omega  -46.00   42.00   2.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -       20.7416  -57.0000  -90.0000 44

#__ type_ start__ end____ width___ exp.time_
  6 omega   -8.00   24.00   2.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      -17.3041  -99.0000 -180.0000 16
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      0.0881534000
_diffrn_orient_matrix_UB_12      0.0645019000
_diffrn_orient_matrix_UB_13      0.0291813000
_diffrn_orient_matrix_UB_21      0.0238688000
_diffrn_orient_matrix_UB_22      0.0011589000
_diffrn_orient_matrix_UB_23      -0.0670313000
_diffrn_orient_matrix_UB_31      -0.0397509000
_diffrn_orient_matrix_UB_32      0.0712879000
_diffrn_orient_matrix_UB_33      0.0059815000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'SuperNova (Mo) X-ray Source'
_diffrn_standards_decay_%        ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_number         ?
_reflns_number_gt                1441
_reflns_number_total             2209
_reflns_odcompleteness_completeness 99.74
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_reflns_threshold_expression     >2sigma(I)
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_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         0.140
_refine_diff_density_min         -0.180
_refine_diff_density_rms         0.036
_refine_ls_extinction_coef       ?
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.127
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     146
_refine_ls_number_reflns         2209
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0887
_refine_ls_R_factor_gt           0.0550
_refine_ls_restrained_S_all      1.127
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0400P)²+0.1096P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1163
_refine_ls_wR_factor_ref         0.1404
_refine_special_details          
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C8(H8), C9(H9), C12(H12)
2.b Secondary CH2 refined with riding coordinates:
 C7(H7A,H7B), C10(H10A,H10B), C11(H11A,H11B)
2.c Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C4(H4)
2.d Idealised Me refined as rotating group:
 C13(H13A,H13B,H13C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_calc_flag
_atom_site_disorder_assembly
_atom_site_disorder_group
_atom_site_refinement_flags_posn
F1 F 0.3199(2) 0.2956(2) 1.15939(15) 0.0784(5) Uani 1 d . . .
O1 O 0.1640(3) 0.3494(3) 0.55598(18) 0.0660(6) Uani 1 d . . .
O2 O 0.3610(2) 0.1796(2) 0.57343(18) 0.0588(5) Uani 1 d . . .
C1 C 0.1335(4) 0.2564(3) 1.1187(3) 0.0539(7) Uani 1 d . . .
C2 C 0.0082(5) 0.2219(3) 1.2108(3) 0.0656(8) Uani 1 d . . .
H2 H 0.0473 0.2236 1.2981 0.079 Uiso 1 calc . . R
C3 C -0.1789(5) 0.1843(3) 1.1690(3) 0.0708(9) Uani 1 d . . .
H3 H -0.2689 0.1596 1.2288 0.085 Uiso 1 calc . . R
C4 C -0.2339(4) 0.1829(3) 1.0388(3) 0.0597(7) Uani 1 d . . .
H4 H -0.3607 0.1570 1.0121 0.072 Uiso 1 calc . . R
C5 C -0.1021(3) 0.2196(3) 0.9469(2) 0.0471(6) Uani 1 d . . .
C6 C 0.0881(3) 0.2576(3) 0.9875(2) 0.0443(6) Uani 1 d . . .
C7 C 0.2419(3) 0.2991(3) 0.8956(2) 0.0479(6) Uani 1 d . . .
H7A H 0.3093 0.4276 0.9280 0.057 Uiso 1 calc . . R
H7B H 0.3302 0.2330 0.9003 0.057 Uiso 1 calc . . R
C8 C 0.1593(3) 0.2458(3) 0.7481(2) 0.0409(5) Uani 1 d . . .
H8 H 0.1141 0.1132 0.7121 0.049 Uiso 1 calc . . R
C9 C -0.0067(3) 0.3160(3) 0.7415(2) 0.0440(6) Uani 1 d . . .
H9 H 0.0307 0.4452 0.7950 0.053 Uiso 1 calc . . R
C10 C -0.1671(3) 0.2177(3) 0.8051(3) 0.0542(7) Uani 1 d . . .
H10A H -0.2184 0.0933 0.7455 0.065 Uiso 1 calc . . R
H10B H -0.2658 0.2752 0.8131 0.065 Uiso 1 calc . . R
C11 C -0.0265(3) 0.2977(4) 0.5899(3) 0.0557(7) Uani 1 d . . .
H11A H -0.0929 0.1739 0.5352 0.067 Uiso 1 calc . . R
H11B H -0.0935 0.3774 0.5740 0.067 Uiso 1 calc . . R
C12 C 0.2823(3) 0.3129(3) 0.6460(2) 0.0457(6) Uani 1 d . . .
H12 H 0.3820 0.4242 0.6952 0.055 Uiso 1 calc . . R
C13 C 0.4900(4) 0.2356(4) 0.4813(3) 0.0723(8) Uani 1 d . . .
H13A H 0.4230 0.2487 0.4063 0.108 Uiso 1 calc . . GR
H13B H 0.5534 0.1462 0.4455 0.108 Uiso 1 calc . . GR
H13C H 0.5805 0.3496 0.5301 0.108 Uiso 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
F1 C1 1.368(3) . ?
O1 C11 1.439(3) . ?
O1 C12 1.419(3) . ?
O2 C12 1.395(2) . ?
O2 C13 1.426(3) . ?
C1 C2 1.362(4) . ?
C1 C6 1.381(3) . ?
C2 H2 0.9300 . ?
C2 C3 1.377(4) . ?
C3 H3 0.9300 . ?
C3 C4 1.383(4) . ?
C4 H4 0.9300 . ?
C4 C5 1.395(3) . ?
C5 C6 1.396(3) . ?
C5 C10 1.517(3) . ?
C6 C7 1.514(3) . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C7 C8 1.508(3) . ?
C8 H8 0.9800 . ?
C8 C9 1.514(3) . ?
C8 C12 1.514(3) . ?
C9 H9 0.9800 . ?
C9 C10 1.506(3) . ?
C9 C11 1.509(3) . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C12 H12 0.9800 . ?
C13 H13A 0.9600 . ?
C13 H13B 0.9600 . ?
C13 H13C 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
C12 O1 C11 109.34(17) . . ?
C12 O2 C13 113.48(18) . . ?
F1 C1 C6 117.0(2) . . ?
C2 C1 F1 117.7(2) . . ?
C2 C1 C6 125.3(3) . . ?
C1 C2 H2 121.4 . . ?
C1 C2 C3 117.2(3) . . ?
C3 C2 H2 121.4 . . ?
C2 C3 H3 119.8 . . ?
C2 C3 C4 120.5(3) . . ?
C4 C3 H3 119.8 . . ?
C3 C4 H4 119.5 . . ?
C3 C4 C5 121.1(3) . . ?
C5 C4 H4 119.5 . . ?
C4 C5 C6 119.2(2) . . ?
C4 C5 C10 119.7(2) . . ?
C6 C5 C10 121.1(2) . . ?
C1 C6 C5 116.8(2) . . ?
C1 C6 C7 119.9(2) . . ?
C5 C6 C7 123.3(2) . . ?
C6 C7 H7A 109.6 . . ?
C6 C7 H7B 109.6 . . ?
H7A C7 H7B 108.1 . . ?
C8 C7 C6 110.33(19) . . ?
C8 C7 H7A 109.6 . . ?
C8 C7 H7B 109.6 . . ?
C7 C8 H8 107.9 . . ?
C7 C8 C9 110.66(18) . . ?
C7 C8 C12 118.5(2) . . ?
C9 C8 H8 107.9 . . ?
C12 C8 H8 107.9 . . ?
C12 C8 C9 103.47(17) . . ?
C8 C9 H9 108.5 . . ?
C10 C9 C8 109.91(18) . . ?
C10 C9 H9 108.5 . . ?
C10 C9 C11 120.2(2) . . ?
C11 C9 C8 100.70(18) . . ?
C11 C9 H9 108.5 . . ?
C5 C10 H10A 109.5 . . ?
C5 C10 H10B 109.5 . . ?
C9 C10 C5 110.8(2) . . ?
C9 C10 H10A 109.5 . . ?
C9 C10 H10B 109.5 . . ?
H10A C10 H10B 108.1 . . ?
O1 C11 C9 104.21(19) . . ?
O1 C11 H11A 110.9 . . ?
O1 C11 H11B 110.9 . . ?
C9 C11 H11A 110.9 . . ?
C9 C11 H11B 110.9 . . ?
H11A C11 H11B 108.9 . . ?
O1 C12 C8 106.42(18) . . ?
O1 C12 H12 109.9 . . ?
O2 C12 O1 111.20(19) . . ?
O2 C12 C8 109.45(17) . . ?
O2 C12 H12 109.9 . . ?
C8 C12 H12 109.9 . . ?
O2 C13 H13A 109.5 . . ?
O2 C13 H13B 109.5 . . ?
O2 C13 H13C 109.5 . . ?
H13A C13 H13B 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 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
F1 C1 C2 C3 179.4(2) . . . . ?
F1 C1 C6 C5 -179.29(19) . . . . ?
F1 C1 C6 C7 0.7(3) . . . . ?
C1 C2 C3 C4 -0.2(4) . . . . ?
C1 C6 C7 C8 165.26(19) . . . . ?
C2 C1 C6 C5 -0.2(3) . . . . ?
C2 C1 C6 C7 179.7(2) . . . . ?
C2 C3 C4 C5 -0.1(4) . . . . ?
C3 C4 C5 C6 0.2(3) . . . . ?
C3 C4 C5 C10 -179.8(2) . . . . ?
C4 C5 C6 C1 -0.1(3) . . . . ?
C4 C5 C6 C7 180.0(2) . . . . ?
C4 C5 C10 C9 162.0(2) . . . . ?
C5 C6 C7 C8 -14.8(3) . . . . ?
C6 C1 C2 C3 0.4(4) . . . . ?
C6 C5 C10 C9 -18.0(3) . . . . ?
C6 C7 C8 C9 47.6(2) . . . . ?
C6 C7 C8 C12 166.74(17) . . . . ?
C7 C8 C9 C10 -68.3(2) . . . . ?
C7 C8 C9 C11 163.86(19) . . . . ?
C7 C8 C12 O1 -143.76(19) . . . . ?
C7 C8 C12 O2 96.0(2) . . . . ?
C8 C9 C10 C5 50.7(2) . . . . ?
C8 C9 C11 O1 -38.8(2) . . . . ?
C9 C8 C12 O1 -20.9(2) . . . . ?
C9 C8 C12 O2 -141.16(19) . . . . ?
C10 C5 C6 C1 179.9(2) . . . . ?
C10 C5 C6 C7 0.0(3) . . . . ?
C10 C9 C11 O1 -159.53(19) . . . . ?
C11 O1 C12 O2 115.3(2) . . . . ?
C11 O1 C12 C8 -3.9(2) . . . . ?
C11 C9 C10 C5 166.74(19) . . . . ?
C12 O1 C11 C9 27.3(2) . . . . ?
C12 C8 C9 C10 163.78(19) . . . . ?
C12 C8 C9 C11 36.0(2) . . . . ?
C13 O2 C12 O1 66.9(3) . . . . ?
C13 O2 C12 C8 -175.8(2) . . . . ?

_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_xiaojian1201
_database_code_depnum_ccdc_archive 'CCDC 1811056'
_audit_update_record             
;
2017-12-13 deposited with the CCDC.
2018-01-29 downloaded from the CCDC.
;
_audit_creation_date             2015-12-04
_audit_creation_method           
;
Olex2 1.2
(compiled 2015.09.30 svn.r3233 for OlexSys, GUI svn.r5103)
;
_chemical_name_common            ?
_chemical_name_systematic        
;
 ? 
;
_chemical_formula_moiety         'C20 H20 O4'
_chemical_formula_sum            'C20 H20 O4'
_chemical_formula_weight         324.36
_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'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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_id
_space_group_symop_operation_xyz
1 'x, y, z'
2 '-x, -y, -z'

_cell_length_a                   6.4202(14)
_cell_length_b                   8.678(2)
_cell_length_c                   15.259(4)
_cell_angle_alpha                77.58(2)
_cell_angle_beta                 82.191(19)
_cell_angle_gamma                85.69(2)
_cell_volume                     821.6(3)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    799
_cell_measurement_temperature    294.06(10)
_cell_measurement_theta_max      22.9540
_cell_measurement_theta_min      3.6400
_exptl_absorpt_coefficient_mu    0.091
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.66608
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.311
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             344
_exptl_crystal_size_max          0.21
_exptl_crystal_size_mid          0.17
_exptl_crystal_size_min          0.14
_exptl_special_details           
;
 ? 
;
_diffrn_reflns_av_R_equivalents  0.0397
_diffrn_reflns_av_unetI/netI     0.0782
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            5016
_diffrn_reflns_theta_full        26.02
_diffrn_reflns_theta_max         26.02
_diffrn_reflns_theta_min         3.26
_diffrn_ambient_environment      air
_diffrn_ambient_temperature      294.06(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.0733
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.985
_diffrn_measured_fraction_theta_max 0.985
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega  -52.00   28.00   2.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       20.5854  -19.0000  -60.0000 40

#__ type_ start__ end____ width___ exp.time_
  2 omega  -19.00   23.00   2.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      -17.1479  -99.0000  -30.0000 21

#__ type_ start__ end____ width___ exp.time_
  3 omega  -16.00   48.00   2.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       20.5854  -99.0000  -60.0000 32

#__ type_ start__ end____ width___ exp.time_
  4 omega  -25.00   39.00   2.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       20.5854  -57.0000 -180.0000 32

#__ type_ start__ end____ width___ exp.time_
  5 omega  -47.00   41.00   2.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -       20.5854  -57.0000   60.0000 44
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      -0.0603916000
_diffrn_orient_matrix_UB_12      0.0715815000
_diffrn_orient_matrix_UB_13      0.0011470000
_diffrn_orient_matrix_UB_21      -0.0530857000
_diffrn_orient_matrix_UB_22      -0.0347475000
_diffrn_orient_matrix_UB_23      0.0427547000
_diffrn_orient_matrix_UB_31      0.0774470000
_diffrn_orient_matrix_UB_32      0.0262570000
_diffrn_orient_matrix_UB_33      0.0217040000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'SuperNova (Mo) X-ray Source'
_diffrn_standards_decay_%        ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_number         ?
_reflns_number_gt                1744
_reflns_number_total             3189
_reflns_odcompleteness_completeness 98.38
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_reflns_threshold_expression     >2sigma(I)
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_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         0.189
_refine_diff_density_min         -0.244
_refine_diff_density_rms         0.056
_refine_ls_extinction_coef       ?
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.055
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     218
_refine_ls_number_reflns         3189
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1187
_refine_ls_R_factor_gt           0.0637
_refine_ls_restrained_S_all      1.055
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0571P)²+0.1094P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1343
_refine_ls_wR_factor_ref         0.1788
_refine_special_details          
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C1(H1), C2(H2), C11(H11), C12(H12)
2.b Secondary CH2 refined with riding coordinates:
 C3(H3A,H3B), C7(H7A,H7B), C13(H13A,H13B)
2.c Aromatic/amide H refined with riding coordinates:
 C5(H5), C9(H9), C16(H16), C17(H17), C18(H18), C19(H19), C20(H20)
2.d Idealised Me refined as rotating group:
 C14(H14A,H14B,H14C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_calc_flag
_atom_site_disorder_assembly
_atom_site_disorder_group
_atom_site_refinement_flags_posn
O1 O 1.2102(4) 0.6343(3) -0.33105(16) 0.0756(8) Uani 1 d . . .
O2 O 1.1434(3) 0.8010(2) -0.22952(16) 0.0584(7) Uani 1 d . . .
O3 O 0.3418(3) 0.1599(2) 0.08346(14) 0.0545(6) Uani 1 d . . .
O4 O 0.1979(3) 0.1053(2) -0.03757(15) 0.0556(6) Uani 1 d . . .
C1 C 1.1580(5) 0.6447(4) -0.2391(2) 0.0455(8) Uani 1 d . . .
H1 H 1.2648 0.5854 -0.2033 0.055 Uiso 1 calc . . R
C2 C 0.9473(4) 0.5708(3) -0.20762(19) 0.0384(7) Uani 1 d . . .
H2 H 0.8360 0.6540 -0.2179 0.046 Uiso 1 calc . . R
C3 C 0.9058(4) 0.4795(3) -0.11150(19) 0.0416(7) Uani 1 d . . .
H3A H 0.8813 0.5528 -0.0709 0.050 Uiso 1 calc . . R
H3B H 1.0288 0.4122 -0.0962 0.050 Uiso 1 calc . . R
C4 C 0.7160(4) 0.3785(3) -0.0987(2) 0.0371(7) Uani 1 d . . .
C5 C 0.6263(4) 0.3185(3) -0.00963(19) 0.0415(7) Uani 1 d . . .
H5 H 0.6825 0.3397 0.0393 0.050 Uiso 1 calc . . R
C6 C 0.4548(4) 0.2283(3) 0.00336(19) 0.0397(7) Uani 1 d . . .
C7 C 0.1779(5) 0.0804(4) 0.0596(2) 0.0527(9) Uani 1 d . . .
H7A H 0.0417 0.1220 0.0825 0.063 Uiso 1 calc . . R
H7B H 0.1897 -0.0316 0.0858 0.063 Uiso 1 calc . . R
C8 C 0.3706(4) 0.1953(3) -0.0684(2) 0.0395(7) Uani 1 d . . .
C9 C 0.4542(4) 0.2510(3) -0.1555(2) 0.0404(7) Uani 1 d . . .
H9 H 0.3955 0.2280 -0.2034 0.048 Uiso 1 calc . . R
C10 C 0.6321(4) 0.3443(3) -0.17157(19) 0.0364(7) Uani 1 d . . .
C11 C 0.7207(4) 0.4084(3) -0.27015(18) 0.0378(7) Uani 1 d . . .
H11 H 0.6323 0.5018 -0.2927 0.045 Uiso 1 calc . . R
C12 C 0.9413(4) 0.4635(4) -0.2732(2) 0.0429(7) Uani 1 d . . .
H12 H 1.0348 0.3704 -0.2560 0.052 Uiso 1 calc . . R
C13 C 1.0427(5) 0.5640(4) -0.3601(2) 0.0612(10) Uani 1 d . . .
H13A H 1.0972 0.4997 -0.4035 0.073 Uiso 1 calc . . R
H13B H 0.9432 0.6441 -0.3869 0.073 Uiso 1 calc . . R
C14 C 1.3385(5) 0.8780(4) -0.2558(3) 0.0738(11) Uani 1 d . . .
H14A H 1.3636 0.9071 -0.3206 0.111 Uiso 1 calc . . GR
H14B H 1.4510 0.8075 -0.2336 0.111 Uiso 1 calc . . GR
H14C H 1.3317 0.9711 -0.2309 0.111 Uiso 1 calc . . GR
C15 C 0.7145(4) 0.2931(3) -0.3316(2) 0.0413(7) Uani 1 d . . .
C16 C 0.8314(5) 0.1517(4) -0.3198(2) 0.0545(9) Uani 1 d . . .
H16 H 0.9105 0.1243 -0.2715 0.065 Uiso 1 calc . . R
C17 C 0.8331(6) 0.0496(4) -0.3785(3) 0.0658(10) Uani 1 d . . .
H17 H 0.9136 -0.0448 -0.3696 0.079 Uiso 1 calc . . R
C18 C 0.7164(6) 0.0876(5) -0.4493(3) 0.0691(11) Uani 1 d . . .
H18 H 0.7194 0.0203 -0.4894 0.083 Uiso 1 calc . . R
C19 C 0.5952(6) 0.2255(5) -0.4610(2) 0.0695(11) Uani 1 d . . .
H19 H 0.5127 0.2505 -0.5081 0.083 Uiso 1 calc . . R
C20 C 0.5952(5) 0.3282(4) -0.4025(2) 0.0548(9) Uani 1 d . . .
H20 H 0.5135 0.4221 -0.4114 0.066 Uiso 1 calc . . R


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes) 
 are estimated using the full covariance matrix.  The cell esds are taken 
 into account individually in the estimation of esds in distances, angles 
 and torsion angles; correlations between esds in cell parameters are only 
 used when they are defined by crystal symmetry.  An approximate (isotropic) 
 treatment of cell esds is used for estimating esds involving l.s. planes. 
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C1 1.419(3) . ?
O1 C13 1.439(3) . ?
O2 C1 1.390(3) . ?
O2 C14 1.432(3) . ?
O3 C6 1.373(3) . ?
O3 C7 1.427(3) . ?
O4 C7 1.441(4) . ?
O4 C8 1.375(3) . ?
C1 H1 0.9800 . ?
C1 C2 1.515(4) . ?
C2 H2 0.9800 . ?
C2 C3 1.508(4) . ?
C2 C12 1.512(4) . ?
C3 H3A 0.9700 . ?
C3 H3B 0.9700 . ?
C3 C4 1.521(4) . ?
C4 C5 1.406(4) . ?
C4 C10 1.395(4) . ?
C5 H5 0.9300 . ?
C5 C6 1.367(4) . ?
C6 C8 1.375(4) . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C8 C9 1.363(4) . ?
C9 H9 0.9300 . ?
C9 C10 1.413(4) . ?
C10 C11 1.533(4) . ?
C11 H11 0.9800 . ?
C11 C12 1.520(4) . ?
C11 C15 1.517(4) . ?
C12 H12 0.9800 . ?
C12 C13 1.514(4) . ?
C13 H13A 0.9700 . ?
C13 H13B 0.9700 . ?
C14 H14A 0.9600 . ?
C14 H14B 0.9600 . ?
C14 H14C 0.9600 . ?
C15 C16 1.381(4) . ?
C15 C20 1.378(4) . ?
C16 H16 0.9300 . ?
C16 C17 1.387(4) . ?
C17 H17 0.9300 . ?
C17 C18 1.367(5) . ?
C18 H18 0.9300 . ?
C18 C19 1.369(5) . ?
C19 H19 0.9300 . ?
C19 C20 1.391(4) . ?
C20 H20 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
C1 O1 C13 109.6(2) . . ?
C1 O2 C14 113.3(2) . . ?
C6 O3 C7 106.0(2) . . ?
C8 O4 C7 105.5(2) . . ?
O1 C1 H1 109.7 . . ?
O1 C1 C2 106.5(2) . . ?
O2 C1 O1 111.2(3) . . ?
O2 C1 H1 109.7 . . ?
O2 C1 C2 110.0(2) . . ?
C2 C1 H1 109.7 . . ?
C1 C2 H2 108.3 . . ?
C3 C2 C1 118.6(2) . . ?
C3 C2 H2 108.3 . . ?
C3 C2 C12 110.4(2) . . ?
C12 C2 C1 102.3(2) . . ?
C12 C2 H2 108.3 . . ?
C2 C3 H3A 109.4 . . ?
C2 C3 H3B 109.4 . . ?
C2 C3 C4 111.4(2) . . ?
H3A C3 H3B 108.0 . . ?
C4 C3 H3A 109.4 . . ?
C4 C3 H3B 109.4 . . ?
C5 C4 C3 117.6(2) . . ?
C10 C4 C3 122.2(3) . . ?
C10 C4 C5 120.2(3) . . ?
C4 C5 H5 120.7 . . ?
C6 C5 C4 118.5(3) . . ?
C6 C5 H5 120.7 . . ?
O3 C6 C8 110.2(2) . . ?
C5 C6 O3 128.4(3) . . ?
C5 C6 C8 121.4(3) . . ?
O3 C7 O4 108.2(2) . . ?
O3 C7 H7A 110.1 . . ?
O3 C7 H7B 110.1 . . ?
O4 C7 H7A 110.1 . . ?
O4 C7 H7B 110.1 . . ?
H7A C7 H7B 108.4 . . ?
C6 C8 O4 110.1(3) . . ?
C9 C8 O4 128.3(3) . . ?
C9 C8 C6 121.6(3) . . ?
C8 C9 H9 120.7 . . ?
C8 C9 C10 118.6(3) . . ?
C10 C9 H9 120.7 . . ?
C4 C10 C9 119.6(3) . . ?
C4 C10 C11 122.6(2) . . ?
C9 C10 C11 117.7(2) . . ?
C10 C11 H11 107.2 . . ?
C12 C11 C10 109.3(2) . . ?
C12 C11 H11 107.2 . . ?
C15 C11 C10 113.7(2) . . ?
C15 C11 H11 107.2 . . ?
C15 C11 C12 112.0(2) . . ?
C2 C12 C11 111.4(2) . . ?
C2 C12 H12 108.3 . . ?
C2 C12 C13 101.0(2) . . ?
C11 C12 H12 108.3 . . ?
C13 C12 C11 118.9(3) . . ?
C13 C12 H12 108.3 . . ?
O1 C13 C12 103.3(2) . . ?
O1 C13 H13A 111.1 . . ?
O1 C13 H13B 111.1 . . ?
C12 C13 H13A 111.1 . . ?
C12 C13 H13B 111.1 . . ?
H13A C13 H13B 109.1 . . ?
O2 C14 H14A 109.5 . . ?
O2 C14 H14B 109.5 . . ?
O2 C14 H14C 109.5 . . ?
H14A C14 H14B 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C16 C15 C11 121.3(3) . . ?
C20 C15 C11 120.8(3) . . ?
C20 C15 C16 117.8(3) . . ?
C15 C16 H16 119.4 . . ?
C15 C16 C17 121.3(3) . . ?
C17 C16 H16 119.4 . . ?
C16 C17 H17 120.0 . . ?
C18 C17 C16 120.1(4) . . ?
C18 C17 H17 120.0 . . ?
C17 C18 H18 120.2 . . ?
C17 C18 C19 119.6(3) . . ?
C19 C18 H18 120.2 . . ?
C18 C19 H19 119.9 . . ?
C18 C19 C20 120.2(3) . . ?
C20 C19 H19 119.9 . . ?
C15 C20 C19 121.0(3) . . ?
C15 C20 H20 119.5 . . ?
C19 C20 H20 119.5 . . ?

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
O1 C1 C2 C3 145.0(3) . . . . ?
O1 C1 C2 C12 23.3(3) . . . . ?
O2 C1 C2 C3 -94.5(3) . . . . ?
O2 C1 C2 C12 143.9(3) . . . . ?
O3 C6 C8 O4 0.6(3) . . . . ?
O3 C6 C8 C9 179.6(2) . . . . ?
O4 C8 C9 C10 179.0(2) . . . . ?
C1 O1 C13 C12 -26.6(3) . . . . ?
C1 C2 C3 C4 -164.9(2) . . . . ?
C1 C2 C12 C11 -165.4(2) . . . . ?
C1 C2 C12 C13 -38.1(3) . . . . ?
C2 C3 C4 C5 -164.4(3) . . . . ?
C2 C3 C4 C10 16.0(4) . . . . ?
C2 C12 C13 O1 39.9(3) . . . . ?
C3 C2 C12 C11 67.5(3) . . . . ?
C3 C2 C12 C13 -165.3(3) . . . . ?
C3 C4 C5 C6 179.6(2) . . . . ?
C3 C4 C10 C9 -179.4(2) . . . . ?
C3 C4 C10 C11 -1.4(4) . . . . ?
C4 C5 C6 O3 -179.2(3) . . . . ?
C4 C5 C6 C8 0.3(4) . . . . ?
C4 C10 C11 C12 18.0(4) . . . . ?
C4 C10 C11 C15 143.9(3) . . . . ?
C5 C4 C10 C9 1.0(4) . . . . ?
C5 C4 C10 C11 179.0(2) . . . . ?
C5 C6 C8 O4 -179.0(2) . . . . ?
C5 C6 C8 C9 0.0(4) . . . . ?
C6 O3 C7 O4 -0.3(3) . . . . ?
C6 C8 C9 C10 0.2(4) . . . . ?
C7 O3 C6 C5 179.4(3) . . . . ?
C7 O3 C6 C8 -0.2(3) . . . . ?
C7 O4 C8 C6 -0.8(3) . . . . ?
C7 O4 C8 C9 -179.7(3) . . . . ?
C8 O4 C7 O3 0.6(3) . . . . ?
C8 C9 C10 C4 -0.7(4) . . . . ?
C8 C9 C10 C11 -178.8(2) . . . . ?
C9 C10 C11 C12 -164.0(2) . . . . ?
C9 C10 C11 C15 -38.1(3) . . . . ?
C10 C4 C5 C6 -0.8(4) . . . . ?
C10 C11 C12 C2 -49.8(3) . . . . ?
C10 C11 C12 C13 -166.6(2) . . . . ?
C10 C11 C15 C16 -64.6(4) . . . . ?
C10 C11 C15 C20 116.9(3) . . . . ?
C11 C12 C13 O1 162.1(2) . . . . ?
C11 C15 C16 C17 -177.0(3) . . . . ?
C11 C15 C20 C19 177.6(3) . . . . ?
C12 C2 C3 C4 -47.3(3) . . . . ?
C12 C11 C15 C16 59.9(4) . . . . ?
C12 C11 C15 C20 -118.6(3) . . . . ?
C13 O1 C1 O2 -117.8(3) . . . . ?
C13 O1 C1 C2 2.1(3) . . . . ?
C14 O2 C1 O1 -63.7(3) . . . . ?
C14 O2 C1 C2 178.5(3) . . . . ?
C15 C11 C12 C2 -176.7(2) . . . . ?
C15 C11 C12 C13 66.5(3) . . . . ?
C15 C16 C17 C18 -0.5(5) . . . . ?
C16 C15 C20 C19 -0.9(5) . . . . ?
C16 C17 C18 C19 -1.2(5) . . . . ?
C17 C18 C19 C20 1.7(6) . . . . ?
C18 C19 C20 C15 -0.7(5) . . . . ?
C20 C15 C16 C17 1.5(5) . . . . ?

_olex2_date_sample_data_collection 2015-12-04
_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_xiaojian0701
_database_code_depnum_ccdc_archive 'CCDC 1811054'
_audit_update_record             
;
2017-12-13 deposited with the CCDC.
2018-01-29 downloaded from the CCDC.
;
_audit_creation_date             2014-07-02
_audit_creation_method           
;
Olex2 1.2
(compiled 2014.06.27 svn.r2953 for OlexSys, GUI svn.r4855)
;
_shelxl_version_number           2013-2
_chemical_name_common            ?
_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         'C14 H16 O4'
_chemical_formula_sum            'C14 H16 O4'
_chemical_formula_weight         248.27
_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 0.0181 0.0091 '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'
O O 0.0492 0.0322 '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/n 1'
_space_group_name_Hall           '-P 2yn'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   5.0801(7)
_cell_length_b                   17.337(3)
_cell_length_c                   13.987(2)
_cell_angle_alpha                90
_cell_angle_beta                 95.513(14)
_cell_angle_gamma                90
_cell_volume                     1226.2(3)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    1465
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      70.4630
_cell_measurement_theta_min      4.0540
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.811
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.79018
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_density_diffrn    1.345
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             528
_exptl_crystal_size_max          0.24
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.02
_exptl_special_details           
;
 ?
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0313
_diffrn_reflns_av_unetI/netI     0.0351
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.974
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            4114
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.974
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         70.780
_diffrn_reflns_theta_min         4.072
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean 16.0733
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.974
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega   35.00   62.00   1.5000    4.0000
omega____ theta____ kappa____ phi______ frames
    -        0.0000   57.0000  -90.0000 18

#__ type_ start__ end____ width___ exp.time_
  2 omega  -67.00  -34.00   1.5000    4.0000
omega____ theta____ kappa____ phi______ frames
    -        0.0000  178.0000 -180.0000 22

#__ type_ start__ end____ width___ exp.time_
  3 omega  -46.00   17.00   1.5000    8.0000
omega____ theta____ kappa____ phi______ frames
    -      -42.5000   25.0000 -150.0000 42

#__ type_ start__ end____ width___ exp.time_
  4 omega   33.00   60.00   1.5000    8.0000
omega____ theta____ kappa____ phi______ frames
    -       56.0000   57.0000  150.0000 18

#__ type_ start__ end____ width___ exp.time_
  5 omega   33.00   81.00   1.5000    8.0000
omega____ theta____ kappa____ phi______ frames
    -       56.0000   57.0000  -30.0000 32

#__ type_ start__ end____ width___ exp.time_
  6 omega   72.00  106.50   1.5000    8.0000
omega____ theta____ kappa____ phi______ frames
    -       56.0000   57.0000  150.0000 23

#__ type_ start__ end____ width___ exp.time_
  7 omega   30.00  126.00   1.5000    8.0000
omega____ theta____ kappa____ phi______ frames
    -       56.0000   66.0000 -122.7986 64

#__ type_ start__ end____ width___ exp.time_
  8 omega   50.00   75.50   1.5000    8.0000
omega____ theta____ kappa____ phi______ frames
    -       56.0000 -125.0000  120.0000 17

#__ type_ start__ end____ width___ exp.time_
  9 omega   34.00   74.50   1.5000    8.0000
omega____ theta____ kappa____ phi______ frames
    -       56.0000 -125.0000  -60.0000 27

#__ type_ start__ end____ width___ exp.time_
 10 omega   44.00   93.50   1.5000    8.5000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -38.0000  120.0000 33

#__ type_ start__ end____ width___ exp.time_
 11 omega   49.00   76.00   1.5000    8.5000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -38.0000   60.0000 18

#__ type_ start__ end____ width___ exp.time_
 12 omega   72.00   99.00   1.5000    8.5000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -50.0000  -90.0000 18

#__ type_ start__ end____ width___ exp.time_
 13 omega   70.00  116.50   1.5000    8.5000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -77.0000  -30.0000 31

#__ type_ start__ end____ width___ exp.time_
 14 omega  147.00  174.00   1.5000    8.5000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  111.0000 -150.0000 18

#__ type_ start__ end____ width___ exp.time_
 15 omega   39.00   88.50   1.5000    8.5000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -38.0000 -180.0000 33

#__ type_ start__ end____ width___ exp.time_
 16 omega   69.00  148.50   1.5000    8.5000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  178.0000   90.0000 53

#__ type_ start__ end____ width___ exp.time_
 17 omega   55.00   92.50   1.5000    8.5000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -25.0000   60.0000 25

#__ type_ start__ end____ width___ exp.time_
 18 omega   48.00   93.00   1.5000    8.5000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -38.0000    0.0000 30

#__ type_ start__ end____ width___ exp.time_
 19 omega  125.00  176.00   1.5000    8.5000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -12.0000 -120.0000 34

#__ type_ start__ end____ width___ exp.time_
 20 omega   36.00  117.00   1.5000    8.5000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -12.0000 -120.0000 54
;
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      0.2430208000
_diffrn_orient_matrix_UB_12      0.0405115000
_diffrn_orient_matrix_UB_13      -0.0351408000
_diffrn_orient_matrix_UB_21      -0.0699176000
_diffrn_orient_matrix_UB_22      -0.0336199000
_diffrn_orient_matrix_UB_23      -0.1011657000
_diffrn_orient_matrix_UB_31      -0.1695581000
_diffrn_orient_matrix_UB_32      0.0717408000
_diffrn_orient_matrix_UB_33      -0.0274501000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'SuperNova (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1721
_reflns_number_total             2298
_reflns_odcompleteness_completeness 99.65
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_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       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2008)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_refine_diff_density_max         0.261
_refine_diff_density_min         -0.252
_refine_diff_density_rms         0.060
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.053
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     164
_refine_ls_number_reflns         2298
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0820
_refine_ls_R_factor_gt           0.0671
_refine_ls_restrained_S_all      1.053
_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)+(0.1279P)²+0.1193P]
 where P=(Fo²+2Fc²)/3
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1855
_refine_ls_wR_factor_ref         0.2069
_refine_special_details          
;
 ?
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C9(H9), C10(H10), C13(H13)
2.b Secondary CH2 refined with riding coordinates:
 C11(H11A,H11B), C12(H12A,H12B), C8(H8A,H8B), C14(H14A,H14B)
2.c Aromatic/amide H refined with riding coordinates:
 C2(H2), C5(H5)
2.d Idealised Me refined as rotating group:
 C15(H15A,H15B,H15C)
;
_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
C3 C -0.0115(4) 0.48321(13) 0.72355(16) 0.0442(5) Uani 1 1 d . . . . .
C4 C 0.0025(4) 0.51771(13) 0.81421(16) 0.0429(5) Uani 1 1 d . . . . .
O2 O 0.5100(4) 0.38768(12) 0.93410(13) 0.0651(6) Uani 1 1 d . . . . .
C2 C 0.1475(4) 0.41878(14) 0.70760(17) 0.0484(6) Uani 1 1 d . . . . .
H2 H 0.1394 0.3954 0.6475 0.058 Uiso 1 1 calc R . . . .
O3 O -0.6114(4) 0.68811(14) 0.64879(14) 0.0701(6) Uani 1 1 d . . . . .
C9 C -0.2716(4) 0.59608(13) 0.65708(17) 0.0457(6) Uani 1 1 d . . . . .
H9 H -0.1133 0.6282 0.6559 0.055 Uiso 1 1 calc R . . . .
O1 O 0.4879(4) 0.33088(11) 0.78388(14) 0.0637(6) Uani 1 1 d . . . . .
O4 O -0.3864(4) 0.66842(11) 0.51475(14) 0.0660(6) Uani 1 1 d . . . . .
C10 C -0.3709(4) 0.60457(14) 0.75500(17) 0.0488(6) Uani 1 1 d . . . . .
H10 H -0.5122 0.5668 0.7605 0.059 Uiso 1 1 calc R . . . .
C11 C -0.1548(5) 0.58978(14) 0.83425(17) 0.0508(6) Uani 1 1 d . . . . .
H11A H -0.2321 0.5835 0.8945 0.061 Uiso 1 1 calc R . . . .
H11B H -0.0369 0.6339 0.8404 0.061 Uiso 1 1 calc R . . . .
C5 C 0.1770(4) 0.48857(14) 0.88980(16) 0.0476(6) Uani 1 1 d . . . . .
H5 H 0.1896 0.5114 0.9502 0.057 Uiso 1 1 calc R . . . .
C6 C 0.3143(4) 0.39143(13) 0.78272(18) 0.0474(6) Uani 1 1 d . . . . .
C7 C 0.3279(4) 0.42570(14) 0.87213(17) 0.0470(6) Uani 1 1 d . . . . .
C12 C -0.4940(5) 0.68435(17) 0.74607(19) 0.0573(7) Uani 1 1 d . . . . .
H12A H -0.6269 0.6906 0.7908 0.069 Uiso 1 1 calc R . . . .
H12B H -0.3605 0.7240 0.7584 0.069 Uiso 1 1 calc R . . . .
C8 C -0.1929(5) 0.51366(14) 0.63991(17) 0.0502(6) Uani 1 1 d . . . . .
H8A H -0.1037 0.5109 0.5817 0.060 Uiso 1 1 calc R . . . .
H8B H -0.3501 0.4817 0.6310 0.060 Uiso 1 1 calc R . . . .
C13 C -0.4886(5) 0.63270(16) 0.59179(19) 0.0538(6) Uani 1 1 d . . . . .
H13 H -0.6178 0.5935 0.5683 0.065 Uiso 1 1 calc R . . . .
C14 C 0.6170(6) 0.32927(18) 0.8784(2) 0.0640(7) Uani 1 1 d . . . . .
H14A H 0.5924 0.2792 0.9073 0.077 Uiso 1 1 calc R . . . .
H14B H 0.8051 0.3377 0.8764 0.077 Uiso 1 1 calc R . . . .
C15 C -0.5859(8) 0.7042(2) 0.4502(2) 0.0922(11) Uani 1 1 d . . . . .
H15A H -0.5085 0.7221 0.3943 0.138 Uiso 1 1 calc GR . . . .
H15B H -0.6606 0.7470 0.4816 0.138 Uiso 1 1 calc GR . . . .
H15C H -0.7222 0.6674 0.4314 0.138 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
C3 C4 1.398(3) . ?
C3 C2 1.409(3) . ?
C3 C8 1.513(3) . ?
C4 C11 1.524(3) . ?
C4 C5 1.407(3) . ?
O2 C7 1.374(3) . ?
O2 C14 1.417(3) . ?
C2 H2 0.9300 . ?
C2 C6 1.369(3) . ?
O3 C12 1.434(3) . ?
O3 C13 1.429(3) . ?
C9 H9 0.9800 . ?
C9 C10 1.511(3) . ?
C9 C8 1.509(3) . ?
C9 C13 1.503(3) . ?
O1 C6 1.370(3) . ?
O1 C14 1.419(3) . ?
O4 C13 1.386(3) . ?
O4 C15 1.432(3) . ?
C10 H10 0.9800 . ?
C10 C11 1.505(3) . ?
C10 C12 1.518(3) . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C5 H5 0.9300 . ?
C5 C7 1.368(3) . ?
C6 C7 1.380(3) . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C13 H13 0.9800 . ?
C14 H14A 0.9700 . ?
C14 H14B 0.9700 . ?
C15 H15A 0.9600 . ?
C15 H15B 0.9600 . ?
C15 H15C 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
C4 C3 C2 120.2(2) . . ?
C4 C3 C8 121.8(2) . . ?
C2 C3 C8 118.0(2) . . ?
C3 C4 C11 122.4(2) . . ?
C3 C4 C5 120.1(2) . . ?
C5 C4 C11 117.4(2) . . ?
C7 O2 C14 105.5(2) . . ?
C3 C2 H2 120.8 . . ?
C6 C2 C3 118.4(2) . . ?
C6 C2 H2 120.8 . . ?
C13 O3 C12 109.56(18) . . ?
C10 C9 H9 107.8 . . ?
C8 C9 H9 107.8 . . ?
C8 C9 C10 110.7(2) . . ?
C13 C9 H9 107.8 . . ?
C13 C9 C10 102.74(19) . . ?
C13 C9 C8 119.6(2) . . ?
C6 O1 C14 105.4(2) . . ?
C13 O4 C15 112.8(2) . . ?
C9 C10 H10 108.4 . . ?
C9 C10 C12 100.6(2) . . ?
C11 C10 C9 111.57(18) . . ?
C11 C10 H10 108.4 . . ?
C11 C10 C12 118.8(2) . . ?
C12 C10 H10 108.4 . . ?
C4 C11 H11A 109.4 . . ?
C4 C11 H11B 109.4 . . ?
C10 C11 C4 111.26(19) . . ?
C10 C11 H11A 109.4 . . ?
C10 C11 H11B 109.4 . . ?
H11A C11 H11B 108.0 . . ?
C4 C5 H5 120.9 . . ?
C7 C5 C4 118.3(2) . . ?
C7 C5 H5 120.9 . . ?
C2 C6 O1 128.6(2) . . ?
C2 C6 C7 121.3(2) . . ?
O1 C6 C7 110.1(2) . . ?
O2 C7 C6 109.7(2) . . ?
C5 C7 O2 128.5(2) . . ?
C5 C7 C6 121.8(2) . . ?
O3 C12 C10 104.5(2) . . ?
O3 C12 H12A 110.9 . . ?
O3 C12 H12B 110.9 . . ?
C10 C12 H12A 110.9 . . ?
C10 C12 H12B 110.9 . . ?
H12A C12 H12B 108.9 . . ?
C3 C8 H8A 109.4 . . ?
C3 C8 H8B 109.4 . . ?
C9 C8 C3 110.99(19) . . ?
C9 C8 H8A 109.4 . . ?
C9 C8 H8B 109.4 . . ?
H8A C8 H8B 108.0 . . ?
O3 C13 C9 106.2(2) . . ?
O3 C13 H13 109.8 . . ?
C9 C13 H13 109.8 . . ?
O4 C13 O3 110.5(2) . . ?
O4 C13 C9 110.7(2) . . ?
O4 C13 H13 109.8 . . ?
O2 C14 O1 109.3(2) . . ?
O2 C14 H14A 109.8 . . ?
O2 C14 H14B 109.8 . . ?
O1 C14 H14A 109.8 . . ?
O1 C14 H14B 109.8 . . ?
H14A C14 H14B 108.3 . . ?
O4 C15 H15A 109.5 . . ?
O4 C15 H15B 109.5 . . ?
O4 C15 H15C 109.5 . . ?
H15A C15 H15B 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 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
C3 C4 C11 C10 15.1(3) . . . . ?
C3 C4 C5 C7 -0.8(3) . . . . ?
C3 C2 C6 O1 -179.1(2) . . . . ?
C3 C2 C6 C7 0.0(3) . . . . ?
C4 C3 C2 C6 -0.1(3) . . . . ?
C4 C3 C8 C9 19.8(3) . . . . ?
C4 C5 C7 O2 180.0(2) . . . . ?
C4 C5 C7 C6 0.7(3) . . . . ?
C2 C3 C4 C11 176.97(19) . . . . ?
C2 C3 C4 C5 0.4(3) . . . . ?
C2 C3 C8 C9 -159.6(2) . . . . ?
C2 C6 C7 O2 -179.7(2) . . . . ?
C2 C6 C7 C5 -0.3(4) . . . . ?
C9 C10 C11 C4 -45.6(3) . . . . ?
C9 C10 C12 O3 37.3(2) . . . . ?
O1 C6 C7 O2 -0.5(3) . . . . ?
O1 C6 C7 C5 178.9(2) . . . . ?
C10 C9 C8 C3 -50.0(2) . . . . ?
C10 C9 C13 O3 27.1(2) . . . . ?
C10 C9 C13 O4 147.0(2) . . . . ?
C11 C4 C5 C7 -177.45(19) . . . . ?
C11 C10 C12 O3 159.3(2) . . . . ?
C5 C4 C11 C10 -168.27(19) . . . . ?
C6 O1 C14 O2 2.3(3) . . . . ?
C7 O2 C14 O1 -2.6(3) . . . . ?
C12 O3 C13 C9 -3.5(3) . . . . ?
C12 O3 C13 O4 -123.6(2) . . . . ?
C12 C10 C11 C4 -161.9(2) . . . . ?
C8 C3 C4 C11 -2.4(3) . . . . ?
C8 C3 C4 C5 -178.88(19) . . . . ?
C8 C3 C2 C6 179.3(2) . . . . ?
C8 C9 C10 C11 65.6(3) . . . . ?
C8 C9 C10 C12 -167.46(19) . . . . ?
C8 C9 C13 O3 150.1(2) . . . . ?
C8 C9 C13 O4 -90.0(3) . . . . ?
C13 O3 C12 C10 -21.6(3) . . . . ?
C13 C9 C10 C11 -165.7(2) . . . . ?
C13 C9 C10 C12 -38.7(2) . . . . ?
C13 C9 C8 C3 -169.0(2) . . . . ?
C14 O2 C7 C5 -177.4(3) . . . . ?
C14 O2 C7 C6 1.9(3) . . . . ?
C14 O1 C6 C2 178.0(2) . . . . ?
C14 O1 C6 C7 -1.1(3) . . . . ?
C15 O4 C13 O3 -62.8(3) . . . . ?
C15 O4 C13 C9 179.9(2) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
