# 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 2016

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_I
_database_code_depnum_ccdc_archive 'CCDC 1062415'
_audit_update_record             
;
2015-08-26 deposited with the CCDC.
2016-01-08 downloaded from the CCDC.
;
#=======================================================================

# 5. CHEMICAL DATA

_chemical_name_systematic        
; ?
;
_chemical_name_common            ?
_chemical_formula_moiety         'C18 H14 N2 O2'
_chemical_formula_structural     ?
_chemical_formula_analytical     ?
_chemical_formula_iupac          ?
_chemical_formula_sum            'C18 H14 N2 O2'
_chemical_formula_weight         290.3
_chemical_melting_point          ?
_chemical_compound_source        ?
_chemical_absolute_configuration .

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

# 6. CRYSTAL DATA

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_symmetry_space_group_name_Hall  '-P 2yabc'
_symmetry_Int_Tables_number      14

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                   6.9512(4)
_cell_length_b                   29.5028(18)
_cell_length_c                   7.4215(5)
_cell_angle_alpha                90
_cell_angle_beta                 108.876(6)
_cell_angle_gamma                90
_cell_volume                     1440.15(16)

loop_
_twin_individual_id
_twin_individual_mass_fraction_refined
_twin_individual_twin_matrix_11
_twin_individual_twin_matrix_12
_twin_individual_twin_matrix_13
_twin_individual_twin_matrix_21
_twin_individual_twin_matrix_22
_twin_individual_twin_matrix_23
_twin_individual_twin_matrix_31
_twin_individual_twin_matrix_32
_twin_individual_twin_matrix_33
? ? ? ? ? ? ? ? ? ? ?

_cell_formula_units_Z            4

_cell_measurement_reflns_used    2407
_cell_measurement_theta_min      6.47
_cell_measurement_theta_max      66.69
_cell_measurement_temperature    120.00(10)
_cell_special_details            
; ?
;

_exptl_crystal_density_diffrn    1.339
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_F_000             608

_exptl_absorpt_coefficient_mu    0.717
_exptl_crystal_description       platelet
_exptl_crystal_size_max          0.352
_exptl_crystal_size_mid          0.23
_exptl_crystal_size_min          0.054
_exptl_crystal_size_rad          ?
_exptl_crystal_colour            colourless
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details   
;
   CrysAlisPro, Agilent Technologies, Version 1.171.37.33a	
   Analytical numeric absorption correction based on crystal shape
;
_exptl_absorpt_correction_T_min  0.857
_exptl_absorpt_correction_T_max  0.963
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
? ? ? ?

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

# 7. EXPERIMENTAL DATA

_exptl_special_details           ?

_diffrn_ambient_temperature      120
_diffrn_source                   'sealed X-ray tube'
_diffrn_source_power             ?
_diffrn_source_voltage           ?
_diffrn_source_current           ?
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_source         'X-ray tube'
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_monochromator  mirror
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Atlas, Gemini ultra'
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.1873
_diffrn_measurement_method       'ω scans'
_diffrn_measurement_specimen_support ?

_diffrn_reflns_number            4356
_diffrn_reflns_theta_min         6.48
_diffrn_reflns_theta_max         66.79
_diffrn_reflns_theta_full        66
_diffrn_measured_fraction_theta_max 0.97
_diffrn_measured_fraction_theta_full 0.98
_diffrn_reflns_av_R_equivalents  0.0258
_diffrn_reflns_av_unetI/netI     0.0361
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -34
_diffrn_reflns_limit_k_max       31
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_limit_l_max       6
_diffrn_reflns_reduction_process ?

_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
loop_
_diffrn_standard_refln_index_h
_diffrn_standard_refln_index_k
_diffrn_standard_refln_index_l
? ? ?

_diffrn_radiation_probe          X-ray

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

# 8. REFINEMENT DATA

_refine_special_details          
; ?
;

_reflns_number_total             2471
_reflns_number_gt                2033
_reflns_threshold_expression     I>3σ(I)

_refine_ls_structure_factor_coef Fsqd
_refine_ls_R_factor_gt           0.0356
_refine_ls_wR_factor_gt          0.0953
_refine_ls_R_factor_all          0.0428
_refine_ls_wR_factor_ref         0.1035
_refine_ls_goodness_of_fit_ref   1.21
_refine_ls_goodness_of_fit_gt    1.24
_refine_ls_restrained_S_gt       ?
_refine_ls_restrained_S_all      ?
_refine_ls_number_reflns         2471
_refine_ls_number_parameters     205
_refine_ls_number_restraints     2
_refine_ls_number_constraints    50
_refine_ls_weighting_scheme      sigma
_refine_ls_weighting_details     w=1/(σ²(I)+0.0016I²)
_refine_ls_hydrogen_treatment    mixed
_refine_ls_shift/su_max          0.0157
_refine_ls_shift/su_mean         0.0015
_refine_diff_density_max         0.14
_refine_diff_density_min         -0.18
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_abs_structure_details ?
_refine_ls_abs_structure_Flack   ?
_refine_ls_abs_structure_Rogers  ?

loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C 0.0181 0.0091 'International Tables Vol C tables 4.2.6.8 and 6.1.1.1'
H 0.0000 0.0000 'International Tables Vol C tables 4.2.6.8 and 6.1.1.1'
N 0.0311 0.0180 'International Tables Vol C tables 4.2.6.8 and 6.1.1.1'
O 0.0492 0.0322 'International Tables Vol C tables 4.2.6.8 and 6.1.1.1'

_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.33a (release 28-03-2014 CrysAlis171 .NET)
(compiled Mar 28 2014,12:25:20)
;
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.33a (release 28-03-2014 CrysAlis171 .NET)
(compiled Mar 28 2014,12:25:20)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.33a (release 28-03-2014 CrysAlis171 .NET)
(compiled Mar 28 2014,12:25:20)
;
_computing_structure_solution    'Superflip (Palatinus et al., 2007).'
_computing_structure_refinement  'Jana2006 (Petricek et al., 2014)'
_computing_molecular_graphics    'Mercury (Macrae et al., 2008)'
_computing_publication_material  
;
enCIFer (Allen et al., 2004), PLATON (Spek, 2009),  
PublCIF (Westrip 2010), WINGX (Farrugia 2012)
;

loop_
_restr_distance_atom_site_label_1
_restr_distance_site_symmetry_1
_restr_distance_atom_site_label_2
_restr_distance_site_symmetry_2
_restr_distance_target
_restr_distance_target_weight_param
H1n2 . N2 . 0.92 0.001
H1o1 . O1 . 0.86 0.001

loop_
_restr_angle_atom_site_label_1
_restr_angle_site_symmetry_1
_restr_angle_atom_site_label_2
_restr_angle_site_symmetry_2
_restr_angle_atom_site_label_3
_restr_angle_site_symmetry_3
_restr_angle_target
_restr_angle_target_weight_param
? ? ? ? ? ? ? ?

loop_
_restr_torsion_atom_site_label_1
_restr_torsion_site_symmetry_1
_restr_torsion_atom_site_label_2
_restr_torsion_site_symmetry_2
_restr_torsion_atom_site_label_3
_restr_torsion_site_symmetry_3
_restr_torsion_atom_site_label_4
_restr_torsion_site_symmetry_4
_restr_torsion_angle_target
_restr_torsion_weight_param
? ? ? ? ? ? ? ? ? ?

loop_
_restr_equal_distance_atom_site_label_1
_restr_equal_distance_site_symmetry_1
_restr_equal_distance_atom_site_label_2
_restr_equal_distance_site_symmetry_2
_restr_equal_distance_class_class_id
_restr_equal_distance_class_target_weight_param
? ? ? ? ? ?

loop_
_restr_equal_angle_atom_site_label_1
_restr_equal_angle_site_symmetry_1
_restr_equal_angle_atom_site_label_2
_restr_equal_angle_site_symmetry_2
_restr_equal_angle_atom_site_label_3
_restr_equal_angle_site_symmetry_3
_restr_equal_angle_class_class_id
_restr_equal_angle_class_target_weight_param
? ? ? ? ? ? ? ?

loop_
_restr_equal_torsion_atom_site_label_1
_restr_equal_torsion_site_symmetry_1
_restr_equal_torsion_atom_site_label_2
_restr_equal_torsion_site_symmetry_2
_restr_equal_torsion_atom_site_label_3
_restr_equal_torsion_site_symmetry_3
_restr_equal_torsion_atom_site_label_4
_restr_equal_torsion_site_symmetry_4
_restr_equal_torsion_class_class_id
_restr_equal_torsion_class_target_weight_param
? ? ? ? ? ? ? ? ? ?


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

# 9. ATOMIC COORDINATES AND DISPLACEMENT PARAMETERS

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_adp_type
_atom_site_U_iso_or_equiv
_atom_site_site_symmetry_multiplicity
_atom_site_occupancy
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.51678(16) 0.19571(4) -0.16916(15) Uani 0.0256(4) 4 1 d . . .
O2 O 0.42709(15) 0.29656(4) 0.14667(14) Uani 0.0240(4) 4 1 d . . .
C1 C 0.6299(2) 0.13850(5) 0.0740(2) Uani 0.0202(5) 4 1 d . . .
C2 C 0.5724(2) 0.15269(5) -0.1144(2) Uani 0.0215(5) 4 1 d . . .
C3 C 0.5711(2) 0.12218(5) -0.2618(2) Uani 0.0252(5) 4 1 d . . .
C4 C 0.6229(2) 0.07804(6) -0.2210(2) Uani 0.0277(6) 4 1 d . . .
C5 C 0.7363(2) 0.01562(6) 0.0100(3) Uani 0.0321(6) 4 1 d . . .
C6 C 0.7885(3) -0.00074(6) 0.1915(3) Uani 0.0357(6) 4 1 d . . .
C7 C 0.7840(2) 0.02859(6) 0.3392(3) Uani 0.0322(6) 4 1 d . . .
C8 C 0.7326(2) 0.07334(6) 0.3038(2) Uani 0.0268(6) 4 1 d . . .
C9 C 0.6808(2) 0.09167(5) 0.1175(2) Uani 0.0209(5) 4 1 d . . .
C10 C 0.6802(2) 0.06134(5) -0.0324(2) Uani 0.0247(5) 4 1 d . . .
C11 C 0.6445(2) 0.17100(5) 0.2254(2) Uani 0.0202(5) 4 1 d . . .
N1 N 0.58161(18) 0.21191(4) 0.18518(17) Uani 0.0210(4) 4 1 d . . .
N2 N 0.61163(18) 0.24095(4) 0.33786(18) Uani 0.0212(4) 4 1 d . . .
C12 C 0.5321(2) 0.28317(5) 0.3053(2) Uani 0.0192(5) 4 1 d . . .
C13 C 0.5822(2) 0.31295(5) 0.4767(2) Uani 0.0193(5) 4 1 d . . .
C14 C 0.6005(2) 0.35922(5) 0.4506(2) Uani 0.0234(5) 4 1 d . . .
C15 C 0.6488(2) 0.38827(6) 0.6061(2) Uani 0.0282(6) 4 1 d . . .
C16 C 0.6745(2) 0.37114(6) 0.7862(2) Uani 0.0296(6) 4 1 d . . .
C17 C 0.6537(2) 0.32521(6) 0.8126(2) Uani 0.0277(5) 4 1 d . . .
C18 C 0.6078(2) 0.29586(5) 0.6586(2) Uani 0.0226(5) 4 1 d . . .
H1c3 H 0.533555 0.132678 -0.39102 Uiso 0.0303 4 1 d . . .
H1c4 H 0.620565 0.057706 -0.32264 Uiso 0.0333 4 1 d . . .
H1c5 H 0.737672 -0.004474 -0.091325 Uiso 0.0385 4 1 d . . .
H1c6 H 0.827819 -0.031864 0.217857 Uiso 0.0429 4 1 d . . .
H1c7 H 0.817251 0.017123 0.466706 Uiso 0.0386 4 1 d . . .
H1c8 H 0.731813 0.092715 0.407455 Uiso 0.0321 4 1 d . . .
H1c11 H 0.701456 0.16183 0.355999 Uiso 0.0243 4 1 d . . .
H1c14 H 0.579767 0.371071 0.325285 Uiso 0.028 4 1 d . . .
H1c15 H 0.664457 0.42014 0.58879 Uiso 0.0338 4 1 d . . .
H1c16 H 0.706836 0.391292 0.893464 Uiso 0.0355 4 1 d . . .
H1c17 H 0.671077 0.31364 0.937782 Uiso 0.0332 4 1 d . . .
H1c18 H 0.593647 0.263974 0.676849 Uiso 0.0271 4 1 d . . .
H1n2 H 0.7051(18) 0.2328(6) 0.4524(12) Uiso 0.0254 4 1 d . . .
H1o1 H 0.528(3) 0.2102(6) -0.0658(15) Uiso 0.0308 4 1 d . . .


loop_
_jana_atom_site_ADP_C_label
_jana_atom_site_ADP_C_type_symbol
_jana_atom_site_ADP_C_111
_jana_atom_site_ADP_C_112
_jana_atom_site_ADP_C_113
_jana_atom_site_ADP_C_122
_jana_atom_site_ADP_C_123
_jana_atom_site_ADP_C_133
_jana_atom_site_ADP_C_222
_jana_atom_site_ADP_C_223
_jana_atom_site_ADP_C_233
_jana_atom_site_ADP_C_333
? ? ? ? ? ? ? ? ? ? ? ?

loop_
_jana_atom_site_ADP_D_label
_jana_atom_site_ADP_D_type_symbol
_jana_atom_site_ADP_D_1111
_jana_atom_site_ADP_D_1112
_jana_atom_site_ADP_D_1113
_jana_atom_site_ADP_D_1122
_jana_atom_site_ADP_D_1123
_jana_atom_site_ADP_D_1133
_jana_atom_site_ADP_D_1222
_jana_atom_site_ADP_D_1223
_jana_atom_site_ADP_D_1233
_jana_atom_site_ADP_D_1333
_jana_atom_site_ADP_D_2222
_jana_atom_site_ADP_D_2223
_jana_atom_site_ADP_D_2233
_jana_atom_site_ADP_D_2333
_jana_atom_site_ADP_D_3333
? ? ? ? ? ? ? ? ? ? ? ? ? ? ? ? ?

loop_
_jana_atom_site_ADP_E_label
_jana_atom_site_ADP_E_type_symbol
_jana_atom_site_ADP_E_11111
_jana_atom_site_ADP_E_11112
_jana_atom_site_ADP_E_11113
_jana_atom_site_ADP_E_11122
_jana_atom_site_ADP_E_11123
_jana_atom_site_ADP_E_11133
_jana_atom_site_ADP_E_11222
_jana_atom_site_ADP_E_11223
_jana_atom_site_ADP_E_11233
_jana_atom_site_ADP_E_11333
_jana_atom_site_ADP_E_12222
_jana_atom_site_ADP_E_12223
_jana_atom_site_ADP_E_12233
_jana_atom_site_ADP_E_12333
_jana_atom_site_ADP_E_13333
_jana_atom_site_ADP_E_22222
_jana_atom_site_ADP_E_22223
_jana_atom_site_ADP_E_22233
_jana_atom_site_ADP_E_22333
_jana_atom_site_ADP_E_23333
_jana_atom_site_ADP_E_33333
? ? ? ? ? ? ? ? ? ? ? ? ? ? ? ? ? ? ? ? ? ? ?

loop_
_jana_atom_site_ADP_F_label
_jana_atom_site_ADP_F_type_symbol
_jana_atom_site_ADP_F_111111
_jana_atom_site_ADP_F_111112
_jana_atom_site_ADP_F_111113
_jana_atom_site_ADP_F_111122
_jana_atom_site_ADP_F_111123
_jana_atom_site_ADP_F_111133
_jana_atom_site_ADP_F_111222
_jana_atom_site_ADP_F_111223
_jana_atom_site_ADP_F_111233
_jana_atom_site_ADP_F_111333
_jana_atom_site_ADP_F_112222
_jana_atom_site_ADP_F_112223
_jana_atom_site_ADP_F_112233
_jana_atom_site_ADP_F_112333
_jana_atom_site_ADP_F_113333
_jana_atom_site_ADP_F_122222
_jana_atom_site_ADP_F_122223
_jana_atom_site_ADP_F_122233
_jana_atom_site_ADP_F_122333
_jana_atom_site_ADP_F_123333
_jana_atom_site_ADP_F_133333
_jana_atom_site_ADP_F_222222
_jana_atom_site_ADP_F_222223
_jana_atom_site_ADP_F_222233
_jana_atom_site_ADP_F_222333
_jana_atom_site_ADP_F_223333
_jana_atom_site_ADP_F_233333
_jana_atom_site_ADP_F_333333
? ? ? ? ? ? ? ? ? ? ? ? ? ? ? ? ? ? ? ? ? ? ? ? ? ? ? ? ? ?


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

# 10. MOLECULAR GEOMETRY


loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_1
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
O1 C2 . . 1.3505(18) ?
O1 H1o1 . . 0.860(13) ?
O2 C12 . . 1.2324(16) ?
C1 C2 . . 1.389(2) ?
C1 C9 . . 1.437(2) ?
C1 C11 . . 1.455(2) ?
C2 C3 . . 1.415(2) ?
C3 C4 . . 1.359(2) ?
C3 H1c3 . . 0.96 ?
C4 C10 . . 1.414(2) ?
C4 H1c4 . . 0.96 ?
C5 C6 . . 1.365(3) ?
C5 C10 . . 1.411(2) ?
C5 H1c5 . . 0.96 ?
C6 C7 . . 1.405(3) ?
C6 H1c6 . . 0.96 ?
C7 C8 . . 1.371(2) ?
C7 H1c7 . . 0.96 ?
C8 C9 . . 1.418(2) ?
C8 H1c8 . . 0.96 ?
C9 C10 . . 1.427(2) ?
C11 N1 . . 1.2857(19) ?
C11 H1c11 . . 0.96 ?
N1 N2 . . 1.3815(18) ?
N2 C12 . . 1.3523(19) ?
N2 H1n2 . . 0.920(9) ?
C12 C13 . . 1.491(2) ?
C13 C14 . . 1.390(2) ?
C13 C18 . . 1.398(2) ?
C14 C15 . . 1.388(2) ?
C14 H1c14 . . 0.96 ?
C15 C16 . . 1.386(2) ?
C15 H1c15 . . 0.96 ?
C16 C17 . . 1.383(2) ?
C16 H1c16 . . 0.96 ?
C17 C18 . . 1.386(2) ?
C17 H1c17 . . 0.96 ?
C18 H1c18 . . 0.96 ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_2
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C2 O1 H1o1 . . . 105.4(10) ?
C2 C1 C9 . . . 119.06(14) ?
C2 C1 C11 . . . 120.26(14) ?
C9 C1 C11 . . . 120.64(13) ?
O1 C2 C1 . . . 123.19(14) ?
O1 C2 C3 . . . 115.83(13) ?
C1 C2 C3 . . . 120.98(14) ?
C2 C3 C4 . . . 120.16(15) ?
C2 C3 H1c3 . . . 119.92 ?
C4 C3 H1c3 . . . 119.92 ?
C3 C4 C10 . . . 121.62(16) ?
C3 C4 H1c4 . . . 119.19 ?
C10 C4 H1c4 . . . 119.19 ?
C6 C5 C10 . . . 121.62(17) ?
C6 C5 H1c5 . . . 119.19 ?
C10 C5 H1c5 . . . 119.19 ?
C5 C6 C7 . . . 119.10(16) ?
C5 C6 H1c6 . . . 120.45 ?
C7 C6 H1c6 . . . 120.45 ?
C6 C7 C8 . . . 120.91(17) ?
C6 C7 H1c7 . . . 119.54 ?
C8 C7 H1c7 . . . 119.55 ?
C7 C8 C9 . . . 121.50(16) ?
C7 C8 H1c8 . . . 119.25 ?
C9 C8 H1c8 . . . 119.25 ?
C1 C9 C8 . . . 123.51(15) ?
C1 C9 C10 . . . 119.31(14) ?
C8 C9 C10 . . . 117.18(14) ?
C4 C10 C5 . . . 121.54(16) ?
C4 C10 C9 . . . 118.81(14) ?
C5 C10 C9 . . . 119.65(15) ?
C1 C11 N1 . . . 120.41(13) ?
C1 C11 H1c11 . . . 119.8 ?
N1 C11 H1c11 . . . 119.79 ?
C11 N1 N2 . . . 116.25(12) ?
N1 N2 C12 . . . 118.69(11) ?
N1 N2 H1n2 . . . 118.0(10) ?
C12 N2 H1n2 . . . 122.2(10) ?
O2 C12 N2 . . . 123.20(14) ?
O2 C12 C13 . . . 121.90(13) ?
N2 C12 C13 . . . 114.90(12) ?
C12 C13 C14 . . . 117.82(14) ?
C12 C13 C18 . . . 122.19(14) ?
C14 C13 C18 . . . 119.98(14) ?
C13 C14 C15 . . . 119.93(15) ?
C13 C14 H1c14 . . . 120.03 ?
C15 C14 H1c14 . . . 120.03 ?
C14 C15 C16 . . . 119.85(15) ?
C14 C15 H1c15 . . . 120.08 ?
C16 C15 H1c15 . . . 120.08 ?
C15 C16 C17 . . . 120.46(16) ?
C15 C16 H1c16 . . . 119.77 ?
C17 C16 H1c16 . . . 119.77 ?
C16 C17 C18 . . . 120.13(16) ?
C16 C17 H1c17 . . . 119.93 ?
C18 C17 H1c17 . . . 119.93 ?
C13 C18 C17 . . . 119.63(15) ?
C13 C18 H1c18 . . . 120.19 ?
C17 C18 H1c18 . . . 120.18 ?

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_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
? ? ? ? ? ? ? ? ? ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_D
_geom_hbond_site_symmetry_H
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_publ_flag
C18 H1c18 O1 . . 1_556 0.96 2.46 3.360(2) 156.34 ?
N2 H1n2 O2 . . 4_555 0.920(9) 1.941(11) 2.8345(15) 163.2(13) ?
O1 H1o1 N1 . . . 0.860(13) 1.778(11) 2.5652(17) 151.2(15) ?


####################################################################### 
# 
# 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_I
_database_code_depnum_ccdc_archive 'CCDC 1062416'
_audit_update_record             
;
2015-08-26 deposited with the CCDC.
2016-01-08 downloaded from the CCDC.
;
#=======================================================================

# 5. CHEMICAL DATA

_chemical_name_systematic        
; ?
;
_chemical_name_common            ?
_chemical_formula_moiety         'C20 H17 N2 O4 V1'
_chemical_formula_structural     ?
_chemical_formula_analytical     ?
_chemical_formula_iupac          ?
_chemical_formula_sum            'C20 H17 N2 O4 V1'
_chemical_formula_weight         400.3
_chemical_melting_point          ?
_chemical_compound_source        ?
_chemical_absolute_configuration .

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

# 6. CRYSTAL DATA

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_symmetry_space_group_name_Hall  '-P 2ycb'
_symmetry_Int_Tables_number      14

loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 x,y,z
2 -x,y+1/2,-z+1/2
3 -x,-y,-z
4 x,-y+1/2,z+1/2

_cell_length_a                   17.8457(18)
_cell_length_b                   5.9203(5)
_cell_length_c                   18.1622(13)
_cell_angle_alpha                90
_cell_angle_beta                 110.679(8)
_cell_angle_gamma                90
_cell_volume                     1795.2(3)

loop_
_twin_individual_id
_twin_individual_mass_fraction_refined
_twin_individual_twin_matrix_11
_twin_individual_twin_matrix_12
_twin_individual_twin_matrix_13
_twin_individual_twin_matrix_21
_twin_individual_twin_matrix_22
_twin_individual_twin_matrix_23
_twin_individual_twin_matrix_31
_twin_individual_twin_matrix_32
_twin_individual_twin_matrix_33
? ? ? ? ? ? ? ? ? ? ?

_cell_formula_units_Z            4

_cell_measurement_reflns_used    2246
_cell_measurement_theta_min      4.96
_cell_measurement_theta_max      66.57
_cell_measurement_temperature    120.00(10)
_cell_special_details            
; ?
;

_exptl_crystal_density_diffrn    1.4811
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_F_000             824

_exptl_absorpt_coefficient_mu    4.862
_exptl_crystal_description       prism
_exptl_crystal_size_max          0.168
_exptl_crystal_size_mid          0.082
_exptl_crystal_size_min          0.033
_exptl_crystal_size_rad          ?
_exptl_crystal_colour            black
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details   
;
   CrysAlisPro, Agilent Technologies, Version 1.171.37.33a	
   Analytical numeric absorption correction based on crystal shape
;
_exptl_absorpt_correction_T_min  0.572
_exptl_absorpt_correction_T_max  0.86
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
? ? ? ?

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

# 7. EXPERIMENTAL DATA

_exptl_special_details           ?

_diffrn_ambient_temperature      120
_diffrn_source                   'sealed X-ray tube'
_diffrn_source_power             ?
_diffrn_source_voltage           ?
_diffrn_source_current           ?
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_source         'X-ray tube'
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_monochromator  mirror
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Atlas, Gemini ultra'
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.1873
_diffrn_measurement_method       'ω scans'
_diffrn_measurement_specimen_support ?

_diffrn_reflns_number            9573
_diffrn_reflns_theta_min         4.94
_diffrn_reflns_theta_max         67.22
_diffrn_reflns_theta_full        66.67
_diffrn_measured_fraction_theta_max 0.97
_diffrn_measured_fraction_theta_full 0.98
_diffrn_reflns_av_R_equivalents  0.0684
_diffrn_reflns_av_unetI/netI     0.0623
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_reduction_process ?

_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
loop_
_diffrn_standard_refln_index_h
_diffrn_standard_refln_index_k
_diffrn_standard_refln_index_l
? ? ?

_diffrn_radiation_probe          X-ray

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

# 8. REFINEMENT DATA

_refine_special_details          
; ?
;

_reflns_number_total             3113
_reflns_number_gt                2288
_reflns_threshold_expression     I>3σ(I)

_refine_ls_structure_factor_coef Fsqd
_refine_ls_R_factor_gt           0.0510
_refine_ls_wR_factor_gt          0.1177
_refine_ls_R_factor_all          0.0700
_refine_ls_wR_factor_ref         0.1320
_refine_ls_goodness_of_fit_ref   1.28
_refine_ls_goodness_of_fit_gt    1.35
_refine_ls_restrained_S_gt       ?
_refine_ls_restrained_S_all      ?
_refine_ls_number_reflns         3113
_refine_ls_number_parameters     244
_refine_ls_number_restraints     0
_refine_ls_number_constraints    68
_refine_ls_weighting_scheme      sigma
_refine_ls_weighting_details     w=1/(σ²(I)+0.0016I²)
_refine_ls_hydrogen_treatment    constr
_refine_ls_shift/su_max          0.0135
_refine_ls_shift/su_mean         0.0005
_refine_diff_density_max         0.63
_refine_diff_density_min         -0.37
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_abs_structure_details ?
_refine_ls_abs_structure_Flack   ?
_refine_ls_abs_structure_Rogers  ?

loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C 0.0181 0.0091 'International Tables Vol C tables 4.2.6.8 and 6.1.1.1'
H 0.0000 0.0000 'International Tables Vol C tables 4.2.6.8 and 6.1.1.1'
N 0.0311 0.0180 'International Tables Vol C tables 4.2.6.8 and 6.1.1.1'
O 0.0492 0.0322 'International Tables Vol C tables 4.2.6.8 and 6.1.1.1'
V 0.0687 2.1097 'International Tables Vol C tables 4.2.6.8 and 6.1.1.1'

_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.33a (release 28-03-2014 CrysAlis171 .NET)
(compiled Mar 28 2014,12:25:20)
;
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.33a (release 28-03-2014 CrysAlis171 .NET)
(compiled Mar 28 2014,12:25:20)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.33a (release 28-03-2014 CrysAlis171 .NET)
(compiled Mar 28 2014,12:25:20)
;
_computing_structure_solution    'Superflip (Palatinus et al., 2007).'
_computing_structure_refinement  'Jana2006 (Petricek et al., 2014)'
_computing_molecular_graphics    'Mercury (Macrae et al., 2008)'
_computing_publication_material  
;
enCIFer (Allen et al., 2004), PLATON (Spek, 2009),  
PublCIF (Westrip 2010), WINGX (Farrugia 2012)
;

loop_
_restr_distance_atom_site_label_1
_restr_distance_site_symmetry_1
_restr_distance_atom_site_label_2
_restr_distance_site_symmetry_2
_restr_distance_target
_restr_distance_target_weight_param
? ? ? ? ? ?

loop_
_restr_angle_atom_site_label_1
_restr_angle_site_symmetry_1
_restr_angle_atom_site_label_2
_restr_angle_site_symmetry_2
_restr_angle_atom_site_label_3
_restr_angle_site_symmetry_3
_restr_angle_target
_restr_angle_target_weight_param
? ? ? ? ? ? ? ?

loop_
_restr_torsion_atom_site_label_1
_restr_torsion_site_symmetry_1
_restr_torsion_atom_site_label_2
_restr_torsion_site_symmetry_2
_restr_torsion_atom_site_label_3
_restr_torsion_site_symmetry_3
_restr_torsion_atom_site_label_4
_restr_torsion_site_symmetry_4
_restr_torsion_angle_target
_restr_torsion_weight_param
? ? ? ? ? ? ? ? ? ?

loop_
_restr_equal_distance_atom_site_label_1
_restr_equal_distance_site_symmetry_1
_restr_equal_distance_atom_site_label_2
_restr_equal_distance_site_symmetry_2
_restr_equal_distance_class_class_id
_restr_equal_distance_class_target_weight_param
? ? ? ? ? ?

loop_
_restr_equal_angle_atom_site_label_1
_restr_equal_angle_site_symmetry_1
_restr_equal_angle_atom_site_label_2
_restr_equal_angle_site_symmetry_2
_restr_equal_angle_atom_site_label_3
_restr_equal_angle_site_symmetry_3
_restr_equal_angle_class_class_id
_restr_equal_angle_class_target_weight_param
? ? ? ? ? ? ? ?

loop_
_restr_equal_torsion_atom_site_label_1
_restr_equal_torsion_site_symmetry_1
_restr_equal_torsion_atom_site_label_2
_restr_equal_torsion_site_symmetry_2
_restr_equal_torsion_atom_site_label_3
_restr_equal_torsion_site_symmetry_3
_restr_equal_torsion_atom_site_label_4
_restr_equal_torsion_site_symmetry_4
_restr_equal_torsion_class_class_id
_restr_equal_torsion_class_target_weight_param
? ? ? ? ? ? ? ? ? ?


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

# 9. ATOMIC COORDINATES AND DISPLACEMENT PARAMETERS

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_adp_type
_atom_site_U_iso_or_equiv
_atom_site_site_symmetry_multiplicity
_atom_site_occupancy
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
V1 V 0.65627(4) 0.29105(11) 0.01709(3) Uani 0.0249(2) 4 1 d . . .
O1v O 0.61958(15) 0.4236(5) 0.07206(15) Uani 0.0329(10) 4 1 d . . .
O1 O 0.70530(14) 0.0388(4) 0.07479(13) Uani 0.0262(9) 4 1 d . . .
O2 O 0.66266(15) 0.5158(5) -0.05722(14) Uani 0.0296(9) 4 1 d . . .
O3 O 0.57897(15) 0.1522(5) -0.05669(15) Uani 0.0332(10) 4 1 d . . .
N1 N 0.77330(17) 0.4177(5) 0.06205(16) Uani 0.0239(10) 4 1 d . . .
N2 N 0.79039(18) 0.6025(5) 0.02328(16) Uani 0.0256(10) 4 1 d . . .
C1 C 0.8252(2) 0.1682(6) 0.17364(19) Uani 0.0236(12) 4 1 d . . .
C2 C 0.7638(2) 0.0138(6) 0.14454(19) Uani 0.0240(12) 4 1 d . . .
C3 C 0.7618(2) -0.1850(7) 0.1876(2) Uani 0.0277(13) 4 1 d . . .
C4 C 0.8193(2) -0.2208(6) 0.2594(2) Uani 0.0267(13) 4 1 d . . .
C5 C 0.9409(2) -0.0991(7) 0.3687(2) Uani 0.0289(13) 4 1 d . . .
C6 C 1.0008(2) 0.0521(7) 0.4010(2) Uani 0.0302(13) 4 1 d . . .
C7 C 1.0052(2) 0.2479(7) 0.3591(2) Uani 0.0293(13) 4 1 d . . .
C8 C 0.9496(2) 0.2881(7) 0.2852(2) Uani 0.0264(12) 4 1 d . . .
C9 C 0.8869(2) 0.1341(6) 0.24997(19) Uani 0.0239(12) 4 1 d . . .
C10 C 0.8828(2) -0.0639(6) 0.29271(20) Uani 0.0252(12) 4 1 d . . .
C11 C 0.8298(2) 0.3595(6) 0.12687(19) Uani 0.0240(12) 4 1 d . . .
C12 C 0.7266(2) 0.6421(6) -0.03890(19) Uani 0.0249(12) 4 1 d . . .
C13 C 0.7269(2) 0.8354(6) -0.0897(2) Uani 0.0261(12) 4 1 d . . .
C14 C 0.6646(2) 0.8610(7) -0.1622(2) Uani 0.0288(13) 4 1 d . . .
C15 C 0.6637(2) 1.0462(7) -0.2090(2) Uani 0.0346(14) 4 1 d . . .
C16 C 0.7238(2) 1.2053(7) -0.1851(2) Uani 0.0325(14) 4 1 d . . .
C17 C 0.7862(2) 1.1813(7) -0.1132(2) Uani 0.0303(13) 4 1 d . . .
C18 C 0.7877(2) 0.9960(7) -0.0660(2) Uani 0.0280(13) 4 1 d . . .
C19 C 0.4957(3) 0.1761(10) -0.0923(3) Uani 0.061(2) 4 1 d . . .
C20 C 0.4619(3) 0.0025(10) -0.1535(3) Uani 0.0539(19) 4 1 d . . .
H1c3 H 0.719832 -0.293889 0.166107 Uiso 0.0332 4 1 d . . .
H1c4 H 0.817067 -0.354963 0.288195 Uiso 0.032 4 1 d . . .
H1c5 H 0.937885 -0.231996 0.397807 Uiso 0.0347 4 1 d . . .
H1c6 H 1.039901 0.025191 0.452284 Uiso 0.0362 4 1 d . . .
H1c7 H 1.047435 0.354887 0.382138 Uiso 0.0352 4 1 d . . .
H1c8 H 0.953631 0.422764 0.257378 Uiso 0.0316 4 1 d . . .
H1c11 H 0.877496 0.449908 0.144637 Uiso 0.0288 4 1 d . . .
H1c14 H 0.622703 0.750318 -0.179475 Uiso 0.0345 4 1 d . . .
H1c15 H 0.620727 1.064081 -0.258589 Uiso 0.0415 4 1 d . . .
H1c16 H 0.722707 1.332987 -0.218028 Uiso 0.039 4 1 d . . .
H1c17 H 0.828053 1.292321 -0.09645 Uiso 0.0364 4 1 d . . .
H1c18 H 0.83087 0.978472 -0.016583 Uiso 0.0336 4 1 d . . .
H1c19 H 0.483532 0.323458 -0.115522 Uiso 0.0729 4 1 d . . .
H2c19 H 0.471357 0.163608 -0.053086 Uiso 0.0729 4 1 d . . .
H1c20 H 0.405302 0.026079 -0.178184 Uiso 0.0647 4 1 d . . .
H2c20 H 0.486953 0.013291 -0.192267 Uiso 0.0647 4 1 d . . .
H3c20 H 0.471542 -0.144646 -0.129797 Uiso 0.0647 4 1 d . . .


loop_
_jana_atom_site_ADP_C_label
_jana_atom_site_ADP_C_type_symbol
_jana_atom_site_ADP_C_111
_jana_atom_site_ADP_C_112
_jana_atom_site_ADP_C_113
_jana_atom_site_ADP_C_122
_jana_atom_site_ADP_C_123
_jana_atom_site_ADP_C_133
_jana_atom_site_ADP_C_222
_jana_atom_site_ADP_C_223
_jana_atom_site_ADP_C_233
_jana_atom_site_ADP_C_333
? ? ? ? ? ? ? ? ? ? ? ?

loop_
_jana_atom_site_ADP_D_label
_jana_atom_site_ADP_D_type_symbol
_jana_atom_site_ADP_D_1111
_jana_atom_site_ADP_D_1112
_jana_atom_site_ADP_D_1113
_jana_atom_site_ADP_D_1122
_jana_atom_site_ADP_D_1123
_jana_atom_site_ADP_D_1133
_jana_atom_site_ADP_D_1222
_jana_atom_site_ADP_D_1223
_jana_atom_site_ADP_D_1233
_jana_atom_site_ADP_D_1333
_jana_atom_site_ADP_D_2222
_jana_atom_site_ADP_D_2223
_jana_atom_site_ADP_D_2233
_jana_atom_site_ADP_D_2333
_jana_atom_site_ADP_D_3333
? ? ? ? ? ? ? ? ? ? ? ? ? ? ? ? ?

loop_
_jana_atom_site_ADP_E_label
_jana_atom_site_ADP_E_type_symbol
_jana_atom_site_ADP_E_11111
_jana_atom_site_ADP_E_11112
_jana_atom_site_ADP_E_11113
_jana_atom_site_ADP_E_11122
_jana_atom_site_ADP_E_11123
_jana_atom_site_ADP_E_11133
_jana_atom_site_ADP_E_11222
_jana_atom_site_ADP_E_11223
_jana_atom_site_ADP_E_11233
_jana_atom_site_ADP_E_11333
_jana_atom_site_ADP_E_12222
_jana_atom_site_ADP_E_12223
_jana_atom_site_ADP_E_12233
_jana_atom_site_ADP_E_12333
_jana_atom_site_ADP_E_13333
_jana_atom_site_ADP_E_22222
_jana_atom_site_ADP_E_22223
_jana_atom_site_ADP_E_22233
_jana_atom_site_ADP_E_22333
_jana_atom_site_ADP_E_23333
_jana_atom_site_ADP_E_33333
? ? ? ? ? ? ? ? ? ? ? ? ? ? ? ? ? ? ? ? ? ? ?

loop_
_jana_atom_site_ADP_F_label
_jana_atom_site_ADP_F_type_symbol
_jana_atom_site_ADP_F_111111
_jana_atom_site_ADP_F_111112
_jana_atom_site_ADP_F_111113
_jana_atom_site_ADP_F_111122
_jana_atom_site_ADP_F_111123
_jana_atom_site_ADP_F_111133
_jana_atom_site_ADP_F_111222
_jana_atom_site_ADP_F_111223
_jana_atom_site_ADP_F_111233
_jana_atom_site_ADP_F_111333
_jana_atom_site_ADP_F_112222
_jana_atom_site_ADP_F_112223
_jana_atom_site_ADP_F_112233
_jana_atom_site_ADP_F_112333
_jana_atom_site_ADP_F_113333
_jana_atom_site_ADP_F_122222
_jana_atom_site_ADP_F_122223
_jana_atom_site_ADP_F_122233
_jana_atom_site_ADP_F_122333
_jana_atom_site_ADP_F_123333
_jana_atom_site_ADP_F_133333
_jana_atom_site_ADP_F_222222
_jana_atom_site_ADP_F_222223
_jana_atom_site_ADP_F_222233
_jana_atom_site_ADP_F_222333
_jana_atom_site_ADP_F_223333
_jana_atom_site_ADP_F_233333
_jana_atom_site_ADP_F_333333
? ? ? ? ? ? ? ? ? ? ? ? ? ? ? ? ? ? ? ? ? ? ? ? ? ? ? ? ? ?


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

# 10. MOLECULAR GEOMETRY


loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_1
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
V1 O1v . . 1.582(3) ?
V1 O1 . . 1.856(2) ?
V1 O2 . . 1.927(3) ?
V1 O3 . . 1.752(2) ?
V1 N1 . . 2.094(3) ?
O1 C2 . . 1.335(4) ?
O2 C12 . . 1.306(4) ?
O3 C19 . . 1.402(5) ?
N1 N2 . . 1.392(4) ?
N1 C11 . . 1.297(4) ?
N2 C12 . . 1.311(4) ?
C1 C2 . . 1.381(5) ?
C1 C9 . . 1.448(4) ?
C1 C11 . . 1.435(5) ?
C2 C3 . . 1.421(5) ?
C3 C4 . . 1.362(4) ?
C3 H1c3 . . 0.96 ?
C4 C10 . . 1.424(5) ?
C4 H1c4 . . 0.96 ?
C5 C6 . . 1.357(5) ?
C5 C10 . . 1.419(4) ?
C5 H1c5 . . 0.96 ?
C6 C7 . . 1.404(6) ?
C6 H1c6 . . 0.96 ?
C7 C8 . . 1.379(4) ?
C7 H1c7 . . 0.96 ?
C8 C9 . . 1.409(5) ?
C8 H1c8 . . 0.96 ?
C9 C10 . . 1.422(5) ?
C11 H1c11 . . 0.96 ?
C12 C13 . . 1.472(5) ?
C13 C14 . . 1.400(4) ?
C13 C18 . . 1.391(5) ?
C14 C15 . . 1.384(6) ?
C14 H1c14 . . 0.96 ?
C15 C16 . . 1.378(6) ?
C15 H1c15 . . 0.96 ?
C16 C17 . . 1.392(5) ?
C16 H1c16 . . 0.96 ?
C17 C18 . . 1.387(6) ?
C17 H1c17 . . 0.96 ?
C18 H1c18 . . 0.96 ?
C19 C20 . . 1.477(7) ?
C19 H1c19 . . 0.96 ?
C19 H2c19 . . 0.96 ?
C20 H1c20 . . 0.96 ?
C20 H2c20 . . 0.96 ?
C20 H3c20 . . 0.96 ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_2
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
O1v V1 O1 . . . 105.10(13) ?
O1v V1 O2 . . . 103.85(13) ?
O1v V1 O3 . . . 109.02(14) ?
O1v V1 N1 . . . 98.88(13) ?
O1 V1 O2 . . . 144.89(13) ?
O1 V1 O3 . . . 98.11(12) ?
O1 V1 N1 . . . 82.03(11) ?
O2 V1 O3 . . . 90.79(12) ?
O2 V1 N1 . . . 74.24(11) ?
O3 V1 N1 . . . 150.89(14) ?
V1 O1 C2 . . . 132.8(2) ?
V1 O2 C12 . . . 118.7(2) ?
V1 O3 C19 . . . 136.5(3) ?
V1 N1 N2 . . . 116.78(18) ?
V1 N1 C11 . . . 127.4(3) ?
N2 N1 C11 . . . 115.4(3) ?
N1 N2 C12 . . . 107.3(3) ?
C2 C1 C9 . . . 120.4(3) ?
C2 C1 C11 . . . 119.9(3) ?
C9 C1 C11 . . . 119.6(3) ?
O1 C2 C1 . . . 122.6(3) ?
O1 C2 C3 . . . 116.8(3) ?
C1 C2 C3 . . . 120.6(3) ?
C2 C3 C4 . . . 119.9(3) ?
C2 C3 H1c3 . . . 120.05 ?
C4 C3 H1c3 . . . 120.05 ?
C3 C4 C10 . . . 121.6(4) ?
C3 C4 H1c4 . . . 119.21 ?
C10 C4 H1c4 . . . 119.22 ?
C6 C5 C10 . . . 121.1(4) ?
C6 C5 H1c5 . . . 119.45 ?
C10 C5 H1c5 . . . 119.45 ?
C5 C6 C7 . . . 119.8(3) ?
C5 C6 H1c6 . . . 120.11 ?
C7 C6 H1c6 . . . 120.11 ?
C6 C7 C8 . . . 120.7(3) ?
C6 C7 H1c7 . . . 119.64 ?
C8 C7 H1c7 . . . 119.64 ?
C7 C8 C9 . . . 120.9(4) ?
C7 C8 H1c8 . . . 119.57 ?
C9 C8 H1c8 . . . 119.57 ?
C1 C9 C8 . . . 123.9(3) ?
C1 C9 C10 . . . 118.0(3) ?
C8 C9 C10 . . . 118.1(3) ?
C4 C10 C5 . . . 121.1(3) ?
C4 C10 C9 . . . 119.5(3) ?
C5 C10 C9 . . . 119.4(3) ?
N1 C11 C1 . . . 123.9(3) ?
N1 C11 H1c11 . . . 118.03 ?
C1 C11 H1c11 . . . 118.03 ?
O2 C12 N2 . . . 122.1(3) ?
O2 C12 C13 . . . 118.8(3) ?
N2 C12 C13 . . . 119.0(3) ?
C12 C13 C14 . . . 119.8(3) ?
C12 C13 C18 . . . 120.8(3) ?
C14 C13 C18 . . . 119.4(3) ?
C13 C14 C15 . . . 119.8(3) ?
C13 C14 H1c14 . . . 120.11 ?
C15 C14 H1c14 . . . 120.1 ?
C14 C15 C16 . . . 120.6(3) ?
C14 C15 H1c15 . . . 119.72 ?
C16 C15 H1c15 . . . 119.72 ?
C15 C16 C17 . . . 120.2(4) ?
C15 C16 H1c16 . . . 119.92 ?
C17 C16 H1c16 . . . 119.92 ?
C16 C17 C18 . . . 119.7(4) ?
C16 C17 H1c17 . . . 120.18 ?
C18 C17 H1c17 . . . 120.17 ?
C13 C18 C17 . . . 120.4(3) ?
C13 C18 H1c18 . . . 119.78 ?
C17 C18 H1c18 . . . 119.78 ?
O3 C19 C20 . . . 111.2(4) ?
O3 C19 H1c19 . . . 109.47 ?
O3 C19 H2c19 . . . 109.47 ?
C20 C19 H1c19 . . . 109.47 ?
C20 C19 H2c19 . . . 109.47 ?
H1c19 C19 H2c19 . . . 107.67 ?
C19 C20 H1c20 . . . 109.47 ?
C19 C20 H2c20 . . . 109.47 ?
C19 C20 H3c20 . . . 109.47 ?
H1c20 C20 H2c20 . . . 109.47 ?
H1c20 C20 H3c20 . . . 109.47 ?
H2c20 C20 H3c20 . . . 109.47 ?

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_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
? ? ? ? ? ? ? ? ? ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_D
_geom_hbond_site_symmetry_H
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_publ_flag
? ? ? ? ? ? ? ? ? ? ?
####################################################################### 
# 
# 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_I
_database_code_depnum_ccdc_archive 'CCDC 1062417'
_audit_update_record             
;
2015-08-26 deposited with the CCDC.
2016-01-08 downloaded from the CCDC.
;
#=======================================================================

# 5. CHEMICAL DATA

_chemical_name_systematic        
; ?
;
_chemical_name_common            ?
_chemical_formula_moiety         'C21 H19 N2 O4 V1'
_chemical_formula_structural     ?
_chemical_formula_analytical     ?
_chemical_formula_iupac          ?
_chemical_formula_sum            'C21 H19 N2 O4 V1'
_chemical_formula_weight         414.3
_chemical_melting_point          ?
_chemical_compound_source        ?
_chemical_absolute_configuration .

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

# 6. CRYSTAL DATA

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'C 1 2/c 1'
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_Int_Tables_number      15

loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 x,y,z
2 -x,y,-z+1/2
3 -x,-y,-z
4 x,-y,z+1/2
5 x+1/2,y+1/2,z
6 -x+1/2,y+1/2,-z+1/2
7 -x+1/2,-y+1/2,-z
8 x+1/2,-y+1/2,z+1/2

_cell_length_a                   34.6714(16)
_cell_length_b                   6.0918(3)
_cell_length_c                   17.8955(5)
_cell_angle_alpha                90
_cell_angle_beta                 97.143(3)
_cell_angle_gamma                90
_cell_volume                     3750.4(3)

loop_
_twin_individual_id
_twin_individual_mass_fraction_refined
_twin_individual_twin_matrix_11
_twin_individual_twin_matrix_12
_twin_individual_twin_matrix_13
_twin_individual_twin_matrix_21
_twin_individual_twin_matrix_22
_twin_individual_twin_matrix_23
_twin_individual_twin_matrix_31
_twin_individual_twin_matrix_32
_twin_individual_twin_matrix_33
? ? ? ? ? ? ? ? ? ? ?

_cell_formula_units_Z            8

_cell_measurement_reflns_used    2889
_cell_measurement_theta_min      4.98
_cell_measurement_theta_max      66.86
_cell_measurement_temperature    120.00(10)
_cell_special_details            
; ?
;

_exptl_crystal_density_diffrn    1.4676
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_F_000             1712

_exptl_absorpt_coefficient_mu    4.691
_exptl_crystal_description       platelet
_exptl_crystal_size_max          0.295
_exptl_crystal_size_mid          0.095
_exptl_crystal_size_min          0.015
_exptl_crystal_size_rad          ?
_exptl_crystal_colour            black
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details   
;
   CrysAlisPro, Agilent Technologies, Version 1.171.37.33a	
   Analytical numeric absorption correction based on crystal shape
;
_exptl_absorpt_correction_T_min  0.471
_exptl_absorpt_correction_T_max  0.929
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
? ? ? ?

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

# 7. EXPERIMENTAL DATA

_exptl_special_details           ?

_diffrn_ambient_temperature      120
_diffrn_source                   'sealed X-ray tube'
_diffrn_source_power             ?
_diffrn_source_voltage           ?
_diffrn_source_current           ?
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_source         'X-ray tube'
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_monochromator  mirror
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Atlas, Gemini ultra'
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.1873
_diffrn_measurement_method       'ω scans'
_diffrn_measurement_specimen_support ?

_diffrn_reflns_number            10825
_diffrn_reflns_theta_min         4.98
_diffrn_reflns_theta_max         66.98
_diffrn_reflns_theta_full        66.98
_diffrn_measured_fraction_theta_max 0.98
_diffrn_measured_fraction_theta_full 0.98
_diffrn_reflns_av_R_equivalents  0.0562
_diffrn_reflns_av_unetI/netI     0.0484
_diffrn_reflns_limit_h_min       -35
_diffrn_reflns_limit_h_max       40
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_reduction_process ?

_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
loop_
_diffrn_standard_refln_index_h
_diffrn_standard_refln_index_k
_diffrn_standard_refln_index_l
? ? ?

_diffrn_radiation_probe          X-ray

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

# 8. REFINEMENT DATA

_refine_special_details          
; ?
;

_reflns_number_total             3292
_reflns_number_gt                2410
_reflns_threshold_expression     I>3σ(I)

_refine_ls_structure_factor_coef Fsqd
_refine_ls_R_factor_gt           0.0385
_refine_ls_wR_factor_gt          0.0887
_refine_ls_R_factor_all          0.0592
_refine_ls_wR_factor_ref         0.1001
_refine_ls_goodness_of_fit_ref   1.14
_refine_ls_goodness_of_fit_gt    1.20
_refine_ls_restrained_S_gt       ?
_refine_ls_restrained_S_all      ?
_refine_ls_number_reflns         3292
_refine_ls_number_parameters     263
_refine_ls_number_restraints     6
_refine_ls_number_constraints    141
_refine_ls_weighting_scheme      sigma
_refine_ls_weighting_details     w=1/(σ²(I)+0.0016I²)
_refine_ls_hydrogen_treatment    constr
_refine_ls_shift/su_max          0.0274
_refine_ls_shift/su_mean         0.0010
_refine_diff_density_max         0.25
_refine_diff_density_min         -0.23
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_abs_structure_details ?
_refine_ls_abs_structure_Flack   ?
_refine_ls_abs_structure_Rogers  ?

loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C 0.0181 0.0091 'International Tables Vol C tables 4.2.6.8 and 6.1.1.1'
H 0.0000 0.0000 'International Tables Vol C tables 4.2.6.8 and 6.1.1.1'
N 0.0311 0.0180 'International Tables Vol C tables 4.2.6.8 and 6.1.1.1'
O 0.0492 0.0322 'International Tables Vol C tables 4.2.6.8 and 6.1.1.1'
V 0.0687 2.1097 'International Tables Vol C tables 4.2.6.8 and 6.1.1.1'

_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.33a (release 28-03-2014 CrysAlis171 .NET)
(compiled Mar 28 2014,12:25:20)
;
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.33a (release 28-03-2014 CrysAlis171 .NET)
(compiled Mar 28 2014,12:25:20)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.33a (release 28-03-2014 CrysAlis171 .NET)
(compiled Mar 28 2014,12:25:20)
;
_computing_structure_solution    'Superflip (Palatinus et al., 2007).'
_computing_structure_refinement  'Jana2006 (Petricek et al., 2014)'
_computing_molecular_graphics    'Mercury (Macrae et al., 2008)'
_computing_publication_material  
;
enCIFer (Allen et al., 2004), PLATON (Spek, 2009),  
PublCIF (Westrip 2010), WINGX (Farrugia 2012)
;

loop_
_restr_distance_atom_site_label_1
_restr_distance_site_symmetry_1
_restr_distance_atom_site_label_2
_restr_distance_site_symmetry_2
_restr_distance_target
_restr_distance_target_weight_param
O3 . C19 . 1.46 0.05
O3 . C22 . 1.46 0.05
C19 . C20 . 1.51 0.05
C22 . C23 . 1.51 0.05
C20 . C21 . 1.54 0.05
C23 . C24 . 1.54 0.05

loop_
_restr_angle_atom_site_label_1
_restr_angle_site_symmetry_1
_restr_angle_atom_site_label_2
_restr_angle_site_symmetry_2
_restr_angle_atom_site_label_3
_restr_angle_site_symmetry_3
_restr_angle_target
_restr_angle_target_weight_param
? ? ? ? ? ? ? ?

loop_
_restr_torsion_atom_site_label_1
_restr_torsion_site_symmetry_1
_restr_torsion_atom_site_label_2
_restr_torsion_site_symmetry_2
_restr_torsion_atom_site_label_3
_restr_torsion_site_symmetry_3
_restr_torsion_atom_site_label_4
_restr_torsion_site_symmetry_4
_restr_torsion_angle_target
_restr_torsion_weight_param
? ? ? ? ? ? ? ? ? ?

loop_
_restr_equal_distance_atom_site_label_1
_restr_equal_distance_site_symmetry_1
_restr_equal_distance_atom_site_label_2
_restr_equal_distance_site_symmetry_2
_restr_equal_distance_class_class_id
_restr_equal_distance_class_target_weight_param
? ? ? ? ? ?

loop_
_restr_equal_angle_atom_site_label_1
_restr_equal_angle_site_symmetry_1
_restr_equal_angle_atom_site_label_2
_restr_equal_angle_site_symmetry_2
_restr_equal_angle_atom_site_label_3
_restr_equal_angle_site_symmetry_3
_restr_equal_angle_class_class_id
_restr_equal_angle_class_target_weight_param
? ? ? ? ? ? ? ?

loop_
_restr_equal_torsion_atom_site_label_1
_restr_equal_torsion_site_symmetry_1
_restr_equal_torsion_atom_site_label_2
_restr_equal_torsion_site_symmetry_2
_restr_equal_torsion_atom_site_label_3
_restr_equal_torsion_site_symmetry_3
_restr_equal_torsion_atom_site_label_4
_restr_equal_torsion_site_symmetry_4
_restr_equal_torsion_class_class_id
_restr_equal_torsion_class_target_weight_param
? ? ? ? ? ? ? ? ? ?


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

# 9. ATOMIC COORDINATES AND DISPLACEMENT PARAMETERS

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_adp_type
_atom_site_U_iso_or_equiv
_atom_site_site_symmetry_multiplicity
_atom_site_occupancy
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
V1 V 0.916565(13) 0.05243(8) 0.17079(3) Uani 0.02274(14) 8 1 d . . .
O1v O 0.93531(6) 0.1829(3) 0.24300(12) Uani 0.0342(7) 8 1 d . . .
O1 O 0.89350(5) -0.1936(3) 0.20658(10) Uani 0.0235(6) 8 1 d . . .
O2 O 0.91243(5) 0.2723(3) 0.09235(11) Uani 0.0257(6) 8 1 d . . .
O3 O 0.95340(6) -0.0770(3) 0.12875(12) Uani 0.0329(7) 8 1 d . . .
N1 N 0.85998(6) 0.1756(4) 0.16473(12) Uani 0.0202(6) 8 1 d . . .
N2 N 0.85129(6) 0.3568(4) 0.11854(12) Uani 0.0221(7) 8 1 d . . .
C1 C 0.83520(7) -0.0736(4) 0.25197(14) Uani 0.0211(8) 8 1 d . . .
C2 C 0.86520(8) -0.2246(4) 0.24970(14) Uani 0.0221(8) 8 1 d . . .
C3 C 0.86658(8) -0.4205(5) 0.29265(15) Uani 0.0248(8) 8 1 d . . .
C4 C 0.83860(8) -0.4618(5) 0.33797(15) Uani 0.0250(8) 8 1 d . . .
C5 C 0.77951(8) -0.3515(5) 0.39289(15) Uani 0.0272(9) 8 1 d . . .
C6 C 0.75038(8) -0.2053(5) 0.39966(16) Uani 0.0281(9) 8 1 d . . .
C7 C 0.74798(8) -0.0110(5) 0.35662(15) Uani 0.0270(9) 8 1 d . . .
C8 C 0.77483(8) 0.0332(5) 0.30833(15) Uani 0.0245(8) 8 1 d . . .
C9 C 0.80550(8) -0.1151(4) 0.30015(14) Uani 0.0216(8) 8 1 d . . .
C10 C 0.80768(8) -0.3103(5) 0.34368(15) Uani 0.0238(8) 8 1 d . . .
C11 C 0.83274(8) 0.1148(4) 0.20414(14) Uani 0.0211(8) 8 1 d . . .
C12 C 0.88145(8) 0.3969(4) 0.08397(15) Uani 0.0218(8) 8 1 d . . .
C13 C 0.88085(8) 0.5876(4) 0.03285(14) Uani 0.0225(8) 8 1 d . . .
C14 C 0.85160(8) 0.7444(5) 0.03105(15) Uani 0.0243(8) 8 1 d . . .
C15 C 0.85198(8) 0.9264(5) -0.01519(15) Uani 0.0262(9) 8 1 d . . .
C16 C 0.88158(9) 0.9529(5) -0.06025(15) Uani 0.0288(9) 8 1 d . . .
C17 C 0.91045(8) 0.7960(5) -0.05943(16) Uani 0.0297(9) 8 1 d . . .
C18 C 0.91024(8) 0.6134(5) -0.01271(15) Uani 0.0261(9) 8 1 d . . .
C19 C 0.99243(15) -0.0353(10) 0.1148(3) Uani 0.0364(15) 8 0.812(7) d . . .
C20 C 1.01191(12) -0.2356(7) 0.0941(3) Uani 0.0477(16) 8 0.812(7) d . . .
C21 C 1.0135(2) -0.4189(13) 0.1516(4) Uani 0.073(3) 8 0.812(7) d . . .
C22 C 0.9919(7) -0.041(5) 0.1414(14) Uani 0.0364(15) 8 0.188(7) d . . .
C23 C 1.0187(5) -0.223(3) 0.1546(14) Uani 0.0477(16) 8 0.188(7) d . . .
C24 C 1.0056(12) -0.440(6) 0.119(2) Uani 0.073(3) 8 0.188(7) d . . .
H1c3 H 0.887209 -0.524153 0.289822 Uiso 0.0298 8 1 d . . .
H1c4 H 0.839708 -0.59538 0.366615 Uiso 0.03 8 1 d . . .
H1c5 H 0.780953 -0.484403 0.421931 Uiso 0.0327 8 1 d . . .
H1c6 H 0.73161 -0.23463 0.433564 Uiso 0.0337 8 1 d . . .
H1c7 H 0.727363 0.091548 0.361096 Uiso 0.0323 8 1 d . . .
H1c8 H 0.772788 0.16675 0.27965 Uiso 0.0294 8 1 d . . .
H1c11 H 0.809536 0.201991 0.200871 Uiso 0.0254 8 1 d . . .
H1c14 H 0.831095 0.726489 0.061969 Uiso 0.0292 8 1 d . . .
H1c15 H 0.831775 1.034461 -0.016176 Uiso 0.0315 8 1 d . . .
H1c16 H 0.881965 1.080025 -0.091864 Uiso 0.0346 8 1 d . . .
H1c17 H 0.930659 0.813051 -0.09111 Uiso 0.0356 8 1 d . . .
H1c18 H 0.93041 0.505134 -0.011942 Uiso 0.0313 8 1 d . . .
H1c19 H 1.006799 0.027871 0.158903 Uiso 0.0437 8 0.812(7) d . . .
H2c19 H 0.992359 0.070826 0.075124 Uiso 0.0437 8 0.812(7) d . . .
H1c20 H 1.037792 -0.200703 0.084189 Uiso 0.0573 8 0.812(7) d . . .
H2c20 H 0.999601 -0.287968 0.046437 Uiso 0.0573 8 0.812(7) d . . .
H1c21 H 1.025611 -0.545528 0.132676 Uiso 0.0882 8 0.812(7) d . . .
H2c21 H 1.028295 -0.371698 0.197711 Uiso 0.0882 8 0.812(7) d . . .
H3c21 H 0.987583 -0.455646 0.160845 Uiso 0.0882 8 0.812(7) d . . .
H1c22 H 0.997368 0.064873 0.180917 Uiso 0.0437 8 0.188(7) d . . .
H2c22 H 0.999663 0.050464 0.102315 Uiso 0.0437 8 0.188(7) d . . .
H1c23 H 1.025621 -0.242581 0.207752 Uiso 0.0573 8 0.188(7) d . . .
H2c23 H 1.043251 -0.183017 0.139112 Uiso 0.0573 8 0.188(7) d . . .
H1c24 H 0.990752 -0.414113 0.070995 Uiso 0.0882 8 0.188(7) d . . .
H2c24 H 1.027897 -0.527788 0.112771 Uiso 0.0882 8 0.188(7) d . . .
H3c24 H 0.98973 -0.515439 0.15125 Uiso 0.0882 8 0.188(7) d . . .


loop_
_jana_atom_site_ADP_C_label
_jana_atom_site_ADP_C_type_symbol
_jana_atom_site_ADP_C_111
_jana_atom_site_ADP_C_112
_jana_atom_site_ADP_C_113
_jana_atom_site_ADP_C_122
_jana_atom_site_ADP_C_123
_jana_atom_site_ADP_C_133
_jana_atom_site_ADP_C_222
_jana_atom_site_ADP_C_223
_jana_atom_site_ADP_C_233
_jana_atom_site_ADP_C_333
? ? ? ? ? ? ? ? ? ? ? ?

loop_
_jana_atom_site_ADP_D_label
_jana_atom_site_ADP_D_type_symbol
_jana_atom_site_ADP_D_1111
_jana_atom_site_ADP_D_1112
_jana_atom_site_ADP_D_1113
_jana_atom_site_ADP_D_1122
_jana_atom_site_ADP_D_1123
_jana_atom_site_ADP_D_1133
_jana_atom_site_ADP_D_1222
_jana_atom_site_ADP_D_1223
_jana_atom_site_ADP_D_1233
_jana_atom_site_ADP_D_1333
_jana_atom_site_ADP_D_2222
_jana_atom_site_ADP_D_2223
_jana_atom_site_ADP_D_2233
_jana_atom_site_ADP_D_2333
_jana_atom_site_ADP_D_3333
? ? ? ? ? ? ? ? ? ? ? ? ? ? ? ? ?

loop_
_jana_atom_site_ADP_E_label
_jana_atom_site_ADP_E_type_symbol
_jana_atom_site_ADP_E_11111
_jana_atom_site_ADP_E_11112
_jana_atom_site_ADP_E_11113
_jana_atom_site_ADP_E_11122
_jana_atom_site_ADP_E_11123
_jana_atom_site_ADP_E_11133
_jana_atom_site_ADP_E_11222
_jana_atom_site_ADP_E_11223
_jana_atom_site_ADP_E_11233
_jana_atom_site_ADP_E_11333
_jana_atom_site_ADP_E_12222
_jana_atom_site_ADP_E_12223
_jana_atom_site_ADP_E_12233
_jana_atom_site_ADP_E_12333
_jana_atom_site_ADP_E_13333
_jana_atom_site_ADP_E_22222
_jana_atom_site_ADP_E_22223
_jana_atom_site_ADP_E_22233
_jana_atom_site_ADP_E_22333
_jana_atom_site_ADP_E_23333
_jana_atom_site_ADP_E_33333
? ? ? ? ? ? ? ? ? ? ? ? ? ? ? ? ? ? ? ? ? ? ?

loop_
_jana_atom_site_ADP_F_label
_jana_atom_site_ADP_F_type_symbol
_jana_atom_site_ADP_F_111111
_jana_atom_site_ADP_F_111112
_jana_atom_site_ADP_F_111113
_jana_atom_site_ADP_F_111122
_jana_atom_site_ADP_F_111123
_jana_atom_site_ADP_F_111133
_jana_atom_site_ADP_F_111222
_jana_atom_site_ADP_F_111223
_jana_atom_site_ADP_F_111233
_jana_atom_site_ADP_F_111333
_jana_atom_site_ADP_F_112222
_jana_atom_site_ADP_F_112223
_jana_atom_site_ADP_F_112233
_jana_atom_site_ADP_F_112333
_jana_atom_site_ADP_F_113333
_jana_atom_site_ADP_F_122222
_jana_atom_site_ADP_F_122223
_jana_atom_site_ADP_F_122233
_jana_atom_site_ADP_F_122333
_jana_atom_site_ADP_F_123333
_jana_atom_site_ADP_F_133333
_jana_atom_site_ADP_F_222222
_jana_atom_site_ADP_F_222223
_jana_atom_site_ADP_F_222233
_jana_atom_site_ADP_F_222333
_jana_atom_site_ADP_F_223333
_jana_atom_site_ADP_F_233333
_jana_atom_site_ADP_F_333333
? ? ? ? ? ? ? ? ? ? ? ? ? ? ? ? ? ? ? ? ? ? ? ? ? ? ? ? ? ?


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

# 10. MOLECULAR GEOMETRY


loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_1
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
V1 O1v . . 1.586(2) ?
V1 O1 . . 1.8501(19) ?
V1 O2 . . 1.933(2) ?
V1 O3 . . 1.748(2) ?
V1 N1 . . 2.091(2) ?
O1 C2 . . 1.335(3) ?
O2 C12 . . 1.308(3) ?
O3 C19 . . 1.429(6) ?
O3 C22 . . 1.34(2) ?
N1 N2 . . 1.389(3) ?
N1 C11 . . 1.301(4) ?
N2 C12 . . 1.303(4) ?
C1 C2 . . 1.393(4) ?
C1 C9 . . 1.445(4) ?
C1 C11 . . 1.428(4) ?
C2 C3 . . 1.417(4) ?
C3 C4 . . 1.363(4) ?
C3 H1c3 . . 0.96 ?
C4 C10 . . 1.428(4) ?
C4 H1c4 . . 0.96 ?
C5 C6 . . 1.363(4) ?
C5 C10 . . 1.416(4) ?
C5 H1c5 . . 0.96 ?
C6 C7 . . 1.409(4) ?
C6 H1c6 . . 0.96 ?
C7 C8 . . 1.373(4) ?
C7 H1c7 . . 0.96 ?
C8 C9 . . 1.417(4) ?
C8 H1c8 . . 0.96 ?
C9 C10 . . 1.419(4) ?
C11 H1c11 . . 0.96 ?
C12 C13 . . 1.477(4) ?
C13 C14 . . 1.391(4) ?
C13 C18 . . 1.391(4) ?
C14 C15 . . 1.384(4) ?
C14 H1c14 . . 0.96 ?
C15 C16 . . 1.391(4) ?
C15 H1c15 . . 0.96 ?
C16 C17 . . 1.383(4) ?
C16 H1c16 . . 0.96 ?
C17 C18 . . 1.392(4) ?
C17 H1c17 . . 0.96 ?
C18 H1c18 . . 0.96 ?
C19 C20 . . 1.464(7) ?
C19 H1c19 . . 0.96 ?
C19 H2c19 . . 0.96 ?
C20 C21 . . 1.514(9) ?
C20 H1c20 . . 0.96 ?
C20 H2c20 . . 0.96 ?
C21 C23 . . 1.21(2) ?
C21 H1c21 . . 0.96 ?
C21 H2c21 . . 0.96 ?
C21 H3c21 . . 0.96 ?
C22 C23 . . 1.44(3) ?
C22 H1c22 . . 0.96 ?
C22 H2c22 . . 0.96 ?
C23 C24 . . 1.51(4) ?
C23 H1c23 . . 0.96 ?
C23 H2c23 . . 0.96 ?
C24 H1c24 . . 0.96 ?
C24 H2c24 . . 0.96 ?
C24 H3c24 . . 0.96 ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_2
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
O1v V1 O1 . . . 105.96(10) ?
O1v V1 O2 . . . 103.30(10) ?
O1v V1 O3 . . . 109.22(10) ?
O1v V1 N1 . . . 98.58(10) ?
O1 V1 O2 . . . 144.75(8) ?
O1 V1 O3 . . . 98.87(9) ?
O1 V1 N1 . . . 82.26(8) ?
O2 V1 O3 . . . 89.55(9) ?
O2 V1 N1 . . . 74.29(8) ?
O3 V1 N1 . . . 150.50(9) ?
V1 O1 C2 . . . 134.04(17) ?
V1 O2 C12 . . . 118.09(17) ?
V1 O3 C19 . . . 138.9(3) ?
V1 O3 C22 . . . 128.2(12) ?
C19 O3 C22 . . . 19.6(11) ?
V1 N1 N2 . . . 116.65(16) ?
V1 N1 C11 . . . 127.55(18) ?
N2 N1 C11 . . . 115.5(2) ?
N1 N2 C12 . . . 107.7(2) ?
C2 C1 C9 . . . 119.5(2) ?
C2 C1 C11 . . . 120.2(2) ?
C9 C1 C11 . . . 120.3(2) ?
O1 C2 C1 . . . 121.9(2) ?
O1 C2 C3 . . . 117.1(2) ?
C1 C2 C3 . . . 121.0(3) ?
C2 C3 C4 . . . 120.0(3) ?
C2 C3 H1c3 . . . 120.01 ?
C4 C3 H1c3 . . . 120.02 ?
C3 C4 C10 . . . 121.3(3) ?
C3 C4 H1c4 . . . 119.34 ?
C10 C4 H1c4 . . . 119.34 ?
C6 C5 C10 . . . 121.0(3) ?
C6 C5 H1c5 . . . 119.48 ?
C10 C5 H1c5 . . . 119.49 ?
C5 C6 C7 . . . 119.6(3) ?
C5 C6 H1c6 . . . 120.19 ?
C7 C6 H1c6 . . . 120.19 ?
C6 C7 C8 . . . 120.7(3) ?
C6 C7 H1c7 . . . 119.67 ?
C8 C7 H1c7 . . . 119.68 ?
C7 C8 C9 . . . 121.1(3) ?
C7 C8 H1c8 . . . 119.45 ?
C9 C8 H1c8 . . . 119.45 ?
C1 C9 C8 . . . 123.4(2) ?
C1 C9 C10 . . . 118.8(2) ?
C8 C9 C10 . . . 117.9(2) ?
C4 C10 C5 . . . 120.8(3) ?
C4 C10 C9 . . . 119.4(3) ?
C5 C10 C9 . . . 119.7(3) ?
N1 C11 C1 . . . 124.1(2) ?
N1 C11 H1c11 . . . 117.94 ?
C1 C11 H1c11 . . . 117.94 ?
O2 C12 N2 . . . 122.2(2) ?
O2 C12 C13 . . . 118.4(2) ?
N2 C12 C13 . . . 119.4(2) ?
C12 C13 C14 . . . 120.6(2) ?
C12 C13 C18 . . . 119.8(2) ?
C14 C13 C18 . . . 119.6(2) ?
C13 C14 C15 . . . 120.2(3) ?
C13 C14 H1c14 . . . 119.9 ?
C15 C14 H1c14 . . . 119.91 ?
C14 C15 C16 . . . 120.1(3) ?
C14 C15 H1c15 . . . 119.93 ?
C16 C15 H1c15 . . . 119.93 ?
C15 C16 C17 . . . 119.9(3) ?
C15 C16 H1c16 . . . 120.04 ?
C17 C16 H1c16 . . . 120.04 ?
C16 C17 C18 . . . 120.1(3) ?
C16 C17 H1c17 . . . 119.97 ?
C18 C17 H1c17 . . . 119.97 ?
C13 C18 C17 . . . 120.1(3) ?
C13 C18 H1c18 . . . 119.96 ?
C17 C18 H1c18 . . . 119.96 ?
O3 C19 C20 . . . 111.9(4) ?
O3 C19 H1c19 . . . 109.47 ?
O3 C19 H2c19 . . . 109.47 ?
C20 C19 C22 . . . 105(4) ?
C20 C19 H1c19 . . . 109.47 ?
C20 C19 H2c19 . . . 109.47 ?
H1c19 C19 H2c19 . . . 106.94 ?
C19 C20 C21 . . . 114.9(5) ?
C19 C20 H1c20 . . . 109.47 ?
C19 C20 H2c20 . . . 109.47 ?
C21 C20 H1c20 . . . 109.47 ?
C21 C20 H2c20 . . . 109.47 ?
H1c20 C20 H2c20 . . . 103.38 ?
C20 C21 H1c21 . . . 109.47 ?
C20 C21 H2c21 . . . 109.47 ?
C20 C21 H3c21 . . . 109.47 ?
H1c21 C21 H2c21 . . . 109.47 ?
H1c21 C21 H3c21 . . . 109.47 ?
H2c21 C21 H3c21 . . . 109.47 ?
O3 C22 C23 . . . 121(2) ?
O3 C22 H1c22 . . . 109.47 ?
O3 C22 H2c22 . . . 109.47 ?
C23 C22 H1c22 . . . 109.47 ?
C23 C22 H2c22 . . . 109.47 ?
H1c22 C22 H2c22 . . . 95.52 ?
C22 C23 C24 . . . 117(2) ?
C22 C23 H1c23 . . . 109.47 ?
C22 C23 H2c23 . . . 109.47 ?
C24 C23 H1c23 . . . 109.47 ?
C24 C23 H2c23 . . . 109.47 ?
H1c23 C23 H2c23 . . . 101.19 ?
C23 C24 H1c24 . . . 109.47 ?
C23 C24 H2c24 . . . 109.47 ?
C23 C24 H3c24 . . . 109.47 ?
H1c24 C24 H2c24 . . . 109.47 ?
H1c24 C24 H3c24 . . . 109.47 ?
H2c24 C24 H3c24 . . . 109.47 ?

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_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
? ? ? ? ? ? ? ? ? ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_D
_geom_hbond_site_symmetry_H
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_publ_flag
? ? ? ? ? ? ? ? ? ? ?

####################################################################### 
# 
# 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_I
_database_code_depnum_ccdc_archive 'CCDC 1062606'
_audit_update_record             
;
2015-08-26 deposited with the CCDC.
2016-01-08 downloaded from the CCDC.
;
#=======================================================================

# 5. CHEMICAL DATA

_chemical_name_systematic        
; ?
;
_chemical_name_common            ?
_chemical_formula_moiety         'C20 H19 N2 O5 V1'
_chemical_formula_structural     ?
_chemical_formula_analytical     ?
_chemical_formula_iupac          ?
_chemical_formula_sum            'C20 H19 N2 O5 V1'
_chemical_formula_weight         418.3
_chemical_melting_point          ?
_chemical_compound_source        ?
_chemical_absolute_configuration .

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

# 6. CRYSTAL DATA

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_symmetry_space_group_name_Hall  '-P 2yabc'
_symmetry_Int_Tables_number      14

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                   12.7970(8)
_cell_length_b                   7.8400(4)
_cell_length_c                   19.3207(13)
_cell_angle_alpha                90
_cell_angle_beta                 104.308(5)
_cell_angle_gamma                90
_cell_volume                     1878.3(2)

loop_
_twin_individual_id
_twin_individual_mass_fraction_refined
_twin_individual_twin_matrix_11
_twin_individual_twin_matrix_12
_twin_individual_twin_matrix_13
_twin_individual_twin_matrix_21
_twin_individual_twin_matrix_22
_twin_individual_twin_matrix_23
_twin_individual_twin_matrix_31
_twin_individual_twin_matrix_32
_twin_individual_twin_matrix_33
? ? ? ? ? ? ? ? ? ? ?

_cell_formula_units_Z            4

_cell_measurement_reflns_used    15462
_cell_measurement_theta_min      3.12
_cell_measurement_theta_max      29.38
_cell_measurement_temperature    121(2)
_cell_special_details            
; ?
;

_exptl_crystal_density_diffrn    1.4793
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_F_000             864

_exptl_absorpt_coefficient_mu    0.563
_exptl_crystal_description       prism
_exptl_crystal_size_max          0.366
_exptl_crystal_size_mid          0.33
_exptl_crystal_size_min          0.158
_exptl_crystal_size_rad          ?
_exptl_crystal_colour            black
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details   
;
   CrysAlisPro, Agilent Technologies, Version 1.171.37.33a	
   Analytical numeric absorption correction based on crystal shape
;
_exptl_absorpt_correction_T_min  0.962
_exptl_absorpt_correction_T_max  0.98
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
? ? ? ?

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

# 7. EXPERIMENTAL DATA

_exptl_special_details           ?

_diffrn_ambient_temperature      121
_diffrn_source                   'Enhance (Mo) X-ray Source'
_diffrn_source_power             ?
_diffrn_source_voltage           ?
_diffrn_source_current           ?
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_source         'X-ray tube'
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Atlas, Gemini ultra'
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.3745
_diffrn_measurement_method       'ω scans'
_diffrn_measurement_specimen_support ?

_diffrn_reflns_number            27921
_diffrn_reflns_theta_min         3.08
_diffrn_reflns_theta_max         29.21
_diffrn_reflns_theta_full        28.41
_diffrn_measured_fraction_theta_max 0.94
_diffrn_measured_fraction_theta_full 0.98
_diffrn_reflns_av_R_equivalents  0.0254
_diffrn_reflns_av_unetI/netI     0.0158
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_reduction_process ?

_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
loop_
_diffrn_standard_refln_index_h
_diffrn_standard_refln_index_k
_diffrn_standard_refln_index_l
? ? ?

_diffrn_radiation_probe          X-ray

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

# 8. REFINEMENT DATA

_refine_special_details          
; ?
;

_reflns_number_total             4751
_reflns_number_gt                4208
_reflns_threshold_expression     I>3σ(I)

_refine_ls_structure_factor_coef Fsqd
_refine_ls_R_factor_gt           0.0324
_refine_ls_wR_factor_gt          0.0969
_refine_ls_R_factor_all          0.0378
_refine_ls_wR_factor_ref         0.1007
_refine_ls_goodness_of_fit_ref   1.83
_refine_ls_goodness_of_fit_gt    1.88
_refine_ls_restrained_S_gt       ?
_refine_ls_restrained_S_all      ?
_refine_ls_number_reflns         4751
_refine_ls_number_parameters     260
_refine_ls_number_restraints     3
_refine_ls_number_constraints    98
_refine_ls_weighting_scheme      sigma
_refine_ls_weighting_details     w=1/(σ²(I)+0.0016I²)
_refine_ls_hydrogen_treatment    mixed
_refine_ls_shift/su_max          0.0245
_refine_ls_shift/su_mean         0.0011
_refine_diff_density_max         0.33
_refine_diff_density_min         -0.36
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_abs_structure_details ?
_refine_ls_abs_structure_Flack   ?
_refine_ls_abs_structure_Rogers  ?

loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C 0.0033 0.0016 'International Tables Vol C tables 4.2.6.8 and 6.1.1.1'
H 0.0000 0.0000 'International Tables Vol C tables 4.2.6.8 and 6.1.1.1'
N 0.0061 0.0033 'International Tables Vol C tables 4.2.6.8 and 6.1.1.1'
O 0.0106 0.0060 'International Tables Vol C tables 4.2.6.8 and 6.1.1.1'
V 0.3005 0.5294 'International Tables Vol C tables 4.2.6.8 and 6.1.1.1'

_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.33a (release 28-03-2014 CrysAlis171 .NET)
(compiled Mar 28 2014,12:25:20)
;
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.33a (release 28-03-2014 CrysAlis171 .NET)
(compiled Mar 28 2014,12:25:20)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.33a (release 28-03-2014 CrysAlis171 .NET)
(compiled Mar 28 2014,12:25:20)
;
_computing_structure_solution    'Superflip (Palatinus et al., 2007).'
_computing_structure_refinement  'Jana2006 (Petricek et al., 2014)'
_computing_molecular_graphics    'Mercury (Macrae et al., 2008)'
_computing_publication_material  
;
enCIFer (Allen et al., 2004), PLATON (Spek, 2009),  
PublCIF (Westrip 2010), WINGX (Farrugia 2012)
;

loop_
_restr_distance_atom_site_label_1
_restr_distance_site_symmetry_1
_restr_distance_atom_site_label_2
_restr_distance_site_symmetry_2
_restr_distance_target
_restr_distance_target_weight_param
H1o4 . O4 . 0.86 0.001

loop_
_restr_angle_atom_site_label_1
_restr_angle_site_symmetry_1
_restr_angle_atom_site_label_2
_restr_angle_site_symmetry_2
_restr_angle_atom_site_label_3
_restr_angle_site_symmetry_3
_restr_angle_target
_restr_angle_target_weight_param
? ? ? ? ? ? ? ?

loop_
_restr_torsion_atom_site_label_1
_restr_torsion_site_symmetry_1
_restr_torsion_atom_site_label_2
_restr_torsion_site_symmetry_2
_restr_torsion_atom_site_label_3
_restr_torsion_site_symmetry_3
_restr_torsion_atom_site_label_4
_restr_torsion_site_symmetry_4
_restr_torsion_angle_target
_restr_torsion_weight_param
? ? ? ? ? ? ? ? ? ?

loop_
_restr_equal_distance_atom_site_label_1
_restr_equal_distance_site_symmetry_1
_restr_equal_distance_atom_site_label_2
_restr_equal_distance_site_symmetry_2
_restr_equal_distance_class_class_id
_restr_equal_distance_class_target_weight_param
O3 . C19 . 1 0.001
O4 . C20 . 1 0.001
O4 . C20' . 1 0.001

loop_
_restr_equal_angle_atom_site_label_1
_restr_equal_angle_site_symmetry_1
_restr_equal_angle_atom_site_label_2
_restr_equal_angle_site_symmetry_2
_restr_equal_angle_atom_site_label_3
_restr_equal_angle_site_symmetry_3
_restr_equal_angle_class_class_id
_restr_equal_angle_class_target_weight_param
? ? ? ? ? ? ? ?

loop_
_restr_equal_torsion_atom_site_label_1
_restr_equal_torsion_site_symmetry_1
_restr_equal_torsion_atom_site_label_2
_restr_equal_torsion_site_symmetry_2
_restr_equal_torsion_atom_site_label_3
_restr_equal_torsion_site_symmetry_3
_restr_equal_torsion_atom_site_label_4
_restr_equal_torsion_site_symmetry_4
_restr_equal_torsion_class_class_id
_restr_equal_torsion_class_target_weight_param
? ? ? ? ? ? ? ? ? ?


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

# 9. ATOMIC COORDINATES AND DISPLACEMENT PARAMETERS

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_adp_type
_atom_site_U_iso_or_equiv
_atom_site_site_symmetry_multiplicity
_atom_site_occupancy
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
V1 V 0.765799(16) 0.94834(3) 0.010215(11) Uani 0.01637(8) 4 1 d . . .
O1v O 0.81652(7) 0.79070(12) -0.02201(5) Uani 0.0227(3) 4 1 d . . .
O1 O 0.75677(7) 1.10412(12) -0.06436(5) Uani 0.0212(3) 4 1 d . . .
O2 O 0.70304(7) 0.81975(12) 0.07756(5) Uani 0.0215(3) 4 1 d . . .
O3 O 0.87906(7) 1.02667(12) 0.07549(5) Uani 0.0217(3) 4 1 d . . .
O4 O 0.67994(8) 1.16201(13) 0.05536(5) Uani 0.0274(3) 4 1 d . . .
N1 N 0.60519(8) 0.89453(13) -0.04591(5) Uani 0.0150(3) 4 1 d . . .
N2 N 0.54214(8) 0.80985(13) -0.00733(6) Uani 0.0156(3) 4 1 d . . .
C1 C 0.61374(10) 1.00555(16) -0.16100(7) Uani 0.0158(4) 4 1 d . . .
C2 C 0.71045(10) 1.09512(16) -0.13398(7) Uani 0.0174(4) 4 1 d . . .
C3 C 0.75943(10) 1.18771(16) -0.18085(7) Uani 0.0209(4) 4 1 d . . .
C4 C 0.71513(11) 1.18489(16) -0.25269(7) Uani 0.0221(4) 4 1 d . . .
C5 C 0.57406(12) 1.09144(17) -0.35796(7) Uani 0.0246(4) 4 1 d . . .
C6 C 0.47963(13) 1.00717(19) -0.38733(8) Uani 0.0280(5) 4 1 d . . .
C7 C 0.42610(12) 0.92120(18) -0.34226(8) Uani 0.0255(4) 4 1 d . . .
C8 C 0.46825(11) 0.91934(17) -0.26938(7) Uani 0.0211(4) 4 1 d . . .
C9 C 0.56562(10) 1.00549(16) -0.23718(7) Uani 0.0166(4) 4 1 d . . .
C10 C 0.61858(11) 1.09411(16) -0.28319(7) Uani 0.0196(4) 4 1 d . . .
C11 C 0.56047(10) 0.92195(15) -0.11289(7) Uani 0.0155(4) 4 1 d . . .
C12 C 0.60266(10) 0.77324(15) 0.05656(7) Uani 0.0162(3) 4 1 d . . .
C13 C 0.55498(10) 0.67608(16) 0.10705(7) Uani 0.0180(4) 4 1 d . . .
C14 C 0.45734(11) 0.58893(16) 0.08291(7) Uani 0.0202(4) 4 1 d . . .
C15 C 0.41163(12) 0.50250(18) 0.13092(8) Uani 0.0236(4) 4 1 d . . .
C16 C 0.46343(13) 0.50180(19) 0.20299(8) Uani 0.0272(5) 4 1 d . . .
C17 C 0.56146(13) 0.58555(20) 0.22752(8) Uani 0.0303(5) 4 1 d . . .
C18 C 0.60733(11) 0.67297(17) 0.17962(7) Uani 0.0235(4) 4 1 d . . .
C19 C 0.98702(10) 0.97339(19) 0.09160(8) Uani 0.0261(4) 4 1 d . . .
C20 C 0.7126(2) 1.2378(4) 0.12300(11) Uani 0.0322(8) 4 0.584(2) d . . .
C20' C 0.7272(3) 1.3094(4) 0.0904(2) Uani 0.0322(8) 4 0.416(2) d . . .
H1c3 H 0.823853 1.252371 -0.161887 Uiso 0.025 4 1 d . . .
H1c4 H 0.750222 1.246105 -0.283611 Uiso 0.0265 4 1 d . . .
H1c5 H 0.610762 1.149849 -0.388723 Uiso 0.0295 4 1 d . . .
H1c6 H 0.450378 1.006876 -0.438119 Uiso 0.0335 4 1 d . . .
H1c7 H 0.359483 0.863186 -0.362476 Uiso 0.0306 4 1 d . . .
H1c8 H 0.430868 0.858337 -0.239713 Uiso 0.0254 4 1 d . . .
H1c11 H 0.48754 0.884262 -0.131465 Uiso 0.0186 4 1 d . . .
H1c14 H 0.421773 0.588857 0.03295 Uiso 0.0242 4 1 d . . .
H1c15 H 0.344385 0.443449 0.114248 Uiso 0.0283 4 1 d . . .
H1c16 H 0.431416 0.443096 0.236212 Uiso 0.0326 4 1 d . . .
H1c17 H 0.597419 0.583088 0.277397 Uiso 0.0364 4 1 d . . .
H1c18 H 0.674892 0.731042 0.19647 Uiso 0.0282 4 1 d . . .
H1c19 H 1.009679 0.943022 0.141195 Uiso 0.0313 4 1 d . . .
H2c19 H 0.993833 0.876215 0.062804 Uiso 0.0313 4 1 d . . .
H3c19 H 1.031425 1.064476 0.081827 Uiso 0.0313 4 1 d . . .
H1c20 H 0.714783 1.153015 0.159174 Uiso 0.0387 4 0.584(2) d . . .
H2c20 H 0.782999 1.286721 0.128829 Uiso 0.0387 4 0.584(2) d . . .
H3c20 H 0.662295 1.325652 0.127314 Uiso 0.0387 4 0.584(2) d . . .
H1c20' H 0.783817 1.34741 0.069452 Uiso 0.0387 4 0.416(2) d . . .
H2c20' H 0.673668 1.397233 0.085733 Uiso 0.0387 4 0.416(2) d . . .
H3c20' H 0.756697 1.284749 0.140074 Uiso 0.0387 4 0.416(2) d . . .
H1o4 H 0.6118(3) 1.173(2) 0.0372(8) Uiso 0.0329 4 1 d . . .


loop_
_jana_atom_site_ADP_C_label
_jana_atom_site_ADP_C_type_symbol
_jana_atom_site_ADP_C_111
_jana_atom_site_ADP_C_112
_jana_atom_site_ADP_C_113
_jana_atom_site_ADP_C_122
_jana_atom_site_ADP_C_123
_jana_atom_site_ADP_C_133
_jana_atom_site_ADP_C_222
_jana_atom_site_ADP_C_223
_jana_atom_site_ADP_C_233
_jana_atom_site_ADP_C_333
? ? ? ? ? ? ? ? ? ? ? ?

loop_
_jana_atom_site_ADP_D_label
_jana_atom_site_ADP_D_type_symbol
_jana_atom_site_ADP_D_1111
_jana_atom_site_ADP_D_1112
_jana_atom_site_ADP_D_1113
_jana_atom_site_ADP_D_1122
_jana_atom_site_ADP_D_1123
_jana_atom_site_ADP_D_1133
_jana_atom_site_ADP_D_1222
_jana_atom_site_ADP_D_1223
_jana_atom_site_ADP_D_1233
_jana_atom_site_ADP_D_1333
_jana_atom_site_ADP_D_2222
_jana_atom_site_ADP_D_2223
_jana_atom_site_ADP_D_2233
_jana_atom_site_ADP_D_2333
_jana_atom_site_ADP_D_3333
? ? ? ? ? ? ? ? ? ? ? ? ? ? ? ? ?

loop_
_jana_atom_site_ADP_E_label
_jana_atom_site_ADP_E_type_symbol
_jana_atom_site_ADP_E_11111
_jana_atom_site_ADP_E_11112
_jana_atom_site_ADP_E_11113
_jana_atom_site_ADP_E_11122
_jana_atom_site_ADP_E_11123
_jana_atom_site_ADP_E_11133
_jana_atom_site_ADP_E_11222
_jana_atom_site_ADP_E_11223
_jana_atom_site_ADP_E_11233
_jana_atom_site_ADP_E_11333
_jana_atom_site_ADP_E_12222
_jana_atom_site_ADP_E_12223
_jana_atom_site_ADP_E_12233
_jana_atom_site_ADP_E_12333
_jana_atom_site_ADP_E_13333
_jana_atom_site_ADP_E_22222
_jana_atom_site_ADP_E_22223
_jana_atom_site_ADP_E_22233
_jana_atom_site_ADP_E_22333
_jana_atom_site_ADP_E_23333
_jana_atom_site_ADP_E_33333
? ? ? ? ? ? ? ? ? ? ? ? ? ? ? ? ? ? ? ? ? ? ?

loop_
_jana_atom_site_ADP_F_label
_jana_atom_site_ADP_F_type_symbol
_jana_atom_site_ADP_F_111111
_jana_atom_site_ADP_F_111112
_jana_atom_site_ADP_F_111113
_jana_atom_site_ADP_F_111122
_jana_atom_site_ADP_F_111123
_jana_atom_site_ADP_F_111133
_jana_atom_site_ADP_F_111222
_jana_atom_site_ADP_F_111223
_jana_atom_site_ADP_F_111233
_jana_atom_site_ADP_F_111333
_jana_atom_site_ADP_F_112222
_jana_atom_site_ADP_F_112223
_jana_atom_site_ADP_F_112233
_jana_atom_site_ADP_F_112333
_jana_atom_site_ADP_F_113333
_jana_atom_site_ADP_F_122222
_jana_atom_site_ADP_F_122223
_jana_atom_site_ADP_F_122233
_jana_atom_site_ADP_F_122333
_jana_atom_site_ADP_F_123333
_jana_atom_site_ADP_F_133333
_jana_atom_site_ADP_F_222222
_jana_atom_site_ADP_F_222223
_jana_atom_site_ADP_F_222233
_jana_atom_site_ADP_F_222333
_jana_atom_site_ADP_F_223333
_jana_atom_site_ADP_F_233333
_jana_atom_site_ADP_F_333333
? ? ? ? ? ? ? ? ? ? ? ? ? ? ? ? ? ? ? ? ? ? ? ? ? ? ? ? ? ?


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

# 10. MOLECULAR GEOMETRY


loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_1
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
V1 O1v . . 1.5926(10) ?
V1 O1 . . 1.8705(10) ?
V1 O2 . . 1.9675(10) ?
V1 O3 . . 1.7791(9) ?
V1 N1 . . 2.1158(10) ?
O1 C2 . . 1.3310(15) ?
O2 C12 . . 1.3000(15) ?
O3 C19 . . 1.4026(15) ?
O4 C20 . . 1.402(2) ?
O4 C20' . . 1.399(3) ?
O4 H1o4 . . 0.860(5) ?
N1 N2 . . 1.3945(16) ?
N1 C11 . . 1.2970(16) ?
N2 C12 . . 1.3166(15) ?
C1 C2 . . 1.4063(17) ?
C1 C9 . . 1.4482(17) ?
C1 C11 . . 1.439(2) ?
C2 C3 . . 1.421(2) ?
C3 C4 . . 1.3636(19) ?
C3 H1c3 . . 0.96 ?
C4 C10 . . 1.4215(18) ?
C4 H1c4 . . 0.96 ?
C5 C6 . . 1.371(2) ?
C5 C10 . . 1.4159(19) ?
C5 H1c5 . . 0.96 ?
C6 C7 . . 1.406(2) ?
C6 H1c6 . . 0.96 ?
C7 C8 . . 1.3778(19) ?
C7 H1c7 . . 0.96 ?
C8 C9 . . 1.4188(18) ?
C8 H1c8 . . 0.96 ?
C9 C10 . . 1.425(2) ?
C11 H1c11 . . 0.96 ?
C12 C13 . . 1.4826(19) ?
C13 C14 . . 1.3992(18) ?
C13 C18 . . 1.3970(17) ?
C14 C15 . . 1.389(2) ?
C14 H1c14 . . 0.96 ?
C15 C16 . . 1.386(2) ?
C15 H1c15 . . 0.96 ?
C16 C17 . . 1.391(2) ?
C16 H1c16 . . 0.96 ?
C17 C18 . . 1.393(2) ?
C17 H1c17 . . 0.96 ?
C18 H1c18 . . 0.96 ?
C19 H1c19 . . 0.96 ?
C19 H2c19 . . 0.96 ?
C19 H3c19 . . 0.96 ?
C20 H1c20 . . 0.96 ?
C20 H2c20 . . 0.96 ?
C20 H3c20 . . 0.96 ?
C20' H1c20' . . 0.96 ?
C20' H2c20' . . 0.96 ?
C20' H3c20' . . 0.96 ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_2
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
O1v V1 O1 . . . 99.15(5) ?
O1v V1 O2 . . . 97.66(5) ?
O1v V1 O3 . . . 101.87(4) ?
O1v V1 N1 . . . 94.76(4) ?
O1 V1 O2 . . . 152.43(4) ?
O1 V1 O3 . . . 101.84(4) ?
O1 V1 N1 . . . 82.42(4) ?
O2 V1 O3 . . . 95.87(4) ?
O2 V1 N1 . . . 74.52(4) ?
O3 V1 N1 . . . 161.84(5) ?
V1 O1 C2 . . . 132.16(8) ?
V1 O2 C12 . . . 118.08(8) ?
V1 O3 C19 . . . 129.77(9) ?
C20 O4 H1o4 . . . 112.1(11) ?
C20' O4 H1o4 . . . 112.9(11) ?
V1 N1 N2 . . . 115.98(7) ?
V1 N1 C11 . . . 127.70(9) ?
N2 N1 C11 . . . 116.19(10) ?
N1 N2 C12 . . . 108.72(10) ?
C2 C1 C9 . . . 119.44(12) ?
C2 C1 C11 . . . 120.10(11) ?
C9 C1 C11 . . . 120.39(11) ?
O1 C2 C1 . . . 122.20(12) ?
O1 C2 C3 . . . 117.41(11) ?
C1 C2 C3 . . . 120.31(11) ?
C2 C3 C4 . . . 120.15(12) ?
C2 C3 H1c3 . . . 119.92 ?
C4 C3 H1c3 . . . 119.92 ?
C3 C4 C10 . . . 122.02(14) ?
C3 C4 H1c4 . . . 118.99 ?
C10 C4 H1c4 . . . 118.99 ?
C6 C5 C10 . . . 121.37(14) ?
C6 C5 H1c5 . . . 119.31 ?
C10 C5 H1c5 . . . 119.31 ?
C5 C6 C7 . . . 119.29(13) ?
C5 C6 H1c6 . . . 120.36 ?
C7 C6 H1c6 . . . 120.36 ?
C6 C7 C8 . . . 120.69(13) ?
C6 C7 H1c7 . . . 119.65 ?
C8 C7 H1c7 . . . 119.65 ?
C7 C8 C9 . . . 121.51(14) ?
C7 C8 H1c8 . . . 119.24 ?
C9 C8 H1c8 . . . 119.24 ?
C1 C9 C8 . . . 123.55(13) ?
C1 C9 C10 . . . 119.05(11) ?
C8 C9 C10 . . . 117.39(11) ?
C4 C10 C5 . . . 121.32(14) ?
C4 C10 C9 . . . 118.96(12) ?
C5 C10 C9 . . . 119.73(12) ?
N1 C11 C1 . . . 123.86(11) ?
N1 C11 H1c11 . . . 118.07 ?
C1 C11 H1c11 . . . 118.07 ?
O2 C12 N2 . . . 122.57(12) ?
O2 C12 C13 . . . 118.32(10) ?
N2 C12 C13 . . . 119.11(11) ?
C12 C13 C14 . . . 120.69(11) ?
C12 C13 C18 . . . 119.74(11) ?
C14 C13 C18 . . . 119.56(13) ?
C13 C14 C15 . . . 120.28(12) ?
C13 C14 H1c14 . . . 119.86 ?
C15 C14 H1c14 . . . 119.86 ?
C14 C15 C16 . . . 119.79(13) ?
C14 C15 H1c15 . . . 120.1 ?
C16 C15 H1c15 . . . 120.1 ?
C15 C16 C17 . . . 120.49(15) ?
C15 C16 H1c16 . . . 119.76 ?
C17 C16 H1c16 . . . 119.76 ?
C16 C17 C18 . . . 119.91(13) ?
C16 C17 H1c17 . . . 120.05 ?
C18 C17 H1c17 . . . 120.05 ?
C13 C18 C17 . . . 119.95(13) ?
C13 C18 H1c18 . . . 120.02 ?
C17 C18 H1c18 . . . 120.02 ?
O3 C19 H1c19 . . . 109.47 ?
O3 C19 H2c19 . . . 109.47 ?
O3 C19 H3c19 . . . 109.47 ?
H1c19 C19 H2c19 . . . 109.47 ?
H1c19 C19 H3c19 . . . 109.47 ?
H2c19 C19 H3c19 . . . 109.47 ?
O4 C20 H1c20 . . . 109.47 ?
O4 C20 H2c20 . . . 109.47 ?
O4 C20 H3c20 . . . 109.47 ?
H1c20 C20 H2c20 . . . 109.47 ?
H1c20 C20 H3c20 . . . 109.47 ?
H2c20 C20 H3c20 . . . 109.47 ?
O4 C20' H1c20' . . . 109.47 ?
O4 C20' H2c20' . . . 109.47 ?
O4 C20' H3c20' . . . 109.47 ?
H1c20' C20' H2c20' . . . 109.47 ?
H1c20' C20' H3c20' . . . 109.47 ?
H2c20' C20' H3c20' . . . 109.47 ?


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_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
? ? ? ? ? ? ? ? ? ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_D
_geom_hbond_site_symmetry_H
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_publ_flag
C5 H1c5 O1v . . 2_654 0.96 2.42 3.3740(19) 172.91 ?
O4 H1o4 N2 . . 3_675 0.860(5) 1.916(4) 2.7718(14) 173.5(16) ?

