# Electronic Supplementary Material (ESI) for CrystEngComm.
# 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_VS-SP-HCl-EtOH
_database_code_depnum_ccdc_archive 'CCDC 1824248'
_audit_update_record             
;
2018-02-15 deposited with the CCDC.
2018-04-06 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2016/4
_shelx_SHELXL_version_number     2016/4
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C19 H20 N O, Cl'
_chemical_formula_sum            'C19 H20 Cl N O'
_chemical_formula_weight         313.81

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 '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 21/n'
_space_group_name_Hall           '-P 2yn'

_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.
;

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                   8.3825(4)
_cell_length_b                   14.3515(8)
_cell_length_c                   13.3425(7)
_cell_angle_alpha                90
_cell_angle_beta                 96.835(5)
_cell_angle_gamma                90
_cell_volume                     1593.71(14)
_cell_formula_units_Z            4
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    4765
_cell_measurement_theta_min      2.9800
_cell_measurement_theta_max      25.1720

_exptl_crystal_description       block
_exptl_crystal_colour            orange-red
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.308
_exptl_crystal_F_000             664
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.16
_exptl_crystal_size_mid          0.11
_exptl_crystal_size_min          0.06
_exptl_absorpt_coefficient_mu    0.241
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.84102
_exptl_absorpt_correction_T_max  1.00000
_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_absorpt_special_details   ?




_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'Rigaku UltraX 18 rotating anode'
_diffrn_radiation_monochromator  'Xenocs Fox3D mirror'
_diffrn_measurement_device_type  'MAR345 image plate'
_diffrn_measurement_method       '120 images, ΔΦ 2.0° '
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            9468
_diffrn_reflns_av_unetI/netI     0.0455
_diffrn_reflns_av_R_equivalents  0.0539
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         3.041
_diffrn_reflns_theta_max         25.237
_diffrn_reflns_theta_full        25.000
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measured_fraction_theta_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_point_group_measured_fraction_full 0.994
_reflns_number_total             2851
_reflns_number_gt                2320
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_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.
;

_computing_data_collection       MAR
_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_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_structure_solution    'SHELXT (Sheldrick, 2015)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'MERCURY (Macrae et al., 2008)'
_computing_publication_material  
;
'MERCURY (Macrae et al., 2008), Platon (Spek, 2009)'
;
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0403P)²+0.8802P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         2851
_refine_ls_number_parameters     202
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0564
_refine_ls_R_factor_gt           0.0424
_refine_ls_wR_factor_ref         0.1038
_refine_ls_wR_factor_gt          0.0972
_refine_ls_goodness_of_fit_ref   1.047
_refine_ls_restrained_S_all      1.047
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

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
CL01 Cl 0.27783(7) 0.55296(4) 0.24574(4) 0.03094(17) Uani 1 1 d . . . . .
O1 O -0.09114(18) 0.36636(11) 0.59557(12) 0.0324(4) Uani 1 1 d . . . . .
H1 H -0.146766 0.389947 0.635334 0.049 Uiso 1 1 calc R U . . .
C3 C -0.2779(2) 0.44983(14) 0.47802(17) 0.0267(5) Uani 1 1 d . . . . .
H3 H -0.346540 0.459336 0.526918 0.032 Uiso 1 1 calc R U . . .
C2 C -0.1347(2) 0.40080(13) 0.50235(16) 0.0224(5) Uani 1 1 d . . . . .
C4 C -0.3178(3) 0.48403(15) 0.38232(18) 0.0290(5) Uani 1 1 d . . . . .
H4 H -0.414087 0.515971 0.366657 0.035 Uiso 1 1 calc R U . . .
C5 C -0.2154(3) 0.47138(15) 0.30810(18) 0.0322(5) Uani 1 1 d . . . . .
H5 H -0.242700 0.495059 0.243456 0.039 Uiso 1 1 calc R U . . .
C6 C -0.0742(3) 0.42369(15) 0.33165(17) 0.0277(5) Uani 1 1 d . . . . .
H6 H -0.005510 0.415985 0.282416 0.033 Uiso 1 1 calc R U . . .
C7 C -0.0304(2) 0.38606(13) 0.42852(16) 0.0211(4) Uani 1 1 d . . . . .
C9 C 0.2330(2) 0.32152(14) 0.39363(16) 0.0227(5) Uani 1 1 d . . . . .
H9 H 0.219722 0.351250 0.331256 0.027 Uiso 1 1 calc R U . . .
C8 C 0.1151(2) 0.33285(14) 0.45354(16) 0.0224(5) Uani 1 1 d . . . . .
H8 H 0.128922 0.303847 0.516304 0.027 Uiso 1 1 calc R U . . .
C10 C 0.3754(2) 0.26821(13) 0.41754(15) 0.0198(4) Uani 1 1 d . . . . .
C11 C 0.4280(2) 0.21142(13) 0.51228(15) 0.0194(4) Uani 1 1 d . . . . .
C12 C 0.3107(2) 0.13042(14) 0.52466(17) 0.0251(5) Uani 1 1 d . . . . .
H12A H 0.290892 0.096685 0.462288 0.038 Uiso 1 1 calc R U . . .
H12B H 0.211240 0.154938 0.542416 0.038 Uiso 1 1 calc R U . . .
H12C H 0.356918 0.089284 0.576977 0.038 Uiso 1 1 calc R U . . .
C13 C 0.4538(3) 0.27253(15) 0.60782(16) 0.0253(5) Uani 1 1 d . . . . .
H13A H 0.532740 0.319442 0.599448 0.038 Uiso 1 1 calc R U . . .
H13B H 0.490331 0.234368 0.665064 0.038 Uiso 1 1 calc R U . . .
H13C H 0.354224 0.301858 0.618460 0.038 Uiso 1 1 calc R U . . .
C14 C 0.5881(2) 0.17419(13) 0.48787(15) 0.0191(4) Uani 1 1 d . . . . .
C15 C 0.7003(2) 0.11837(14) 0.54334(16) 0.0245(5) Uani 1 1 d . . . . .
H15 H 0.681937 0.095282 0.606093 0.029 Uiso 1 1 calc R U . . .
C16 C 0.8419(3) 0.09760(15) 0.50253(17) 0.0281(5) Uani 1 1 d . . . . .
H16 H 0.919132 0.060450 0.538966 0.034 Uiso 1 1 calc R U . . .
C17 C 0.8697(3) 0.13120(15) 0.40889(18) 0.0291(5) Uani 1 1 d . . . . .
H17 H 0.965271 0.116507 0.383575 0.035 Uiso 1 1 calc R U . . .
C18 C 0.7566(3) 0.18656(15) 0.35228(17) 0.0264(5) Uani 1 1 d . . . . .
H18 H 0.773434 0.208968 0.288974 0.032 Uiso 1 1 calc R U . . .
C19 C 0.6181(2) 0.20670(13) 0.39458(15) 0.0205(4) Uani 1 1 d . . . . .
N20 N 0.48525(19) 0.26313(11) 0.35454(12) 0.0201(4) Uani 1 1 d . . . . .
C21 C 0.4732(3) 0.30528(16) 0.25355(16) 0.0310(5) Uani 1 1 d . . . . .
H21A H 0.577224 0.305710 0.230262 0.047 Uiso 1 1 calc R U . . .
H21B H 0.434397 0.368032 0.256645 0.047 Uiso 1 1 calc R U . . .
H21C H 0.400052 0.269643 0.207752 0.047 Uiso 1 1 calc R U . . .


_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 C2 1.348(2) . ?
O1 H1 0.8200 . ?
C3 C4 1.372(3) . ?
C3 C2 1.396(3) . ?
C3 H3 0.9300 . ?
C2 C7 1.408(3) . ?
C4 C5 1.398(3) . ?
C4 H4 0.9300 . ?
C5 C6 1.371(3) . ?
C5 H5 0.9300 . ?
C6 C7 1.408(3) . ?
C6 H6 0.9300 . ?
C7 C8 1.444(3) . ?
C9 C8 1.353(3) . ?
C9 C10 1.422(3) . ?
C9 H9 0.9300 . ?
C8 H8 0.9300 . ?
C10 N20 1.321(3) . ?
C10 C11 1.525(3) . ?
C11 C14 1.515(3) . ?
C11 C13 1.541(3) . ?
C11 C12 1.544(3) . ?
C12 H12A 0.9600 . ?
C12 H12B 0.9600 . ?
C12 H12C 0.9600 . ?
C13 H13A 0.9600 . ?
C13 H13B 0.9600 . ?
C13 H13C 0.9600 . ?
C14 C19 1.380(3) . ?
C14 C15 1.381(3) . ?
C15 C16 1.396(3) . ?
C15 H15 0.9300 . ?
C16 C17 1.385(3) . ?
C16 H16 0.9300 . ?
C17 C18 1.389(3) . ?
C17 H17 0.9300 . ?
C18 C19 1.381(3) . ?
C18 H18 0.9300 . ?
C19 N20 1.428(2) . ?
N20 C21 1.470(3) . ?
C21 H21A 0.9600 . ?
C21 H21B 0.9600 . ?
C21 H21C 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
C2 O1 H1 109.5 . . ?
C4 C3 C2 120.3(2) . . ?
C4 C3 H3 119.8 . . ?
C2 C3 H3 119.8 . . ?
O1 C2 C3 122.02(19) . . ?
O1 C2 C7 117.91(18) . . ?
C3 C2 C7 120.07(19) . . ?
C3 C4 C5 120.7(2) . . ?
C3 C4 H4 119.6 . . ?
C5 C4 H4 119.6 . . ?
C6 C5 C4 119.3(2) . . ?
C6 C5 H5 120.4 . . ?
C4 C5 H5 120.4 . . ?
C5 C6 C7 121.7(2) . . ?
C5 C6 H6 119.2 . . ?
C7 C6 H6 119.2 . . ?
C2 C7 C6 117.96(18) . . ?
C2 C7 C8 119.67(19) . . ?
C6 C7 C8 122.37(19) . . ?
C8 C9 C10 125.8(2) . . ?
C8 C9 H9 117.1 . . ?
C10 C9 H9 117.1 . . ?
C9 C8 C7 125.7(2) . . ?
C9 C8 H8 117.2 . . ?
C7 C8 H8 117.2 . . ?
N20 C10 C9 121.15(19) . . ?
N20 C10 C11 110.07(17) . . ?
C9 C10 C11 128.78(18) . . ?
C14 C11 C10 100.76(16) . . ?
C14 C11 C13 109.77(16) . . ?
C10 C11 C13 112.32(16) . . ?
C14 C11 C12 110.44(16) . . ?
C10 C11 C12 111.45(16) . . ?
C13 C11 C12 111.60(17) . . ?
C11 C12 H12A 109.5 . . ?
C11 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
C11 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C11 C13 H13A 109.5 . . ?
C11 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
C11 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
C19 C14 C15 119.59(19) . . ?
C19 C14 C11 109.62(17) . . ?
C15 C14 C11 130.76(19) . . ?
C14 C15 C16 118.1(2) . . ?
C14 C15 H15 121.0 . . ?
C16 C15 H15 121.0 . . ?
C17 C16 C15 121.3(2) . . ?
C17 C16 H16 119.3 . . ?
C15 C16 H16 119.3 . . ?
C16 C17 C18 120.8(2) . . ?
C16 C17 H17 119.6 . . ?
C18 C17 H17 119.6 . . ?
C19 C18 C17 116.7(2) . . ?
C19 C18 H18 121.6 . . ?
C17 C18 H18 121.6 . . ?
C14 C19 C18 123.39(19) . . ?
C14 C19 N20 108.13(17) . . ?
C18 C19 N20 128.47(19) . . ?
C10 N20 C19 111.41(17) . . ?
C10 N20 C21 125.72(17) . . ?
C19 N20 C21 122.81(17) . . ?
N20 C21 H21A 109.5 . . ?
N20 C21 H21B 109.5 . . ?
H21A C21 H21B 109.5 . . ?
N20 C21 H21C 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 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
C4 C3 C2 O1 179.84(19) . . . . ?
C4 C3 C2 C7 -0.1(3) . . . . ?
C2 C3 C4 C5 -0.7(3) . . . . ?
C3 C4 C5 C6 0.4(3) . . . . ?
C4 C5 C6 C7 0.8(3) . . . . ?
O1 C2 C7 C6 -178.71(18) . . . . ?
C3 C2 C7 C6 1.3(3) . . . . ?
O1 C2 C7 C8 1.9(3) . . . . ?
C3 C2 C7 C8 -178.12(18) . . . . ?
C5 C6 C7 C2 -1.6(3) . . . . ?
C5 C6 C7 C8 177.8(2) . . . . ?
C10 C9 C8 C7 -179.15(19) . . . . ?
C2 C7 C8 C9 -172.85(19) . . . . ?
C6 C7 C8 C9 7.8(3) . . . . ?
C8 C9 C10 N20 -178.5(2) . . . . ?
C8 C9 C10 C11 1.0(3) . . . . ?
N20 C10 C11 C14 -0.2(2) . . . . ?
C9 C10 C11 C14 -179.75(19) . . . . ?
N20 C10 C11 C13 116.52(18) . . . . ?
C9 C10 C11 C13 -63.0(3) . . . . ?
N20 C10 C11 C12 -117.41(18) . . . . ?
C9 C10 C11 C12 63.1(3) . . . . ?
C10 C11 C14 C19 0.5(2) . . . . ?
C13 C11 C14 C19 -118.09(18) . . . . ?
C12 C11 C14 C19 118.45(18) . . . . ?
C10 C11 C14 C15 178.9(2) . . . . ?
C13 C11 C14 C15 60.3(3) . . . . ?
C12 C11 C14 C15 -63.2(3) . . . . ?
C19 C14 C15 C16 0.6(3) . . . . ?
C11 C14 C15 C16 -177.66(19) . . . . ?
C14 C15 C16 C17 -0.4(3) . . . . ?
C15 C16 C17 C18 -0.3(3) . . . . ?
C16 C17 C18 C19 0.7(3) . . . . ?
C15 C14 C19 C18 -0.1(3) . . . . ?
C11 C14 C19 C18 178.48(19) . . . . ?
C15 C14 C19 N20 -179.23(17) . . . . ?
C11 C14 C19 N20 -0.6(2) . . . . ?
C17 C18 C19 C14 -0.6(3) . . . . ?
C17 C18 C19 N20 178.39(19) . . . . ?
C9 C10 N20 C19 179.42(17) . . . . ?
C11 C10 N20 C19 -0.1(2) . . . . ?
C9 C10 N20 C21 -3.4(3) . . . . ?
C11 C10 N20 C21 177.02(18) . . . . ?
C14 C19 N20 C10 0.5(2) . . . . ?
C18 C19 N20 C10 -178.6(2) . . . . ?
C14 C19 N20 C21 -176.76(17) . . . . ?
C18 C19 N20 C21 4.2(3) . . . . ?

_refine_diff_density_max         0.245
_refine_diff_density_min         -0.190
_refine_diff_density_rms         0.048


_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: Ethanol'
####################################################################### 
# 
# 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_(IIc)
_database_code_depnum_ccdc_archive 'CCDC 1824252'
_audit_update_record             
;
2018-02-15 deposited with the CCDC.
2018-04-06 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C23 H22 N O, N O3'
_chemical_formula_sum            'C23 H22 N2 O4'
_chemical_formula_weight         390.42

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           61
_space_group_name_H-M_alt        'P b c a'
_space_group_name_Hall           '-P 2ac 2ab'

_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.
;

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

_cell_length_a                   14.9120(4)
_cell_length_b                   6.9922(2)
_cell_length_c                   37.2099(13)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     3879.8(2)
_cell_formula_units_Z            8
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    6502
_cell_measurement_theta_min      3.2580
_cell_measurement_theta_max      25.6150

_exptl_crystal_description       plate
_exptl_crystal_colour            red
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.337
_exptl_crystal_F_000             1648
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.01
_exptl_absorpt_coefficient_mu    0.092
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_T_min  0.84097
_exptl_absorpt_correction_T_max  1.00000
_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_absorpt_special_details   ?




_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'Rigaku UltraX 18 rotating anode'
_diffrn_radiation_monochromator  'Xenocs Fox3D mirror'
_diffrn_measurement_device_type  'MAR345 image plate'
_diffrn_measurement_method       '150 images, ΔΦ 1.2° '
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            21363
_diffrn_reflns_av_unetI/netI     0.0323
_diffrn_reflns_av_R_equivalents  0.0609
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -44
_diffrn_reflns_limit_l_max       39
_diffrn_reflns_theta_min         3.264
_diffrn_reflns_theta_max         25.241
_diffrn_reflns_theta_full        25.241
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_point_group_measured_fraction_full 0.997
_reflns_number_total             3508
_reflns_number_gt                2737
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_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.
;

_computing_data_collection       MAR
_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_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_structure_solution    'SHELXT (Sheldrick, 2015)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'MERCURY (Macrae et al., 2008)'
_computing_publication_material  
;

'MERCURY (Macrae et al., 2008), Platon (Spek, 2009)'



;








_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0440P)²+3.0479P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3508
_refine_ls_number_parameters     266
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0657
_refine_ls_R_factor_gt           0.0475
_refine_ls_wR_factor_ref         0.1163
_refine_ls_wR_factor_gt          0.1080
_refine_ls_goodness_of_fit_ref   1.029
_refine_ls_restrained_S_all      1.029
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.21463(9) 0.3270(2) 0.37627(4) 0.0324(4) Uani 1 1 d . . . . .
H1 H 0.1605 0.3307 0.3701 0.049 Uiso 1 1 calc R U . . .
C2 C 0.22023(13) 0.2874(3) 0.41128(5) 0.0240(4) Uani 1 1 d . . . . .
C3 C 0.14086(13) 0.2625(3) 0.43171(5) 0.0265(5) Uani 1 1 d . . . . .
H3 H 0.0840 0.2742 0.4204 0.032 Uiso 1 1 calc R U . . .
C4 C 0.14580(13) 0.2221(3) 0.46725(5) 0.0261(5) Uani 1 1 d . . . . .
H4 H 0.0919 0.2050 0.4805 0.031 Uiso 1 1 calc R U . . .
C5 C 0.22915(13) 0.2046(3) 0.48526(5) 0.0234(4) Uani 1 1 d . . . . .
C6 C 0.31021(12) 0.2299(3) 0.46524(5) 0.0223(4) Uani 1 1 d . . . . .
C7 C 0.30522(12) 0.2729(3) 0.42708(5) 0.0222(4) Uani 1 1 d . . . . .
C8 C 0.38669(13) 0.3023(3) 0.40682(5) 0.0241(4) Uani 1 1 d . . . . .
H8 H 0.4407 0.2937 0.4203 0.029 Uiso 1 1 calc R U . . .
C9 C 0.39697(12) 0.3403(3) 0.37132(5) 0.0242(4) Uani 1 1 d . . . . .
H9 H 0.3444 0.3508 0.3571 0.029 Uiso 1 1 calc R U . . .
C10 C 0.48119(13) 0.3656(3) 0.35402(5) 0.0230(4) Uani 1 1 d . . . . .
C11 C 0.57561(12) 0.3569(3) 0.37007(5) 0.0233(4) Uani 1 1 d . . . . .
C12 C 0.59022(13) 0.5242(3) 0.39647(5) 0.0282(5) Uani 1 1 d . . . . .
H12A H 0.6533 0.5281 0.4038 0.042 Uiso 1 1 calc R U . . .
H12B H 0.5523 0.5060 0.4177 0.042 Uiso 1 1 calc R U . . .
H12C H 0.5743 0.6449 0.3847 0.042 Uiso 1 1 calc R U . . .
C13 C 0.59726(14) 0.1638(3) 0.38753(6) 0.0300(5) Uani 1 1 d . . . . .
H13A H 0.5838 0.0605 0.3706 0.045 Uiso 1 1 calc R U . . .
H13B H 0.5609 0.1478 0.4092 0.045 Uiso 1 1 calc R U . . .
H13C H 0.6610 0.1597 0.3939 0.045 Uiso 1 1 calc R U . . .
C14 C 0.63241(13) 0.3876(3) 0.33686(5) 0.0251(4) Uani 1 1 d . . . . .
C15 C 0.72425(13) 0.3896(3) 0.33214(6) 0.0308(5) Uani 1 1 d . . . . .
H15 H 0.7633 0.3697 0.3520 0.037 Uiso 1 1 calc R U . . .
C16 C 0.75854(14) 0.4213(3) 0.29795(6) 0.0371(6) Uani 1 1 d . . . . .
H16 H 0.8216 0.4237 0.2944 0.044 Uiso 1 1 calc R U . . .
C17 C 0.70153(15) 0.4496(3) 0.26897(6) 0.0372(6) Uani 1 1 d . . . . .
H17 H 0.7264 0.4706 0.2458 0.045 Uiso 1 1 calc R U . . .
C18 C 0.60873(14) 0.4480(3) 0.27302(6) 0.0318(5) Uani 1 1 d . . . . .
H18 H 0.5694 0.4674 0.2533 0.038 Uiso 1 1 calc R U . . .
C19 C 0.57723(13) 0.4163(3) 0.30743(5) 0.0263(5) Uani 1 1 d . . . . .
N20 N 0.48664(10) 0.4044(2) 0.31930(4) 0.0241(4) Uani 1 1 d . . . . .
C21 C 0.41085(13) 0.4334(4) 0.29462(5) 0.0331(5) Uani 1 1 d . . . . .
H21A H 0.3770 0.3139 0.2923 0.050 Uiso 0.5 1 calc R U P . .
H21B H 0.4335 0.4720 0.2710 0.050 Uiso 0.5 1 calc R U P . .
H21C H 0.3715 0.5337 0.3041 0.050 Uiso 0.5 1 calc R U P . .
H21D H 0.4110 0.5658 0.2860 0.050 Uiso 0.5 1 calc R U P . .
H21E H 0.3545 0.4077 0.3073 0.050 Uiso 0.5 1 calc R U P . .
H21F H 0.4165 0.3461 0.2741 0.050 Uiso 0.5 1 calc R U P . .
C22 C 0.23241(14) 0.1636(3) 0.52225(5) 0.0277(5) Uani 1 1 d . . . . .
H22 H 0.1780 0.1473 0.5352 0.033 Uiso 1 1 calc R U . . .
C23 C 0.31215(15) 0.1467(3) 0.53993(6) 0.0299(5) Uani 1 1 d . . . . .
H23 H 0.3133 0.1197 0.5649 0.036 Uiso 1 1 calc R U . . .
C24 C 0.39203(14) 0.1695(3) 0.52080(5) 0.0312(5) Uani 1 1 d . . . . .
H24 H 0.4478 0.1565 0.5329 0.037 Uiso 1 1 calc R U . . .
C25 C 0.39113(13) 0.2104(3) 0.48475(5) 0.0282(5) Uani 1 1 d . . . . .
H25 H 0.4465 0.2261 0.4725 0.034 Uiso 1 1 calc R U . . .
N31 N 0.05058(12) 0.4155(3) 0.32267(5) 0.0323(4) Uani 1 1 d . . . . .
O32 O 0.04866(10) 0.3245(2) 0.35229(4) 0.0378(4) Uani 1 1 d . . . . .
O33 O -0.01927(11) 0.4449(3) 0.30598(5) 0.0630(6) Uani 1 1 d . . . . .
O34 O 0.12317(11) 0.4770(3) 0.31148(4) 0.0479(5) Uani 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C2 1.334(2) . ?
O1 H1 0.8400 . ?
C2 C7 1.401(3) . ?
C2 C3 1.417(3) . ?
C3 C4 1.354(3) . ?
C3 H3 0.9500 . ?
C4 C5 1.417(3) . ?
C4 H4 0.9500 . ?
C5 C22 1.407(3) . ?
C5 C6 1.431(3) . ?
C6 C25 1.415(3) . ?
C6 C7 1.453(3) . ?
C7 C8 1.445(3) . ?
C8 C9 1.356(3) . ?
C8 H8 0.9500 . ?
C9 C10 1.422(3) . ?
C9 H9 0.9500 . ?
C10 N20 1.322(2) . ?
C10 C11 1.531(3) . ?
C11 C14 1.513(3) . ?
C11 C13 1.533(3) . ?
C11 C12 1.543(3) . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12C 0.9800 . ?
C13 H13A 0.9800 . ?
C13 H13B 0.9800 . ?
C13 H13C 0.9800 . ?
C14 C15 1.381(3) . ?
C14 C19 1.384(3) . ?
C15 C16 1.389(3) . ?
C15 H15 0.9500 . ?
C16 C17 1.387(3) . ?
C16 H16 0.9500 . ?
C17 C18 1.392(3) . ?
C17 H17 0.9500 . ?
C18 C19 1.382(3) . ?
C18 H18 0.9500 . ?
C19 N20 1.424(2) . ?
N20 C21 1.470(2) . ?
C21 H21A 0.9800 . ?
C21 H21B 0.9800 . ?
C21 H21C 0.9800 . ?
C21 H21D 0.9800 . ?
C21 H21E 0.9800 . ?
C21 H21F 0.9800 . ?
C22 C23 1.364(3) . ?
C22 H22 0.9500 . ?
C23 C24 1.397(3) . ?
C23 H23 0.9500 . ?
C24 C25 1.372(3) . ?
C24 H24 0.9500 . ?
C25 H25 0.9500 . ?
N31 O33 1.230(2) . ?
N31 O34 1.237(2) . ?
N31 O32 1.273(2) . ?

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
C2 O1 H1 109.5 . . ?
O1 C2 C7 118.78(17) . . ?
O1 C2 C3 119.79(17) . . ?
C7 C2 C3 121.43(18) . . ?
C4 C3 C2 120.26(18) . . ?
C4 C3 H3 119.9 . . ?
C2 C3 H3 119.9 . . ?
C3 C4 C5 121.83(18) . . ?
C3 C4 H4 119.1 . . ?
C5 C4 H4 119.1 . . ?
C22 C5 C4 120.70(18) . . ?
C22 C5 C6 120.35(18) . . ?
C4 C5 C6 118.95(18) . . ?
C25 C6 C5 116.21(18) . . ?
C25 C6 C7 124.39(17) . . ?
C5 C6 C7 119.40(17) . . ?
C2 C7 C8 122.11(17) . . ?
C2 C7 C6 118.13(17) . . ?
C8 C7 C6 119.75(17) . . ?
C9 C8 C7 129.15(18) . . ?
C9 C8 H8 115.4 . . ?
C7 C8 H8 115.4 . . ?
C8 C9 C10 124.41(18) . . ?
C8 C9 H9 117.8 . . ?
C10 C9 H9 117.8 . . ?
N20 C10 C9 121.46(17) . . ?
N20 C10 C11 109.44(16) . . ?
C9 C10 C11 129.09(17) . . ?
C14 C11 C10 100.99(15) . . ?
C14 C11 C13 110.67(16) . . ?
C10 C11 C13 113.23(16) . . ?
C14 C11 C12 109.47(17) . . ?
C10 C11 C12 110.37(16) . . ?
C13 C11 C12 111.61(16) . . ?
C11 C12 H12A 109.5 . . ?
C11 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
C11 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C11 C13 H13A 109.5 . . ?
C11 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
C11 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
C15 C14 C19 119.18(19) . . ?
C15 C14 C11 131.33(18) . . ?
C19 C14 C11 109.49(17) . . ?
C14 C15 C16 118.9(2) . . ?
C14 C15 H15 120.6 . . ?
C16 C15 H15 120.6 . . ?
C17 C16 C15 120.6(2) . . ?
C17 C16 H16 119.7 . . ?
C15 C16 H16 119.7 . . ?
C16 C17 C18 121.6(2) . . ?
C16 C17 H17 119.2 . . ?
C18 C17 H17 119.2 . . ?
C19 C18 C17 116.1(2) . . ?
C19 C18 H18 122.0 . . ?
C17 C18 H18 122.0 . . ?
C18 C19 C14 123.65(19) . . ?
C18 C19 N20 128.28(18) . . ?
C14 C19 N20 108.06(17) . . ?
C10 N20 C19 111.92(16) . . ?
C10 N20 C21 126.25(17) . . ?
C19 N20 C21 121.82(16) . . ?
N20 C21 H21A 109.5 . . ?
N20 C21 H21B 109.5 . . ?
H21A C21 H21B 109.5 . . ?
N20 C21 H21C 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
N20 C21 H21D 109.5 . . ?
H21A C21 H21D 141.1 . . ?
H21B C21 H21D 56.3 . . ?
H21C C21 H21D 56.3 . . ?
N20 C21 H21E 109.5 . . ?
H21A C21 H21E 56.3 . . ?
H21B C21 H21E 141.1 . . ?
H21C C21 H21E 56.3 . . ?
H21D C21 H21E 109.5 . . ?
N20 C21 H21F 109.5 . . ?
H21A C21 H21F 56.3 . . ?
H21B C21 H21F 56.3 . . ?
H21C C21 H21F 141.1 . . ?
H21D C21 H21F 109.5 . . ?
H21E C21 H21F 109.5 . . ?
C23 C22 C5 121.31(19) . . ?
C23 C22 H22 119.3 . . ?
C5 C22 H22 119.3 . . ?
C22 C23 C24 119.20(19) . . ?
C22 C23 H23 120.4 . . ?
C24 C23 H23 120.4 . . ?
C25 C24 C23 120.92(19) . . ?
C25 C24 H24 119.5 . . ?
C23 C24 H24 119.5 . . ?
C24 C25 C6 122.02(19) . . ?
C24 C25 H25 119.0 . . ?
C6 C25 H25 119.0 . . ?
O33 N31 O34 120.9(2) . . ?
O33 N31 O32 120.13(19) . . ?
O34 N31 O32 119.00(17) . . ?

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 C2 C3 C4 179.93(19) . . . . ?
C7 C2 C3 C4 -0.6(3) . . . . ?
C2 C3 C4 C5 0.4(3) . . . . ?
C3 C4 C5 C22 179.7(2) . . . . ?
C3 C4 C5 C6 -0.2(3) . . . . ?
C22 C5 C6 C25 0.3(3) . . . . ?
C4 C5 C6 C25 -179.93(18) . . . . ?
C22 C5 C6 C7 -179.76(18) . . . . ?
C4 C5 C6 C7 0.1(3) . . . . ?
O1 C2 C7 C8 0.9(3) . . . . ?
C3 C2 C7 C8 -178.54(19) . . . . ?
O1 C2 C7 C6 179.96(18) . . . . ?
C3 C2 C7 C6 0.5(3) . . . . ?
C25 C6 C7 C2 179.8(2) . . . . ?
C5 C6 C7 C2 -0.2(3) . . . . ?
C25 C6 C7 C8 -1.2(3) . . . . ?
C5 C6 C7 C8 178.83(18) . . . . ?
C2 C7 C8 C9 -2.2(3) . . . . ?
C6 C7 C8 C9 178.8(2) . . . . ?
C7 C8 C9 C10 -179.6(2) . . . . ?
C8 C9 C10 N20 -179.3(2) . . . . ?
C8 C9 C10 C11 0.0(3) . . . . ?
N20 C10 C11 C14 -3.0(2) . . . . ?
C9 C10 C11 C14 177.6(2) . . . . ?
N20 C10 C11 C13 -121.33(19) . . . . ?
C9 C10 C11 C13 59.3(3) . . . . ?
N20 C10 C11 C12 112.74(19) . . . . ?
C9 C10 C11 C12 -66.6(3) . . . . ?
C10 C11 C14 C15 -177.5(2) . . . . ?
C13 C11 C14 C15 -57.3(3) . . . . ?
C12 C11 C14 C15 66.1(3) . . . . ?
C10 C11 C14 C19 2.1(2) . . . . ?
C13 C11 C14 C19 122.25(19) . . . . ?
C12 C11 C14 C19 -114.32(19) . . . . ?
C19 C14 C15 C16 0.3(3) . . . . ?
C11 C14 C15 C16 179.8(2) . . . . ?
C14 C15 C16 C17 -0.3(3) . . . . ?
C15 C16 C17 C18 0.2(4) . . . . ?
C16 C17 C18 C19 -0.1(4) . . . . ?
C17 C18 C19 C14 0.1(3) . . . . ?
C17 C18 C19 N20 -179.0(2) . . . . ?
C15 C14 C19 C18 -0.1(3) . . . . ?
C11 C14 C19 C18 -179.8(2) . . . . ?
C15 C14 C19 N20 179.08(18) . . . . ?
C11 C14 C19 N20 -0.6(2) . . . . ?
C9 C10 N20 C19 -177.67(18) . . . . ?
C11 C10 N20 C19 2.9(2) . . . . ?
C9 C10 N20 C21 2.4(3) . . . . ?
C11 C10 N20 C21 -177.03(19) . . . . ?
C18 C19 N20 C10 177.7(2) . . . . ?
C14 C19 N20 C10 -1.5(2) . . . . ?
C18 C19 N20 C21 -2.4(3) . . . . ?
C14 C19 N20 C21 178.44(19) . . . . ?
C4 C5 C22 C23 -179.9(2) . . . . ?
C6 C5 C22 C23 -0.1(3) . . . . ?
C5 C22 C23 C24 -0.4(3) . . . . ?
C22 C23 C24 C25 0.7(3) . . . . ?
C23 C24 C25 C6 -0.5(3) . . . . ?
C5 C6 C25 C24 0.0(3) . . . . ?
C7 C6 C25 C24 -180.0(2) . . . . ?

_refine_diff_density_max         0.270
_refine_diff_density_min         -0.207
_refine_diff_density_rms         0.041


_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: Acetone'
####################################################################### 
# 
# 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_V532_132_100K
_database_code_depnum_ccdc_archive 'CCDC 1824249'
_audit_update_record             
;
2018-02-15 deposited with the CCDC.
2018-04-06 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C19 H20 N O, Br'
_chemical_formula_sum            'C19 H20 Br N O'
_chemical_formula_weight         358.27

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0030 0.0020 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0060 0.0030 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0110 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.4010 2.4850 '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 21/n'
_space_group_name_Hall           '-P 2yn'

_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.
;

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                   8.3080(4)
_cell_length_b                   13.9039(8)
_cell_length_c                   13.6580(6)
_cell_angle_alpha                90
_cell_angle_beta                 96.642(4)
_cell_angle_gamma                90
_cell_volume                     1567.10(14)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    3293
_cell_measurement_theta_min      2.0870
_cell_measurement_theta_max      31.7590

_exptl_crystal_description       needle
_exptl_crystal_colour            orange
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.519
_exptl_crystal_F_000             736
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.01
_exptl_crystal_size_min          0.01
_exptl_absorpt_coefficient_mu    2.625
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_T_min  0.65581
_exptl_absorpt_correction_T_max  1.00000
_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_absorpt_special_details   ?






_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.7149
_diffrn_radiation_type           synchrotron
_diffrn_radiation_source         synchrotron
_diffrn_radiation_monochromator  Si(111)
_diffrn_measurement_device_type  'pilatus 2M'
_diffrn_measurement_method       
;
'359 images, ΔΦ 1.0° '
'359 images, ΔΦ 1.0° (2nd orientation)'
;
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            19811
_diffrn_reflns_av_unetI/netI     0.0673
_diffrn_reflns_av_R_equivalents  0.0971
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         2.110
_diffrn_reflns_theta_max         28.055
_diffrn_reflns_theta_full        25.400
_diffrn_measured_fraction_theta_max 0.980
_diffrn_measured_fraction_theta_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.980
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.980
_diffrn_reflns_point_group_measured_fraction_full 0.994
_reflns_number_total             3653
_reflns_number_gt                2828
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_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.
;

_computing_data_collection       'SNBL Pilatus control'
_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_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_structure_solution    'SHELXT (Sheldrick, 2015)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'MERCURY (Macrae et al., 2008)'
_computing_publication_material  
;

'MERCURY (Macrae et al., 2008), Platon (Spek, 2009)'



;


_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0727P)²+1.5061P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3653
_refine_ls_number_parameters     202
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0721
_refine_ls_R_factor_gt           0.0531
_refine_ls_wR_factor_ref         0.1393
_refine_ls_wR_factor_gt          0.1300
_refine_ls_goodness_of_fit_ref   1.042
_refine_ls_restrained_S_all      1.042
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 1.0682(3) 0.3790(2) 0.4137(2) 0.0289(6) Uani 1 1 d . . . . .
H1 H 1.1345 0.3963 0.3751 0.043 Uiso 1 1 calc R U . . .
C2 C 1.1240(5) 0.4039(3) 0.5055(3) 0.0236(8) Uani 1 1 d . . . . .
C3 C 1.2684(5) 0.4529(3) 0.5276(3) 0.0257(8) Uani 1 1 d . . . . .
H3 H 1.3316 0.4699 0.4765 0.031 Uiso 1 1 calc R U . . .
C4 C 1.3199(5) 0.4768(3) 0.6235(3) 0.0282(9) Uani 1 1 d . . . . .
H4 H 1.4209 0.5086 0.6386 0.034 Uiso 1 1 calc R U . . .
C5 C 1.2284(5) 0.4557(3) 0.6978(3) 0.0287(8) Uani 1 1 d . . . . .
H5 H 1.2651 0.4734 0.7638 0.034 Uiso 1 1 calc R U . . .
C6 C 1.0838(5) 0.4088(3) 0.6765(3) 0.0263(8) Uani 1 1 d . . . . .
H6 H 1.0193 0.3952 0.7278 0.032 Uiso 1 1 calc R U . . .
C7 C 1.0300(5) 0.3809(3) 0.5803(3) 0.0212(7) Uani 1 1 d . . . . .
C8 C 0.8814(5) 0.3287(3) 0.5551(3) 0.0221(7) Uani 1 1 d . . . . .
H8 H 0.8622 0.3027 0.4905 0.026 Uiso 1 1 calc R U . . .
C9 C 0.7680(5) 0.3141(3) 0.6158(3) 0.0235(8) Uani 1 1 d . . . . .
H9 H 0.7869 0.3397 0.6806 0.028 Uiso 1 1 calc R U . . .
C10 C 0.6228(5) 0.2632(3) 0.5899(3) 0.0217(7) Uani 1 1 d . . . . .
C11 C 0.5648(5) 0.2113(3) 0.4945(3) 0.0216(7) Uani 1 1 d . . . . .
C12 C 0.6771(5) 0.1289(3) 0.4756(3) 0.0258(8) Uani 1 1 d . . . . .
H12A H 0.7046 0.0924 0.5366 0.039 Uiso 1 1 calc R U . . .
H12B H 0.7763 0.1546 0.4531 0.039 Uiso 1 1 calc R U . . .
H12C H 0.6228 0.0864 0.4248 0.039 Uiso 1 1 calc R U . . .
C13 C 0.5419(5) 0.2810(3) 0.4067(3) 0.0255(8) Uani 1 1 d . . . . .
H13A H 0.4913 0.2469 0.3483 0.038 Uiso 1 1 calc R U . . .
H13B H 0.6475 0.3061 0.3937 0.038 Uiso 1 1 calc R U . . .
H13C H 0.4721 0.3344 0.4221 0.038 Uiso 1 1 calc R U . . .
C14 C 0.4039(4) 0.1753(3) 0.5168(3) 0.0212(7) Uani 1 1 d . . . . .
C15 C 0.2882(5) 0.1243(3) 0.4603(3) 0.0254(8) Uani 1 1 d . . . . .
H15 H 0.3039 0.1048 0.3954 0.030 Uiso 1 1 calc R U . . .
C16 C 0.1468(5) 0.1013(3) 0.4997(3) 0.0288(8) Uani 1 1 d . . . . .
H16 H 0.0637 0.0671 0.4607 0.035 Uiso 1 1 calc R U . . .
C17 C 0.1248(5) 0.1273(3) 0.5947(3) 0.0268(8) Uani 1 1 d . . . . .
H17 H 0.0272 0.1102 0.6205 0.032 Uiso 1 1 calc R U . . .
C18 C 0.2424(5) 0.1778(3) 0.6528(3) 0.0251(8) Uani 1 1 d . . . . .
H18 H 0.2290 0.1955 0.7185 0.030 Uiso 1 1 calc R U . . .
C19 C 0.3792(5) 0.2011(3) 0.6114(3) 0.0219(8) Uani 1 1 d . . . . .
N20 N 0.5155(4) 0.2542(2) 0.6521(2) 0.0207(6) Uani 1 1 d . . . . .
C21 C 0.5352(5) 0.2899(3) 0.7528(3) 0.0272(8) Uani 1 1 d . . . . .
H21A H 0.6253 0.2561 0.7908 0.041 Uiso 1 1 calc R U . . .
H21B H 0.4353 0.2786 0.7828 0.041 Uiso 1 1 calc R U . . .
H21C H 0.5583 0.3590 0.7525 0.041 Uiso 1 1 calc R U . . .
Br31 Br 0.26951(5) 0.44959(3) 0.24537(3) 0.02464(14) Uani 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C2 1.332(5) . ?
O1 H1 0.8400 . ?
C2 C3 1.381(6) . ?
C2 C7 1.394(5) . ?
C3 C4 1.372(6) . ?
C3 H3 0.9500 . ?
C4 C5 1.368(6) . ?
C4 H4 0.9500 . ?
C5 C6 1.368(6) . ?
C5 H5 0.9500 . ?
C6 C7 1.392(5) . ?
C6 H6 0.9500 . ?
C7 C8 1.439(5) . ?
C8 C9 1.340(5) . ?
C8 H8 0.9500 . ?
C9 C10 1.408(5) . ?
C9 H9 0.9500 . ?
C10 N20 1.307(5) . ?
C10 C11 1.518(5) . ?
C11 C14 1.492(5) . ?
C11 C12 1.519(5) . ?
C11 C13 1.536(5) . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12C 0.9800 . ?
C13 H13A 0.9800 . ?
C13 H13B 0.9800 . ?
C13 H13C 0.9800 . ?
C14 C15 1.361(6) . ?
C14 C19 1.380(5) . ?
C15 C16 1.384(6) . ?
C15 H15 0.9500 . ?
C16 C17 1.380(6) . ?
C16 H16 0.9500 . ?
C17 C18 1.377(6) . ?
C17 H17 0.9500 . ?
C18 C19 1.366(5) . ?
C18 H18 0.9500 . ?
C19 N20 1.411(5) . ?
N20 C21 1.452(5) . ?
C21 H21A 0.9800 . ?
C21 H21B 0.9800 . ?
C21 H21C 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
C2 O1 H1 109.5 . . ?
O1 C2 C3 122.2(3) . . ?
O1 C2 C7 117.9(3) . . ?
C3 C2 C7 119.9(4) . . ?
C4 C3 C2 119.7(4) . . ?
C4 C3 H3 120.2 . . ?
C2 C3 H3 120.2 . . ?
C5 C4 C3 121.2(4) . . ?
C5 C4 H4 119.4 . . ?
C3 C4 H4 119.4 . . ?
C6 C5 C4 119.6(4) . . ?
C6 C5 H5 120.2 . . ?
C4 C5 H5 120.2 . . ?
C5 C6 C7 120.8(4) . . ?
C5 C6 H6 119.6 . . ?
C7 C6 H6 119.6 . . ?
C6 C7 C2 118.8(4) . . ?
C6 C7 C8 122.6(3) . . ?
C2 C7 C8 118.6(3) . . ?
C9 C8 C7 125.0(4) . . ?
C9 C8 H8 117.5 . . ?
C7 C8 H8 117.5 . . ?
C8 C9 C10 124.3(4) . . ?
C8 C9 H9 117.8 . . ?
C10 C9 H9 117.8 . . ?
N20 C10 C9 120.9(3) . . ?
N20 C10 C11 109.9(3) . . ?
C9 C10 C11 129.2(3) . . ?
C14 C11 C10 100.8(3) . . ?
C14 C11 C12 111.3(3) . . ?
C10 C11 C12 111.4(3) . . ?
C14 C11 C13 109.8(3) . . ?
C10 C11 C13 111.6(3) . . ?
C12 C11 C13 111.5(3) . . ?
C11 C12 H12A 109.5 . . ?
C11 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
C11 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C11 C13 H13A 109.5 . . ?
C11 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
C11 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
C15 C14 C19 119.6(3) . . ?
C15 C14 C11 130.6(4) . . ?
C19 C14 C11 109.8(3) . . ?
C14 C15 C16 118.4(4) . . ?
C14 C15 H15 120.8 . . ?
C16 C15 H15 120.8 . . ?
C17 C16 C15 121.0(4) . . ?
C17 C16 H16 119.5 . . ?
C15 C16 H16 119.5 . . ?
C18 C17 C16 120.9(4) . . ?
C18 C17 H17 119.6 . . ?
C16 C17 H17 119.6 . . ?
C19 C18 C17 116.9(4) . . ?
C19 C18 H18 121.6 . . ?
C17 C18 H18 121.6 . . ?
C18 C19 C14 123.2(4) . . ?
C18 C19 N20 129.0(4) . . ?
C14 C19 N20 107.8(3) . . ?
C10 N20 C19 111.7(3) . . ?
C10 N20 C21 124.9(3) . . ?
C19 N20 C21 123.3(3) . . ?
N20 C21 H21A 109.5 . . ?
N20 C21 H21B 109.5 . . ?
H21A C21 H21B 109.5 . . ?
N20 C21 H21C 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 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
O1 C2 C3 C4 179.9(4) . . . . ?
C7 C2 C3 C4 1.4(6) . . . . ?
C2 C3 C4 C5 -2.0(6) . . . . ?
C3 C4 C5 C6 0.8(6) . . . . ?
C4 C5 C6 C7 1.1(6) . . . . ?
C5 C6 C7 C2 -1.7(6) . . . . ?
C5 C6 C7 C8 177.9(4) . . . . ?
O1 C2 C7 C6 -178.1(3) . . . . ?
C3 C2 C7 C6 0.5(6) . . . . ?
O1 C2 C7 C8 2.3(5) . . . . ?
C3 C2 C7 C8 -179.2(3) . . . . ?
C6 C7 C8 C9 10.7(6) . . . . ?
C2 C7 C8 C9 -169.7(4) . . . . ?
C7 C8 C9 C10 179.7(4) . . . . ?
C8 C9 C10 N20 -178.0(4) . . . . ?
C8 C9 C10 C11 3.0(7) . . . . ?
N20 C10 C11 C14 1.6(4) . . . . ?
C9 C10 C11 C14 -179.4(4) . . . . ?
N20 C10 C11 C12 -116.6(4) . . . . ?
C9 C10 C11 C12 62.5(5) . . . . ?
N20 C10 C11 C13 118.0(4) . . . . ?
C9 C10 C11 C13 -62.9(5) . . . . ?
C10 C11 C14 C15 178.6(4) . . . . ?
C12 C11 C14 C15 -63.2(5) . . . . ?
C13 C11 C14 C15 60.7(5) . . . . ?
C10 C11 C14 C19 -1.5(4) . . . . ?
C12 C11 C14 C19 116.7(4) . . . . ?
C13 C11 C14 C19 -119.4(3) . . . . ?
C19 C14 C15 C16 1.1(6) . . . . ?
C11 C14 C15 C16 -179.0(4) . . . . ?
C14 C15 C16 C17 -1.5(6) . . . . ?
C15 C16 C17 C18 0.6(6) . . . . ?
C16 C17 C18 C19 0.7(6) . . . . ?
C17 C18 C19 C14 -1.1(6) . . . . ?
C17 C18 C19 N20 178.0(4) . . . . ?
C15 C14 C19 C18 0.1(6) . . . . ?
C11 C14 C19 C18 -179.8(4) . . . . ?
C15 C14 C19 N20 -179.1(3) . . . . ?
C11 C14 C19 N20 1.0(4) . . . . ?
C9 C10 N20 C19 179.8(3) . . . . ?
C11 C10 N20 C19 -1.1(4) . . . . ?
C9 C10 N20 C21 -2.9(6) . . . . ?
C11 C10 N20 C21 176.2(3) . . . . ?
C18 C19 N20 C10 -179.1(4) . . . . ?
C14 C19 N20 C10 0.1(4) . . . . ?
C18 C19 N20 C21 3.5(6) . . . . ?
C14 C19 N20 C21 -177.3(3) . . . . ?

_refine_diff_density_max         1.525
_refine_diff_density_min         -0.726
_refine_diff_density_rms         0.121


_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: Acetone'
####################################################################### 
# 
# 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_vs32-1d6d2
_database_code_depnum_ccdc_archive 'CCDC 1824259'
_audit_update_record             
;
2018-02-15 deposited with the CCDC.
2018-04-06 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C19 H20 N O, N O3'
_chemical_formula_sum            'C19 H20 N2 O4'
_chemical_formula_weight         340.37

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           33
_space_group_name_H-M_alt        'P n a 21'
_space_group_name_Hall           'P 2c -2n'

_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.
;

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

_cell_length_a                   10.4953(9)
_cell_length_b                   19.9612(19)
_cell_length_c                   8.1903(7)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1715.9(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    2703
_cell_measurement_theta_min      3.3040
_cell_measurement_theta_max      24.7040

_exptl_crystal_description       rod
_exptl_crystal_colour            orange
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.318
_exptl_crystal_F_000             720
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.07
_exptl_crystal_size_min          0.05
_exptl_absorpt_coefficient_mu    0.093
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_T_min  0.85405
_exptl_absorpt_correction_T_max  1.00000
_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_absorpt_special_details   ?



_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'Rigaku UltraX 18 rotating anode'
_diffrn_radiation_monochromator  'Xenocs Fox3D mirror'
_diffrn_measurement_device_type  'MAR345 image plate'
_diffrn_measurement_method       '113 images, ΔΦ 2.0° '
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            8028
_diffrn_reflns_av_unetI/netI     0.0826
_diffrn_reflns_av_R_equivalents  0.0980
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_theta_min         3.316
_diffrn_reflns_theta_max         25.257
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.980
_diffrn_measured_fraction_theta_full 0.981
_diffrn_reflns_Laue_measured_fraction_max 0.980
_diffrn_reflns_Laue_measured_fraction_full 0.981
_diffrn_reflns_point_group_measured_fraction_max 0.862
_diffrn_reflns_point_group_measured_fraction_full 0.864
_reflns_number_total             2671
_reflns_number_gt                1703
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.636
_reflns_Friedel_fraction_max     0.725
_reflns_Friedel_fraction_full    0.727

_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.
;

_computing_data_collection       MAR
_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_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_structure_solution    'SHELXT (Sheldrick, 2015)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'MERCURY (Macrae et al., 2008)'
_computing_publication_material  
;

'MERCURY (Macrae et al., 2008), Platon (Spek, 2009)'



;







_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0328P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Flack x determined using 474 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -1.9(10)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         2671
_refine_ls_number_parameters     304
_refine_ls_number_restraints     152
_refine_ls_R_factor_all          0.1027
_refine_ls_R_factor_gt           0.0564
_refine_ls_wR_factor_ref         0.1144
_refine_ls_wR_factor_gt          0.0973
_refine_ls_goodness_of_fit_ref   1.036
_refine_ls_restrained_S_all      1.027
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.7575(3) 0.49131(17) -0.1327(5) 0.0635(11) Uani 1 1 d . . . . .
H1 H 0.7518 0.4633 -0.2056 0.095 Uiso 1 1 calc R U . . .
C2 C 0.8575(5) 0.5328(3) -0.1642(7) 0.0465(14) Uani 1 1 d . . . . .
C3 C 0.9324(5) 0.5250(3) -0.3022(8) 0.0602(17) Uani 1 1 d . . . . .
H3 H 0.9144 0.4911 -0.3764 0.072 Uiso 1 1 calc R U . . .
C4 C 1.0318(5) 0.5668(3) -0.3288(9) 0.0675(17) Uani 1 1 d . . . . .
H4 H 1.0825 0.5606 -0.4206 0.081 Uiso 1 1 calc R U . . .
C5 C 1.0591(6) 0.6181(3) -0.2236(9) 0.0685(17) Uani 1 1 d . . . . .
H5 H 1.1272 0.6467 -0.2442 0.082 Uiso 1 1 calc R U . . .
C6 C 0.9853(5) 0.6268(3) -0.0882(8) 0.0565(15) Uani 1 1 d . . . . .
H6 H 1.0037 0.6616 -0.0167 0.068 Uiso 1 1 calc R U . . .
C7 C 0.8823(4) 0.5844(2) -0.0544(7) 0.0447(13) Uani 1 1 d . . . . .
C8 C 0.8062(5) 0.5905(3) 0.0906(7) 0.0476(14) Uani 1 1 d . . . . .
H8 H 0.7328 0.5646 0.0952 0.057 Uiso 1 1 calc R U . . .
C9 C 0.8300(4) 0.6299(3) 0.2206(7) 0.0471(14) Uani 1 1 d . . . . .
H9 H 0.9035 0.6559 0.2181 0.057 Uiso 1 1 calc R U . . .
C10 C 0.7525(5) 0.6348(2) 0.3597(7) 0.0428(12) Uani 1 1 d . . . . .
C11 C 0.6278(4) 0.5988(2) 0.3942(7) 0.0442(13) Uani 1 1 d . . . . .
C12 C 0.6455(6) 0.5231(2) 0.4078(8) 0.0680(18) Uani 1 1 d . . . . .
H12A H 0.6776 0.5059 0.3064 0.102 Uiso 1 1 calc R U . . .
H12B H 0.5651 0.5024 0.4320 0.102 Uiso 1 1 calc R U . . .
H12C H 0.7050 0.5133 0.4937 0.102 Uiso 1 1 calc R U . . .
C13 C 0.5252(5) 0.6160(3) 0.2674(8) 0.0634(17) Uani 1 1 d . . . . .
H13A H 0.5203 0.6638 0.2547 0.095 Uiso 1 1 calc R U . . .
H13B H 0.4443 0.5992 0.3035 0.095 Uiso 1 1 calc R U . . .
H13C H 0.5469 0.5959 0.1647 0.095 Uiso 1 1 calc R U . . .
C14 C 0.5925(6) 0.6273(2) 0.5590(7) 0.0489(14) Uani 1 1 d . . . . .
C15 C 0.4892(6) 0.6165(3) 0.6584(8) 0.0664(17) Uani 1 1 d . . . . .
H15 H 0.4245 0.5875 0.6265 0.080 Uiso 1 1 calc R U . . .
C16 C 0.4831(7) 0.6492(3) 0.8060(8) 0.0733(19) Uani 1 1 d . . . . .
H16 H 0.4135 0.6423 0.8743 0.088 Uiso 1 1 calc R U . . .
C17 C 0.5799(7) 0.6924(3) 0.8540(8) 0.0707(18) Uani 1 1 d . . . . .
H17 H 0.5751 0.7132 0.9553 0.085 Uiso 1 1 calc R U . . .
C18 C 0.6820(6) 0.7048(3) 0.7552(8) 0.0598(16) Uani 1 1 d . . . . .
H18 H 0.7460 0.7344 0.7858 0.072 Uiso 1 1 calc R U . . .
C19 C 0.6862(5) 0.6714(3) 0.6081(7) 0.0494(14) Uani 1 1 d . . . . .
N20 N 0.7801(4) 0.67459(19) 0.4828(6) 0.0447(10) Uani 1 1 d . . . . .
C21 C 0.8880(4) 0.7205(3) 0.4943(9) 0.0677(18) Uani 1 1 d . . . . .
H21A H 0.9595 0.7021 0.4364 0.102 Uiso 1 1 calc R U . . .
H21B H 0.9104 0.7268 0.6069 0.102 Uiso 1 1 calc R U . . .
H21C H 0.8652 0.7629 0.4470 0.102 Uiso 1 1 calc R U . . .
N51 N 0.785(2) 0.3346(7) 0.694(2) 0.058(5) Uani 0.47(2) 1 d D U P A 1
O52 O 0.752(2) 0.3895(8) 0.640(2) 0.068(5) Uani 0.47(2) 1 d D U P A 1
O53 O 0.837(3) 0.3304(13) 0.829(3) 0.143(10) Uani 0.47(2) 1 d D U P A 1
O54 O 0.754(3) 0.2829(7) 0.620(2) 0.125(8) Uani 0.47(2) 1 d D U P A 1
N51B N 0.808(4) 0.3333(11) 0.760(3) 0.062(8) Uani 0.31(2) 1 d D U P B 2
O52B O 0.782(5) 0.3816(14) 0.672(4) 0.090(12) Uani 0.31(2) 1 d D U P B 2
O53B O 0.799(3) 0.3384(14) 0.910(3) 0.093(8) Uani 0.31(2) 1 d D U P B 2
O54B O 0.833(4) 0.2781(13) 0.699(4) 0.087(11) Uani 0.31(2) 1 d D U P B 2
N51C N 0.805(5) 0.3214(18) 0.721(5) 0.059(10) Uani 0.220(16) 1 d D U P C 3
O52C O 0.873(4) 0.2714(14) 0.723(4) 0.064(8) Uani 0.220(16) 1 d D U P C 3
O53C O 0.739(3) 0.335(2) 0.599(3) 0.110(12) Uani 0.220(16) 1 d D U P C 3
O54C O 0.823(4) 0.3659(13) 0.824(4) 0.086(11) Uani 0.220(16) 1 d D U P C 3


_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 C2 1.362(6) . ?
O1 H1 0.8200 . ?
C2 C3 1.385(7) . ?
C2 C7 1.392(6) . ?
C3 C4 1.353(7) . ?
C3 H3 0.9300 . ?
C4 C5 1.369(8) . ?
C4 H4 0.9300 . ?
C5 C6 1.364(8) . ?
C5 H5 0.9300 . ?
C6 C7 1.400(6) . ?
C6 H6 0.9300 . ?
C7 C8 1.436(7) . ?
C8 C9 1.347(6) . ?
C8 H8 0.9300 . ?
C9 C10 1.403(7) . ?
C9 H9 0.9300 . ?
C10 N20 1.315(6) . ?
C10 C11 1.520(7) . ?
C11 C14 1.511(7) . ?
C11 C12 1.528(6) . ?
C11 C13 1.535(7) . ?
C12 H12A 0.9600 . ?
C12 H12B 0.9600 . ?
C12 H12C 0.9600 . ?
C13 H13A 0.9600 . ?
C13 H13B 0.9600 . ?
C13 H13C 0.9600 . ?
C14 C15 1.372(8) . ?
C14 C19 1.379(7) . ?
C15 C16 1.375(8) . ?
C15 H15 0.9300 . ?
C16 C17 1.390(8) . ?
C16 H16 0.9300 . ?
C17 C18 1.366(8) . ?
C17 H17 0.9300 . ?
C18 C19 1.377(7) . ?
C18 H18 0.9300 . ?
C19 N20 1.424(6) . ?
N20 C21 1.460(6) . ?
C21 H21A 0.9600 . ?
C21 H21B 0.9600 . ?
C21 H21C 0.9600 . ?
N51 O52 1.232(12) . ?
N51 O53 1.235(13) . ?
N51 O54 1.239(12) . ?
N51B O52B 1.232(13) . ?
N51B O53B 1.233(14) . ?
N51B O54B 1.239(13) . ?
N51C O52C 1.230(15) . ?
N51C O53C 1.235(16) . ?
N51C O54C 1.242(16) . ?

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
C2 O1 H1 109.5 . . ?
O1 C2 C3 121.6(5) . . ?
O1 C2 C7 118.1(5) . . ?
C3 C2 C7 120.3(5) . . ?
C4 C3 C2 120.0(6) . . ?
C4 C3 H3 120.0 . . ?
C2 C3 H3 120.0 . . ?
C3 C4 C5 121.4(6) . . ?
C3 C4 H4 119.3 . . ?
C5 C4 H4 119.3 . . ?
C6 C5 C4 119.2(6) . . ?
C6 C5 H5 120.4 . . ?
C4 C5 H5 120.4 . . ?
C5 C6 C7 121.6(6) . . ?
C5 C6 H6 119.2 . . ?
C7 C6 H6 119.2 . . ?
C2 C7 C6 117.6(5) . . ?
C2 C7 C8 119.6(5) . . ?
C6 C7 C8 122.8(5) . . ?
C9 C8 C7 126.9(5) . . ?
C9 C8 H8 116.5 . . ?
C7 C8 H8 116.5 . . ?
C8 C9 C10 125.1(5) . . ?
C8 C9 H9 117.4 . . ?
C10 C9 H9 117.4 . . ?
N20 C10 C9 122.4(5) . . ?
N20 C10 C11 109.4(5) . . ?
C9 C10 C11 128.1(5) . . ?
C14 C11 C10 101.5(4) . . ?
C14 C11 C12 109.7(4) . . ?
C10 C11 C12 112.1(4) . . ?
C14 C11 C13 110.4(4) . . ?
C10 C11 C13 111.8(4) . . ?
C12 C11 C13 110.9(4) . . ?
C11 C12 H12A 109.5 . . ?
C11 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
C11 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C11 C13 H13A 109.5 . . ?
C11 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
C11 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
C15 C14 C19 119.4(5) . . ?
C15 C14 C11 131.6(5) . . ?
C19 C14 C11 109.0(5) . . ?
C14 C15 C16 118.9(6) . . ?
C14 C15 H15 120.6 . . ?
C16 C15 H15 120.6 . . ?
C15 C16 C17 120.6(6) . . ?
C15 C16 H16 119.7 . . ?
C17 C16 H16 119.7 . . ?
C18 C17 C16 121.2(6) . . ?
C18 C17 H17 119.4 . . ?
C16 C17 H17 119.4 . . ?
C17 C18 C19 117.1(6) . . ?
C17 C18 H18 121.4 . . ?
C19 C18 H18 121.4 . . ?
C18 C19 C14 122.7(6) . . ?
C18 C19 N20 129.1(5) . . ?
C14 C19 N20 108.2(5) . . ?
C10 N20 C19 111.9(4) . . ?
C10 N20 C21 126.8(5) . . ?
C19 N20 C21 121.2(4) . . ?
N20 C21 H21A 109.5 . . ?
N20 C21 H21B 109.5 . . ?
H21A C21 H21B 109.5 . . ?
N20 C21 H21C 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
O52 N51 O53 120.6(15) . . ?
O52 N51 O54 119.3(14) . . ?
O53 N51 O54 119.7(15) . . ?
O52B N51B O53B 120.0(16) . . ?
O52B N51B O54B 120.5(17) . . ?
O53B N51B O54B 119.4(16) . . ?
O52C N51C O53C 120.7(19) . . ?
O52C N51C O54C 118.6(19) . . ?
O53C N51C O54C 119(2) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O1 C2 C3 C4 -179.4(5) . . . . ?
C7 C2 C3 C4 1.3(8) . . . . ?
C2 C3 C4 C5 -1.4(9) . . . . ?
C3 C4 C5 C6 0.6(10) . . . . ?
C4 C5 C6 C7 0.1(9) . . . . ?
O1 C2 C7 C6 -179.9(4) . . . . ?
C3 C2 C7 C6 -0.6(7) . . . . ?
O1 C2 C7 C8 2.6(7) . . . . ?
C3 C2 C7 C8 -178.1(5) . . . . ?
C5 C6 C7 C2 -0.1(7) . . . . ?
C5 C6 C7 C8 177.3(5) . . . . ?
C2 C7 C8 C9 168.3(5) . . . . ?
C6 C7 C8 C9 -9.0(8) . . . . ?
C7 C8 C9 C10 179.5(5) . . . . ?
C8 C9 C10 N20 -179.6(5) . . . . ?
C8 C9 C10 C11 -0.6(8) . . . . ?
N20 C10 C11 C14 0.6(5) . . . . ?
C9 C10 C11 C14 -178.4(5) . . . . ?
N20 C10 C11 C12 -116.4(5) . . . . ?
C9 C10 C11 C12 64.5(7) . . . . ?
N20 C10 C11 C13 118.3(5) . . . . ?
C9 C10 C11 C13 -60.8(7) . . . . ?
C10 C11 C14 C15 178.9(6) . . . . ?
C12 C11 C14 C15 -62.3(7) . . . . ?
C13 C11 C14 C15 60.2(7) . . . . ?
C10 C11 C14 C19 -1.1(5) . . . . ?
C12 C11 C14 C19 117.7(5) . . . . ?
C13 C11 C14 C19 -119.8(5) . . . . ?
C19 C14 C15 C16 -1.0(8) . . . . ?
C11 C14 C15 C16 178.9(5) . . . . ?
C14 C15 C16 C17 -0.1(9) . . . . ?
C15 C16 C17 C18 1.5(9) . . . . ?
C16 C17 C18 C19 -1.5(9) . . . . ?
C17 C18 C19 C14 0.3(8) . . . . ?
C17 C18 C19 N20 -180.0(5) . . . . ?
C15 C14 C19 C18 1.0(8) . . . . ?
C11 C14 C19 C18 -179.0(5) . . . . ?
C15 C14 C19 N20 -178.8(5) . . . . ?
C11 C14 C19 N20 1.2(6) . . . . ?
C9 C10 N20 C19 179.2(4) . . . . ?
C11 C10 N20 C19 0.1(6) . . . . ?
C9 C10 N20 C21 2.6(8) . . . . ?
C11 C10 N20 C21 -176.5(5) . . . . ?
C18 C19 N20 C10 179.4(5) . . . . ?
C14 C19 N20 C10 -0.9(6) . . . . ?
C18 C19 N20 C21 -3.8(8) . . . . ?
C14 C19 N20 C21 176.0(5) . . . . ?

_refine_diff_density_max         0.120
_refine_diff_density_min         -0.118
_refine_diff_density_rms         0.030


_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: Ethanol'
####################################################################### 
# 
# 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_VS-KC-SPOMe-HCl
_database_code_depnum_ccdc_archive 'CCDC 1824258'
_audit_update_record             
;
2018-02-15 deposited with the CCDC.
2018-04-06 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2016/4
_shelx_SHELXL_version_number     2016/4
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C20 H22 N O2 1+, Cl 1-, 2(H2 O)'
_chemical_formula_sum            'C20 H26 Cl N O4'
_chemical_formula_weight         379.87

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 '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 21/c'
_space_group_name_Hall           '-P 2ybc'

_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.
;

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

_cell_length_a                   11.5183(3)
_cell_length_b                   24.4350(7)
_cell_length_c                   7.1002(2)
_cell_angle_alpha                90
_cell_angle_beta                 98.786(3)
_cell_angle_gamma                90
_cell_volume                     1974.90(11)
_cell_formula_units_Z            4
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    8842
_cell_measurement_theta_min      3.0560
_cell_measurement_theta_max      26.0810

_exptl_crystal_description       bar
_exptl_crystal_colour            orange
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.278
_exptl_crystal_F_000             808

_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.10
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.06
_exptl_absorpt_coefficient_mu    0.217
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.55866
_exptl_absorpt_correction_T_max  1.00000

_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_absorpt_special_details   ?
_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'Rigaku UltraX 18 rotating anode'
_diffrn_radiation_monochromator  'Xenocs Fox3D mirror'
_diffrn_measurement_device_type  'MAR345 image plate'
_diffrn_measurement_method       '150 images, ΔΦ 1.2° '
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            18299
_diffrn_reflns_av_unetI/netI     0.0508
_diffrn_reflns_av_R_equivalents  0.0871
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -30
_diffrn_reflns_limit_k_max       30
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_theta_min         3.075
_diffrn_reflns_theta_max         26.162
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             3922
_reflns_number_gt                3270
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_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.
;

_computing_data_collection       MAR
_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_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_structure_solution    'SHELXT (Sheldrick, 2015)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'MERCURY (Macrae et al., 2008)'
_computing_publication_material  
;

'MERCURY (Macrae et al., 2008), Platon (Spek, 2009)'



;

_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0610P)²+0.8630P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3922
_refine_ls_number_parameters     247
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0578
_refine_ls_R_factor_gt           0.0480
_refine_ls_wR_factor_ref         0.1257
_refine_ls_wR_factor_gt          0.1197
_refine_ls_goodness_of_fit_ref   1.034
_refine_ls_restrained_S_all      1.034
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O -0.04805(12) 0.37387(6) -0.2596(2) 0.0307(3) Uani 1 1 d . . . . .
H1 H -0.112(2) 0.3595(5) -0.3024(15) 0.046 Uiso 1 1 calc R U . . .
C2 C 0.03979(15) 0.34648(7) -0.3237(3) 0.0220(4) Uani 1 1 d . . . . .
C3 C 0.02216(16) 0.31827(7) -0.4990(3) 0.0233(4) Uani 1 1 d . . . . .
C4 C 0.11381(16) 0.28993(8) -0.5582(3) 0.0252(4) Uani 1 1 d . . . . .
H4 H 0.101676 0.270615 -0.672343 0.030 Uiso 1 1 calc R U . . .
C5 C 0.22518(16) 0.29022(8) -0.4462(3) 0.0268(4) Uani 1 1 d . . . . .
H5 H 0.286136 0.270480 -0.485726 0.032 Uiso 1 1 calc R U . . .
C6 C 0.24541(16) 0.31933(8) -0.2787(3) 0.0239(4) Uani 1 1 d . . . . .
H6 H 0.320322 0.320166 -0.207918 0.029 Uiso 1 1 calc R U . . .
C7 C 0.15252(15) 0.34799(7) -0.2138(3) 0.0219(4) Uani 1 1 d . . . . .
C8 C 0.16758(16) 0.38025(7) -0.0408(3) 0.0232(4) Uani 1 1 d . . . . .
H8 H 0.104861 0.402617 -0.022862 0.028 Uiso 1 1 calc R U . . .
C9 C 0.26208(16) 0.38168(8) 0.0977(3) 0.0236(4) Uani 1 1 d . . . . .
H9 H 0.324438 0.358081 0.089360 0.028 Uiso 1 1 calc R U . . .
C10 C 0.26966(15) 0.41815(7) 0.2564(3) 0.0214(4) Uani 1 1 d . . . . .
C11 C 0.19122(15) 0.46742(7) 0.2807(3) 0.0205(4) Uani 1 1 d . . . . .
C12 C 0.06497(15) 0.45126(8) 0.3069(3) 0.0274(4) Uani 1 1 d . . . . .
H12A H 0.022983 0.483269 0.336653 0.041 Uiso 1 1 calc R U . . .
H12B H 0.068004 0.425300 0.408974 0.041 Uiso 1 1 calc R U . . .
H12C H 0.025499 0.435176 0.191196 0.041 Uiso 1 1 calc R U . . .
C13 C 0.19187(18) 0.50851(8) 0.1156(3) 0.0279(4) Uani 1 1 d . . . . .
H13A H 0.271427 0.518217 0.105406 0.042 Uiso 1 1 calc R U . . .
H13B H 0.149100 0.540786 0.140329 0.042 Uiso 1 1 calc R U . . .
H13C H 0.155476 0.492085 -0.001459 0.042 Uiso 1 1 calc R U . . .
C14 C 0.25391(15) 0.49192(7) 0.4634(3) 0.0206(4) Uani 1 1 d . . . . .
C15 C 0.23113(16) 0.53900(8) 0.5587(3) 0.0242(4) Uani 1 1 d . . . . .
H15 H 0.165612 0.560405 0.516126 0.029 Uiso 1 1 calc R U . . .
C16 C 0.30926(17) 0.55352(8) 0.7209(3) 0.0282(4) Uani 1 1 d . . . . .
H16 H 0.296292 0.585331 0.786471 0.034 Uiso 1 1 calc R U . . .
C17 C 0.40634(17) 0.52106(8) 0.7857(3) 0.0290(4) Uani 1 1 d . . . . .
H17 H 0.457461 0.531942 0.893446 0.035 Uiso 1 1 calc R U . . .
C18 C 0.42925(17) 0.47275(8) 0.6942(3) 0.0272(4) Uani 1 1 d . . . . .
H18 H 0.492897 0.450441 0.739119 0.033 Uiso 1 1 calc R U . . .
C19 C 0.35099(15) 0.46003(8) 0.5315(3) 0.0218(4) Uani 1 1 d . . . . .
N20 N 0.35613(12) 0.41565(6) 0.4031(2) 0.0211(3) Uani 1 1 d . . . . .
C21 C 0.44957(16) 0.37431(8) 0.4354(3) 0.0271(4) Uani 1 1 d . . . . .
H21A H 0.459886 0.362726 0.566045 0.041 Uiso 1 1 calc R U . . .
H21B H 0.521623 0.389766 0.407293 0.041 Uiso 1 1 calc R U . . .
H21C H 0.428293 0.343418 0.353843 0.041 Uiso 1 1 calc R U . . .
O22 O -0.08868(11) 0.32329(6) -0.5984(2) 0.0294(3) Uani 1 1 d . . . . .
C23 C -0.11197(19) 0.29784(10) -0.7826(3) 0.0365(5) Uani 1 1 d . . . . .
H23A H -0.104680 0.258861 -0.768537 0.055 Uiso 1 1 calc R U . . .
H23B H -0.056585 0.310843 -0.860543 0.055 Uiso 1 1 calc R U . . .
H23C H -0.190202 0.306799 -0.842005 0.055 Uiso 1 1 calc R U . . .
CL1 Cl 0.55520(4) 0.34106(2) -0.03835(7) 0.02941(16) Uani 1 1 d . . . . .
O1X O 0.73788(13) 0.34288(7) 0.6661(2) 0.0393(4) Uani 1 1 d G . . . .
H11X H 0.693790 0.342608 0.746548 0.059 Uiso 1 1 d G U . . .
H12X H 0.705526 0.323067 0.580666 0.053(9) Uiso 1 1 d G . . . .
O1Y O 0.62099(16) 0.28192(6) 0.3733(2) 0.0430(4) Uani 1 1 d G . . . .
H11Y H 0.603422 0.289467 0.259975 0.065 Uiso 1 1 d G U . . .
H12Y H 0.603030 0.249589 0.380439 0.065 Uiso 1 1 d G U . . .


_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 C2 1.349(2) . ?
O1 H1 0.83(3) . ?
C2 C7 1.409(3) . ?
C2 C3 1.411(3) . ?
C3 O22 1.367(2) . ?
C3 C4 1.380(3) . ?
C4 C5 1.402(3) . ?
C4 H4 0.9300 . ?
C5 C6 1.375(3) . ?
C5 H5 0.9300 . ?
C6 C7 1.413(3) . ?
C6 H6 0.9300 . ?
C7 C8 1.447(3) . ?
C8 C9 1.351(3) . ?
C8 H8 0.9300 . ?
C9 C10 1.429(3) . ?
C9 H9 0.9300 . ?
C10 N20 1.328(2) . ?
C10 C11 1.531(2) . ?
C11 C14 1.509(3) . ?
C11 C13 1.544(3) . ?
C11 C12 1.545(2) . ?
C12 H12A 0.9600 . ?
C12 H12B 0.9600 . ?
C12 H12C 0.9600 . ?
C13 H13A 0.9600 . ?
C13 H13B 0.9600 . ?
C13 H13C 0.9600 . ?
C14 C15 1.380(3) . ?
C14 C19 1.388(3) . ?
C15 C16 1.394(3) . ?
C15 H15 0.9300 . ?
C16 C17 1.391(3) . ?
C16 H16 0.9300 . ?
C17 C18 1.392(3) . ?
C17 H17 0.9300 . ?
C18 C19 1.387(3) . ?
C18 H18 0.9300 . ?
C19 N20 1.424(2) . ?
N20 C21 1.468(2) . ?
C21 H21A 0.9600 . ?
C21 H21B 0.9600 . ?
C21 H21C 0.9600 . ?
O22 C23 1.436(2) . ?
C23 H23A 0.9600 . ?
C23 H23B 0.9600 . ?
C23 H23C 0.9600 . ?
O1X H11X 0.8200 . ?
O1X H12X 0.8200 . ?
O1Y H11Y 0.8200 . ?
O1Y H12Y 0.8201 . ?

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
C2 O1 H1 109.5 . . ?
O1 C2 C7 118.39(17) . . ?
O1 C2 C3 121.74(16) . . ?
C7 C2 C3 119.84(16) . . ?
O22 C3 C4 125.84(18) . . ?
O22 C3 C2 114.15(16) . . ?
C4 C3 C2 120.00(17) . . ?
C3 C4 C5 120.05(18) . . ?
C3 C4 H4 120.0 . . ?
C5 C4 H4 120.0 . . ?
C6 C5 C4 120.85(17) . . ?
C6 C5 H5 119.6 . . ?
C4 C5 H5 119.6 . . ?
C5 C6 C7 120.10(17) . . ?
C5 C6 H6 120.0 . . ?
C7 C6 H6 120.0 . . ?
C2 C7 C6 119.08(17) . . ?
C2 C7 C8 117.69(16) . . ?
C6 C7 C8 123.21(17) . . ?
C9 C8 C7 127.62(17) . . ?
C9 C8 H8 116.2 . . ?
C7 C8 H8 116.2 . . ?
C8 C9 C10 122.38(16) . . ?
C8 C9 H9 118.8 . . ?
C10 C9 H9 118.8 . . ?
N20 C10 C9 122.54(16) . . ?
N20 C10 C11 109.44(15) . . ?
C9 C10 C11 127.83(16) . . ?
C14 C11 C10 101.28(14) . . ?
C14 C11 C13 109.73(15) . . ?
C10 C11 C13 110.76(15) . . ?
C14 C11 C12 109.49(15) . . ?
C10 C11 C12 113.27(15) . . ?
C13 C11 C12 111.78(15) . . ?
C11 C12 H12A 109.5 . . ?
C11 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
C11 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C11 C13 H13A 109.5 . . ?
C11 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
C11 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
C15 C14 C19 120.05(18) . . ?
C15 C14 C11 130.58(17) . . ?
C19 C14 C11 109.33(16) . . ?
C14 C15 C16 118.02(18) . . ?
C14 C15 H15 121.0 . . ?
C16 C15 H15 121.0 . . ?
C17 C16 C15 120.87(19) . . ?
C17 C16 H16 119.6 . . ?
C15 C16 H16 119.6 . . ?
C16 C17 C18 121.95(19) . . ?
C16 C17 H17 119.0 . . ?
C18 C17 H17 119.0 . . ?
C19 C18 C17 115.67(18) . . ?
C19 C18 H18 122.2 . . ?
C17 C18 H18 122.2 . . ?
C18 C19 C14 123.41(18) . . ?
C18 C19 N20 128.19(17) . . ?
C14 C19 N20 108.35(16) . . ?
C10 N20 C19 111.56(15) . . ?
C10 N20 C21 126.75(16) . . ?
C19 N20 C21 121.68(15) . . ?
N20 C21 H21A 109.5 . . ?
N20 C21 H21B 109.5 . . ?
H21A C21 H21B 109.5 . . ?
N20 C21 H21C 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
C3 O22 C23 117.47(15) . . ?
O22 C23 H23A 109.5 . . ?
O22 C23 H23B 109.5 . . ?
H23A C23 H23B 109.5 . . ?
O22 C23 H23C 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 109.5 . . ?
H11X O1X H12X 104.5 . . ?
H11Y O1Y H12Y 104.5 . . ?

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 C2 C3 O22 2.5(3) . . . . ?
C7 C2 C3 O22 -175.33(16) . . . . ?
O1 C2 C3 C4 -178.87(18) . . . . ?
C7 C2 C3 C4 3.3(3) . . . . ?
O22 C3 C4 C5 176.89(17) . . . . ?
C2 C3 C4 C5 -1.5(3) . . . . ?
C3 C4 C5 C6 -1.2(3) . . . . ?
C4 C5 C6 C7 2.1(3) . . . . ?
O1 C2 C7 C6 179.76(17) . . . . ?
C3 C2 C7 C6 -2.3(3) . . . . ?
O1 C2 C7 C8 -1.7(3) . . . . ?
C3 C2 C7 C8 176.29(16) . . . . ?
C5 C6 C7 C2 -0.4(3) . . . . ?
C5 C6 C7 C8 -178.88(18) . . . . ?
C2 C7 C8 C9 170.32(18) . . . . ?
C6 C7 C8 C9 -11.2(3) . . . . ?
C7 C8 C9 C10 175.66(17) . . . . ?
C8 C9 C10 N20 172.43(17) . . . . ?
C8 C9 C10 C11 -13.1(3) . . . . ?
N20 C10 C11 C14 1.90(18) . . . . ?
C9 C10 C11 C14 -173.20(17) . . . . ?
N20 C10 C11 C13 118.24(17) . . . . ?
C9 C10 C11 C13 -56.9(2) . . . . ?
N20 C10 C11 C12 -115.24(17) . . . . ?
C9 C10 C11 C12 69.7(2) . . . . ?
C10 C11 C14 C15 176.31(18) . . . . ?
C13 C11 C14 C15 59.2(2) . . . . ?
C12 C11 C14 C15 -63.8(2) . . . . ?
C10 C11 C14 C19 -1.16(18) . . . . ?
C13 C11 C14 C19 -118.26(17) . . . . ?
C12 C11 C14 C19 118.71(16) . . . . ?
C19 C14 C15 C16 1.2(3) . . . . ?
C11 C14 C15 C16 -176.04(17) . . . . ?
C14 C15 C16 C17 -0.8(3) . . . . ?
C15 C16 C17 C18 -0.7(3) . . . . ?
C16 C17 C18 C19 1.8(3) . . . . ?
C17 C18 C19 C14 -1.4(3) . . . . ?
C17 C18 C19 N20 175.70(17) . . . . ?
C15 C14 C19 C18 0.0(3) . . . . ?
C11 C14 C19 C18 177.74(17) . . . . ?
C15 C14 C19 N20 -177.66(15) . . . . ?
C11 C14 C19 N20 0.11(19) . . . . ?
C9 C10 N20 C19 173.42(16) . . . . ?
C11 C10 N20 C19 -1.98(19) . . . . ?
C9 C10 N20 C21 -5.2(3) . . . . ?
C11 C10 N20 C21 179.36(16) . . . . ?
C18 C19 N20 C10 -176.27(18) . . . . ?
C14 C19 N20 C10 1.2(2) . . . . ?
C18 C19 N20 C21 2.5(3) . . . . ?
C14 C19 N20 C21 179.94(15) . . . . ?
C4 C3 O22 C23 -1.3(3) . . . . ?
C2 C3 O22 C23 177.15(17) . . . . ?

_refine_diff_density_max         0.599
_refine_diff_density_min         -0.243
_refine_diff_density_rms         0.060


_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: Acetone'
####################################################################### 
# 
# 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_vs_spome_hno3_acn
_database_code_depnum_ccdc_archive 'CCDC 1824253'
_audit_update_record             
;
2018-02-15 deposited with the CCDC.
2018-04-06 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2016/4
_shelx_SHELXL_version_number     2016/4
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C20 H22 N O2, N O3, H2 O'
_chemical_formula_sum            'C20 H24 N2 O6'
_chemical_formula_weight         388.41

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

_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.
;

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

_cell_length_a                   10.9418(7)
_cell_length_b                   22.2438(13)
_cell_length_c                   8.0740(6)
_cell_angle_alpha                90
_cell_angle_beta                 99.632(7)
_cell_angle_gamma                90
_cell_volume                     1937.4(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    3235
_cell_measurement_theta_min      3.0400
_cell_measurement_theta_max      25.1920

_exptl_crystal_description       rod
_exptl_crystal_colour            yellow-orange
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.332
_exptl_crystal_F_000             824
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.07
_exptl_absorpt_coefficient_mu    0.099
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_T_min  0.92215
_exptl_absorpt_correction_T_max  1.00000
_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_absorpt_special_details   ?
_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'Rigaku UltraX 18 rotating anode'
_diffrn_radiation_monochromator  'Xenocs Fox3D mirror'
_diffrn_measurement_device_type  'MAR345 image plate'
_diffrn_measurement_method       '81 images, ΔΦ 2.0° '
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            10899
_diffrn_reflns_av_unetI/netI     0.0636
_diffrn_reflns_av_R_equivalents  0.0668
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -26
_diffrn_reflns_limit_k_max       26
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_theta_min         3.056
_diffrn_reflns_theta_max         25.241
_diffrn_reflns_theta_full        25.000
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measured_fraction_theta_full 0.992
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_Laue_measured_fraction_full 0.992
_diffrn_reflns_point_group_measured_fraction_max 0.992
_diffrn_reflns_point_group_measured_fraction_full 0.992
_reflns_number_total             3471
_reflns_number_gt                2478
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_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.
;

_computing_data_collection       MAR
_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_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_structure_solution    'SHELXT (Sheldrick, 2015)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'MERCURY (Macrae et al., 2008)'
_computing_publication_material  
;
'MERCURY (Macrae et al., 2008), Platon (Spek, 2009)'
;
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0290P)²+0.7508P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3471
_refine_ls_number_parameters     261
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0898
_refine_ls_R_factor_gt           0.0539
_refine_ls_wR_factor_ref         0.1074
_refine_ls_wR_factor_gt          0.0960
_refine_ls_goodness_of_fit_ref   1.060
_refine_ls_restrained_S_all      1.060
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.46555(14) 0.61825(7) 0.2209(2) 0.0289(4) Uani 1 1 d . . . . .
H1 H 0.397912 0.633850 0.177065 0.043 Uiso 1 1 calc R U . . .
C2 C 0.5601(2) 0.64824(9) 0.1700(3) 0.0199(5) Uani 1 1 d . . . . .
C3 C 0.5424(2) 0.67858(10) 0.0148(3) 0.0231(5) Uani 1 1 d . . . . .
C4 C 0.6388(2) 0.71037(10) -0.0324(3) 0.0269(6) Uani 1 1 d . . . . .
H4 H 0.626734 0.731484 -0.136178 0.032 Uiso 1 1 calc R U . . .
C5 C 0.7547(2) 0.71168(10) 0.0718(3) 0.0278(6) Uani 1 1 d . . . . .
H5 H 0.820534 0.734189 0.039106 0.033 Uiso 1 1 calc R U . . .
C6 C 0.7739(2) 0.68071(10) 0.2209(3) 0.0238(5) Uani 1 1 d . . . . .
H6 H 0.853584 0.681038 0.289102 0.029 Uiso 1 1 calc R U . . .
C7 C 0.6767(2) 0.64848(9) 0.2734(3) 0.0205(5) Uani 1 1 d . . . . .
C8 C 0.6900(2) 0.61590(10) 0.4305(3) 0.0223(5) Uani 1 1 d . . . . .
H8 H 0.625085 0.588928 0.444099 0.027 Uiso 1 1 calc R U . . .
C9 C 0.7859(2) 0.62005(10) 0.5601(3) 0.0225(5) Uani 1 1 d . . . . .
H9 H 0.852482 0.646296 0.548926 0.027 Uiso 1 1 calc R U . . .
C10 C 0.7916(2) 0.58692(9) 0.7126(3) 0.0206(5) Uani 1 1 d . . . . .
C11 C 0.7106(2) 0.53459(10) 0.7514(3) 0.0207(5) Uani 1 1 d . . . . .
C12 C 0.5729(2) 0.55059(11) 0.7463(3) 0.0286(6) Uani 1 1 d . . . . .
H121 H 0.529884 0.516377 0.787084 0.043 Uiso 1 1 calc R U . . .
H122 H 0.534669 0.559973 0.630625 0.043 Uiso 1 1 calc R U . . .
H123 H 0.566515 0.585605 0.818095 0.043 Uiso 1 1 calc R U . . .
C13 C 0.7242(2) 0.48180(10) 0.6315(3) 0.0240(5) Uani 1 1 d . . . . .
H131 H 0.812180 0.471791 0.638538 0.036 Uiso 1 1 calc R U . . .
H132 H 0.689751 0.493431 0.516038 0.036 Uiso 1 1 calc R U . . .
H133 H 0.679452 0.446710 0.663800 0.036 Uiso 1 1 calc R U . . .
C14 C 0.7687(2) 0.51964(10) 0.9301(3) 0.0228(5) Uani 1 1 d . . . . .
C15 C 0.7382(2) 0.47774(11) 1.0416(3) 0.0283(6) Uani 1 1 d . . . . .
H15 H 0.670358 0.451151 1.009997 0.034 Uiso 1 1 calc R U . . .
C16 C 0.8089(2) 0.47507(12) 1.2020(3) 0.0350(6) Uani 1 1 d . . . . .
H16 H 0.789830 0.445966 1.279921 0.042 Uiso 1 1 calc R U . . .
C17 C 0.9072(2) 0.51471(12) 1.2490(3) 0.0365(7) Uani 1 1 d . . . . .
H17 H 0.953390 0.512477 1.359494 0.044 Uiso 1 1 calc R U . . .
C18 C 0.9390(2) 0.55706(11) 1.1392(3) 0.0306(6) Uani 1 1 d . . . . .
H18 H 1.006136 0.584080 1.170673 0.037 Uiso 1 1 calc R U . . .
C19 C 0.8677(2) 0.55806(10) 0.9800(3) 0.0237(5) Uani 1 1 d . . . . .
N20 N 0.87958(17) 0.59725(8) 0.8443(2) 0.0227(5) Uani 1 1 d . . . . .
C21 C 0.9790(2) 0.64211(11) 0.8560(3) 0.0334(6) Uani 1 1 d . . . . .
H21A H 1.007175 0.652555 0.974141 0.050 Uiso 0.5 1 calc R U P . .
H21B H 0.947689 0.678246 0.793440 0.050 Uiso 0.5 1 calc R U P . .
H21C H 1.048419 0.625508 0.808285 0.050 Uiso 0.5 1 calc R U P . .
H21D H 0.995014 0.651651 0.743103 0.050 Uiso 0.5 1 calc R U P . .
H21E H 1.054500 0.625960 0.923804 0.050 Uiso 0.5 1 calc R U P . .
H21F H 0.953770 0.678698 0.908960 0.050 Uiso 0.5 1 calc R U P . .
O22 O 0.42612(14) 0.67221(7) -0.0770(2) 0.0311(4) Uani 1 1 d . . . . .
C23 C 0.4007(3) 0.70283(13) -0.2354(3) 0.0429(7) Uani 1 1 d . . . . .
H231 H 0.411451 0.746197 -0.217184 0.064 Uiso 1 1 calc R U . . .
H232 H 0.315222 0.694539 -0.289032 0.064 Uiso 1 1 calc R U . . .
H233 H 0.457976 0.688660 -0.308103 0.064 Uiso 1 1 calc R U . . .
N31 N 0.10371(19) 0.70484(10) 0.4762(3) 0.0334(5) Uani 1 1 d . . . . .
O32 O 0.02507(16) 0.72818(8) 0.5504(2) 0.0403(5) Uani 1 1 d . . . . .
O33 O 0.19096(16) 0.73586(9) 0.4394(2) 0.0445(5) Uani 1 1 d . . . . .
O34 O 0.0958(2) 0.65058(9) 0.4389(3) 0.0689(7) Uani 1 1 d . . . . .
O35 O 0.23940(16) 0.65894(8) 0.1465(2) 0.0338(4) Uani 1 1 d G . . . .
H351 H 0.220795 0.688419 0.086584 0.051 Uiso 1 1 d G U . . .
H352 H 0.212769 0.666514 0.233250 0.051 Uiso 1 1 d G U . . .


_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 C2 1.351(3) . ?
O1 H1 0.8400 . ?
C2 C7 1.403(3) . ?
C2 C3 1.408(3) . ?
C3 O22 1.368(3) . ?
C3 C4 1.376(3) . ?
C4 C5 1.400(3) . ?
C4 H4 0.9500 . ?
C5 C6 1.372(3) . ?
C5 H5 0.9500 . ?
C6 C7 1.406(3) . ?
C6 H6 0.9500 . ?
C7 C8 1.446(3) . ?
C8 C9 1.355(3) . ?
C8 H8 0.9500 . ?
C9 C10 1.427(3) . ?
C9 H9 0.9500 . ?
C10 N20 1.329(3) . ?
C10 C11 1.527(3) . ?
C11 C14 1.513(3) . ?
C11 C12 1.542(3) . ?
C11 C13 1.545(3) . ?
C12 H121 0.9800 . ?
C12 H122 0.9800 . ?
C12 H123 0.9800 . ?
C13 H131 0.9800 . ?
C13 H132 0.9800 . ?
C13 H133 0.9800 . ?
C14 C15 1.375(3) . ?
C14 C19 1.385(3) . ?
C15 C16 1.394(3) . ?
C15 H15 0.9500 . ?
C16 C17 1.394(4) . ?
C16 H16 0.9500 . ?
C17 C18 1.378(4) . ?
C17 H17 0.9500 . ?
C18 C19 1.388(3) . ?
C18 H18 0.9500 . ?
C19 N20 1.423(3) . ?
N20 C21 1.467(3) . ?
C21 H21A 0.9800 . ?
C21 H21B 0.9800 . ?
C21 H21C 0.9800 . ?
C21 H21D 0.9800 . ?
C21 H21E 0.9800 . ?
C21 H21F 0.9800 . ?
O22 C23 1.434(3) . ?
C23 H231 0.9800 . ?
C23 H232 0.9800 . ?
C23 H233 0.9800 . ?
N31 O32 1.241(3) . ?
N31 O34 1.244(3) . ?
N31 O33 1.253(3) . ?
O35 H351 0.8200 . ?
O35 H352 0.8200 . ?

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
C2 O1 H1 109.5 . . ?
O1 C2 C7 119.15(19) . . ?
O1 C2 C3 120.58(19) . . ?
C7 C2 C3 120.3(2) . . ?
O22 C3 C4 126.1(2) . . ?
O22 C3 C2 114.2(2) . . ?
C4 C3 C2 119.7(2) . . ?
C3 C4 C5 120.2(2) . . ?
C3 C4 H4 119.9 . . ?
C5 C4 H4 119.9 . . ?
C6 C5 C4 120.5(2) . . ?
C6 C5 H5 119.8 . . ?
C4 C5 H5 119.8 . . ?
C5 C6 C7 120.5(2) . . ?
C5 C6 H6 119.7 . . ?
C7 C6 H6 119.7 . . ?
C2 C7 C6 118.7(2) . . ?
C2 C7 C8 117.9(2) . . ?
C6 C7 C8 123.4(2) . . ?
C9 C8 C7 126.5(2) . . ?
C9 C8 H8 116.8 . . ?
C7 C8 H8 116.8 . . ?
C8 C9 C10 123.2(2) . . ?
C8 C9 H9 118.4 . . ?
C10 C9 H9 118.4 . . ?
N20 C10 C9 121.5(2) . . ?
N20 C10 C11 109.59(19) . . ?
C9 C10 C11 128.84(18) . . ?
C14 C11 C10 101.38(17) . . ?
C14 C11 C12 109.21(19) . . ?
C10 C11 C12 114.64(18) . . ?
C14 C11 C13 111.18(18) . . ?
C10 C11 C13 109.28(19) . . ?
C12 C11 C13 110.82(18) . . ?
C11 C12 H121 109.5 . . ?
C11 C12 H122 109.5 . . ?
H121 C12 H122 109.5 . . ?
C11 C12 H123 109.5 . . ?
H121 C12 H123 109.5 . . ?
H122 C12 H123 109.5 . . ?
C11 C13 H131 109.5 . . ?
C11 C13 H132 109.5 . . ?
H131 C13 H132 109.5 . . ?
C11 C13 H133 109.5 . . ?
H131 C13 H133 109.5 . . ?
H132 C13 H133 109.5 . . ?
C15 C14 C19 119.4(2) . . ?
C15 C14 C11 131.6(2) . . ?
C19 C14 C11 109.0(2) . . ?
C14 C15 C16 118.6(2) . . ?
C14 C15 H15 120.7 . . ?
C16 C15 H15 120.7 . . ?
C15 C16 C17 120.6(2) . . ?
C15 C16 H16 119.7 . . ?
C17 C16 H16 119.7 . . ?
C18 C17 C16 121.6(2) . . ?
C18 C17 H17 119.2 . . ?
C16 C17 H17 119.2 . . ?
C17 C18 C19 116.3(2) . . ?
C17 C18 H18 121.8 . . ?
C19 C18 H18 121.8 . . ?
C14 C19 C18 123.4(2) . . ?
C14 C19 N20 108.78(18) . . ?
C18 C19 N20 127.8(2) . . ?
C10 N20 C19 111.26(18) . . ?
C10 N20 C21 126.8(2) . . ?
C19 N20 C21 121.95(17) . . ?
N20 C21 H21A 109.5 . . ?
N20 C21 H21B 109.5 . . ?
H21A C21 H21B 109.5 . . ?
N20 C21 H21C 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
N20 C21 H21D 109.5 . . ?
H21A C21 H21D 141.1 . . ?
H21B C21 H21D 56.3 . . ?
H21C C21 H21D 56.3 . . ?
N20 C21 H21E 109.5 . . ?
H21A C21 H21E 56.3 . . ?
H21B C21 H21E 141.1 . . ?
H21C C21 H21E 56.3 . . ?
H21D C21 H21E 109.5 . . ?
N20 C21 H21F 109.5 . . ?
H21A C21 H21F 56.3 . . ?
H21B C21 H21F 56.3 . . ?
H21C C21 H21F 141.1 . . ?
H21D C21 H21F 109.5 . . ?
H21E C21 H21F 109.5 . . ?
C3 O22 C23 117.26(19) . . ?
O22 C23 H231 109.5 . . ?
O22 C23 H232 109.5 . . ?
H231 C23 H232 109.5 . . ?
O22 C23 H233 109.5 . . ?
H231 C23 H233 109.5 . . ?
H232 C23 H233 109.5 . . ?
O32 N31 O34 119.8(2) . . ?
O32 N31 O33 120.1(2) . . ?
O34 N31 O33 120.1(2) . . ?
H351 O35 H352 104.5 . . ?

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 C2 C3 O22 -2.7(3) . . . . ?
C7 C2 C3 O22 176.87(19) . . . . ?
O1 C2 C3 C4 178.1(2) . . . . ?
C7 C2 C3 C4 -2.4(3) . . . . ?
O22 C3 C4 C5 -178.0(2) . . . . ?
C2 C3 C4 C5 1.1(3) . . . . ?
C3 C4 C5 C6 0.9(4) . . . . ?
C4 C5 C6 C7 -1.7(4) . . . . ?
O1 C2 C7 C6 -178.9(2) . . . . ?
C3 C2 C7 C6 1.6(3) . . . . ?
O1 C2 C7 C8 0.4(3) . . . . ?
C3 C2 C7 C8 -179.2(2) . . . . ?
C5 C6 C7 C2 0.5(3) . . . . ?
C5 C6 C7 C8 -178.7(2) . . . . ?
C2 C7 C8 C9 -166.4(2) . . . . ?
C6 C7 C8 C9 12.8(4) . . . . ?
C7 C8 C9 C10 179.1(2) . . . . ?
C8 C9 C10 N20 -172.0(2) . . . . ?
C8 C9 C10 C11 11.7(4) . . . . ?
N20 C10 C11 C14 1.5(2) . . . . ?
C9 C10 C11 C14 178.1(2) . . . . ?
N20 C10 C11 C12 119.0(2) . . . . ?
C9 C10 C11 C12 -64.4(3) . . . . ?
N20 C10 C11 C13 -115.9(2) . . . . ?
C9 C10 C11 C13 60.7(3) . . . . ?
C10 C11 C14 C15 178.1(2) . . . . ?
C12 C11 C14 C15 56.7(3) . . . . ?
C13 C11 C14 C15 -65.9(3) . . . . ?
C10 C11 C14 C19 -0.5(2) . . . . ?
C12 C11 C14 C19 -121.8(2) . . . . ?
C13 C11 C14 C19 115.6(2) . . . . ?
C19 C14 C15 C16 -0.4(3) . . . . ?
C11 C14 C15 C16 -178.8(2) . . . . ?
C14 C15 C16 C17 1.0(4) . . . . ?
C15 C16 C17 C18 -0.9(4) . . . . ?
C16 C17 C18 C19 0.2(4) . . . . ?
C15 C14 C19 C18 -0.4(4) . . . . ?
C11 C14 C19 C18 178.4(2) . . . . ?
C15 C14 C19 N20 -179.4(2) . . . . ?
C11 C14 C19 N20 -0.6(3) . . . . ?
C17 C18 C19 C14 0.4(4) . . . . ?
C17 C18 C19 N20 179.3(2) . . . . ?
C9 C10 N20 C19 -178.9(2) . . . . ?
C11 C10 N20 C19 -2.0(2) . . . . ?
C9 C10 N20 C21 0.7(3) . . . . ?
C11 C10 N20 C21 177.6(2) . . . . ?
C14 C19 N20 C10 1.7(3) . . . . ?
C18 C19 N20 C10 -177.3(2) . . . . ?
C14 C19 N20 C21 -177.9(2) . . . . ?
C18 C19 N20 C21 3.1(4) . . . . ?
C4 C3 O22 C23 -1.9(3) . . . . ?
C2 C3 O22 C23 178.9(2) . . . . ?

_refine_diff_density_max         0.233
_refine_diff_density_min         -0.180
_refine_diff_density_rms         0.043


_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: Acetonitrile'
####################################################################### 
# 
# 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_nt0141_Vanessa_KC-SPB_HCl_DCM11_300
_database_code_depnum_ccdc_archive 'CCDC 1824255'
_audit_update_record             
;
2018-02-15 deposited with the CCDC.
2018-04-06 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2016/6
_shelx_SHELXL_version_number     2016/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C23 H22 N O 1+, Cl 1-'
_chemical_formula_sum            'C23 H22 Cl N O'
_chemical_formula_weight         363.86

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'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

_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.
;

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

_cell_length_a                   17.6960(6)
_cell_length_b                   15.1030(4)
_cell_length_c                   6.9665(3)
_cell_angle_alpha                90
_cell_angle_beta                 92.410(4)
_cell_angle_gamma                90
_cell_volume                     1860.24(11)
_cell_formula_units_Z            4
_cell_measurement_temperature    295(2)
_cell_measurement_reflns_used    5996
_cell_measurement_theta_min      2.6600
_cell_measurement_theta_max      31.8360

_exptl_crystal_description       plate
_exptl_crystal_colour            red
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.299
_exptl_crystal_F_000             768
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.683
_exptl_crystal_size_mid          0.371
_exptl_crystal_size_min          0.049
_exptl_absorpt_coefficient_mu    0.217
_shelx_estimated_absorpt_T_min   0.866
_shelx_estimated_absorpt_T_max   0.989
_exptl_absorpt_correction_T_min  0.904
_exptl_absorpt_correction_T_max  0.989
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.46 (Rigaku Oxford Diffraction, 2015)
Numerical absorption correction based on gaussian integration over
a multifaceted crystal model
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      295(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  
;
Oxford Diffraction Xcalibur, Ruby, Gemini ultra
;
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean 10.3712
_diffrn_reflns_number            6241
_diffrn_reflns_av_unetI/netI     0.0283
_diffrn_reflns_av_R_equivalents  ?
_diffrn_reflns_limit_h_min       -23
_diffrn_reflns_limit_h_max       23
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_theta_min         2.304
_diffrn_reflns_theta_max         28.279
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             6241
_reflns_number_gt                4655
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 _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.
;

_computing_data_collection       'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_cell_refinement       'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_structure_solution    'SHELXT (Sheldrick, 2015)'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          'Refined as a 2-component twin.,Twin'
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0627P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   dual
_atom_sites_solution_hydrogens   difmap
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         6241
_refine_ls_number_parameters     240
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0588
_refine_ls_R_factor_gt           0.0409
_refine_ls_wR_factor_ref         0.1049
_refine_ls_wR_factor_gt          0.0997
_refine_ls_goodness_of_fit_ref   1.011
_refine_ls_restrained_S_all      1.011
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.21606(6) 0.78486(6) 0.27192(19) 0.0464(3) Uani 1 1 d . . . . .
H1 H 0.200316 0.835883 0.275050 0.070 Uiso 1 1 calc R U . . .
N20 N 0.11965(6) 0.49286(7) 0.25822(17) 0.0295(3) Uani 1 1 d . . . . .
C2 C 0.29137(9) 0.78567(9) 0.2588(2) 0.0325(3) Uani 1 1 d . . . . .
C3 C 0.33023(10) 0.86746(9) 0.2523(2) 0.0375(4) Uani 1 1 d . . . . .
H3 H 0.303436 0.920317 0.257504 0.045 Uiso 1 1 calc R U . . .
C4 C 0.40610(10) 0.86893(10) 0.2384(2) 0.0405(4) Uani 1 1 d . . . . .
H4 H 0.430572 0.923333 0.233791 0.049 Uiso 1 1 calc R U . . .
C5 C 0.44964(9) 0.79052(9) 0.2308(2) 0.0341(4) Uani 1 1 d . . . . .
C6 C 0.41200(9) 0.70760(9) 0.2391(2) 0.0301(3) Uani 1 1 d . . . . .
C7 C 0.33061(9) 0.70520(9) 0.2530(2) 0.0298(3) Uani 1 1 d . . . . .
C8 C 0.29346(9) 0.62072(8) 0.2583(2) 0.0320(3) Uani 1 1 d . . . . .
H8 H 0.325998 0.572340 0.261037 0.038 Uiso 1 1 calc R U . . .
C9 C 0.21964(8) 0.59967(9) 0.2600(2) 0.0333(3) Uani 1 1 d . . . . .
H9 H 0.184451 0.645395 0.260586 0.040 Uiso 1 1 calc R U . . .
C10 C 0.19277(8) 0.51106(8) 0.2608(2) 0.0286(3) Uani 1 1 d . . . . .
C11 C 0.23808(8) 0.42467(8) 0.2656(2) 0.0298(3) Uani 1 1 d . . . . .
C12 C 0.28505(10) 0.41372(10) 0.0861(2) 0.0403(4) Uani 1 1 d . . . . .
H12A H 0.304250 0.354344 0.081184 0.060 Uiso 1 1 calc R U . . .
H12B H 0.326526 0.454737 0.092086 0.060 Uiso 1 1 calc R U . . .
H12C H 0.253678 0.425236 -0.026903 0.060 Uiso 1 1 calc R U . . .
C13 C 0.28692(10) 0.41631(10) 0.4524(2) 0.0391(4) Uani 1 1 d . . . . .
H13A H 0.256339 0.427512 0.560356 0.059 Uiso 1 1 calc R U . . .
H13B H 0.327414 0.458591 0.451494 0.059 Uiso 1 1 calc R U . . .
H13C H 0.307535 0.357602 0.461971 0.059 Uiso 1 1 calc R U . . .
C14 C 0.17495(8) 0.35727(9) 0.2631(2) 0.0311(3) Uani 1 1 d . . . . .
C15 C 0.17615(10) 0.26567(9) 0.2638(3) 0.0406(4) Uani 1 1 d . . . . .
H15 H 0.221867 0.235241 0.266570 0.049 Uiso 1 1 calc R U . . .
C16 C 0.10857(11) 0.22020(10) 0.2604(3) 0.0484(4) Uani 1 1 d . . . . .
H16 H 0.108787 0.158619 0.260835 0.058 Uiso 1 1 calc R U . . .
C17 C 0.04087(11) 0.26488(10) 0.2565(3) 0.0511(4) Uani 1 1 d . . . . .
H17 H -0.003955 0.232684 0.254041 0.061 Uiso 1 1 calc R U . . .
C18 C 0.03749(9) 0.35686(9) 0.2560(2) 0.0408(4) Uani 1 1 d . . . . .
H18 H -0.008241 0.387264 0.253759 0.049 Uiso 1 1 calc R U . . .
C19 C 0.10608(8) 0.40019(8) 0.2591(2) 0.0307(3) Uani 1 1 d . . . . .
C21 C 0.05888(9) 0.55800(9) 0.2537(3) 0.0434(4) Uani 1 1 d . . . . .
H21A H 0.061699 0.593691 0.140151 0.065 Uiso 1 1 calc R U . . .
H21B H 0.063926 0.595121 0.365326 0.065 Uiso 1 1 calc R U . . .
H21C H 0.010986 0.528121 0.252488 0.065 Uiso 1 1 calc R U . . .
C22 C 0.52886(10) 0.79366(11) 0.2153(2) 0.0436(4) Uani 1 1 d . . . . .
H22 H 0.552855 0.848335 0.209993 0.052 Uiso 1 1 calc R U . . .
C23 C 0.57071(10) 0.71860(11) 0.2081(3) 0.0472(4) Uani 1 1 d . . . . .
H23 H 0.622877 0.721785 0.197886 0.057 Uiso 1 1 calc R U . . .
C24 C 0.53500(10) 0.63717(11) 0.2160(3) 0.0481(4) Uani 1 1 d . . . . .
H24 H 0.563552 0.585593 0.211006 0.058 Uiso 1 1 calc R U . . .
C25 C 0.45822(9) 0.63150(9) 0.2311(2) 0.0408(4) Uani 1 1 d . . . . .
H25 H 0.435835 0.575890 0.236362 0.049 Uiso 1 1 calc R U . . .
Cl1 Cl 0.14449(2) 0.96676(2) 0.25943(7) 0.04440(13) Uani 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C2 1.3398(18) . ?
O1 H1 0.8200 . ?
N20 C10 1.3222(17) . ?
N20 C19 1.4200(16) . ?
N20 C21 1.4568(17) . ?
C2 C7 1.4010(19) . ?
C2 C3 1.4155(19) . ?
C3 C4 1.350(2) . ?
C3 H3 0.9300 . ?
C4 C5 1.415(2) . ?
C4 H4 0.9300 . ?
C5 C22 1.411(2) . ?
C5 C6 1.4207(19) . ?
C6 C25 1.413(2) . ?
C6 C7 1.448(2) . ?
C7 C8 1.4364(18) . ?
C8 C9 1.345(2) . ?
C8 H8 0.9300 . ?
C9 C10 1.4204(18) . ?
C9 H9 0.9300 . ?
C10 C11 1.5311(18) . ?
C11 C14 1.5109(19) . ?
C11 C13 1.537(2) . ?
C11 C12 1.539(2) . ?
C12 H12A 0.9600 . ?
C12 H12B 0.9600 . ?
C12 H12C 0.9600 . ?
C13 H13A 0.9600 . ?
C13 H13B 0.9600 . ?
C13 H13C 0.9600 . ?
C14 C19 1.380(2) . ?
C14 C15 1.3835(18) . ?
C15 C16 1.378(2) . ?
C15 H15 0.9300 . ?
C16 C17 1.374(2) . ?
C16 H16 0.9300 . ?
C17 C18 1.3904(19) . ?
C17 H17 0.9300 . ?
C18 C19 1.378(2) . ?
C18 H18 0.9300 . ?
C21 H21A 0.9600 . ?
C21 H21B 0.9600 . ?
C21 H21C 0.9600 . ?
C22 C23 1.356(2) . ?
C22 H22 0.9300 . ?
C23 C24 1.385(2) . ?
C23 H23 0.9300 . ?
C24 C25 1.370(2) . ?
C24 H24 0.9300 . ?
C25 H25 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
C2 O1 H1 109.5 . . ?
C10 N20 C19 111.74(11) . . ?
C10 N20 C21 125.52(11) . . ?
C19 N20 C21 122.75(12) . . ?
O1 C2 C7 119.32(12) . . ?
O1 C2 C3 119.74(13) . . ?
C7 C2 C3 120.94(14) . . ?
C4 C3 C2 120.16(14) . . ?
C4 C3 H3 119.9 . . ?
C2 C3 H3 119.9 . . ?
C3 C4 C5 122.25(14) . . ?
C3 C4 H4 118.9 . . ?
C5 C4 H4 118.9 . . ?
C22 C5 C4 121.26(14) . . ?
C22 C5 C6 120.11(14) . . ?
C4 C5 C6 118.63(14) . . ?
C25 C6 C5 116.24(14) . . ?
C25 C6 C7 124.14(13) . . ?
C5 C6 C7 119.62(13) . . ?
C2 C7 C8 122.81(14) . . ?
C2 C7 C6 118.40(12) . . ?
C8 C7 C6 118.79(12) . . ?
C9 C8 C7 130.99(13) . . ?
C9 C8 H8 114.5 . . ?
C7 C8 H8 114.5 . . ?
C8 C9 C10 123.24(13) . . ?
C8 C9 H9 118.4 . . ?
C10 C9 H9 118.4 . . ?
N20 C10 C9 121.56(12) . . ?
N20 C10 C11 109.54(11) . . ?
C9 C10 C11 128.90(13) . . ?
C14 C11 C10 100.82(11) . . ?
C14 C11 C13 110.11(12) . . ?
C10 C11 C13 111.34(12) . . ?
C14 C11 C12 110.02(12) . . ?
C10 C11 C12 111.96(12) . . ?
C13 C11 C12 112.04(13) . . ?
C11 C12 H12A 109.5 . . ?
C11 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
C11 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C11 C13 H13A 109.5 . . ?
C11 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
C11 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
C19 C14 C15 118.91(14) . . ?
C19 C14 C11 109.61(11) . . ?
C15 C14 C11 131.48(14) . . ?
C16 C15 C14 119.01(15) . . ?
C16 C15 H15 120.5 . . ?
C14 C15 H15 120.5 . . ?
C17 C16 C15 120.70(14) . . ?
C17 C16 H16 119.7 . . ?
C15 C16 H16 119.7 . . ?
C16 C17 C18 121.88(15) . . ?
C16 C17 H17 119.1 . . ?
C18 C17 H17 119.1 . . ?
C19 C18 C17 115.88(15) . . ?
C19 C18 H18 122.1 . . ?
C17 C18 H18 122.1 . . ?
C18 C19 C14 123.62(13) . . ?
C18 C19 N20 128.08(13) . . ?
C14 C19 N20 108.30(12) . . ?
N20 C21 H21A 109.5 . . ?
N20 C21 H21B 109.5 . . ?
H21A C21 H21B 109.5 . . ?
N20 C21 H21C 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
C23 C22 C5 121.37(14) . . ?
C23 C22 H22 119.3 . . ?
C5 C22 H22 119.3 . . ?
C22 C23 C24 119.33(16) . . ?
C22 C23 H23 120.3 . . ?
C24 C23 H23 120.3 . . ?
C25 C24 C23 120.96(15) . . ?
C25 C24 H24 119.5 . . ?
C23 C24 H24 119.5 . . ?
C24 C25 C6 121.99(14) . . ?
C24 C25 H25 119.0 . . ?
C6 C25 H25 119.0 . . ?

_refine_diff_density_max         0.211
_refine_diff_density_min         -0.236
_refine_diff_density_rms         0.048


_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: Dichlormethane'
####################################################################### 
# 
# 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_nt0143_Vanessa_KC-SPNO2_H2SO4_ACN
_database_code_depnum_ccdc_archive 'CCDC 1824257'
_audit_update_record             
;
2018-02-15 deposited with the CCDC.
2018-04-06 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        
'2-[(E)-2-(2-hydroxy-5-nitrophenyl)ethenyl]-1,3,3-trimethyl-3H-indol-1-ium hydrogen sulfate'
_chemical_name_common            
'2-[(E)-2-(2-hydroxy-5-nitrophenyl)ethenyl]-1,3,3-trimethyl-3H-indol-1-ium hydrogen sulfate'
_chemical_melting_point          ?
_chemical_formula_moiety         'C19 H19 N2 O3, H O4 S'
_chemical_formula_sum            'C19 H20 N2 O7 S'
_chemical_formula_weight         420.43

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'
N N 0.0311 0.0180 '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'
S S 0.3331 0.5567 '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 21/c'
_space_group_name_Hall           '-P 2ybc'

_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.
;

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

_cell_length_a                   11.768(3)
_cell_length_b                   25.295(5)
_cell_length_c                   7.006(2)
_cell_angle_alpha                90
_cell_angle_beta                 104.70(3)
_cell_angle_gamma                90
_cell_volume                     2017.2(10)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    1148
_cell_measurement_theta_min      6.7800
_cell_measurement_theta_max      53.8490

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.384
_exptl_crystal_F_000             880
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.11
_exptl_crystal_size_min          0.056
_exptl_absorpt_coefficient_mu    1.817
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_T_min  0.43995
_exptl_absorpt_correction_T_max  1.00000
_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_absorpt_special_details   ?
_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_type           CuK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_radiation_monochromator  'multilayer mirror'
_diffrn_measurement_device_type  
;
Oxford Diffraction Xcalibur, Ruby, Gemini ultra
;
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean 5.1856
_diffrn_reflns_number            3479
_diffrn_reflns_av_unetI/netI     0.0392
_diffrn_reflns_av_R_equivalents  ?
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -25
_diffrn_reflns_limit_k_max       25
_diffrn_reflns_limit_l_min       -6
_diffrn_reflns_limit_l_max       6
_diffrn_reflns_theta_min         4.259
_diffrn_reflns_theta_max         50.534
_diffrn_reflns_theta_full        50.534
_diffrn_measured_fraction_theta_max 0.965
_diffrn_measured_fraction_theta_full 0.965
_diffrn_reflns_Laue_measured_fraction_max 0.965
_diffrn_reflns_Laue_measured_fraction_full 0.965
_diffrn_reflns_point_group_measured_fraction_max 0.965
_diffrn_reflns_point_group_measured_fraction_full 0.965
_reflns_number_total             3479
_reflns_number_gt                1505
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 _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.
;

_computing_data_collection       'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_cell_refinement       'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_structure_solution    'SHELXT (Sheldrick, 2015)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          'Refined as a 2-component twin.,Twin'
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0500P)²+0.3000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3479
_refine_ls_number_parameters     332
_refine_ls_number_restraints     121
_refine_ls_R_factor_all          0.1193
_refine_ls_R_factor_gt           0.0611
_refine_ls_wR_factor_ref         0.1500
_refine_ls_wR_factor_gt          0.1371
_refine_ls_goodness_of_fit_ref   1.027
_refine_ls_restrained_S_all      1.044
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

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
S1 S 0.9496(9) -0.0754(3) 0.4570(18) 0.213(10) Uani 0.452(4) 1 d G U P A 1
O2 O 0.8667(15) -0.1197(5) 0.438(3) 0.211(11) Uani 0.452(4) 1 d G U P A 1
O3 O 1.0494(13) -0.0908(6) 0.377(3) 0.221(8) Uani 0.452(4) 1 d G U P A 1
O4 O 0.9940(19) -0.0612(8) 0.6661(17) 0.201(10) Uani 0.452(4) 1 d G U P A 1
H4 H 1.0403 -0.0365 0.6762 0.302 Uiso 0.452(4) 1 calc R U P A 1
O5 O 0.8888(13) -0.0298(4) 0.345(3) 0.208(7) Uani 0.452(4) 1 d G U P A 1
S1B S 0.9546(9) -0.0727(3) 0.4981(19) 0.171(8) Uani 0.324(4) 1 d G U P B 2
O2B O 0.8770(15) -0.1161(5) 0.406(3) 0.169(12) Uani 0.324(4) 1 d G U P B 2
O3B O 1.0083(18) -0.0480(7) 0.352(2) 0.125(8) Uani 0.324(4) 1 d G U P B 2
O4B O 1.0481(13) -0.0932(7) 0.662(3) 0.210(11) Uani 0.324(4) 1 d G U P B 2
O5B O 0.8850(12) -0.0328(5) 0.572(3) 0.140(5) Uani 0.324(4) 1 d G U P B 2
H5B H 0.9279 -0.0084 0.6235 0.209 Uiso 0.324(4) 1 calc R U P B 2
S1C S 0.9542(15) -0.0801(6) 0.440(3) 0.148(12) Uani 0.223(4) 1 d G U P C 3
O2C O 0.989(2) -0.1360(7) 0.459(5) 0.276(13) Uani 0.223(4) 1 d G U P C 3
O3C O 1.017(3) -0.0508(11) 0.617(3) 0.160(14) Uani 0.223(4) 1 d G U P C 3
H3C H 0.9976 -0.0196 0.6064 0.240 Uiso 0.223(4) 1 calc R U P C 3
O4C O 0.8271(15) -0.0757(11) 0.421(5) 0.235(13) Uani 0.223(4) 1 d G U P C 3
O5C O 0.983(3) -0.0574(11) 0.265(3) 0.170(14) Uani 0.223(4) 1 d G U P C 3
O11 O 0.1210(4) 0.28029(15) 0.0672(8) 0.196(2) Uani 1 1 d . . . . .
H11 H 0.1095 0.3122 0.0681 0.294 Uiso 1 1 d R U . . .
O33 O -0.3853(5) 0.1937(3) -0.2062(10) 0.249(3) Uani 1 1 d . . . . .
O34 O -0.2928(5) 0.1207(2) -0.1373(12) 0.240(3) Uani 1 1 d . . . . .
N30 N 0.2982(4) 0.0500(2) 0.1488(9) 0.1540(18) Uani 1 1 d . . . . .
N32 N -0.2926(7) 0.1689(3) -0.1521(13) 0.197(2) Uani 1 1 d . . . . .
C12 C 0.0198(7) 0.2548(3) 0.0142(11) 0.147(2) Uani 1 1 d . . . . .
C13 C -0.0858(8) 0.2804(3) -0.0414(11) 0.170(3) Uani 1 1 d . . . . .
H13 H -0.0865 0.3172 -0.0415 0.205 Uiso 1 1 calc R U . . .
C14 C -0.1904(8) 0.2539(3) -0.0967(10) 0.158(2) Uani 1 1 d . . . . .
H14 H -0.2617 0.2717 -0.1368 0.190 Uiso 1 1 calc R U . . .
C15 C -0.1846(7) 0.1988(3) -0.0898(11) 0.147(2) Uani 1 1 d . . . . .
C16 C -0.0813(7) 0.1715(2) -0.0381(9) 0.153(2) Uani 1 1 d . . . . .
H16 H -0.0811 0.1348 -0.0404 0.184 Uiso 1 1 calc R U . . .
C17 C 0.0219(6) 0.1989(2) 0.0170(10) 0.138(2) Uani 1 1 d . . . . .
C18 C 0.1352(5) 0.1744(2) 0.0742(10) 0.165(2) Uani 1 1 d . . . . .
H18 H 0.1992 0.1972 0.1094 0.199 Uiso 1 1 calc R U . . .
C19 C 0.1608(5) 0.1219(2) 0.0832(9) 0.159(2) Uani 1 1 d . . . . .
H19 H 0.0987 0.0981 0.0491 0.191 Uiso 1 1 calc R U . . .
C20 C 0.2770(6) 0.1011(3) 0.1416(10) 0.1404(19) Uani 1 1 d . . . . .
C21 C 0.3896(6) 0.1316(3) 0.2052(17) 0.160(2) Uani 1 1 d . . . . .
C22 C 0.4086(7) 0.1663(3) 0.0329(14) 0.214(4) Uani 1 1 d . . . . .
H22A H 0.3437 0.1902 -0.0092 0.321 Uiso 1 1 calc R U . . .
H22B H 0.4138 0.1439 -0.0753 0.321 Uiso 1 1 calc R U . . .
H22C H 0.4800 0.1861 0.0767 0.321 Uiso 1 1 calc R U . . .
C23 C 0.3948(6) 0.1649(3) 0.3931(13) 0.203(3) Uani 1 1 d . . . . .
H23A H 0.4715 0.1802 0.4386 0.305 Uiso 1 1 calc R U . . .
H23B H 0.3792 0.1425 0.4942 0.305 Uiso 1 1 calc R U . . .
H23C H 0.3370 0.1924 0.3628 0.305 Uiso 1 1 calc R U . . .
C24 C 0.4768(7) 0.0881(3) 0.2462(11) 0.154(2) Uani 1 1 d . . . . .
C25 C 0.5965(7) 0.0889(3) 0.3090(12) 0.188(3) Uani 1 1 d . . . . .
H25 H 0.6362 0.1210 0.3345 0.226 Uiso 1 1 calc R U . . .
C26 C 0.6583(7) 0.0420(5) 0.3343(13) 0.195(3) Uani 1 1 d . . . . .
H26 H 0.7399 0.0424 0.3730 0.233 Uiso 1 1 calc R U . . .
C27 C 0.5990(8) -0.0051(4) 0.3025(12) 0.182(3) Uani 1 1 d . . . . .
H27 H 0.6415 -0.0365 0.3253 0.218 Uiso 1 1 calc R U . . .
C28 C 0.4785(7) -0.0074(3) 0.2377(10) 0.165(2) Uani 1 1 d . . . . .
H28 H 0.4388 -0.0394 0.2118 0.198 Uiso 1 1 calc R U . . .
C29 C 0.4202(6) 0.0398(3) 0.2133(11) 0.151(2) Uani 1 1 d . . . . .
C31 C 0.2121(5) 0.0070(2) 0.1017(12) 0.196(3) Uani 1 1 d . . . . .
H31A H 0.2138 -0.0084 -0.0228 0.294 Uiso 1 1 calc R U . . .
H31B H 0.1350 0.0207 0.0941 0.294 Uiso 1 1 calc R U . . .
H31C H 0.2312 -0.0195 0.2029 0.294 Uiso 1 1 calc R U . . .


_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
S1 O2 1.4693 . ?
S1 O4 1.4701 . ?
S1 O5 1.4738 . ?
S1 O3 1.4739 . ?
O4 H4 0.8200 . ?
S1B O2B 1.4693 . ?
S1B O4B 1.4701 . ?
S1B O3B 1.4738 . ?
S1B O5B 1.4739 . ?
O5B H5B 0.8200 . ?
S1C O2C 1.4693 . ?
S1C O4C 1.4701 . ?
S1C O5C 1.4738 . ?
S1C O3C 1.4739 . ?
O3C H3C 0.8200 . ?
O11 C12 1.322(6) . ?
O11 H11 0.8194 . ?
O33 N32 1.232(6) . ?
O34 N32 1.224(6) . ?
N30 C20 1.317(6) . ?
N30 C29 1.415(7) . ?
N30 C31 1.466(6) . ?
N32 C15 1.447(8) . ?
C12 C13 1.368(8) . ?
C12 C17 1.412(7) . ?
C13 C14 1.369(7) . ?
C13 H13 0.9300 . ?
C14 C15 1.396(7) . ?
C14 H14 0.9300 . ?
C15 C16 1.364(7) . ?
C16 C17 1.366(7) . ?
C16 H16 0.9300 . ?
C17 C18 1.433(7) . ?
C18 C19 1.359(7) . ?
C18 H18 0.9300 . ?
C19 C20 1.425(7) . ?
C19 H19 0.9300 . ?
C20 C21 1.499(7) . ?
C21 C24 1.484(7) . ?
C21 C23 1.549(9) . ?
C21 C22 1.553(9) . ?
C22 H22A 0.9600 . ?
C22 H22B 0.9600 . ?
C22 H22C 0.9600 . ?
C23 H23A 0.9600 . ?
C23 H23B 0.9600 . ?
C23 H23C 0.9600 . ?
C24 C25 1.365(7) . ?
C24 C29 1.380(7) . ?
C25 C26 1.379(9) . ?
C25 H25 0.9300 . ?
C26 C27 1.371(8) . ?
C26 H26 0.9300 . ?
C27 C28 1.376(8) . ?
C27 H27 0.9300 . ?
C28 C29 1.367(7) . ?
C28 H28 0.9300 . ?
C31 H31A 0.9600 . ?
C31 H31B 0.9600 . ?
C31 H31C 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
O2 S1 O4 109.7 . . ?
O2 S1 O5 109.1 . . ?
O4 S1 O5 109.8 . . ?
O2 S1 O3 109.9 . . ?
O4 S1 O3 109.0 . . ?
O5 S1 O3 109.3 . . ?
S1 O4 H4 109.5 . . ?
O2B S1B O4B 109.7 . . ?
O2B S1B O3B 109.9 . . ?
O4B S1B O3B 109.0 . . ?
O2B S1B O5B 109.1 . . ?
O4B S1B O5B 109.8 . . ?
O3B S1B O5B 109.3 . . ?
S1B O5B H5B 109.5 . . ?
O2C S1C O4C 109.7 . . ?
O2C S1C O5C 109.1 . . ?
O4C S1C O5C 109.8 . . ?
O2C S1C O3C 109.9 . . ?
O4C S1C O3C 109.0 . . ?
O5C S1C O3C 109.3 . . ?
S1C O3C H3C 109.5 . . ?
C12 O11 H11 110.2 . . ?
C20 N30 C29 110.9(5) . . ?
C20 N30 C31 127.4(5) . . ?
C29 N30 C31 121.7(5) . . ?
O34 N32 O33 120.8(8) . . ?
O34 N32 C15 121.0(7) . . ?
O33 N32 C15 117.9(7) . . ?
O11 C12 C13 122.4(6) . . ?
O11 C12 C17 118.2(6) . . ?
C13 C12 C17 119.3(7) . . ?
C12 C13 C14 122.3(6) . . ?
C12 C13 H13 118.8 . . ?
C14 C13 H13 118.8 . . ?
C13 C14 C15 116.5(7) . . ?
C13 C14 H14 121.7 . . ?
C15 C14 H14 121.7 . . ?
C16 C15 C14 123.1(7) . . ?
C16 C15 N32 118.1(7) . . ?
C14 C15 N32 118.6(8) . . ?
C15 C16 C17 119.1(6) . . ?
C15 C16 H16 120.4 . . ?
C17 C16 H16 120.4 . . ?
C16 C17 C12 119.5(6) . . ?
C16 C17 C18 123.8(5) . . ?
C12 C17 C18 116.7(6) . . ?
C19 C18 C17 128.0(5) . . ?
C19 C18 H18 116.0 . . ?
C17 C18 H18 116.0 . . ?
C18 C19 C20 124.0(5) . . ?
C18 C19 H19 118.0 . . ?
C20 C19 H19 118.0 . . ?
N30 C20 C19 122.2(6) . . ?
N30 C20 C21 110.5(5) . . ?
C19 C20 C21 127.3(5) . . ?
C24 C21 C20 101.0(5) . . ?
C24 C21 C23 111.2(7) . . ?
C20 C21 C23 111.9(7) . . ?
C24 C21 C22 109.9(7) . . ?
C20 C21 C22 110.5(7) . . ?
C23 C21 C22 111.8(6) . . ?
C21 C22 H22A 109.5 . . ?
C21 C22 H22B 109.5 . . ?
H22A C22 H22B 109.5 . . ?
C21 C22 H22C 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
C21 C23 H23A 109.5 . . ?
C21 C23 H23B 109.5 . . ?
H23A C23 H23B 109.5 . . ?
C21 C23 H23C 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 109.5 . . ?
C25 C24 C29 118.9(7) . . ?
C25 C24 C21 131.1(7) . . ?
C29 C24 C21 110.1(6) . . ?
C24 C25 C26 119.7(7) . . ?
C24 C25 H25 120.2 . . ?
C26 C25 H25 120.2 . . ?
C27 C26 C25 119.8(7) . . ?
C27 C26 H26 120.1 . . ?
C25 C26 H26 120.1 . . ?
C26 C27 C28 121.9(7) . . ?
C26 C27 H27 119.0 . . ?
C28 C27 H27 119.0 . . ?
C29 C28 C27 116.6(7) . . ?
C29 C28 H28 121.7 . . ?
C27 C28 H28 121.7 . . ?
C28 C29 C24 123.1(7) . . ?
C28 C29 N30 129.4(7) . . ?
C24 C29 N30 107.5(6) . . ?
N30 C31 H31A 109.5 . . ?
N30 C31 H31B 109.5 . . ?
H31A C31 H31B 109.5 . . ?
N30 C31 H31C 109.5 . . ?
H31A C31 H31C 109.5 . . ?
H31B C31 H31C 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
O11 C12 C13 C14 179.8(7) . . . . ?
C17 C12 C13 C14 -0.7(12) . . . . ?
C12 C13 C14 C15 1.3(12) . . . . ?
C13 C14 C15 C16 -2.3(12) . . . . ?
C13 C14 C15 N32 -178.3(7) . . . . ?
O34 N32 C15 C16 8.4(14) . . . . ?
O33 N32 C15 C16 -177.1(8) . . . . ?
O34 N32 C15 C14 -175.5(9) . . . . ?
O33 N32 C15 C14 -0.9(13) . . . . ?
C14 C15 C16 C17 2.6(11) . . . . ?
N32 C15 C16 C17 178.6(7) . . . . ?
C15 C16 C17 C12 -1.8(11) . . . . ?
C15 C16 C17 C18 180.0(7) . . . . ?
O11 C12 C17 C16 -179.6(6) . . . . ?
C13 C12 C17 C16 0.8(11) . . . . ?
O11 C12 C17 C18 -1.2(10) . . . . ?
C13 C12 C17 C18 179.2(7) . . . . ?
C16 C17 C18 C19 0.4(12) . . . . ?
C12 C17 C18 C19 -178.0(7) . . . . ?
C17 C18 C19 C20 179.8(7) . . . . ?
C29 N30 C20 C19 -179.3(6) . . . . ?
C31 N30 C20 C19 -0.2(12) . . . . ?
C29 N30 C20 C21 -0.2(9) . . . . ?
C31 N30 C20 C21 178.9(7) . . . . ?
C18 C19 C20 N30 179.9(7) . . . . ?
C18 C19 C20 C21 1.0(12) . . . . ?
N30 C20 C21 C24 0.7(10) . . . . ?
C19 C20 C21 C24 179.7(7) . . . . ?
N30 C20 C21 C23 -117.7(7) . . . . ?
C19 C20 C21 C23 61.3(10) . . . . ?
N30 C20 C21 C22 117.0(7) . . . . ?
C19 C20 C21 C22 -64.0(10) . . . . ?
C20 C21 C24 C25 179.6(8) . . . . ?
C23 C21 C24 C25 -61.5(11) . . . . ?
C22 C21 C24 C25 62.9(12) . . . . ?
C20 C21 C24 C29 -1.0(10) . . . . ?
C23 C21 C24 C29 117.9(7) . . . . ?
C22 C21 C24 C29 -117.7(7) . . . . ?
C29 C24 C25 C26 1.3(12) . . . . ?
C21 C24 C25 C26 -179.4(10) . . . . ?
C24 C25 C26 C27 -2.1(14) . . . . ?
C25 C26 C27 C28 2.6(15) . . . . ?
C26 C27 C28 C29 -2.3(13) . . . . ?
C27 C28 C29 C24 1.5(12) . . . . ?
C27 C28 C29 N30 179.7(7) . . . . ?
C25 C24 C29 C28 -1.0(12) . . . . ?
C21 C24 C29 C28 179.5(8) . . . . ?
C25 C24 C29 N30 -179.6(7) . . . . ?
C21 C24 C29 N30 0.9(9) . . . . ?
C20 N30 C29 C28 -178.9(8) . . . . ?
C31 N30 C29 C28 2.0(12) . . . . ?
C20 N30 C29 C24 -0.4(9) . . . . ?
C31 N30 C29 C24 -179.6(7) . . . . ?

_refine_diff_density_max         0.124
_refine_diff_density_min         -0.177
_refine_diff_density_rms         0.032


# start Validation Reply Form
_vrf_THETM01_nt0143_Vanessa_KC-SPNO2_H2SO4_ACN 
;
PROBLEM: The value of sine(theta_max)/wavelength is less than 0.550
RESPONSE: Even the best selected crystal was weakly diffracting,
despite the use of Cu radiation and presence of S atom in the structure. 
All tested crystal had high mosaicity and were twinned, also the sulfate anion 
in the structure is disordered. The lack of reflections also led to a number 
of aditional problems (see below). 
However, all the non-H atoms could be located in the 
electron difference map, and the overall shape of the molecule as well as the
packing of molecules can be considered to be reasonably determined.
 
;
_vrf_PLAT088_nt0143_Vanessa_KC-SPNO2_H2SO4_ACN 
;
PROBLEM: Poor Data / Parameter Ratio ....................       6.11 Note  
RESPONSE: Even the best selected crystal was weakly diffracting,
despite the use of Cu radiation and presence of S atom in the structure.
All hydrogen atoms are already refined in riding mode to 
minimize number of parameters.
;
_vrf_PLAT214_nt0143_Vanessa_KC-SPNO2_H2SO4_ACN 
;
PROBLEM: Atom O2B       (Anion/Solvent) ADP max/min Ratio        5.3 prolat
RESPONSE: See above.
;
_vrf_PLAT340_nt0143_Vanessa_KC-SPNO2_H2SO4_ACN 
;
PROBLEM: Low Bond Precision on  C-C Bonds ...............    0.01132 Ang.  
RESPONSE: See above.
;
# start Validation Reply Form
_vrf_PLAT026_nt0143_Vanessa_KC-SPNO2_H2SO4_ACN 
;
PROBLEM: Ratio Observed / Unique Reflections (too) Low ..        43% Check 
RESPONSE: See above.
;
_vrf_PLAT029_nt0143_Vanessa_KC-SPNO2_H2SO4_ACN 
;
PROBLEM: _diffrn_measured_fraction_theta_full value Low .      0.965 Why?  
RESPONSE: See above.
;
_vrf_PLAT230_nt0143_Vanessa_KC-SPNO2_H2SO4_ACN 
;
PROBLEM: Hirshfeld Test Diff for  N32      --C15       ..        5.2 s.u.  
RESPONSE: See above.
;
_vrf_PLAT234_nt0143_Vanessa_KC-SPNO2_H2SO4_ACN 
;
PROBLEM: Large Hirshfeld Difference N30      -- C31             0.19 Ang.  
RESPONSE: See above.
;
_vrf_PLAT241_nt0143_Vanessa_KC-SPNO2_H2SO4_ACN 
;
PROBLEM: High   'MainMol' Ueq as Compared to Neighbors of        C13 Check 
RESPONSE: See above.
;
_vrf_PLAT242_nt0143_Vanessa_KC-SPNO2_H2SO4_ACN 
;
PROBLEM: Low    'MainMol' Ueq as Compared to Neighbors of        C12 Check 
RESPONSE: See above.
;
_vrf_PLAT250_nt0143_Vanessa_KC-SPNO2_H2SO4_ACN 
;
PROBLEM: Large U3/U1 Ratio for Average U(i,j) Tensor ....        2.3 Note  
RESPONSE: ...
;
_vrf_PLAT334_nt0143_Vanessa_KC-SPNO2_H2SO4_ACN 
;
PROBLEM: Small Aver. Benzene C-C Dist C24      -C29             1.37 Ang.  
RESPONSE: See above.
;
_vrf_PLAT906_nt0143_Vanessa_KC-SPNO2_H2SO4_ACN 
;
PROBLEM: Large K Value in the Analysis of Variance ......      8.805 Check 
RESPONSE: See above.
;
_vrf_PLAT910_nt0143_Vanessa_KC-SPNO2_H2SO4_ACN 
;
PROBLEM: Missing # of FCF Reflection(s) Below Theta(Min).          8 Note  
RESPONSE: These reflections are missing because of the instrument
 geometry limitation.
;
_vrf_PLAT911_nt0143_Vanessa_KC-SPNO2_H2SO4_ACN 
;
PROBLEM: Missing FCF Refl Between Thmin & STh/L=    0.501         73 Report
RESPONSE: These reflections are missing because of the instrument
 geometry limitation.
;
_vrf_PLAT913_nt0143_Vanessa_KC-SPNO2_H2SO4_ACN 
;
PROBLEM: Missing # of Very Strong Reflections in FCF ....          7 Note  
RESPONSE: These reflections are missing because of the instrument
 geometry limitation.
;
# end Validation Reply Form
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: Acetonitrile'
####################################################################### 
# 
# 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_VS-SPNO2-HNO3-ACN-gr
_database_code_depnum_ccdc_archive 'CCDC 1824263'
_audit_update_record             
;
2018-02-15 deposited with the CCDC.
2018-04-06 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2016/4
_shelx_SHELXL_version_number     2016/4
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C19 H17 N3 O5'
_chemical_formula_sum            'C19 H17 N3 O5'
_chemical_formula_weight         367.35

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

_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.
;

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

_cell_length_a                   18.8741(12)
_cell_length_b                   6.2632(3)
_cell_length_c                   14.2571(7)
_cell_angle_alpha                90
_cell_angle_beta                 98.548(6)
_cell_angle_gamma                90
_cell_volume                     1666.65(16)
_cell_formula_units_Z            4
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    4346
_cell_measurement_theta_min      3.2350
_cell_measurement_theta_max      25.4830

_exptl_crystal_description       block
_exptl_crystal_colour            'pale green'
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.464
_exptl_crystal_F_000             768
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.400
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.150
_exptl_absorpt_coefficient_mu    0.108
_shelx_estimated_absorpt_T_min   0.958
_shelx_estimated_absorpt_T_max   0.984
_exptl_absorpt_correction_T_min  0.87056
_exptl_absorpt_correction_T_max  1.00000
_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_absorpt_special_details   ?
_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'Rigaku UltraX 18 rotating anode'
_diffrn_measurement_device_type  'MAR345 image plate'
_diffrn_measurement_method       '113 images, ΔΦ 2.0° '
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            3092
_diffrn_reflns_av_unetI/netI     0.0429
_diffrn_reflns_av_R_equivalents  ?
_diffrn_reflns_limit_h_min       -22
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         3.237
_diffrn_reflns_theta_max         25.573
_diffrn_reflns_theta_full        25.000
_diffrn_measured_fraction_theta_max 0.990
_diffrn_measured_fraction_theta_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.990
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.990
_diffrn_reflns_point_group_measured_fraction_full 0.995
_reflns_number_total             3092
_reflns_number_gt                2804
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 _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.
;

_computing_data_collection       MAR
_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_structure_solution    'SHELXT (Sheldrick, 2015)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'MERCURY (Macrae et al., 2008)'
_computing_publication_material  
;
'MERCURY (Macrae et al., 2008), Platon (Spek, 2009)'
;

_refine_special_details          'Refined as a 2-component twin.,Twin'
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0541P)²+3.7000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3092
_refine_ls_number_parameters     248
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0782
_refine_ls_R_factor_gt           0.0713
_refine_ls_wR_factor_ref         0.1773
_refine_ls_wR_factor_gt          0.1728
_refine_ls_goodness_of_fit_ref   1.063
_refine_ls_restrained_S_all      1.063
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.69871(12) 0.6024(4) 0.44209(16) 0.0327(6) Uani 1 1 d . . . . .
C2 C 0.62916(17) 0.5459(5) 0.4198(2) 0.0290(7) Uani 1 1 d . . . . .
C3 C 0.58242(18) 0.6965(6) 0.3736(2) 0.0334(8) Uani 1 1 d . . . . .
H3 H 0.599645 0.833345 0.359220 0.040 Uiso 1 1 calc R U . . .
C4 C 0.51091(18) 0.6466(6) 0.3486(2) 0.0347(8) Uani 1 1 d . . . . .
H4 H 0.478603 0.748040 0.316426 0.042 Uiso 1 1 calc R U . . .
C5 C 0.48684(18) 0.4468(6) 0.3710(2) 0.0342(8) Uani 1 1 d . . . . .
C6 C 0.53200(19) 0.2986(6) 0.4196(2) 0.0346(8) Uani 1 1 d . . . . .
H6 H 0.513764 0.164361 0.435808 0.041 Uiso 1 1 calc R U . . .
C7 C 0.60399(18) 0.3451(5) 0.4448(2) 0.0316(7) Uani 1 1 d . . . . .
C8 C 0.6544(2) 0.2042(6) 0.5010(2) 0.0358(8) Uani 1 1 d . . . . .
H8 H 0.637816 0.079331 0.528710 0.043 Uiso 1 1 calc R U . . .
C9 C 0.72364(19) 0.2499(6) 0.5138(2) 0.0366(8) Uani 1 1 d . . . . .
H9 H 0.755411 0.158290 0.553058 0.044 Uiso 1 1 calc R U . . .
C10 C 0.75444(18) 0.4383(6) 0.4694(2) 0.0320(7) Uani 1 1 d . . . . .
C11 C 0.79305(18) 0.3822(6) 0.3808(2) 0.0309(7) Uani 1 1 d . . . . .
C12 C 0.8176(2) 0.1496(6) 0.3852(3) 0.0410(9) Uani 1 1 d . . . . .
H12A H 0.848192 0.124075 0.336498 0.061 Uiso 1 1 calc R U . . .
H12B H 0.775712 0.055595 0.374112 0.061 Uiso 1 1 calc R U . . .
H12C H 0.844759 0.119856 0.447965 0.061 Uiso 1 1 calc R U . . .
C13 C 0.74629(19) 0.4273(7) 0.2860(2) 0.0405(9) Uani 1 1 d . . . . .
H13A H 0.729905 0.575910 0.284627 0.061 Uiso 1 1 calc R U . . .
H13B H 0.704731 0.331675 0.278390 0.061 Uiso 1 1 calc R U . . .
H13C H 0.774198 0.403320 0.234278 0.061 Uiso 1 1 calc R U . . .
C14 C 0.85862(18) 0.5247(5) 0.3989(2) 0.0300(7) Uani 1 1 d . . . . .
C15 C 0.91056(18) 0.5601(5) 0.3430(2) 0.0310(7) Uani 1 1 d . . . . .
H15 H 0.905726 0.508093 0.279768 0.037 Uiso 1 1 calc R U . . .
C16 C 0.97097(17) 0.6757(5) 0.3828(2) 0.0311(7) Uani 1 1 d . . . . .
C17 C 0.97898(18) 0.7523(6) 0.4744(2) 0.0345(8) Uani 1 1 d . . . . .
H17 H 1.021516 0.826196 0.499667 0.041 Uiso 1 1 calc R U . . .
C18 C 0.92568(19) 0.7226(6) 0.5296(2) 0.0347(8) Uani 1 1 d . . . . .
H18 H 0.929815 0.779809 0.591851 0.042 Uiso 1 1 calc R U . . .
N20 N 0.80875(15) 0.5449(5) 0.53379(19) 0.0353(7) Uani 1 1 d . . . . .
C21 C 0.7964(2) 0.6213(7) 0.6265(2) 0.0437(9) Uani 1 1 d . . . . .
H21A H 0.838813 0.592400 0.673372 0.066 Uiso 1 1 calc R U . . .
H21B H 0.754875 0.547585 0.645155 0.066 Uiso 1 1 calc R U . . .
H21C H 0.787258 0.775360 0.623425 0.066 Uiso 1 1 calc R U . . .
N22 N 0.41104(17) 0.3924(6) 0.3439(2) 0.0438(8) Uani 1 1 d . . . . .
O23 O 0.39028(16) 0.2182(6) 0.3670(2) 0.0594(9) Uani 1 1 d . . . . .
O24 O 0.37225(15) 0.5234(5) 0.2976(2) 0.0557(8) Uani 1 1 d . . . . .
N25 N 1.02965(15) 0.7003(5) 0.3282(2) 0.0348(7) Uani 1 1 d . . . . .
O26 O 1.02375(14) 0.6252(5) 0.24771(19) 0.0449(7) Uani 1 1 d . . . . .
O27 O 1.08448(13) 0.7954(4) 0.36477(19) 0.0444(7) Uani 1 1 d . . . . .
C28 C 0.86572(18) 0.6060(5) 0.4910(2) 0.0309(7) Uani 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C2 1.351(4) . ?
O1 C10 1.481(4) . ?
C2 C3 1.389(5) . ?
C2 C7 1.409(5) . ?
C3 C4 1.380(5) . ?
C3 H3 0.9500 . ?
C4 C5 1.385(5) . ?
C4 H4 0.9500 . ?
C5 C6 1.376(5) . ?
C5 N22 1.466(5) . ?
C6 C7 1.384(5) . ?
C6 H6 0.9500 . ?
C7 C8 1.449(5) . ?
C8 C9 1.323(5) . ?
C8 H8 0.9500 . ?
C9 C10 1.497(5) . ?
C9 H9 0.9500 . ?
C10 N20 1.435(4) . ?
C10 C11 1.589(5) . ?
C11 C14 1.517(5) . ?
C11 C13 1.526(5) . ?
C11 C12 1.527(5) . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12C 0.9800 . ?
C13 H13A 0.9800 . ?
C13 H13B 0.9800 . ?
C13 H13C 0.9800 . ?
C14 C15 1.370(5) . ?
C14 C28 1.396(5) . ?
C15 C16 1.398(5) . ?
C15 H15 0.9500 . ?
C16 C17 1.378(5) . ?
C16 N25 1.454(4) . ?
C17 C18 1.379(5) . ?
C17 H17 0.9500 . ?
C18 C28 1.390(5) . ?
C18 H18 0.9500 . ?
N20 C28 1.367(4) . ?
N20 C21 1.457(4) . ?
C21 H21A 0.9800 . ?
C21 H21B 0.9800 . ?
C21 H21C 0.9800 . ?
N22 O23 1.221(5) . ?
N22 O24 1.225(4) . ?
N25 O26 1.230(4) . ?
N25 O27 1.240(4) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 O1 C10 120.5(3) . . ?
O1 C2 C3 117.4(3) . . ?
O1 C2 C7 121.8(3) . . ?
C3 C2 C7 120.8(3) . . ?
C4 C3 C2 119.8(3) . . ?
C4 C3 H3 120.1 . . ?
C2 C3 H3 120.1 . . ?
C3 C4 C5 119.1(3) . . ?
C3 C4 H4 120.4 . . ?
C5 C4 H4 120.4 . . ?
C6 C5 C4 121.7(3) . . ?
C6 C5 N22 118.9(3) . . ?
C4 C5 N22 119.4(3) . . ?
C5 C6 C7 120.0(3) . . ?
C5 C6 H6 120.0 . . ?
C7 C6 H6 120.0 . . ?
C6 C7 C2 118.5(3) . . ?
C6 C7 C8 123.7(3) . . ?
C2 C7 C8 117.7(3) . . ?
C9 C8 C7 119.9(3) . . ?
C9 C8 H8 120.1 . . ?
C7 C8 H8 120.1 . . ?
C8 C9 C10 123.4(3) . . ?
C8 C9 H9 118.3 . . ?
C10 C9 H9 118.3 . . ?
N20 C10 O1 104.9(3) . . ?
N20 C10 C9 112.5(3) . . ?
O1 C10 C9 110.7(3) . . ?
N20 C10 C11 104.1(3) . . ?
O1 C10 C11 109.6(2) . . ?
C9 C10 C11 114.5(3) . . ?
C14 C11 C13 113.0(3) . . ?
C14 C11 C12 108.6(3) . . ?
C13 C11 C12 110.2(3) . . ?
C14 C11 C10 101.2(3) . . ?
C13 C11 C10 112.9(3) . . ?
C12 C11 C10 110.5(3) . . ?
C11 C12 H12A 109.5 . . ?
C11 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
C11 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C11 C13 H13A 109.5 . . ?
C11 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
C11 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
C15 C14 C28 120.7(3) . . ?
C15 C14 C11 129.2(3) . . ?
C28 C14 C11 109.7(3) . . ?
C14 C15 C16 117.3(3) . . ?
C14 C15 H15 121.4 . . ?
C16 C15 H15 121.4 . . ?
C17 C16 C15 122.2(3) . . ?
C17 C16 N25 119.1(3) . . ?
C15 C16 N25 118.5(3) . . ?
C16 C17 C18 120.5(3) . . ?
C16 C17 H17 119.8 . . ?
C18 C17 H17 119.8 . . ?
C17 C18 C28 117.8(3) . . ?
C17 C18 H18 121.1 . . ?
C28 C18 H18 121.1 . . ?
C28 N20 C10 112.3(3) . . ?
C28 N20 C21 123.7(3) . . ?
C10 N20 C21 122.5(3) . . ?
N20 C21 H21A 109.5 . . ?
N20 C21 H21B 109.5 . . ?
H21A C21 H21B 109.5 . . ?
N20 C21 H21C 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
O23 N22 O24 123.6(3) . . ?
O23 N22 C5 118.5(3) . . ?
O24 N22 C5 117.9(3) . . ?
O26 N25 O27 122.0(3) . . ?
O26 N25 C16 119.3(3) . . ?
O27 N25 C16 118.7(3) . . ?
N20 C28 C18 128.2(3) . . ?
N20 C28 C14 110.2(3) . . ?
C18 C28 C14 121.5(3) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C10 O1 C2 C3 -165.0(3) . . . . ?
C10 O1 C2 C7 17.0(4) . . . . ?
O1 C2 C3 C4 179.6(3) . . . . ?
C7 C2 C3 C4 -2.4(5) . . . . ?
C2 C3 C4 C5 0.6(5) . . . . ?
C3 C4 C5 C6 1.6(5) . . . . ?
C3 C4 C5 N22 -179.5(3) . . . . ?
C4 C5 C6 C7 -2.0(5) . . . . ?
N22 C5 C6 C7 179.1(3) . . . . ?
C5 C6 C7 C2 0.1(5) . . . . ?
C5 C6 C7 C8 176.0(3) . . . . ?
O1 C2 C7 C6 180.0(3) . . . . ?
C3 C2 C7 C6 2.1(5) . . . . ?
O1 C2 C7 C8 3.8(5) . . . . ?
C3 C2 C7 C8 -174.0(3) . . . . ?
C6 C7 C8 C9 172.9(3) . . . . ?
C2 C7 C8 C9 -11.2(5) . . . . ?
C7 C8 C9 C10 -2.6(5) . . . . ?
C2 O1 C10 N20 -149.6(3) . . . . ?
C2 O1 C10 C9 -28.1(4) . . . . ?
C2 O1 C10 C11 99.1(3) . . . . ?
C8 C9 C10 N20 138.2(4) . . . . ?
C8 C9 C10 O1 21.1(5) . . . . ?
C8 C9 C10 C11 -103.3(4) . . . . ?
N20 C10 C11 C14 -15.5(3) . . . . ?
O1 C10 C11 C14 96.3(3) . . . . ?
C9 C10 C11 C14 -138.7(3) . . . . ?
N20 C10 C11 C13 -136.6(3) . . . . ?
O1 C10 C11 C13 -24.8(4) . . . . ?
C9 C10 C11 C13 100.2(4) . . . . ?
N20 C10 C11 C12 99.4(3) . . . . ?
O1 C10 C11 C12 -148.8(3) . . . . ?
C9 C10 C11 C12 -23.8(4) . . . . ?
C13 C11 C14 C15 -53.6(5) . . . . ?
C12 C11 C14 C15 69.0(4) . . . . ?
C10 C11 C14 C15 -174.7(3) . . . . ?
C13 C11 C14 C28 133.4(3) . . . . ?
C12 C11 C14 C28 -104.0(3) . . . . ?
C10 C11 C14 C28 12.4(3) . . . . ?
C28 C14 C15 C16 1.4(5) . . . . ?
C11 C14 C15 C16 -170.9(3) . . . . ?
C14 C15 C16 C17 0.0(5) . . . . ?
C14 C15 C16 N25 174.9(3) . . . . ?
C15 C16 C17 C18 -2.1(5) . . . . ?
N25 C16 C17 C18 -176.9(3) . . . . ?
C16 C17 C18 C28 2.6(5) . . . . ?
O1 C10 N20 C28 -100.7(3) . . . . ?
C9 C10 N20 C28 139.0(3) . . . . ?
C11 C10 N20 C28 14.5(4) . . . . ?
O1 C10 N20 C21 66.1(4) . . . . ?
C9 C10 N20 C21 -54.3(4) . . . . ?
C11 C10 N20 C21 -178.8(3) . . . . ?
C6 C5 N22 O23 1.3(5) . . . . ?
C4 C5 N22 O23 -177.6(3) . . . . ?
C6 C5 N22 O24 -177.3(3) . . . . ?
C4 C5 N22 O24 3.8(5) . . . . ?
C17 C16 N25 O26 177.3(3) . . . . ?
C15 C16 N25 O26 2.3(5) . . . . ?
C17 C16 N25 O27 -2.2(5) . . . . ?
C15 C16 N25 O27 -177.2(3) . . . . ?
C10 N20 C28 C18 176.0(3) . . . . ?
C21 N20 C28 C18 9.5(6) . . . . ?
C10 N20 C28 C14 -7.0(4) . . . . ?
C21 N20 C28 C14 -173.5(3) . . . . ?
C17 C18 C28 N20 175.5(3) . . . . ?
C17 C18 C28 C14 -1.2(5) . . . . ?
C15 C14 C28 N20 -178.1(3) . . . . ?
C11 C14 C28 N20 -4.4(4) . . . . ?
C15 C14 C28 C18 -0.9(5) . . . . ?
C11 C14 C28 C18 172.8(3) . . . . ?

_refine_diff_density_max         0.269
_refine_diff_density_min         -0.250
_refine_diff_density_rms         0.053


_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: acetonitrile'
####################################################################### 
# 
# 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_nt0159_KC-SPOMe_H3PO4_ACN
_database_code_depnum_ccdc_archive 'CCDC 1824256'
_audit_update_record             
;
2018-02-15 deposited with the CCDC.
2018-04-06 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/1
_shelx_SHELXL_version_number     2018/1
_chemical_name_systematic        
'tetrakis(2-[(E)-2-(2-hydroxy-3-methoxyphenyl)ethenyl]-1,3,3-trimethyl-3H-indol-1-ium) tris(phosphoric acid) nonahydrate tetradihydrogen phosphate'
_chemical_name_common            
'tetrakis(2-[(E)-2-(2-hydroxy-3-methoxyphenyl)ethenyl]-1,3,3-trimethyl-3H-indol-1-ium) tris(phosphoric acid) nonahydrate tetradihydrogen phosphate'
_chemical_melting_point          ?
_chemical_formula_moiety         
'2(C20 H22 N O2), 2(H2 O4 P), 1.5(H3 O4 P), 4.5(H2O)'
_chemical_formula_sum            'C40 H60.50 N2 O22.50 P3.50'
_chemical_formula_weight         1037.80

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'
N N 0.0311 0.0180 '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'
P P 0.2955 0.4335 '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'

_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.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   12.0289(5)
_cell_length_b                   12.4435(5)
_cell_length_c                   17.4047(7)
_cell_angle_alpha                76.128(4)
_cell_angle_beta                 81.814(4)
_cell_angle_gamma                79.953(4)
_cell_volume                     2476.57(19)
_cell_formula_units_Z            2
_cell_measurement_temperature    295(2)
_cell_measurement_reflns_used    5428
_cell_measurement_theta_min      2.6230
_cell_measurement_theta_max      62.0630

_exptl_crystal_description       block
_exptl_crystal_colour            red
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.392
_exptl_crystal_F_000             1094
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.110
_exptl_crystal_size_mid          0.090
_exptl_crystal_size_min          0.080
_exptl_absorpt_coefficient_mu    1.971
_shelx_estimated_absorpt_T_min   0.812
_shelx_estimated_absorpt_T_max   0.858
_exptl_absorpt_correction_T_min  0.866
_exptl_absorpt_correction_T_max  0.891
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.46 (Rigaku Oxford Diffraction, 2015)
Analytical numeric absorption correction using a multifaceted crystal
model based on expressions derived by R.C. Clark & J.S. Reid.
(Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      295(2)
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_type           CuK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_radiation_monochromator  'multilayer mirror'
_diffrn_measurement_device_type  
;
Oxford Diffraction Xcalibur, Ruby, Gemini ultra
;
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean 5.1856
_diffrn_reflns_number            15421
_diffrn_reflns_av_unetI/netI     0.0330
_diffrn_reflns_av_R_equivalents  0.0244
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         2.630
_diffrn_reflns_theta_max         62.520
_diffrn_reflns_theta_full        62.520
_diffrn_measured_fraction_theta_max 0.970
_diffrn_measured_fraction_theta_full 0.970
_diffrn_reflns_Laue_measured_fraction_max 0.970
_diffrn_reflns_Laue_measured_fraction_full 0.970
_diffrn_reflns_point_group_measured_fraction_max 0.970
_diffrn_reflns_point_group_measured_fraction_full 0.970
_reflns_number_total             7672
_reflns_number_gt                5767
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_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.
;

_computing_data_collection       'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_cell_refinement       'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_structure_solution    'SHELXT (Sheldrick, 2015)'
_computing_structure_refinement  'SHELXL-2018/1 (Sheldrick, 2018)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0889P)²+0.9168P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         7672
_refine_ls_number_parameters     722
_refine_ls_number_restraints     133
_refine_ls_R_factor_all          0.0726
_refine_ls_R_factor_gt           0.0536
_refine_ls_wR_factor_ref         0.1599
_refine_ls_wR_factor_gt          0.1423
_refine_ls_goodness_of_fit_ref   1.012
_refine_ls_restrained_S_all      1.022
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

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
O1A O 0.47059(17) 0.27248(17) 0.89184(13) 0.0640(6) Uani 1 1 d . . . . .
H1A H 0.427775 0.326500 0.903428 0.096 Uiso 1 1 calc R U . . .
C2A C 0.4204(2) 0.2270(3) 0.84545(17) 0.0550(7) Uani 1 1 d . . . . .
C3A C 0.3187(3) 0.2812(3) 0.81544(18) 0.0601(8) Uani 1 1 d . . . . .
C4A C 0.2691(3) 0.2376(3) 0.76588(19) 0.0713(9) Uani 1 1 d . . . . .
H4A H 0.200720 0.273717 0.746849 0.086 Uiso 1 1 calc R U . . .
C5A C 0.3215(3) 0.1396(4) 0.7445(2) 0.0813(10) Uani 1 1 d . . . . .
H5A H 0.289380 0.111267 0.709340 0.098 Uiso 1 1 calc R U . . .
C6A C 0.4203(3) 0.0835(3) 0.7743(2) 0.0757(10) Uani 1 1 d . . . . .
H6A H 0.453856 0.017418 0.759312 0.091 Uiso 1 1 calc R U . . .
C7A C 0.4718(3) 0.1243(3) 0.82728(18) 0.0619(8) Uani 1 1 d . . . . .
C8A C 0.5712(3) 0.0574(3) 0.86122(19) 0.0642(8) Uani 1 1 d . . . . .
H8A H 0.604666 -0.002520 0.838521 0.077 Uiso 1 1 calc R U . . .
C9A C 0.6210(3) 0.0717(3) 0.92185(19) 0.0616(8) Uani 1 1 d . . . . .
H9A H 0.590321 0.133283 0.943463 0.074 Uiso 1 1 calc R U . . .
C10A C 0.7163(3) 0.0014(2) 0.95597(17) 0.0557(7) Uani 1 1 d . . . . .
C11A C 0.7863(3) -0.1034(2) 0.93330(18) 0.0581(7) Uani 1 1 d . . . . .
C12A C 0.7123(3) -0.1965(3) 0.9440(2) 0.0761(9) Uani 1 1 d . . . . .
H12A H 0.759909 -0.265017 0.937907 0.114 Uiso 1 1 calc R U . . .
H12B H 0.659488 -0.175440 0.904589 0.114 Uiso 1 1 calc R U . . .
H12C H 0.671293 -0.207070 0.996128 0.114 Uiso 1 1 calc R U . . .
C13A C 0.8451(3) -0.0764(3) 0.84756(19) 0.0707(9) Uani 1 1 d . . . . .
H13A H 0.886465 -0.015015 0.841371 0.106 Uiso 1 1 calc R U . . .
H13B H 0.788844 -0.056629 0.810618 0.106 Uiso 1 1 calc R U . . .
H13C H 0.896516 -0.140909 0.837357 0.106 Uiso 1 1 calc R U . . .
C14A C 0.8714(3) -0.1345(2) 0.99315(18) 0.0571(7) Uani 1 1 d . . . . .
C15A C 0.9597(3) -0.2226(3) 1.0065(2) 0.0697(9) Uani 1 1 d . . . . .
H15A H 0.975157 -0.274769 0.974623 0.084 Uiso 1 1 calc R U . . .
C16A C 1.0239(3) -0.2312(3) 1.0677(2) 0.0750(9) Uani 1 1 d . . . . .
H16A H 1.082905 -0.290296 1.077288 0.090 Uiso 1 1 calc R U . . .
C17A C 1.0025(3) -0.1536(3) 1.1153(2) 0.0730(9) Uani 1 1 d . . . . .
H17A H 1.047781 -0.161094 1.155887 0.088 Uiso 1 1 calc R U . . .
C18A C 0.9152(3) -0.0655(3) 1.10331(19) 0.0657(8) Uani 1 1 d . . . . .
H18A H 0.899853 -0.013129 1.135041 0.079 Uiso 1 1 calc R U . . .
C19A C 0.8519(3) -0.0590(2) 1.04183(18) 0.0563(7) Uani 1 1 d . . . . .
N20A N 0.7572(2) 0.02150(19) 1.01701(15) 0.0572(6) Uani 1 1 d . . . . .
C21A C 0.7154(3) 0.1140(3) 1.0572(2) 0.0748(10) Uani 1 1 d . . . . .
H21A H 0.697347 0.084533 1.112993 0.112 Uiso 0.5 1 calc R U P . .
H21B H 0.648464 0.156890 1.034953 0.112 Uiso 0.5 1 calc R U P . .
H21C H 0.772885 0.161266 1.049954 0.112 Uiso 0.5 1 calc R U P . .
H21D H 0.715117 0.183927 1.018940 0.112 Uiso 0.5 1 calc R U P . .
H21E H 0.764000 0.111569 1.096980 0.112 Uiso 0.5 1 calc R U P . .
H21F H 0.639579 0.107193 1.081979 0.112 Uiso 0.5 1 calc R U P . .
O22A O 0.27887(19) 0.3790(2) 0.84001(14) 0.0745(6) Uani 1 1 d . . . . .
C23A C 0.1745(3) 0.4409(3) 0.8154(3) 0.0882(11) Uani 1 1 d . . . . .
H23A H 0.181486 0.464900 0.758465 0.132 Uiso 1 1 calc R U . . .
H23B H 0.155798 0.505134 0.838758 0.132 Uiso 1 1 calc R U . . .
H23C H 0.115669 0.394609 0.832342 0.132 Uiso 1 1 calc R U . . .
O1B O -0.03219(16) 0.46297(18) 0.71676(12) 0.0633(5) Uani 1 1 d . . . . .
H1B H -0.072106 0.498472 0.747210 0.095 Uiso 1 1 calc R U . . .
C2B C -0.0853(2) 0.3803(3) 0.70887(17) 0.0542(7) Uani 1 1 d . . . . .
C3B C -0.1876(2) 0.3602(3) 0.75589(18) 0.0606(8) Uani 1 1 d . . . . .
C4B C -0.2433(3) 0.2761(3) 0.7490(2) 0.0733(9) Uani 1 1 d . . . . .
H4B H -0.312306 0.264851 0.779049 0.088 Uiso 1 1 calc R U . . .
C5B C -0.1957(3) 0.2082(3) 0.6967(2) 0.0806(10) Uani 1 1 d . . . . .
H5B H -0.231784 0.149528 0.693157 0.097 Uiso 1 1 calc R U . . .
C6B C -0.0963(3) 0.2264(3) 0.6503(2) 0.0757(9) Uani 1 1 d . . . . .
H6B H -0.065939 0.179539 0.615840 0.091 Uiso 1 1 calc R U . . .
C7B C -0.0385(2) 0.3142(3) 0.65318(18) 0.0595(7) Uani 1 1 d . . . . .
C8B C 0.0606(3) 0.3346(3) 0.59815(18) 0.0621(8) Uani 1 1 d . . . . .
H8B H 0.089611 0.280236 0.569176 0.074 Uiso 1 1 calc R U . . .
C9B C 0.1165(3) 0.4239(3) 0.58379(18) 0.0612(8) Uani 1 1 d . . . . .
H9B H 0.090681 0.476151 0.614971 0.073 Uiso 1 1 calc R U . . .
C10B C 0.2102(2) 0.4462(3) 0.52634(17) 0.0564(7) Uani 1 1 d . . . . .
C11B C 0.2754(2) 0.3761(2) 0.46918(17) 0.0545(7) Uani 1 1 d . . . . .
C12B C 0.3344(3) 0.2633(3) 0.5143(2) 0.0717(9) Uani 1 1 d . . . . .
H12D H 0.382178 0.225160 0.477056 0.108 Uiso 1 1 calc R U . . .
H12E H 0.278047 0.218097 0.542480 0.108 Uiso 1 1 calc R U . . .
H12F H 0.379636 0.276218 0.551451 0.108 Uiso 1 1 calc R U . . .
C13B C 0.1976(3) 0.3575(3) 0.4125(2) 0.0776(10) Uani 1 1 d . . . . .
H13D H 0.154285 0.427642 0.390080 0.116 Uiso 1 1 calc R U . . .
H13E H 0.147064 0.306416 0.441355 0.116 Uiso 1 1 calc R U . . .
H13F H 0.242876 0.326876 0.370597 0.116 Uiso 1 1 calc R U . . .
C14B C 0.3609(3) 0.4508(3) 0.42473(17) 0.0572(7) Uani 1 1 d . . . . .
C15B C 0.4446(3) 0.4389(3) 0.36301(19) 0.0715(9) Uani 1 1 d . . . . .
H15B H 0.456887 0.375192 0.342058 0.086 Uiso 1 1 calc R U . . .
C16B C 0.5098(3) 0.5238(4) 0.3331(2) 0.0800(10) Uani 1 1 d . . . . .
H16B H 0.566437 0.516796 0.291481 0.096 Uiso 1 1 calc R U . . .
C17B C 0.4926(3) 0.6184(3) 0.3635(2) 0.0778(10) Uani 1 1 d . . . . .
H17B H 0.537570 0.674143 0.341801 0.093 Uiso 1 1 calc R U . . .
C18B C 0.4102(3) 0.6324(3) 0.4253(2) 0.0736(9) Uani 1 1 d . . . . .
H18B H 0.398738 0.695682 0.446593 0.088 Uiso 1 1 calc R U . . .
C19B C 0.3455(3) 0.5468(3) 0.45390(17) 0.0592(7) Uani 1 1 d . . . . .
N20B N 0.2535(2) 0.5397(2) 0.51513(14) 0.0606(6) Uani 1 1 d . . . . .
C21B C 0.2140(4) 0.6315(3) 0.5572(2) 0.0920(12) Uani 1 1 d . . . . .
H21G H 0.220319 0.603676 0.613106 0.138 Uiso 1 1 calc R U . . .
H21H H 0.136242 0.660497 0.549094 0.138 Uiso 1 1 calc R U . . .
H21I H 0.259944 0.690030 0.536861 0.138 Uiso 1 1 calc R U . . .
O22B O -0.22082(18) 0.4312(2) 0.80601(14) 0.0765(6) Uani 1 1 d . . . . .
C23B C -0.3256(3) 0.4258(4) 0.8539(2) 0.0922(12) Uani 1 1 d . . . . .
H23D H -0.386266 0.443852 0.820597 0.138 Uiso 1 1 calc R U . . .
H23E H -0.335218 0.478242 0.887655 0.138 Uiso 1 1 calc R U . . .
H23F H -0.326429 0.351546 0.886195 0.138 Uiso 1 1 calc R U . . .
P1C P 0.38500(6) 0.57965(7) 0.91335(4) 0.0585(2) Uani 1 1 d D . . . .
O2C O 0.41859(19) 0.45751(17) 0.94546(13) 0.0695(6) Uani 1 1 d D . . . .
O3C O 0.4555(2) 0.64820(19) 0.94604(15) 0.0834(7) Uani 1 1 d D . . . .
H3C H 0.518615 0.612423 0.953151 0.125 Uiso 1 1 calc R U . . .
O4C O 0.4158(2) 0.6097(2) 0.82174(13) 0.0899(8) Uani 1 1 d D . . . .
H4C H 0.358813 0.641055 0.800162 0.135 Uiso 1 1 calc R U . . .
O5C O 0.26058(18) 0.6205(2) 0.93271(12) 0.0716(6) Uani 1 1 d D . . . .
P1D P 0.15719(7) 0.77974(8) 0.75644(5) 0.0662(3) Uani 1 1 d . . . . .
O2D O 0.1277(2) 0.7435(3) 0.84539(14) 0.1064(10) Uani 1 1 d . . . . .
H2D H 0.174388 0.760509 0.868692 0.160 Uiso 1 1 calc R U . . .
O3D O 0.2716(2) 0.7266(2) 0.72753(13) 0.0817(7) Uani 1 1 d . . . . .
O4D O 0.0640(3) 0.7485(2) 0.71868(19) 0.1032(9) Uani 1 1 d . . . . .
H4D H 0.066345 0.780317 0.671531 0.155 Uiso 1 1 calc R U . . .
O5D O 0.1469(2) 0.9086(2) 0.73819(16) 0.0857(7) Uani 1 1 d . . . . .
H5D H 0.174392 0.931269 0.692451 0.129 Uiso 1 1 calc R U . . .
P1E P 0.35206(9) 0.93705(9) 0.55938(7) 0.0856(3) Uani 1 1 d . . . . .
O2E O 0.4302(3) 0.9840(3) 0.60124(16) 0.1129(10) Uani 1 1 d . . . . .
H2E H 0.488103 0.996126 0.571525 0.169 Uiso 1 1 calc R U . . .
O3E O 0.2342(3) 0.9817(3) 0.59146(19) 0.1108(10) Uani 1 1 d . . . . .
O4E O 0.3805(3) 0.9653(3) 0.47174(17) 0.1114(10) Uani 1 1 d . . . . .
O5E O 0.3708(3) 0.8088(2) 0.5857(2) 0.1209(11) Uani 1 1 d . . . . .
H5E H 0.337773 0.789861 0.630237 0.181 Uiso 1 1 calc R U . . .
P1F P 0.0796(13) 1.0411(13) 0.4489(8) 0.120(5) Uani 0.185(9) 1 d D U P A 1
O2F O -0.0270(13) 0.9875(13) 0.4762(9) 0.073(6) Uani 0.185(9) 1 d D U P A 1
H2F H -0.014962 0.933744 0.513328 0.110 Uiso 0.185(9) 1 calc R U P A 1
O3F O 0.107(2) 1.091(2) 0.5171(14) 0.183(19) Uani 0.185(9) 1 d D U P A 1
H3F H 0.118159 1.040372 0.556521 0.274 Uiso 0.185(9) 1 calc R U P A 1
O4F O 0.1829(14) 0.952(2) 0.4366(15) 0.135(9) Uani 0.185(9) 1 d D U P A 1
H4F H 0.240804 0.981113 0.425567 0.203 Uiso 0.185(9) 1 calc R U P A 1
O5F O 0.065(2) 1.1403(18) 0.3800(11) 0.085(8) Uani 0.185(9) 1 d D U P A 1
P1G P 0.0427(6) 1.0754(5) 0.4485(3) 0.0731(17) Uani 0.315(9) 1 d D U P A 2
O2G O -0.0501(12) 1.0036(15) 0.4783(13) 0.188(11) Uani 0.315(9) 1 d D U P A 2
H2G H -0.023175 0.942080 0.503152 0.283 Uiso 0.315(9) 1 calc R U P A 2
O3G O 0.0966(8) 1.0978(7) 0.5175(5) 0.066(3) Uani 0.315(9) 1 d D U P A 2
H3G H 0.124934 1.038206 0.544126 0.099 Uiso 0.315(9) 1 calc R U P A 2
O4G O 0.1389(13) 1.0191(12) 0.3964(8) 0.161(6) Uani 0.315(9) 1 d D U P A 2
H4G H 0.186199 1.061388 0.378620 0.242 Uiso 0.315(9) 1 calc R U P A 2
O5G O -0.0055(11) 1.1890(7) 0.4045(5) 0.087(3) Uani 0.315(9) 1 d D U P A 2
O1W O -0.0757(11) 0.9073(13) 0.6408(6) 0.155(5) Uani 0.5 1 d . U P B 3
O2W O 0.3476(5) 1.2748(5) 0.2288(3) 0.128(3) Uani 0.703(11) 1 d . U P . .
O3W O 0.3016(4) 1.0663(4) 0.3229(3) 0.136(2) Uani 0.809(9) 1 d . U P . .
O4W O -0.1071(3) 0.6171(3) 0.80481(17) 0.0940(8) Uani 1 1 d G U . . .
H4WA H -0.057047 0.656327 0.787612 0.141 Uiso 1 1 d G U . . .
H4WB H -0.100424 0.595382 0.852493 0.141 Uiso 1 1 d G U . . .
O5W O 0.1034(3) 0.4812(3) 1.0334(2) 0.1166(10) Uani 1 1 d G U . . .
H5WA H 0.136845 0.528175 1.042429 0.175 Uiso 1 1 d G U . . .
H5WB H 0.142823 0.459413 0.996042 0.175 Uiso 1 1 d G U . . .
O6W O 0.4722(12) 1.1915(10) 0.2405(10) 0.157(7) Uani 0.313(9) 1 d . U P . .
O7W O 0.2534(19) 1.2179(18) 0.2637(11) 0.120(10) Uani 0.176(10) 1 d . U P . .


_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
O1A C2A 1.346(3) . ?
O1A H1A 0.8200 . ?
C2A C3A 1.397(4) . ?
C2A C7A 1.407(4) . ?
C3A C4A 1.370(4) . ?
C3A O22A 1.371(4) . ?
C4A C5A 1.381(5) . ?
C4A H4A 0.9300 . ?
C5A C6A 1.372(5) . ?
C5A H5A 0.9300 . ?
C6A C7A 1.410(4) . ?
C6A H6A 0.9300 . ?
C7A C8A 1.445(5) . ?
C8A C9A 1.346(4) . ?
C8A H8A 0.9300 . ?
C9A C10A 1.424(4) . ?
C9A H9A 0.9300 . ?
C10A N20A 1.324(4) . ?
C10A C11A 1.528(4) . ?
C11A C14A 1.501(4) . ?
C11A C12A 1.543(4) . ?
C11A C13A 1.543(4) . ?
C12A H12A 0.9600 . ?
C12A H12B 0.9600 . ?
C12A H12C 0.9600 . ?
C13A H13A 0.9600 . ?
C13A H13B 0.9600 . ?
C13A H13C 0.9600 . ?
C14A C19A 1.380(4) . ?
C14A C15A 1.387(4) . ?
C15A C16A 1.376(5) . ?
C15A H15A 0.9300 . ?
C16A C17A 1.386(5) . ?
C16A H16A 0.9300 . ?
C17A C18A 1.378(5) . ?
C17A H17A 0.9300 . ?
C18A C19A 1.379(4) . ?
C18A H18A 0.9300 . ?
C19A N20A 1.422(4) . ?
N20A C21A 1.467(4) . ?
C21A H21A 0.9600 . ?
C21A H21B 0.9600 . ?
C21A H21C 0.9600 . ?
C21A H21D 0.9600 . ?
C21A H21E 0.9600 . ?
C21A H21F 0.9600 . ?
O22A C23A 1.418(4) . ?
C23A H23A 0.9600 . ?
C23A H23B 0.9600 . ?
C23A H23C 0.9600 . ?
O1B C2B 1.345(3) . ?
O1B H1B 0.8200 . ?
C2B C3B 1.402(4) . ?
C2B C7B 1.413(4) . ?
C3B O22B 1.360(4) . ?
C3B C4B 1.374(5) . ?
C4B C5B 1.386(5) . ?
C4B H4B 0.9300 . ?
C5B C6B 1.365(5) . ?
C5B H5B 0.9300 . ?
C6B C7B 1.407(4) . ?
C6B H6B 0.9300 . ?
C7B C8B 1.438(4) . ?
C8B C9B 1.352(4) . ?
C8B H8B 0.9300 . ?
C9B C10B 1.415(4) . ?
C9B H9B 0.9300 . ?
C10B N20B 1.317(4) . ?
C10B C11B 1.523(4) . ?
C11B C14B 1.511(4) . ?
C11B C13B 1.533(4) . ?
C11B C12B 1.541(4) . ?
C12B H12D 0.9600 . ?
C12B H12E 0.9600 . ?
C12B H12F 0.9600 . ?
C13B H13D 0.9600 . ?
C13B H13E 0.9600 . ?
C13B H13F 0.9600 . ?
C14B C19B 1.380(4) . ?
C14B C15B 1.381(4) . ?
C15B C16B 1.382(5) . ?
C15B H15B 0.9300 . ?
C16B C17B 1.375(5) . ?
C16B H16B 0.9300 . ?
C17B C18B 1.377(5) . ?
C17B H17B 0.9300 . ?
C18B C19B 1.383(5) . ?
C18B H18B 0.9300 . ?
C19B N20B 1.422(4) . ?
N20B C21B 1.477(4) . ?
C21B H21G 0.9600 . ?
C21B H21H 0.9600 . ?
C21B H21I 0.9600 . ?
O22B C23B 1.411(4) . ?
C23B H23D 0.9600 . ?
C23B H23E 0.9600 . ?
C23B H23F 0.9600 . ?
P1C O2C 1.493(2) . ?
P1C O5C 1.512(2) . ?
P1C O3C 1.547(2) . ?
P1C O4C 1.554(2) . ?
O3C H3C 0.8200 . ?
O4C H4C 0.8200 . ?
P1D O3D 1.493(2) . ?
P1D O2D 1.514(3) . ?
P1D O4D 1.525(3) . ?
P1D O5D 1.544(3) . ?
O2D H2D 0.8200 . ?
O4D H4D 0.8200 . ?
O5D H5D 0.8200 . ?
P1E O4E 1.484(3) . ?
P1E O3E 1.510(3) . ?
P1E O2E 1.532(3) . ?
P1E O5E 1.536(3) . ?
O2E H2E 0.8200 . ?
O5E H5E 0.8200 . ?
P1F O5F 1.506(9) . ?
P1F O2F 1.512(8) . ?
P1F O4F 1.543(9) . ?
P1F O3F 1.561(8) . ?
O2F H2F 0.8200 . ?
O3F H3F 0.8200 . ?
O4F H4F 0.8200 . ?
P1G O5G 1.497(7) . ?
P1G O2G 1.508(8) . ?
P1G O4G 1.541(8) . ?
P1G O3G 1.544(6) . ?
O2G H2G 0.8200 . ?
O3G H3G 0.8200 . ?
O4G H4G 0.8200 . ?
O4W H4WA 0.8200 . ?
O4W H4WB 0.8199 . ?
O5W H5WA 0.8200 . ?
O5W H5WB 0.8200 . ?

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
C2A O1A H1A 109.5 . . ?
O1A C2A C3A 120.5(3) . . ?
O1A C2A C7A 119.3(3) . . ?
C3A C2A C7A 120.2(3) . . ?
C4A C3A O22A 126.2(3) . . ?
C4A C3A C2A 120.9(3) . . ?
O22A C3A C2A 112.9(2) . . ?
C3A C4A C5A 119.4(3) . . ?
C3A C4A H4A 120.3 . . ?
C5A C4A H4A 120.3 . . ?
C6A C5A C4A 120.8(3) . . ?
C6A C5A H5A 119.6 . . ?
C4A C5A H5A 119.6 . . ?
C5A C6A C7A 121.2(3) . . ?
C5A C6A H6A 119.4 . . ?
C7A C6A H6A 119.4 . . ?
C2A C7A C6A 117.2(3) . . ?
C2A C7A C8A 124.1(3) . . ?
C6A C7A C8A 118.6(3) . . ?
C9A C8A C7A 127.6(3) . . ?
C9A C8A H8A 116.2 . . ?
C7A C8A H8A 116.2 . . ?
C8A C9A C10A 126.1(3) . . ?
C8A C9A H9A 117.0 . . ?
C10A C9A H9A 117.0 . . ?
N20A C10A C9A 121.3(2) . . ?
N20A C10A C11A 109.1(3) . . ?
C9A C10A C11A 129.6(3) . . ?
C14A C11A C10A 101.2(2) . . ?
C14A C11A C12A 110.9(3) . . ?
C10A C11A C12A 111.0(3) . . ?
C14A C11A C13A 111.2(3) . . ?
C10A C11A C13A 111.2(3) . . ?
C12A C11A C13A 111.0(3) . . ?
C11A C12A H12A 109.5 . . ?
C11A C12A H12B 109.5 . . ?
H12A C12A H12B 109.5 . . ?
C11A C12A H12C 109.5 . . ?
H12A C12A H12C 109.5 . . ?
H12B C12A H12C 109.5 . . ?
C11A C13A H13A 109.5 . . ?
C11A C13A H13B 109.5 . . ?
H13A C13A H13B 109.5 . . ?
C11A C13A H13C 109.5 . . ?
H13A C13A H13C 109.5 . . ?
H13B C13A H13C 109.5 . . ?
C19A C14A C15A 118.5(3) . . ?
C19A C14A C11A 110.0(3) . . ?
C15A C14A C11A 131.5(3) . . ?
C16A C15A C14A 118.8(3) . . ?
C16A C15A H15A 120.6 . . ?
C14A C15A H15A 120.6 . . ?
C15A C16A C17A 121.3(3) . . ?
C15A C16A H16A 119.3 . . ?
C17A C16A H16A 119.3 . . ?
C18A C17A C16A 121.0(3) . . ?
C18A C17A H17A 119.5 . . ?
C16A C17A H17A 119.5 . . ?
C17A C18A C19A 116.5(3) . . ?
C17A C18A H18A 121.7 . . ?
C19A C18A H18A 121.7 . . ?
C18A C19A C14A 123.9(3) . . ?
C18A C19A N20A 128.4(3) . . ?
C14A C19A N20A 107.7(3) . . ?
C10A N20A C19A 112.0(2) . . ?
C10A N20A C21A 127.0(3) . . ?
C19A N20A C21A 121.0(2) . . ?
N20A C21A H21A 109.5 . . ?
N20A C21A H21B 109.5 . . ?
H21A C21A H21B 109.5 . . ?
N20A C21A H21C 109.5 . . ?
H21A C21A H21C 109.5 . . ?
H21B C21A H21C 109.5 . . ?
N20A C21A H21D 109.5 . . ?
H21A C21A H21D 141.1 . . ?
H21B C21A H21D 56.3 . . ?
H21C C21A H21D 56.3 . . ?
N20A C21A H21E 109.5 . . ?
H21A C21A H21E 56.3 . . ?
H21B C21A H21E 141.1 . . ?
H21C C21A H21E 56.3 . . ?
H21D C21A H21E 109.5 . . ?
N20A C21A H21F 109.5 . . ?
H21A C21A H21F 56.3 . . ?
H21B C21A H21F 56.3 . . ?
H21C C21A H21F 141.1 . . ?
H21D C21A H21F 109.5 . . ?
H21E C21A H21F 109.5 . . ?
C3A O22A C23A 118.6(3) . . ?
O22A C23A H23A 109.5 . . ?
O22A C23A H23B 109.5 . . ?
H23A C23A H23B 109.5 . . ?
O22A C23A H23C 109.5 . . ?
H23A C23A H23C 109.5 . . ?
H23B C23A H23C 109.5 . . ?
C2B O1B H1B 109.5 . . ?
O1B C2B C3B 119.7(3) . . ?
O1B C2B C7B 120.1(3) . . ?
C3B C2B C7B 120.2(3) . . ?
O22B C3B C4B 126.6(3) . . ?
O22B C3B C2B 112.7(3) . . ?
C4B C3B C2B 120.7(3) . . ?
C3B C4B C5B 119.4(3) . . ?
C3B C4B H4B 120.3 . . ?
C5B C4B H4B 120.3 . . ?
C6B C5B C4B 120.7(3) . . ?
C6B C5B H5B 119.6 . . ?
C4B C5B H5B 119.6 . . ?
C5B C6B C7B 121.9(3) . . ?
C5B C6B H6B 119.1 . . ?
C7B C6B H6B 119.1 . . ?
C6B C7B C2B 117.0(3) . . ?
C6B C7B C8B 119.0(3) . . ?
C2B C7B C8B 123.9(3) . . ?
C9B C8B C7B 127.4(3) . . ?
C9B C8B H8B 116.3 . . ?
C7B C8B H8B 116.3 . . ?
C8B C9B C10B 126.9(3) . . ?
C8B C9B H9B 116.6 . . ?
C10B C9B H9B 116.6 . . ?
N20B C10B C9B 121.1(3) . . ?
N20B C10B C11B 109.4(2) . . ?
C9B C10B C11B 129.6(3) . . ?
C14B C11B C10B 101.1(2) . . ?
C14B C11B C13B 110.9(3) . . ?
C10B C11B C13B 111.2(2) . . ?
C14B C11B C12B 111.3(2) . . ?
C10B C11B C12B 111.4(2) . . ?
C13B C11B C12B 110.5(3) . . ?
C11B C12B H12D 109.5 . . ?
C11B C12B H12E 109.5 . . ?
H12D C12B H12E 109.5 . . ?
C11B C12B H12F 109.5 . . ?
H12D C12B H12F 109.5 . . ?
H12E C12B H12F 109.5 . . ?
C11B C13B H13D 109.5 . . ?
C11B C13B H13E 109.5 . . ?
H13D C13B H13E 109.5 . . ?
C11B C13B H13F 109.5 . . ?
H13D C13B H13F 109.5 . . ?
H13E C13B H13F 109.5 . . ?
C19B C14B C15B 118.8(3) . . ?
C19B C14B C11B 109.5(2) . . ?
C15B C14B C11B 131.6(3) . . ?
C14B C15B C16B 118.5(3) . . ?
C14B C15B H15B 120.8 . . ?
C16B C15B H15B 120.8 . . ?
C17B C16B C15B 121.4(3) . . ?
C17B C16B H16B 119.3 . . ?
C15B C16B H16B 119.3 . . ?
C16B C17B C18B 121.5(3) . . ?
C16B C17B H17B 119.2 . . ?
C18B C17B H17B 119.2 . . ?
C17B C18B C19B 116.1(3) . . ?
C17B C18B H18B 121.9 . . ?
C19B C18B H18B 121.9 . . ?
C14B C19B C18B 123.7(3) . . ?
C14B C19B N20B 107.8(3) . . ?
C18B C19B N20B 128.5(3) . . ?
C10B N20B C19B 112.2(2) . . ?
C10B N20B C21B 126.8(3) . . ?
C19B N20B C21B 121.0(3) . . ?
N20B C21B H21G 109.5 . . ?
N20B C21B H21H 109.5 . . ?
H21G C21B H21H 109.5 . . ?
N20B C21B H21I 109.5 . . ?
H21G C21B H21I 109.5 . . ?
H21H C21B H21I 109.5 . . ?
C3B O22B C23B 119.4(3) . . ?
O22B C23B H23D 109.5 . . ?
O22B C23B H23E 109.5 . . ?
H23D C23B H23E 109.5 . . ?
O22B C23B H23F 109.5 . . ?
H23D C23B H23F 109.5 . . ?
H23E C23B H23F 109.5 . . ?
O2C P1C O5C 113.82(14) . . ?
O2C P1C O3C 110.10(12) . . ?
O5C P1C O3C 108.28(14) . . ?
O2C P1C O4C 110.53(13) . . ?
O5C P1C O4C 109.20(12) . . ?
O3C P1C O4C 104.48(16) . . ?
P1C O3C H3C 109.5 . . ?
P1C O4C H4C 109.5 . . ?
O3D P1D O2D 113.43(13) . . ?
O3D P1D O4D 111.02(17) . . ?
O2D P1D O4D 105.56(18) . . ?
O3D P1D O5D 112.11(15) . . ?
O2D P1D O5D 105.95(16) . . ?
O4D P1D O5D 108.37(15) . . ?
P1D O2D H2D 109.5 . . ?
P1D O4D H4D 109.5 . . ?
P1D O5D H5D 109.5 . . ?
O4E P1E O3E 117.0(2) . . ?
O4E P1E O2E 110.95(17) . . ?
O3E P1E O2E 103.79(19) . . ?
O4E P1E O5E 107.01(19) . . ?
O3E P1E O5E 109.15(17) . . ?
O2E P1E O5E 108.7(2) . . ?
P1E O2E H2E 109.5 . . ?
P1E O5E H5E 109.5 . . ?
O5F P1F O2F 112.7(9) . . ?
O5F P1F O4F 115.1(11) . . ?
O2F P1F O4F 110.5(9) . . ?
O5F P1F O3F 104.3(10) . . ?
O2F P1F O3F 108.9(11) . . ?
O4F P1F O3F 104.6(10) . . ?
P1F O4F H4F 109.5 . . ?
O5G P1G O2G 110.2(8) . . ?
O5G P1G O4G 111.3(6) . . ?
O2G P1G O4G 111.3(9) . . ?
O5G P1G O3G 104.7(5) . . ?
O2G P1G O3G 112.0(8) . . ?
O4G P1G O3G 107.2(7) . . ?
P1G O2G H2G 109.5 . . ?
P1G O3G H3G 109.5 . . ?
H3G O3G H2G 94.7 . 2_576 ?
P1G O4G H4G 109.5 . . ?
O7W O2W O6W 112.4(10) . . ?
H4WA O4W H4WB 104.5 . . ?
H5WA O5W H5WB 104.5 . . ?

_refine_diff_density_max         0.542
_refine_diff_density_min         -0.401
_refine_diff_density_rms         0.044


# start Validation Reply Form
_vrf_PLAT430_nt0159_KC-SPOMe_H3PO4_ACN 
;
PROBLEM: Short Inter D...A Contact  O1W      ..O3W              2.68 Ang.  
RESPONSE: Disordered water molecules.
;
# end Validation Reply Form
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: Acetonitrile'
####################################################################### 
# 
# 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_nt0158_Vanessa_KC-SPOMe_HBr_EtOH
_database_code_depnum_ccdc_archive 'CCDC 1824251'
_audit_update_record             
;
2018-02-15 deposited with the CCDC.
2018-04-06 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2016/6
_shelx_SHELXL_version_number     2016/6
_chemical_name_systematic        
'2-[(E)-2-(2-hydroxy-3-methoxyphenyl)ethenyl]-1,3,3-trimethyl-3H-indol-1-ium dihydrate bromide'
_chemical_name_common            
'2-[(E)-2-(2-hydroxy-3-methoxyphenyl)ethenyl]-1,3,3-trimethyl-3H-indol-1-ium dihydrate bromide'
_chemical_melting_point          ?
_chemical_formula_moiety         'C20 H22 N O2 1+, Br 1-, 2(H2 O)'
_chemical_formula_sum            'C20 H26 Br N O4'
_chemical_formula_weight         424.33

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'
Br Br -0.6763 1.2805 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 '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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

_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.
;

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

_cell_length_a                   11.5976(3)
_cell_length_b                   23.9015(6)
_cell_length_c                   7.36093(15)
_cell_angle_alpha                90
_cell_angle_beta                 98.766(2)
_cell_angle_gamma                90
_cell_volume                     2016.61(8)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    4756
_cell_measurement_theta_min      3.6880
_cell_measurement_theta_max      66.8320

_exptl_crystal_description       plate
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.398
_exptl_crystal_F_000             880
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.223
_exptl_crystal_size_mid          0.089
_exptl_crystal_size_min          0.026
_exptl_absorpt_coefficient_mu    2.976
_shelx_estimated_absorpt_T_min   0.557
_shelx_estimated_absorpt_T_max   0.927
_exptl_absorpt_correction_T_min  0.679
_exptl_absorpt_correction_T_max  0.927
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.46 (Rigaku Oxford Diffraction, 2015)
Analytical numeric absorption correction using a multifaceted crystal
model based on expressions derived by R.C. Clark & J.S. Reid.
(Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_type           CuK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_radiation_monochromator  'multilayer mirror'
_diffrn_measurement_device_type  
;
Oxford Diffraction Xcalibur, Ruby, Gemini ultra
;
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean 5.1856
_diffrn_reflns_number            8366
_diffrn_reflns_av_unetI/netI     0.0399
_diffrn_reflns_av_R_equivalents  0.0352
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -27
_diffrn_reflns_limit_k_max       27
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_limit_l_max       6
_diffrn_reflns_theta_min         3.699
_diffrn_reflns_theta_max         67.104
_diffrn_reflns_theta_full        67.104
_diffrn_measured_fraction_theta_max 0.951
_diffrn_measured_fraction_theta_full 0.951
_diffrn_reflns_Laue_measured_fraction_max 0.951
_diffrn_reflns_Laue_measured_fraction_full 0.951
_diffrn_reflns_point_group_measured_fraction_max 0.951
_diffrn_reflns_point_group_measured_fraction_full 0.951
_reflns_number_total             3431
_reflns_number_gt                3027
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_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.
;

_computing_data_collection       'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_cell_refinement       'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_structure_solution    'SHELXT (Sheldrick, 2015)'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0530P)²+0.2228P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   dual
_atom_sites_solution_hydrogens   difmap
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3431
_refine_ls_number_parameters     254
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0395
_refine_ls_R_factor_gt           0.0345
_refine_ls_wR_factor_ref         0.0920
_refine_ls_wR_factor_gt          0.0873
_refine_ls_goodness_of_fit_ref   1.048
_refine_ls_restrained_S_all      1.048
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

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
Br1 Br 0.07493(2) 0.34565(2) 0.45047(3) 0.03180(12) Uani 1 1 d . . . . .
O1 O 0.47084(17) 0.37824(8) 0.2232(2) 0.0344(4) Uani 1 1 d . . . . .
H1 H 0.409(4) 0.3659(16) 0.182(5) 0.052 Uiso 1 1 d . U . . .
O3 O 0.14002(19) 0.28619(9) 0.8669(3) 0.0420(5) Uani 1 1 d . . . . .
H3A H 0.124(4) 0.2544(19) 0.870(5) 0.063 Uiso 1 1 d . U . . .
H3B H 0.124(3) 0.2954(17) 0.758(6) 0.063 Uiso 1 1 d . U . . .
N20 N 0.85876(17) 0.41564(8) 0.8860(2) 0.0271(4) Uani 1 1 d . . . . .
O22 O 0.43458(15) 0.32367(7) -0.0968(2) 0.0332(4) Uani 1 1 d . . . . .
O2 O 0.2634(2) 0.34147(9) 0.1553(3) 0.0467(5) Uani 1 1 d . . . . .
H2A H 0.218(4) 0.3437(16) 0.239(6) 0.070 Uiso 1 1 d . U . . .
H2B H 0.234(4) 0.3247(19) 0.080(6) 0.070 Uiso 1 1 d . U . . .
C21 C 0.9546(2) 0.37491(10) 0.9137(3) 0.0325(5) Uani 1 1 d . . . . .
H21A H 1.023400 0.390882 0.870652 0.049 Uiso 1 1 calc R U . . .
H21B H 0.930861 0.340762 0.844295 0.049 Uiso 1 1 calc R U . . .
H21C H 0.973453 0.365910 1.044785 0.049 Uiso 1 1 calc R U . . .
C14 C 0.7511(2) 0.48996(10) 0.9528(3) 0.0274(5) Uani 1 1 d . . . . .
C9 C 0.7719(2) 0.38380(10) 0.5854(3) 0.0291(5) Uani 1 1 d . . . . .
H9 H 0.835892 0.359514 0.578253 0.035 Uiso 1 1 calc R U . . .
C19 C 0.8486(2) 0.45843(10) 1.0174(3) 0.0282(5) Uani 1 1 d . . . . .
C6 C 0.7624(2) 0.32022(10) 0.2232(3) 0.0292(5) Uani 1 1 d . . . . .
H6 H 0.837472 0.321013 0.296021 0.035 Uiso 1 1 calc R U . . .
C11 C 0.6942(2) 0.46810(9) 0.7696(3) 0.0267(5) Uani 1 1 d . . . . .
C16 C 0.7945(2) 0.54788(10) 1.2172(3) 0.0321(5) Uani 1 1 d . . . . .
H16 H 0.777016 0.579131 1.287965 0.039 Uiso 1 1 calc R U . . .
C12 C 0.5678(2) 0.45047(10) 0.7801(3) 0.0320(5) Uani 1 1 d . . . . .
H12A H 0.567699 0.420907 0.872342 0.048 Uiso 1 1 calc R U . . .
H12B H 0.531158 0.436460 0.659905 0.048 Uiso 1 1 calc R U . . .
H12C H 0.523897 0.482802 0.814675 0.048 Uiso 1 1 calc R U . . .
C15 C 0.7223(2) 0.53556(10) 1.0553(3) 0.0291(5) Uani 1 1 d . . . . .
H15 H 0.654887 0.557476 1.014856 0.035 Uiso 1 1 calc R U . . .
C4 C 0.6356(2) 0.28884(10) -0.0479(3) 0.0315(5) Uani 1 1 d . . . . .
H4 H 0.624821 0.267708 -0.158527 0.038 Uiso 1 1 calc R U . . .
C13 C 0.6983(2) 0.51315(10) 0.6197(3) 0.0302(5) Uani 1 1 d . . . . .
H13A H 0.652469 0.545758 0.646560 0.045 Uiso 1 1 calc R U . . .
H13B H 0.665536 0.497769 0.499460 0.045 Uiso 1 1 calc R U . . .
H13C H 0.779332 0.524464 0.618184 0.045 Uiso 1 1 calc R U . . .
C2 C 0.5595(2) 0.34911(9) 0.1696(3) 0.0284(5) Uani 1 1 d . . . . .
C18 C 0.9215(2) 0.46902(10) 1.1806(3) 0.0312(5) Uani 1 1 d . . . . .
H18 H 0.987064 0.446136 1.222858 0.037 Uiso 1 1 calc R U . . .
C8 C 0.6808(2) 0.38356(9) 0.4461(3) 0.0289(5) Uani 1 1 d . . . . .
H8 H 0.617552 0.407671 0.459496 0.035 Uiso 1 1 calc R U . . .
C17 C 0.8925(2) 0.51541(10) 1.2791(3) 0.0332(5) Uani 1 1 d . . . . .
H17 H 0.940678 0.525132 1.390856 0.040 Uiso 1 1 calc R U . . .
C10 C 0.7752(2) 0.41918(9) 0.7424(3) 0.0276(5) Uani 1 1 d . . . . .
C3 C 0.5435(2) 0.31886(10) 0.0025(3) 0.0283(5) Uani 1 1 d . . . . .
C23 C 0.4137(3) 0.29656(13) -0.2726(4) 0.0425(6) Uani 1 1 d . . . . .
H23A H 0.472406 0.308741 -0.346855 0.064 Uiso 1 1 calc R U . . .
H23B H 0.335783 0.306490 -0.335456 0.064 Uiso 1 1 calc R U . . .
H23C H 0.418763 0.255922 -0.255449 0.064 Uiso 1 1 calc R U . . .
C7 C 0.6693(2) 0.35059(9) 0.2791(3) 0.0281(5) Uani 1 1 d . . . . .
C5 C 0.7443(2) 0.28960(10) 0.0639(3) 0.0316(5) Uani 1 1 d . . . . .
H5 H 0.806853 0.268535 0.028842 0.038 Uiso 1 1 calc R U . . .


_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 C2 1.350(3) . ?
O1 H1 0.79(4) . ?
O3 H3A 0.78(4) . ?
O3 H3B 0.82(4) . ?
N20 C10 1.324(3) . ?
N20 C19 1.425(3) . ?
N20 C21 1.468(3) . ?
O22 C3 1.365(3) . ?
O22 C23 1.434(3) . ?
O2 H2A 0.87(5) . ?
O2 H2B 0.72(5) . ?
C21 H21A 0.9800 . ?
C21 H21B 0.9800 . ?
C21 H21C 0.9800 . ?
C14 C19 1.381(3) . ?
C14 C15 1.395(3) . ?
C14 C11 1.501(3) . ?
C9 C8 1.355(4) . ?
C9 C10 1.428(3) . ?
C9 H9 0.9500 . ?
C19 C18 1.383(3) . ?
C6 C5 1.372(4) . ?
C6 C7 1.413(3) . ?
C6 H6 0.9500 . ?
C11 C10 1.532(3) . ?
C11 C12 1.539(3) . ?
C11 C13 1.548(3) . ?
C16 C15 1.380(4) . ?
C16 C17 1.395(4) . ?
C16 H16 0.9500 . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12C 0.9800 . ?
C15 H15 0.9500 . ?
C4 C3 1.383(3) . ?
C4 C5 1.397(4) . ?
C4 H4 0.9500 . ?
C13 H13A 0.9800 . ?
C13 H13B 0.9800 . ?
C13 H13C 0.9800 . ?
C2 C7 1.400(4) . ?
C2 C3 1.415(3) . ?
C18 C17 1.393(4) . ?
C18 H18 0.9500 . ?
C8 C7 1.450(3) . ?
C8 H8 0.9500 . ?
C17 H17 0.9500 . ?
C23 H23A 0.9800 . ?
C23 H23B 0.9800 . ?
C23 H23C 0.9800 . ?
C5 H5 0.9500 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 O1 H1 113(3) . . ?
H3A O3 H3B 105(4) . . ?
C10 N20 C19 111.72(19) . . ?
C10 N20 C21 126.88(19) . . ?
C19 N20 C21 121.38(19) . . ?
C3 O22 C23 117.37(19) . . ?
H2A O2 H2B 108(5) . . ?
N20 C21 H21A 109.5 . . ?
N20 C21 H21B 109.5 . . ?
H21A C21 H21B 109.5 . . ?
N20 C21 H21C 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
C19 C14 C15 119.4(2) . . ?
C19 C14 C11 110.1(2) . . ?
C15 C14 C11 130.4(2) . . ?
C8 C9 C10 122.4(2) . . ?
C8 C9 H9 118.8 . . ?
C10 C9 H9 118.8 . . ?
C14 C19 C18 124.0(2) . . ?
C14 C19 N20 107.8(2) . . ?
C18 C19 N20 128.2(2) . . ?
C5 C6 C7 119.9(2) . . ?
C5 C6 H6 120.0 . . ?
C7 C6 H6 120.0 . . ?
C14 C11 C10 100.90(19) . . ?
C14 C11 C12 110.00(18) . . ?
C10 C11 C12 113.91(19) . . ?
C14 C11 C13 109.95(19) . . ?
C10 C11 C13 110.60(17) . . ?
C12 C11 C13 111.02(19) . . ?
C15 C16 C17 121.4(2) . . ?
C15 C16 H16 119.3 . . ?
C17 C16 H16 119.3 . . ?
C11 C12 H12A 109.5 . . ?
C11 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
C11 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C16 C15 C14 118.0(2) . . ?
C16 C15 H15 121.0 . . ?
C14 C15 H15 121.0 . . ?
C3 C4 C5 120.0(2) . . ?
C3 C4 H4 120.0 . . ?
C5 C4 H4 120.0 . . ?
C11 C13 H13A 109.5 . . ?
C11 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
C11 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
O1 C2 C7 119.1(2) . . ?
O1 C2 C3 120.9(2) . . ?
C7 C2 C3 120.1(2) . . ?
C19 C18 C17 115.7(2) . . ?
C19 C18 H18 122.1 . . ?
C17 C18 H18 122.1 . . ?
C9 C8 C7 127.2(2) . . ?
C9 C8 H8 116.4 . . ?
C7 C8 H8 116.4 . . ?
C18 C17 C16 121.4(2) . . ?
C18 C17 H17 119.3 . . ?
C16 C17 H17 119.3 . . ?
N20 C10 C9 122.3(2) . . ?
N20 C10 C11 109.45(19) . . ?
C9 C10 C11 128.1(2) . . ?
O22 C3 C4 126.1(2) . . ?
O22 C3 C2 114.2(2) . . ?
C4 C3 C2 119.6(2) . . ?
O22 C23 H23A 109.5 . . ?
O22 C23 H23B 109.5 . . ?
H23A C23 H23B 109.5 . . ?
O22 C23 H23C 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 109.5 . . ?
C2 C7 C6 119.2(2) . . ?
C2 C7 C8 117.4(2) . . ?
C6 C7 C8 123.4(2) . . ?
C6 C5 C4 121.2(2) . . ?
C6 C5 H5 119.4 . . ?
C4 C5 H5 119.4 . . ?

_refine_diff_density_max         0.623
_refine_diff_density_min         -0.302
_refine_diff_density_rms         0.068


# start Validation Reply Form
_vrf_PLAT029_nt0158_Vanessa_KC-SPOMe_HBr_EtOH 
;
PROBLEM: _diffrn_measured_fraction_theta_full value Low .      0.951 Note  
RESPONSE: The crystal was blown away by flow of nitrogen at the end of 
experiment.
;
_vrf_PLAT094_nt0158_Vanessa_KC-SPOMe_HBr_EtOH 
;
PROBLEM: Ratio of Maximum / Minimum Residual Density ....       2.06 Report
RESPONSE: This is because of truncation error peaks near Br atom.
;
_vrf_PLAT911_nt0158_Vanessa_KC-SPOMe_HBr_EtOH 
;
PROBLEM: Missing # FCF Refl Between THmin & STh/L=  0.597        168 Report
RESPONSE: The crystal was blown away by flow of nitrogen at the end of 
experiment.
;
# end Validation Reply Form

_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: Ethanol'
####################################################################### 
# 
# 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_VS-KC-SP-HBr-yellow
_database_code_depnum_ccdc_archive 'CCDC 1824254'
_audit_update_record             
;
2018-02-15 deposited with the CCDC.
2018-04-06 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2016/4
_shelx_SHELXL_version_number     2016/4
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C19 H21 Br N O1.50'
_chemical_formula_sum            'C19 H21 Br N O1.50'
_chemical_formula_weight         367.28

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.2901 2.4595 '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 21/c'
_space_group_name_Hall           '-P 2ybc'

_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.
;

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

_cell_length_a                   12.8779(5)
_cell_length_b                   10.4911(5)
_cell_length_c                   12.8498(7)
_cell_angle_alpha                90
_cell_angle_beta                 94.836(4)
_cell_angle_gamma                90
_cell_volume                     1729.87(15)
_cell_formula_units_Z            4
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    3945
_cell_measurement_theta_min      3.1600
_cell_measurement_theta_max      26.1280

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.410
_exptl_crystal_F_000             756
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.15
_exptl_absorpt_coefficient_mu    2.382
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.31137
_exptl_absorpt_correction_T_max  1.00000
_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_absorpt_special_details   ?





_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'Rigaku UltraX 18 rotating anode'
_diffrn_radiation_monochromator  'Xenocs Fox3D mirror'
_diffrn_measurement_device_type  'MAR345 image plate'
_diffrn_measurement_method       '75 images, ΔΦ 2.0° '
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            9903
_diffrn_reflns_av_unetI/netI     0.0514
_diffrn_reflns_av_R_equivalents  0.0529
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         3.182
_diffrn_reflns_theta_max         26.182
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.988
_diffrn_measured_fraction_theta_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.988
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.988
_diffrn_reflns_point_group_measured_fraction_full 0.995
_reflns_number_total             3427
_reflns_number_gt                2748
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_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.
;







_computing_data_collection       MAR
_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_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_structure_solution    'SHELXT (Sheldrick, 2015)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'MERCURY (Macrae et al., 2008)'
_computing_publication_material  
;
'MERCURY (Macrae et al., 2008), Platon (Spek, 2009)'
;







_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0456P)²+1.9331P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3427
_refine_ls_number_parameters     216
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0626
_refine_ls_R_factor_gt           0.0459
_refine_ls_wR_factor_ref         0.1086
_refine_ls_wR_factor_gt          0.1022
_refine_ls_goodness_of_fit_ref   1.049
_refine_ls_restrained_S_all      1.049
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 1.11947(18) 0.2652(2) 0.39456(18) 0.0296(5) Uani 1 1 d . . . . .
H1 H 1.166671 0.212721 0.383841 0.044 Uiso 1 1 calc R U . . .
C2 C 1.1028(2) 0.3438(3) 0.3102(3) 0.0239(7) Uani 1 1 d . . . . .
C3 C 1.1778(2) 0.3626(3) 0.2408(3) 0.0273(7) Uani 1 1 d . . . . .
H3 H 1.243091 0.320291 0.251391 0.033 Uiso 1 1 calc R U . . .
C4 C 1.1580(3) 0.4430(3) 0.1561(3) 0.0317(8) Uani 1 1 d . . . . .
H4 H 1.209489 0.455094 0.108230 0.038 Uiso 1 1 calc R U . . .
C5 C 1.0631(3) 0.5060(3) 0.1406(3) 0.0282(7) Uani 1 1 d . . . . .
H5 H 1.049095 0.559740 0.081538 0.034 Uiso 1 1 calc R U . . .
C6 C 0.9894(3) 0.4905(3) 0.2110(3) 0.0285(8) Uani 1 1 d . . . . .
H6 H 0.925221 0.535271 0.200986 0.034 Uiso 1 1 calc R U . . .
C7 C 1.0077(2) 0.4091(3) 0.2976(3) 0.0237(7) Uani 1 1 d . . . . .
C8 C 0.9318(2) 0.3919(3) 0.3738(3) 0.0262(7) Uani 1 1 d . . . . .
H8 H 0.937748 0.317697 0.416320 0.031 Uiso 1 1 calc R U . . .
C9 C 0.8530(2) 0.4737(3) 0.3888(3) 0.0268(7) Uani 1 1 d . . . . .
H9 H 0.846478 0.547660 0.346124 0.032 Uiso 1 1 calc R U . . .
C10 C 0.7790(2) 0.4559(3) 0.4646(3) 0.0227(7) Uani 1 1 d . . . . .
C11 C 0.7601(2) 0.3381(3) 0.5298(3) 0.0236(7) Uani 1 1 d . . . . .
C12 C 0.8535(3) 0.2926(4) 0.6032(3) 0.0316(8) Uani 1 1 d . . . . .
H12A H 0.879527 0.363459 0.647690 0.047 Uiso 1 1 calc R U . . .
H12B H 0.908956 0.262497 0.561563 0.047 Uiso 1 1 calc R U . . .
H12C H 0.831337 0.222824 0.646947 0.047 Uiso 1 1 calc R U . . .
C13 C 0.7192(3) 0.2310(3) 0.4550(3) 0.0295(8) Uani 1 1 d . . . . .
H13A H 0.699449 0.157240 0.495770 0.044 Uiso 1 1 calc R U . . .
H13B H 0.773966 0.206105 0.410516 0.044 Uiso 1 1 calc R U . . .
H13C H 0.658287 0.261618 0.411307 0.044 Uiso 1 1 calc R U . . .
C14 C 0.6741(2) 0.3859(3) 0.5925(3) 0.0250(7) Uani 1 1 d . . . . .
C15 C 0.6240(3) 0.3280(4) 0.6717(3) 0.0316(8) Uani 1 1 d . . . . .
H15 H 0.641115 0.243480 0.693447 0.038 Uiso 1 1 calc R U . . .
C16 C 0.5483(3) 0.3971(4) 0.7183(3) 0.0354(9) Uani 1 1 d . . . . .
H16 H 0.513637 0.359561 0.773012 0.043 Uiso 1 1 calc R U . . .
C17 C 0.5228(3) 0.5200(4) 0.6859(3) 0.0338(8) Uani 1 1 d . . . . .
H17 H 0.470771 0.565208 0.719009 0.041 Uiso 1 1 calc R U . . .
C18 C 0.5712(3) 0.5786(3) 0.6062(3) 0.0290(8) Uani 1 1 d . . . . .
H18 H 0.553487 0.662507 0.583226 0.035 Uiso 1 1 calc R U . . .
C19 C 0.6465(2) 0.5084(3) 0.5623(2) 0.0235(7) Uani 1 1 d . . . . .
N20 N 0.7104(2) 0.5453(3) 0.4820(2) 0.0228(6) Uani 1 1 d . . . . .
C21 C 0.6980(3) 0.6666(3) 0.4262(3) 0.0289(8) Uani 1 1 d . . . . .
H21A H 0.762573 0.716020 0.437263 0.043 Uiso 1 1 calc R U . . .
H21B H 0.640553 0.714754 0.452677 0.043 Uiso 1 1 calc R U . . .
H21C H 0.682581 0.650300 0.351443 0.043 Uiso 1 1 calc R U . . .
BR31 Br 0.30189(3) 0.06543(4) 0.36293(3) 0.03486(14) Uani 1 1 d . . . . .
O41 O 0.4865(5) 0.1173(7) 0.5374(7) 0.075(3) Uani 0.499(10) 1 d G . P . .
H41A H 0.444243 0.082310 0.495432 0.113 Uiso 0.499(10) 1 d G U P . .
H41B H 0.529417 0.061726 0.554306 0.113 Uiso 0.499(10) 1 d G U P . .


_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 C2 1.365(4) . ?
O1 H1 0.8400 . ?
C2 C3 1.382(4) . ?
C2 C7 1.400(4) . ?
C3 C4 1.384(5) . ?
C3 H3 0.9500 . ?
C4 C5 1.389(5) . ?
C4 H4 0.9500 . ?
C5 C6 1.374(5) . ?
C5 H5 0.9500 . ?
C6 C7 1.407(5) . ?
C6 H6 0.9500 . ?
C7 C8 1.453(4) . ?
C8 C9 1.354(5) . ?
C8 H8 0.9500 . ?
C9 C10 1.431(4) . ?
C9 H9 0.9500 . ?
C10 N20 1.320(4) . ?
C10 C11 1.524(4) . ?
C11 C14 1.510(4) . ?
C11 C12 1.540(4) . ?
C11 C13 1.542(5) . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12C 0.9800 . ?
C13 H13A 0.9800 . ?
C13 H13B 0.9800 . ?
C13 H13C 0.9800 . ?
C14 C19 1.380(5) . ?
C14 C15 1.389(5) . ?
C15 C16 1.390(5) . ?
C15 H15 0.9500 . ?
C16 C17 1.386(5) . ?
C16 H16 0.9500 . ?
C17 C18 1.387(5) . ?
C17 H17 0.9500 . ?
C18 C19 1.376(4) . ?
C18 H18 0.9500 . ?
C19 N20 1.427(4) . ?
N20 C21 1.463(4) . ?
C21 H21A 0.9800 . ?
C21 H21B 0.9800 . ?
C21 H21C 0.9800 . ?
O41 H41A 0.8200 . ?
O41 H41B 0.8200 . ?

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
C2 O1 H1 109.5 . . ?
O1 C2 C3 121.8(3) . . ?
O1 C2 C7 117.7(3) . . ?
C3 C2 C7 120.5(3) . . ?
C2 C3 C4 120.1(3) . . ?
C2 C3 H3 120.0 . . ?
C4 C3 H3 120.0 . . ?
C3 C4 C5 120.3(3) . . ?
C3 C4 H4 119.9 . . ?
C5 C4 H4 119.9 . . ?
C6 C5 C4 119.8(3) . . ?
C6 C5 H5 120.1 . . ?
C4 C5 H5 120.1 . . ?
C5 C6 C7 120.9(3) . . ?
C5 C6 H6 119.5 . . ?
C7 C6 H6 119.5 . . ?
C2 C7 C6 118.3(3) . . ?
C2 C7 C8 119.6(3) . . ?
C6 C7 C8 122.1(3) . . ?
C9 C8 C7 124.9(3) . . ?
C9 C8 H8 117.6 . . ?
C7 C8 H8 117.6 . . ?
C8 C9 C10 124.3(3) . . ?
C8 C9 H9 117.8 . . ?
C10 C9 H9 117.8 . . ?
N20 C10 C9 121.1(3) . . ?
N20 C10 C11 110.0(3) . . ?
C9 C10 C11 128.7(3) . . ?
C14 C11 C10 100.5(3) . . ?
C14 C11 C12 110.3(3) . . ?
C10 C11 C12 115.8(3) . . ?
C14 C11 C13 110.3(3) . . ?
C10 C11 C13 108.1(3) . . ?
C12 C11 C13 111.3(3) . . ?
C11 C12 H12A 109.5 . . ?
C11 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
C11 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C11 C13 H13A 109.5 . . ?
C11 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
C11 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
C19 C14 C15 119.3(3) . . ?
C19 C14 C11 110.0(3) . . ?
C15 C14 C11 130.7(3) . . ?
C14 C15 C16 118.2(3) . . ?
C14 C15 H15 120.9 . . ?
C16 C15 H15 120.9 . . ?
C17 C16 C15 120.9(3) . . ?
C17 C16 H16 119.6 . . ?
C15 C16 H16 119.6 . . ?
C16 C17 C18 121.6(3) . . ?
C16 C17 H17 119.2 . . ?
C18 C17 H17 119.2 . . ?
C19 C18 C17 116.2(3) . . ?
C19 C18 H18 121.9 . . ?
C17 C18 H18 121.9 . . ?
C18 C19 C14 123.9(3) . . ?
C18 C19 N20 128.3(3) . . ?
C14 C19 N20 107.8(3) . . ?
C10 N20 C19 111.4(3) . . ?
C10 N20 C21 125.6(3) . . ?
C19 N20 C21 123.0(3) . . ?
N20 C21 H21A 109.5 . . ?
N20 C21 H21B 109.5 . . ?
H21A C21 H21B 109.5 . . ?
N20 C21 H21C 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
H41A O41 H41B 104.5 . . ?

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 C2 C3 C4 179.9(3) . . . . ?
C7 C2 C3 C4 -2.3(5) . . . . ?
C2 C3 C4 C5 0.5(5) . . . . ?
C3 C4 C5 C6 1.3(5) . . . . ?
C4 C5 C6 C7 -1.4(5) . . . . ?
O1 C2 C7 C6 -179.9(3) . . . . ?
C3 C2 C7 C6 2.1(5) . . . . ?
O1 C2 C7 C8 0.4(4) . . . . ?
C3 C2 C7 C8 -177.5(3) . . . . ?
C5 C6 C7 C2 -0.3(5) . . . . ?
C5 C6 C7 C8 179.4(3) . . . . ?
C2 C7 C8 C9 159.7(3) . . . . ?
C6 C7 C8 C9 -20.0(5) . . . . ?
C7 C8 C9 C10 -179.6(3) . . . . ?
C8 C9 C10 N20 173.4(3) . . . . ?
C8 C9 C10 C11 -11.0(6) . . . . ?
N20 C10 C11 C14 -4.7(3) . . . . ?
C9 C10 C11 C14 179.3(3) . . . . ?
N20 C10 C11 C12 -123.5(3) . . . . ?
C9 C10 C11 C12 60.5(5) . . . . ?
N20 C10 C11 C13 110.9(3) . . . . ?
C9 C10 C11 C13 -65.1(4) . . . . ?
C10 C11 C14 C19 2.7(3) . . . . ?
C12 C11 C14 C19 125.5(3) . . . . ?
C13 C11 C14 C19 -111.2(3) . . . . ?
C10 C11 C14 C15 -176.1(3) . . . . ?
C12 C11 C14 C15 -53.4(5) . . . . ?
C13 C11 C14 C15 69.9(4) . . . . ?
C19 C14 C15 C16 -0.6(5) . . . . ?
C11 C14 C15 C16 178.2(3) . . . . ?
C14 C15 C16 C17 0.6(5) . . . . ?
C15 C16 C17 C18 0.1(6) . . . . ?
C16 C17 C18 C19 -0.7(5) . . . . ?
C17 C18 C19 C14 0.7(5) . . . . ?
C17 C18 C19 N20 -178.1(3) . . . . ?
C15 C14 C19 C18 0.0(5) . . . . ?
C11 C14 C19 C18 -179.1(3) . . . . ?
C15 C14 C19 N20 179.0(3) . . . . ?
C11 C14 C19 N20 -0.1(4) . . . . ?
C9 C10 N20 C19 -178.5(3) . . . . ?
C11 C10 N20 C19 5.1(4) . . . . ?
C9 C10 N20 C21 2.6(5) . . . . ?
C11 C10 N20 C21 -173.8(3) . . . . ?
C18 C19 N20 C10 175.7(3) . . . . ?
C14 C19 N20 C10 -3.2(4) . . . . ?
C18 C19 N20 C21 -5.3(5) . . . . ?
C14 C19 N20 C21 175.7(3) . . . . ?

_refine_diff_density_max         0.685
_refine_diff_density_min         -0.387
_refine_diff_density_rms         0.083


_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: Ethanol'
####################################################################### 
# 
# 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_vs_kc_spno2_hno3
_database_code_depnum_ccdc_archive 'CCDC 1824260'
_audit_update_record             
;
2018-02-15 deposited with the CCDC.
2018-04-06 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C19 H19 N2 O3, N O3'
_chemical_formula_sum            'C19 H19 N3 O6'
_chemical_formula_weight         385.37

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_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.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   7.227(3)
_cell_length_b                   10.0542(10)
_cell_length_c                   12.687(3)
_cell_angle_alpha                80.825(14)
_cell_angle_beta                 89.00(2)
_cell_angle_gamma                88.089(18)
_cell_volume                     909.6(4)
_cell_formula_units_Z            2
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    1333
_cell_measurement_theta_min      3.2350
_cell_measurement_theta_max      25.2420

_exptl_crystal_description       block
_exptl_crystal_colour            orange
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.407
_exptl_crystal_F_000             404
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.08
_exptl_absorpt_coefficient_mu    0.106
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_T_min  0.96398
_exptl_absorpt_correction_T_max  1.00000
_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_absorpt_special_details   ?





_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'Rigaku UltraX 18 rotating anode'
_diffrn_radiation_monochromator  'Xenocs Fox3D mirror'
_diffrn_measurement_device_type  'MAR345 image plate'
_diffrn_measurement_method       '59 images, ΔΦ 2.5° '
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            5621
_diffrn_reflns_av_unetI/netI     0.1246
_diffrn_reflns_av_R_equivalents  ?
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         3.253
_diffrn_reflns_theta_max         25.245
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.939
_diffrn_measured_fraction_theta_full 0.940
_diffrn_reflns_Laue_measured_fraction_max 0.939
_diffrn_reflns_Laue_measured_fraction_full 0.940
_diffrn_reflns_point_group_measured_fraction_max 0.939
_diffrn_reflns_point_group_measured_fraction_full 0.940
_reflns_number_total             5621
_reflns_number_gt                2963
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 _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.
;

_computing_data_collection       MAR
_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_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_structure_solution    'SHELXT (Sheldrick, 2015)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'MERCURY (Macrae et al., 2008)'
_computing_publication_material  
;

'MERCURY (Macrae et al., 2008), Platon (Spek, 2009)'



;








_refine_special_details          
;
 Refined as a 2-component twin.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0535P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         5621
_refine_ls_number_parameters     258
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1250
_refine_ls_R_factor_gt           0.0646
_refine_ls_wR_factor_ref         0.1370
_refine_ls_wR_factor_gt          0.1281
_refine_ls_goodness_of_fit_ref   1.046
_refine_ls_restrained_S_all      1.046
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.3964(4) 0.3225(2) 0.68186(19) 0.0292(7) Uani 1 1 d . . . . .
H1 H 0.4431 0.2464 0.6757 0.044 Uiso 1 1 calc R U . . .
C3 C 0.3204(5) 0.3139(3) 0.4997(3) 0.0247(10) Uani 1 1 d . . . . .
H3 H 0.3556 0.2211 0.5071 0.030 Uiso 1 1 calc R U . . .
C4 C 0.2600(5) 0.3810(3) 0.4030(3) 0.0237(9) Uani 1 1 d . . . . .
H4 H 0.2560 0.3353 0.3431 0.028 Uiso 1 1 calc R U . . .
C5 C 0.2048(5) 0.5159(3) 0.3932(3) 0.0212(9) Uani 1 1 d . . . . .
C6 C 0.2099(5) 0.5846(3) 0.4788(3) 0.0221(9) Uani 1 1 d . . . . .
H6 H 0.1727 0.6771 0.4702 0.026 Uiso 1 1 calc R U . . .
C7 C 0.2696(5) 0.5188(3) 0.5776(3) 0.0199(9) Uani 1 1 d . . . . .
C8 C 0.2752(5) 0.5857(3) 0.6709(3) 0.0233(9) Uani 1 1 d . . . . .
H8 H 0.3164 0.5331 0.7357 0.028 Uiso 1 1 calc R U . . .
C9 C 0.2272(5) 0.7155(3) 0.6736(3) 0.0240(9) Uani 1 1 d . . . . .
H9 H 0.1849 0.7684 0.6093 0.029 Uiso 1 1 calc R U . . .
C2 C 0.3301(5) 0.3821(3) 0.5873(3) 0.0215(9) Uani 1 1 d . . . . .
C10 C 0.2350(5) 0.7796(3) 0.7659(3) 0.0192(9) Uani 1 1 d . . . . .
C11 C 0.2961(5) 0.7205(3) 0.8780(3) 0.0209(9) Uani 1 1 d . . . . .
C12 C 0.1653(6) 0.6091(3) 0.9286(3) 0.0298(10) Uani 1 1 d . . . . .
H00D H 0.1909 0.5853 1.0050 0.045 Uiso 1 1 calc R U . . .
H00H H 0.1854 0.5293 0.8940 0.045 Uiso 1 1 calc R U . . .
H00I H 0.0365 0.6418 0.9191 0.045 Uiso 1 1 calc R U . . .
C13 C 0.4998(5) 0.6682(3) 0.8809(3) 0.0280(10) Uani 1 1 d . . . . .
H00A H 0.5778 0.7371 0.8409 0.042 Uiso 1 1 calc R U . . .
H00B H 0.5099 0.5860 0.8485 0.042 Uiso 1 1 calc R U . . .
H00C H 0.5407 0.6482 0.9551 0.042 Uiso 1 1 calc R U . . .
C14 C 0.2747(5) 0.8431(3) 0.9334(3) 0.0218(9) Uani 1 1 d . . . . .
C15 C 0.3081(5) 0.8591(3) 1.0375(3) 0.0273(10) Uani 1 1 d . . . . .
H15 H 0.3509 0.7853 1.0885 0.033 Uiso 1 1 calc R U . . .
C16 C 0.2775(5) 0.9859(4) 1.0654(3) 0.0292(10) Uani 1 1 d . . . . .
H16 H 0.3011 0.9993 1.1363 0.035 Uiso 1 1 calc R U . . .
C17 C 0.2134(5) 1.0928(4) 0.9922(3) 0.0283(10) Uani 1 1 d . . . . .
H17 H 0.1942 1.1784 1.0138 0.034 Uiso 1 1 calc R U . . .
C18 C 0.1761(5) 1.0789(4) 0.8877(3) 0.0275(10) Uani 1 1 d . . . . .
H18 H 0.1301 1.1519 0.8371 0.033 Uiso 1 1 calc R U . . .
C19 C 0.2106(5) 0.9511(3) 0.8620(3) 0.0220(9) Uani 1 1 d . . . . .
N20 N 0.1857(4) 0.9083(3) 0.7616(2) 0.0218(8) Uani 1 1 d . . . . .
C21 C 0.1122(6) 0.9976(4) 0.6669(3) 0.0324(11) Uani 1 1 d . . . . .
H00P H 0.2007 0.9991 0.6073 0.049 Uiso 1 1 calc R U . . .
H00Q H 0.0930 1.0891 0.6834 0.049 Uiso 1 1 calc R U . . .
H00R H -0.0059 0.9641 0.6470 0.049 Uiso 1 1 calc R U . . .
N22 N 0.1454(4) 0.5882(3) 0.2907(2) 0.0276(8) Uani 1 1 d . . . . .
O23 O 0.1528(4) 0.5288(2) 0.2132(2) 0.0406(8) Uani 1 1 d . . . . .
O24 O 0.0907(4) 0.7057(3) 0.2846(2) 0.0444(9) Uani 1 1 d . . . . .
N31 N 0.6242(4) 0.0218(3) 0.6390(3) 0.0250(8) Uani 1 1 d . . . . .
O32 O 0.5102(4) 0.0728(2) 0.6992(2) 0.0336(8) Uani 1 1 d . . . . .
O33 O 0.6784(4) -0.0973(2) 0.6668(2) 0.0446(9) Uani 1 1 d . . . . .
O34 O 0.6800(4) 0.0889(3) 0.5550(2) 0.0438(8) Uani 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C2 1.341(4) . ?
O1 H1 0.8400 . ?
C3 C4 1.373(5) . ?
C3 C2 1.400(5) . ?
C3 H3 0.9500 . ?
C4 C5 1.387(4) . ?
C4 H4 0.9500 . ?
C5 C6 1.378(5) . ?
C5 N22 1.450(4) . ?
C6 C7 1.389(5) . ?
C6 H6 0.9500 . ?
C7 C2 1.415(4) . ?
C7 C8 1.454(5) . ?
C8 C9 1.344(4) . ?
C8 H8 0.9500 . ?
C9 C10 1.427(5) . ?
C9 H9 0.9500 . ?
C10 N20 1.323(4) . ?
C10 C11 1.519(5) . ?
C11 C14 1.516(5) . ?
C11 C12 1.543(5) . ?
C11 C13 1.546(5) . ?
C12 H00D 0.9800 . ?
C12 H00H 0.9800 . ?
C12 H00I 0.9800 . ?
C13 H00A 0.9800 . ?
C13 H00B 0.9800 . ?
C13 H00C 0.9800 . ?
C14 C19 1.372(5) . ?
C14 C15 1.382(5) . ?
C15 C16 1.386(5) . ?
C15 H15 0.9500 . ?
C16 C17 1.377(5) . ?
C16 H16 0.9500 . ?
C17 C18 1.387(5) . ?
C17 H17 0.9500 . ?
C18 C19 1.389(5) . ?
C18 H18 0.9500 . ?
C19 N20 1.424(5) . ?
N20 C21 1.477(4) . ?
C21 H00P 0.9800 . ?
C21 H00Q 0.9800 . ?
C21 H00R 0.9800 . ?
N22 O24 1.224(3) . ?
N22 O23 1.228(4) . ?
N31 O34 1.236(3) . ?
N31 O33 1.244(3) . ?
N31 O32 1.265(3) . ?

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
C2 O1 H1 109.5 . . ?
C4 C3 C2 120.2(3) . . ?
C4 C3 H3 119.9 . . ?
C2 C3 H3 119.9 . . ?
C3 C4 C5 119.7(4) . . ?
C3 C4 H4 120.2 . . ?
C5 C4 H4 120.2 . . ?
C6 C5 C4 121.3(3) . . ?
C6 C5 N22 118.7(3) . . ?
C4 C5 N22 119.9(3) . . ?
C5 C6 C7 120.1(3) . . ?
C5 C6 H6 119.9 . . ?
C7 C6 H6 119.9 . . ?
C6 C7 C2 118.8(3) . . ?
C6 C7 C8 122.5(3) . . ?
C2 C7 C8 118.8(3) . . ?
C9 C8 C7 125.7(3) . . ?
C9 C8 H8 117.1 . . ?
C7 C8 H8 117.1 . . ?
C8 C9 C10 124.9(3) . . ?
C8 C9 H9 117.6 . . ?
C10 C9 H9 117.6 . . ?
O1 C2 C3 122.2(3) . . ?
O1 C2 C7 117.8(3) . . ?
C3 C2 C7 119.9(3) . . ?
N20 C10 C9 121.0(3) . . ?
N20 C10 C11 110.0(3) . . ?
C9 C10 C11 128.9(3) . . ?
C14 C11 C10 100.9(3) . . ?
C14 C11 C12 110.8(3) . . ?
C10 C11 C12 110.8(3) . . ?
C14 C11 C13 110.5(3) . . ?
C10 C11 C13 112.3(3) . . ?
C12 C11 C13 111.2(3) . . ?
C11 C12 H00D 109.5 . . ?
C11 C12 H00H 109.5 . . ?
H00D C12 H00H 109.5 . . ?
C11 C12 H00I 109.5 . . ?
H00D C12 H00I 109.5 . . ?
H00H C12 H00I 109.5 . . ?
C11 C13 H00A 109.5 . . ?
C11 C13 H00B 109.5 . . ?
H00A C13 H00B 109.5 . . ?
C11 C13 H00C 109.5 . . ?
H00A C13 H00C 109.5 . . ?
H00B C13 H00C 109.5 . . ?
C19 C14 C15 119.6(3) . . ?
C19 C14 C11 109.3(3) . . ?
C15 C14 C11 131.1(3) . . ?
C14 C15 C16 118.1(3) . . ?
C14 C15 H15 120.9 . . ?
C16 C15 H15 120.9 . . ?
C17 C16 C15 121.2(4) . . ?
C17 C16 H16 119.4 . . ?
C15 C16 H16 119.4 . . ?
C16 C17 C18 121.9(3) . . ?
C16 C17 H17 119.1 . . ?
C18 C17 H17 119.1 . . ?
C17 C18 C19 115.5(3) . . ?
C17 C18 H18 122.3 . . ?
C19 C18 H18 122.3 . . ?
C14 C19 C18 123.8(4) . . ?
C14 C19 N20 108.7(3) . . ?
C18 C19 N20 127.6(3) . . ?
C10 N20 C19 111.0(3) . . ?
C10 N20 C21 125.5(3) . . ?
C19 N20 C21 123.4(3) . . ?
N20 C21 H00P 109.5 . . ?
N20 C21 H00Q 109.5 . . ?
H00P C21 H00Q 109.5 . . ?
N20 C21 H00R 109.5 . . ?
H00P C21 H00R 109.5 . . ?
H00Q C21 H00R 109.5 . . ?
O24 N22 O23 122.6(3) . . ?
O24 N22 C5 118.9(3) . . ?
O23 N22 C5 118.4(3) . . ?
O34 N31 O33 121.2(3) . . ?
O34 N31 O32 120.6(3) . . ?
O33 N31 O32 118.3(3) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C2 C3 C4 C5 -1.4(6) . . . . ?
C3 C4 C5 C6 0.3(6) . . . . ?
C3 C4 C5 N22 178.4(4) . . . . ?
C4 C5 C6 C7 -0.6(6) . . . . ?
N22 C5 C6 C7 -178.8(3) . . . . ?
C5 C6 C7 C2 2.1(5) . . . . ?
C5 C6 C7 C8 -179.1(4) . . . . ?
C6 C7 C8 C9 -0.7(6) . . . . ?
C2 C7 C8 C9 178.2(4) . . . . ?
C7 C8 C9 C10 -179.5(4) . . . . ?
C4 C3 C2 O1 -176.8(4) . . . . ?
C4 C3 C2 C7 2.9(6) . . . . ?
C6 C7 C2 O1 176.5(3) . . . . ?
C8 C7 C2 O1 -2.4(5) . . . . ?
C6 C7 C2 C3 -3.2(5) . . . . ?
C8 C7 C2 C3 177.9(3) . . . . ?
C8 C9 C10 N20 179.7(4) . . . . ?
C8 C9 C10 C11 0.0(6) . . . . ?
N20 C10 C11 C14 -1.3(4) . . . . ?
C9 C10 C11 C14 178.5(4) . . . . ?
N20 C10 C11 C12 116.1(3) . . . . ?
C9 C10 C11 C12 -64.1(5) . . . . ?
N20 C10 C11 C13 -119.0(3) . . . . ?
C9 C10 C11 C13 60.9(5) . . . . ?
C10 C11 C14 C19 0.4(4) . . . . ?
C12 C11 C14 C19 -116.9(3) . . . . ?
C13 C11 C14 C19 119.4(3) . . . . ?
C10 C11 C14 C15 -179.7(4) . . . . ?
C12 C11 C14 C15 63.0(5) . . . . ?
C13 C11 C14 C15 -60.7(5) . . . . ?
C19 C14 C15 C16 -0.9(6) . . . . ?
C11 C14 C15 C16 179.2(4) . . . . ?
C14 C15 C16 C17 0.8(6) . . . . ?
C15 C16 C17 C18 0.2(6) . . . . ?
C16 C17 C18 C19 -1.0(6) . . . . ?
C15 C14 C19 C18 0.1(6) . . . . ?
C11 C14 C19 C18 180.0(3) . . . . ?
C15 C14 C19 N20 -179.4(3) . . . . ?
C11 C14 C19 N20 0.5(4) . . . . ?
C17 C18 C19 C14 0.8(6) . . . . ?
C17 C18 C19 N20 -179.8(4) . . . . ?
C9 C10 N20 C19 -178.1(3) . . . . ?
C11 C10 N20 C19 1.7(4) . . . . ?
C9 C10 N20 C21 2.6(6) . . . . ?
C11 C10 N20 C21 -177.6(3) . . . . ?
C14 C19 N20 C10 -1.4(4) . . . . ?
C18 C19 N20 C10 179.1(4) . . . . ?
C14 C19 N20 C21 177.9(3) . . . . ?
C18 C19 N20 C21 -1.5(6) . . . . ?
C6 C5 N22 O24 -4.5(5) . . . . ?
C4 C5 N22 O24 177.3(3) . . . . ?
C6 C5 N22 O23 175.3(3) . . . . ?
C4 C5 N22 O23 -2.9(5) . . . . ?

_refine_diff_density_max         0.271
_refine_diff_density_min         -0.281
_refine_diff_density_rms         0.063


_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: Acetone'
####################################################################### 
# 
# 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_VS-KC-SPOMe-H2SO4
_database_code_depnum_ccdc_archive 'CCDC 1824262'
_audit_update_record             
;
2018-02-15 deposited with the CCDC.
2018-04-06 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C20 H22 N O2, H O4 S'
_chemical_formula_sum            'C20 H23 N O6 S'
_chemical_formula_weight         405.45

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           33
_space_group_name_H-M_alt        'P n a 21'
_space_group_name_Hall           'P 2c -2n'

_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.
;

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

_cell_length_a                   7.8327(5)
_cell_length_b                   16.0190(13)
_cell_length_c                   15.1017(19)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1894.9(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    1864
_cell_measurement_theta_min      3.1840
_cell_measurement_theta_max      26.0370

_exptl_crystal_description       rod
_exptl_crystal_colour            orange
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.421
_exptl_crystal_F_000             856
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.50
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.10
_exptl_absorpt_coefficient_mu    0.209
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_T_min  0.87499
_exptl_absorpt_correction_T_max  1.00000
_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_absorpt_special_details   ?




_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'Rigaku UltraX 18 rotating anode'
_diffrn_radiation_monochromator  'Xenocs Fox3D mirror'
_diffrn_measurement_device_type  'MAR345 image plate'
_diffrn_measurement_method       
;
'118 images, ΔΦ 2.0° '
' 21 images, ΔΦ 2.0° (2nd orientation)'
;
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            19542
_diffrn_reflns_av_unetI/netI     0.0234
_diffrn_reflns_av_R_equivalents  0.0377
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         3.194
_diffrn_reflns_theta_max         26.243
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.984
_diffrn_measured_fraction_theta_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.984
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.977
_diffrn_reflns_point_group_measured_fraction_full 0.990
_reflns_number_total             3734
_reflns_number_gt                3641
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.911
_reflns_Friedel_fraction_max     0.970
_reflns_Friedel_fraction_full    0.986

_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.
;

_computing_data_collection       MAR
_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_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_structure_solution    'SHELXT (Sheldrick, 2015)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'MERCURY (Macrae et al., 2008)'
_computing_publication_material  
;

'MERCURY (Macrae et al., 2008), Platon (Spek, 2009)'



;








_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0362P)²+1.1714P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Flack x determined using 1690 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.70(3)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         3734
_refine_ls_number_parameters     259
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0315
_refine_ls_R_factor_gt           0.0302
_refine_ls_wR_factor_ref         0.0780
_refine_ls_wR_factor_gt          0.0774
_refine_ls_goodness_of_fit_ref   1.014
_refine_ls_restrained_S_all      1.014
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.3708(3) 0.54687(14) -0.06102(13) 0.0271(5) Uani 1 1 d . . . . .
H1 H 0.411(2) 0.500(2) -0.0424(10) 0.041 Uiso 1 1 calc R U . . .
C2 C 0.3231(4) 0.59433(17) 0.00921(18) 0.0198(6) Uani 1 1 d . . . . .
C3 C 0.1850(4) 0.65013(17) -0.00614(19) 0.0206(6) Uani 1 1 d . . . . .
C4 C 0.1249(4) 0.70039(19) 0.0608(2) 0.0240(6) Uani 1 1 d . . . . .
H4 H 0.0317 0.7370 0.0502 0.029 Uiso 1 1 calc R U . . .
C5 C 0.2014(4) 0.69742(18) 0.1441(2) 0.0241(6) Uani 1 1 d . . . . .
H5 H 0.1577 0.7308 0.1909 0.029 Uiso 1 1 calc R U . . .
C6 C 0.3398(4) 0.64646(18) 0.15891(18) 0.0213(6) Uani 1 1 d . . . . .
H6 H 0.3920 0.6460 0.2157 0.026 Uiso 1 1 calc R U . . .
C7 C 0.4057(4) 0.59483(17) 0.09130(18) 0.0189(5) Uani 1 1 d . . . . .
C8 C 0.5610(4) 0.54555(18) 0.10464(18) 0.0205(6) Uani 1 1 d . . . . .
H8 H 0.5841 0.5020 0.0636 0.025 Uiso 1 1 calc R U . . .
C9 C 0.6734(4) 0.55747(17) 0.17090(19) 0.0200(6) Uani 1 1 d . . . . .
H9 H 0.6477 0.5987 0.2141 0.024 Uiso 1 1 calc R U . . .
C10 C 0.8305(4) 0.51144(17) 0.18029(18) 0.0179(5) Uani 1 1 d . . . . .
C11 C 0.8959(3) 0.43810(16) 0.12609(18) 0.0173(5) Uani 1 1 d . . . . .
C12 C 0.9230(4) 0.46027(19) 0.02845(19) 0.0233(6) Uani 1 1 d . . . . .
H12A H 0.8121 0.4692 0.0000 0.035 Uiso 1 1 calc R U . . .
H12B H 0.9831 0.4145 -0.0012 0.035 Uiso 1 1 calc R U . . .
H12C H 0.9913 0.5114 0.0241 0.035 Uiso 1 1 calc R U . . .
C13 C 0.7772(4) 0.36196(17) 0.13606(19) 0.0217(6) Uani 1 1 d . . . . .
H13A H 0.7665 0.3475 0.1989 0.033 Uiso 1 1 calc R U . . .
H13B H 0.8253 0.3145 0.1036 0.033 Uiso 1 1 calc R U . . .
H13C H 0.6643 0.3755 0.1120 0.033 Uiso 1 1 calc R U . . .
C14 C 1.0660(3) 0.42121(17) 0.16998(18) 0.0184(5) Uani 1 1 d . . . . .
C15 C 1.1896(4) 0.36193(18) 0.15178(19) 0.0224(6) Uani 1 1 d . . . . .
H15 H 1.1760 0.3236 0.1043 0.027 Uiso 1 1 calc R U . . .
C16 C 1.3342(4) 0.36005(19) 0.2051(2) 0.0237(6) Uani 1 1 d . . . . .
H16 H 1.4200 0.3194 0.1942 0.028 Uiso 1 1 calc R U . . .
C17 C 1.3553(4) 0.41644(19) 0.2739(2) 0.0239(6) Uani 1 1 d . . . . .
H17 H 1.4561 0.4141 0.3088 0.029 Uiso 1 1 calc R U . . .
C18 C 1.2314(4) 0.47662(18) 0.29297(18) 0.0218(6) Uani 1 1 d . . . . .
H18 H 1.2451 0.5156 0.3399 0.026 Uiso 1 1 calc R U . . .
C19 C 1.0872(3) 0.47615(17) 0.23939(17) 0.0177(5) Uani 1 1 d . . . . .
N20 N 0.9419(3) 0.52950(15) 0.24286(15) 0.0189(5) Uani 1 1 d . . . . .
C21 C 0.9222(4) 0.5946(2) 0.3102(2) 0.0275(7) Uani 1 1 d . . . . .
H21A H 0.8868 0.6468 0.2817 0.041 Uiso 1 1 calc R U . . .
H21B H 1.0313 0.6031 0.3406 0.041 Uiso 1 1 calc R U . . .
H21C H 0.8353 0.5774 0.3532 0.041 Uiso 1 1 calc R U . . .
O22 O 0.1208(3) 0.64811(13) -0.09007(14) 0.0282(5) Uani 1 1 d . . . . .
C23 C -0.0165(5) 0.7038(2) -0.1088(2) 0.0342(8) Uani 1 1 d . . . . .
H23A H -0.1145 0.6899 -0.0712 0.051 Uiso 1 1 calc R U . . .
H23B H -0.0492 0.6984 -0.1712 0.051 Uiso 1 1 calc R U . . .
H23C H 0.0196 0.7613 -0.0970 0.051 Uiso 1 1 calc R U . . .
S31 S 0.02248(8) 0.18527(4) 0.92400(5) 0.01822(15) Uani 1 1 d . . . . .
O32 O 0.1996(3) 0.17070(14) 0.87904(17) 0.0313(5) Uani 1 1 d . . . . .
H32 H 0.255(3) 0.220(3) 0.8735(3) 0.047 Uiso 1 1 calc R U . . .
O33 O 0.0403(3) 0.25371(14) 0.98430(14) 0.0301(5) Uani 1 1 d . . . . .
O34 O -0.0128(3) 0.10596(15) 0.96509(17) 0.0383(6) Uani 1 1 d . . . . .
O35 O -0.0965(3) 0.20355(13) 0.85217(13) 0.0255(5) Uani 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C2 1.357(3) . ?
O1 H1 0.86(4) . ?
C2 C7 1.399(4) . ?
C2 C3 1.422(4) . ?
C3 O22 1.364(3) . ?
C3 C4 1.375(4) . ?
C4 C5 1.395(4) . ?
C4 H4 0.9500 . ?
C5 C6 1.375(4) . ?
C5 H5 0.9500 . ?
C6 C7 1.412(4) . ?
C6 H6 0.9500 . ?
C7 C8 1.464(4) . ?
C8 C9 1.347(4) . ?
C8 H8 0.9500 . ?
C9 C10 1.441(4) . ?
C9 H9 0.9500 . ?
C10 N20 1.318(4) . ?
C10 C11 1.521(4) . ?
C11 C14 1.512(4) . ?
C11 C12 1.532(4) . ?
C11 C13 1.541(4) . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12C 0.9800 . ?
C13 H13A 0.9800 . ?
C13 H13B 0.9800 . ?
C13 H13C 0.9800 . ?
C14 C19 1.379(4) . ?
C14 C15 1.384(4) . ?
C15 C16 1.389(4) . ?
C15 H15 0.9500 . ?
C16 C17 1.387(4) . ?
C16 H16 0.9500 . ?
C17 C18 1.398(4) . ?
C17 H17 0.9500 . ?
C18 C19 1.390(4) . ?
C18 H18 0.9500 . ?
C19 N20 1.424(4) . ?
N20 C21 1.464(4) . ?
C21 H21A 0.9800 . ?
C21 H21B 0.9800 . ?
C21 H21C 0.9800 . ?
O22 C23 1.426(4) . ?
C23 H23A 0.9800 . ?
C23 H23B 0.9800 . ?
C23 H23C 0.9800 . ?
S31 O33 1.432(2) . ?
S31 O34 1.441(2) . ?
S31 O35 1.460(2) . ?
S31 O32 1.562(2) . ?
O32 H32 0.91(5) . ?

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
C2 O1 H1 109.5 . . ?
O1 C2 C7 124.6(2) . . ?
O1 C2 C3 115.7(2) . . ?
C7 C2 C3 119.5(2) . . ?
O22 C3 C4 124.8(3) . . ?
O22 C3 C2 114.6(2) . . ?
C4 C3 C2 120.6(3) . . ?
C3 C4 C5 119.8(3) . . ?
C3 C4 H4 120.1 . . ?
C5 C4 H4 120.1 . . ?
C6 C5 C4 120.3(3) . . ?
C6 C5 H5 119.8 . . ?
C4 C5 H5 119.8 . . ?
C5 C6 C7 121.2(3) . . ?
C5 C6 H6 119.4 . . ?
C7 C6 H6 119.4 . . ?
C2 C7 C6 118.4(3) . . ?
C2 C7 C8 120.2(2) . . ?
C6 C7 C8 121.3(3) . . ?
C9 C8 C7 124.7(3) . . ?
C9 C8 H8 117.7 . . ?
C7 C8 H8 117.7 . . ?
C8 C9 C10 124.0(3) . . ?
C8 C9 H9 118.0 . . ?
C10 C9 H9 118.0 . . ?
N20 C10 C9 121.5(2) . . ?
N20 C10 C11 109.4(2) . . ?
C9 C10 C11 129.0(2) . . ?
C14 C11 C10 101.5(2) . . ?
C14 C11 C12 110.0(2) . . ?
C10 C11 C12 112.7(2) . . ?
C14 C11 C13 110.3(2) . . ?
C10 C11 C13 110.8(2) . . ?
C12 C11 C13 111.2(2) . . ?
C11 C12 H12A 109.5 . . ?
C11 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
C11 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C11 C13 H13A 109.5 . . ?
C11 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
C11 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
C19 C14 C15 120.3(3) . . ?
C19 C14 C11 109.0(2) . . ?
C15 C14 C11 130.7(2) . . ?
C14 C15 C16 118.0(3) . . ?
C14 C15 H15 121.0 . . ?
C16 C15 H15 121.0 . . ?
C17 C16 C15 121.1(3) . . ?
C17 C16 H16 119.4 . . ?
C15 C16 H16 119.4 . . ?
C16 C17 C18 121.4(3) . . ?
C16 C17 H17 119.3 . . ?
C18 C17 H17 119.3 . . ?
C19 C18 C17 116.1(3) . . ?
C19 C18 H18 121.9 . . ?
C17 C18 H18 121.9 . . ?
C14 C19 C18 123.0(3) . . ?
C14 C19 N20 108.3(2) . . ?
C18 C19 N20 128.7(2) . . ?
C10 N20 C19 111.8(2) . . ?
C10 N20 C21 125.7(2) . . ?
C19 N20 C21 122.5(2) . . ?
N20 C21 H21A 109.5 . . ?
N20 C21 H21B 109.5 . . ?
H21A C21 H21B 109.5 . . ?
N20 C21 H21C 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
C3 O22 C23 116.6(2) . . ?
O22 C23 H23A 109.5 . . ?
O22 C23 H23B 109.5 . . ?
H23A C23 H23B 109.5 . . ?
O22 C23 H23C 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 109.5 . . ?
O33 S31 O34 114.83(15) . . ?
O33 S31 O35 112.41(13) . . ?
O34 S31 O35 112.00(14) . . ?
O33 S31 O32 107.70(13) . . ?
O34 S31 O32 103.06(14) . . ?
O35 S31 O32 105.91(13) . . ?
S31 O32 H32 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
O1 C2 C3 O22 -0.4(4) . . . . ?
C7 C2 C3 O22 176.1(2) . . . . ?
O1 C2 C3 C4 179.2(3) . . . . ?
C7 C2 C3 C4 -4.4(4) . . . . ?
O22 C3 C4 C5 -179.7(3) . . . . ?
C2 C3 C4 C5 0.8(5) . . . . ?
C3 C4 C5 C6 2.0(5) . . . . ?
C4 C5 C6 C7 -1.3(4) . . . . ?
O1 C2 C7 C6 -178.9(3) . . . . ?
C3 C2 C7 C6 5.0(4) . . . . ?
O1 C2 C7 C8 3.7(4) . . . . ?
C3 C2 C7 C8 -172.3(3) . . . . ?
C5 C6 C7 C2 -2.3(4) . . . . ?
C5 C6 C7 C8 175.1(3) . . . . ?
C2 C7 C8 C9 162.0(3) . . . . ?
C6 C7 C8 C9 -15.3(4) . . . . ?
C7 C8 C9 C10 -176.4(3) . . . . ?
C8 C9 C10 N20 175.2(3) . . . . ?
C8 C9 C10 C11 -5.5(5) . . . . ?
N20 C10 C11 C14 -1.3(3) . . . . ?
C9 C10 C11 C14 179.4(3) . . . . ?
N20 C10 C11 C12 -118.8(3) . . . . ?
C9 C10 C11 C12 61.9(4) . . . . ?
N20 C10 C11 C13 115.9(3) . . . . ?
C9 C10 C11 C13 -63.4(4) . . . . ?
C10 C11 C14 C19 1.4(3) . . . . ?
C12 C11 C14 C19 120.9(3) . . . . ?
C13 C11 C14 C19 -116.1(2) . . . . ?
C10 C11 C14 C15 -179.9(3) . . . . ?
C12 C11 C14 C15 -60.4(4) . . . . ?
C13 C11 C14 C15 62.6(4) . . . . ?
C19 C14 C15 C16 -0.2(4) . . . . ?
C11 C14 C15 C16 -178.8(3) . . . . ?
C14 C15 C16 C17 -0.7(4) . . . . ?
C15 C16 C17 C18 0.8(4) . . . . ?
C16 C17 C18 C19 0.2(4) . . . . ?
C15 C14 C19 C18 1.2(4) . . . . ?
C11 C14 C19 C18 -179.9(2) . . . . ?
C15 C14 C19 N20 -179.9(2) . . . . ?
C11 C14 C19 N20 -1.0(3) . . . . ?
C17 C18 C19 C14 -1.2(4) . . . . ?
C17 C18 C19 N20 -179.8(3) . . . . ?
C9 C10 N20 C19 -179.9(2) . . . . ?
C11 C10 N20 C19 0.7(3) . . . . ?
C9 C10 N20 C21 1.4(4) . . . . ?
C11 C10 N20 C21 -178.0(3) . . . . ?
C14 C19 N20 C10 0.2(3) . . . . ?
C18 C19 N20 C10 179.0(3) . . . . ?
C14 C19 N20 C21 179.0(3) . . . . ?
C18 C19 N20 C21 -2.2(4) . . . . ?
C4 C3 O22 C23 1.2(4) . . . . ?
C2 C3 O22 C23 -179.3(3) . . . . ?

_refine_diff_density_max         0.202
_refine_diff_density_min         -0.164
_refine_diff_density_rms         0.040

####################################################################### 
# 
# 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_VS-KC-SPB-HBr-DCM
_database_code_depnum_ccdc_archive 'CCDC 1824250'
_audit_update_record             
;
2018-02-15 deposited with the CCDC.
2018-04-06 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2016/4
_shelx_SHELXL_version_number     2016/4
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C23 H22 N O, Br'
_chemical_formula_sum            'C23 H22 Br N O'
_chemical_formula_weight         408.32

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.2901 2.4595 '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 21/c'
_space_group_name_Hall           '-P 2ybc'

_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.
;

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

_cell_length_a                   17.8583(18)
_cell_length_b                   15.1686(10)
_cell_length_c                   6.9757(3)
_cell_angle_alpha                90
_cell_angle_beta                 93.704(7)
_cell_angle_gamma                90
_cell_volume                     1885.7(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    297(2)
_cell_measurement_reflns_used    3152
_cell_measurement_theta_min      3.3480
_cell_measurement_theta_max      25.2300

_exptl_crystal_description       needle
_exptl_crystal_colour            red
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.438
_exptl_crystal_F_000             840
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.5
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.2
_exptl_absorpt_coefficient_mu    2.191
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_T_min  0.68028
_exptl_absorpt_correction_T_max  1.00000
_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_absorpt_special_details   ?
_diffrn_ambient_temperature      297(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'Rigaku UltraX 18 rotating anode'
_diffrn_radiation_monochromator  'Xenocs Fox3D mirror'
_diffrn_measurement_device_type  'MAR345 image plate'
_diffrn_measurement_method       '108 images, ΔΦ 1.5° '
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            3400
_diffrn_reflns_av_unetI/netI     0.0728
_diffrn_reflns_av_R_equivalents  0.0787
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_l_min       -6
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_theta_min         3.220
_diffrn_reflns_theta_max         25.237
_diffrn_reflns_theta_full        25.000
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_point_group_measured_fraction_full 0.997
_reflns_number_total             3400
_reflns_number_gt                2711
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 _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.
;

_computing_data_collection       MAR
_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_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_structure_solution    'SHELXT (Sheldrick, 2015)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'MERCURY (Macrae et al., 2008)'
_computing_publication_material  
;
'MERCURY (Macrae et al., 2008), Platon (Spek, 2009)'
;

_refine_special_details          'Refined as a 2-component twin.,Twin'
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0905P)²+6.8780P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3400
_refine_ls_number_parameters     240
_refine_ls_number_restraints     6
_refine_ls_R_factor_all          0.0873
_refine_ls_R_factor_gt           0.0697
_refine_ls_wR_factor_ref         0.1897
_refine_ls_wR_factor_gt          0.1803
_refine_ls_goodness_of_fit_ref   1.055
_refine_ls_restrained_S_all      1.054
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.7763(3) 0.7806(3) 0.7111(9) 0.0285(11) Uani 1 1 d . . . . .
H1 H 0.792490 0.831235 0.716164 0.043 Uiso 1 1 calc R U . . .
C2 C 0.7017(4) 0.7815(4) 0.7305(9) 0.0220(15) Uani 1 1 d . . . . .
C3 C 0.6649(4) 0.8641(5) 0.7443(10) 0.0253(17) Uani 1 1 d . . . . .
H3 H 0.691856 0.916376 0.738611 0.030 Uiso 1 1 calc R U . . .
C4 C 0.5896(4) 0.8657(5) 0.7661(10) 0.0245(16) Uani 1 1 d . . . . .
H4 H 0.565626 0.919842 0.774413 0.029 Uiso 1 1 calc R U . . .
C5 C 0.5466(4) 0.7871(5) 0.7766(9) 0.0239(16) Uani 1 1 d . . . . .
C6 C 0.5833(4) 0.7046(5) 0.7642(9) 0.0221(15) Uani 1 1 d . . . . .
C7 C 0.6639(4) 0.7023(4) 0.7425(9) 0.0219(15) Uani 1 1 d . . . . .
C8 C 0.7003(4) 0.6169(4) 0.7302(10) 0.0219(15) Uani 1 1 d . U . . .
H8 H 0.668120 0.568634 0.721070 0.026 Uiso 1 1 calc R U . . .
C9 C 0.7749(4) 0.5973(4) 0.7299(10) 0.0203(14) Uani 1 1 d . . . . .
H9 H 0.809295 0.643336 0.731311 0.024 Uiso 1 1 calc R U . . .
C10 C 0.8021(4) 0.5093(4) 0.7277(10) 0.0180(13) Uani 1 1 d . . . . .
C11 C 0.7576(4) 0.4227(4) 0.7202(10) 0.0183(13) Uani 1 1 d . . . . .
C12 C 0.7115(4) 0.4103(5) 0.8955(11) 0.0257(16) Uani 1 1 d . . . . .
H12A H 0.692121 0.351304 0.896499 0.039 Uiso 1 1 calc R U . . .
H12B H 0.670588 0.451498 0.889480 0.039 Uiso 1 1 calc R U . . .
H12C H 0.742828 0.420420 1.010416 0.039 Uiso 1 1 calc R U . . .
C13 C 0.7088(4) 0.4144(4) 0.5296(11) 0.0233(14) Uani 1 1 d . . . . .
H13A H 0.738144 0.429799 0.424097 0.035 Uiso 1 1 calc R U . . .
H13B H 0.666544 0.453412 0.532292 0.035 Uiso 1 1 calc R U . . .
H13C H 0.691335 0.354774 0.514279 0.035 Uiso 1 1 calc R U . . .
C14 C 0.8215(4) 0.3561(4) 0.7244(10) 0.0209(13) Uani 1 1 d . . . . .
C15 C 0.8209(4) 0.2652(4) 0.7223(11) 0.0255(15) Uani 1 1 d . . . . .
H15 H 0.775820 0.234393 0.717729 0.031 Uiso 1 1 calc R U . . .
C16 C 0.8887(4) 0.2207(4) 0.7272(11) 0.0279(15) Uani 1 1 d . . . . .
H16 H 0.889112 0.159403 0.725814 0.034 Uiso 1 1 calc R U . . .
C17 C 0.9565(4) 0.2667(4) 0.7341(11) 0.0304(16) Uani 1 1 d . . . . .
H17 H 1.001322 0.235459 0.736329 0.036 Uiso 1 1 calc R U . . .
C18 C 0.9584(4) 0.3582(4) 0.7377(11) 0.0240(15) Uani 1 1 d . . . . .
H18 H 1.003413 0.389162 0.743566 0.029 Uiso 1 1 calc R U . . .
C19 C 0.8903(4) 0.4009(4) 0.7323(10) 0.0180(13) Uani 1 1 d . . . . .
N20 N 0.8750(3) 0.4923(3) 0.7362(8) 0.0185(11) Uani 1 1 d . . . . .
C21 C 0.9345(4) 0.5593(4) 0.7439(11) 0.0246(14) Uani 1 1 d . . . . .
H21A H 0.926915 0.598371 0.636083 0.037 Uiso 1 1 calc R U . . .
H21B H 0.982395 0.531010 0.739920 0.037 Uiso 1 1 calc R U . . .
H21C H 0.932929 0.592449 0.860915 0.037 Uiso 1 1 calc R U . . .
C22 C 0.4691(4) 0.7904(4) 0.8023(10) 0.0238(15) Uani 1 1 d . . . . .
H22 H 0.445897 0.844925 0.812183 0.029 Uiso 1 1 calc R U . . .
C23 C 0.4271(4) 0.7155(4) 0.8130(11) 0.0265(15) Uani 1 1 d . . . . .
H23 H 0.375809 0.719104 0.828149 0.032 Uiso 1 1 calc R U . . .
C24 C 0.4621(4) 0.6335(4) 0.8008(11) 0.0264(16) Uani 1 1 d . . . . .
H24 H 0.434150 0.582086 0.808750 0.032 Uiso 1 1 calc R U . . .
C25 C 0.5379(4) 0.6289(5) 0.7771(10) 0.0247(16) Uani 1 1 d . . . . .
H25 H 0.560132 0.573666 0.769185 0.030 Uiso 1 1 calc R U . . .
BR31 Br 0.85506(4) 0.53122(4) 0.23253(10) 0.0232(2) Uani 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C2 1.348(8) . ?
O1 H1 0.8200 . ?
C2 C7 1.384(9) . ?
C2 C3 1.420(10) . ?
C3 C4 1.363(11) . ?
C3 H3 0.9300 . ?
C4 C5 1.424(10) . ?
C4 H4 0.9300 . ?
C5 C22 1.408(10) . ?
C5 C6 1.417(10) . ?
C6 C25 1.412(10) . ?
C6 C7 1.457(10) . ?
C7 C8 1.456(9) . ?
C8 C9 1.365(9) . ?
C8 H8 0.9300 . ?
C9 C10 1.420(9) . ?
C9 H9 0.9300 . ?
C10 N20 1.325(8) . ?
C10 C11 1.535(8) . ?
C11 C14 1.523(9) . ?
C11 C12 1.529(10) . ?
C11 C13 1.547(9) . ?
C12 H12A 0.9600 . ?
C12 H12B 0.9600 . ?
C12 H12C 0.9600 . ?
C13 H13A 0.9600 . ?
C13 H13B 0.9600 . ?
C13 H13C 0.9600 . ?
C14 C15 1.379(9) . ?
C14 C19 1.402(9) . ?
C15 C16 1.385(10) . ?
C15 H15 0.9300 . ?
C16 C17 1.395(10) . ?
C16 H16 0.9300 . ?
C17 C18 1.389(9) . ?
C17 H17 0.9300 . ?
C18 C19 1.375(9) . ?
C18 H18 0.9300 . ?
C19 N20 1.414(8) . ?
N20 C21 1.468(8) . ?
C21 H21A 0.9600 . ?
C21 H21B 0.9600 . ?
C21 H21C 0.9600 . ?
C22 C23 1.365(10) . ?
C22 H22 0.9300 . ?
C23 C24 1.397(10) . ?
C23 H23 0.9300 . ?
C24 C25 1.377(10) . ?
C24 H24 0.9300 . ?
C25 H25 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
C2 O1 H1 109.5 . . ?
O1 C2 C7 119.2(6) . . ?
O1 C2 C3 118.7(6) . . ?
C7 C2 C3 122.1(6) . . ?
C4 C3 C2 119.2(6) . . ?
C4 C3 H3 120.4 . . ?
C2 C3 H3 120.4 . . ?
C3 C4 C5 122.1(7) . . ?
C3 C4 H4 119.0 . . ?
C5 C4 H4 119.0 . . ?
C22 C5 C6 120.1(6) . . ?
C22 C5 C4 121.0(7) . . ?
C6 C5 C4 118.9(6) . . ?
C25 C6 C5 116.4(6) . . ?
C25 C6 C7 124.2(6) . . ?
C5 C6 C7 119.4(6) . . ?
C2 C7 C8 123.2(6) . . ?
C2 C7 C6 118.4(6) . . ?
C8 C7 C6 118.4(6) . . ?
C9 C8 C7 129.4(6) . . ?
C9 C8 H8 115.3 . . ?
C7 C8 H8 115.3 . . ?
C8 C9 C10 122.6(6) . . ?
C8 C9 H9 118.7 . . ?
C10 C9 H9 118.7 . . ?
N20 C10 C9 121.2(6) . . ?
N20 C10 C11 109.9(5) . . ?
C9 C10 C11 128.9(6) . . ?
C14 C11 C12 110.2(5) . . ?
C14 C11 C10 100.5(5) . . ?
C12 C11 C10 112.4(5) . . ?
C14 C11 C13 110.1(5) . . ?
C12 C11 C13 112.0(5) . . ?
C10 C11 C13 111.1(5) . . ?
C11 C12 H12A 109.5 . . ?
C11 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
C11 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C11 C13 H13A 109.5 . . ?
C11 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
C11 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
C15 C14 C19 119.4(6) . . ?
C15 C14 C11 131.1(6) . . ?
C19 C14 C11 109.5(5) . . ?
C14 C15 C16 118.7(7) . . ?
C14 C15 H15 120.6 . . ?
C16 C15 H15 120.6 . . ?
C15 C16 C17 120.8(6) . . ?
C15 C16 H16 119.6 . . ?
C17 C16 H16 119.6 . . ?
C18 C17 C16 121.4(7) . . ?
C18 C17 H17 119.3 . . ?
C16 C17 H17 119.3 . . ?
C19 C18 C17 116.7(7) . . ?
C19 C18 H18 121.6 . . ?
C17 C18 H18 121.6 . . ?
C18 C19 C14 122.9(6) . . ?
C18 C19 N20 129.2(6) . . ?
C14 C19 N20 107.8(5) . . ?
C10 N20 C19 112.4(5) . . ?
C10 N20 C21 125.0(5) . . ?
C19 N20 C21 122.6(5) . . ?
N20 C21 H21A 109.5 . . ?
N20 C21 H21B 109.5 . . ?
H21A C21 H21B 109.5 . . ?
N20 C21 H21C 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
C23 C22 C5 121.7(6) . . ?
C23 C22 H22 119.2 . . ?
C5 C22 H22 119.2 . . ?
C22 C23 C24 119.2(6) . . ?
C22 C23 H23 120.4 . . ?
C24 C23 H23 120.4 . . ?
C25 C24 C23 120.0(6) . . ?
C25 C24 H24 120.0 . . ?
C23 C24 H24 120.0 . . ?
C24 C25 C6 122.6(7) . . ?
C24 C25 H25 118.7 . . ?
C6 C25 H25 118.7 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O1 C2 C3 C4 -179.3(7) . . . . ?
C7 C2 C3 C4 -1.4(10) . . . . ?
C2 C3 C4 C5 0.4(10) . . . . ?
C3 C4 C5 C22 179.0(7) . . . . ?
C3 C4 C5 C6 0.1(10) . . . . ?
C22 C5 C6 C25 0.6(9) . . . . ?
C4 C5 C6 C25 179.5(6) . . . . ?
C22 C5 C6 C7 -178.5(6) . . . . ?
C4 C5 C6 C7 0.4(9) . . . . ?
O1 C2 C7 C8 -1.7(10) . . . . ?
C3 C2 C7 C8 -179.6(6) . . . . ?
O1 C2 C7 C6 179.8(6) . . . . ?
C3 C2 C7 C6 1.9(10) . . . . ?
C25 C6 C7 C2 179.6(6) . . . . ?
C5 C6 C7 C2 -1.4(9) . . . . ?
C25 C6 C7 C8 1.0(10) . . . . ?
C5 C6 C7 C8 -180.0(6) . . . . ?
C2 C7 C8 C9 9.1(11) . . . . ?
C6 C7 C8 C9 -172.4(7) . . . . ?
C7 C8 C9 C10 176.4(7) . . . . ?
C8 C9 C10 N20 -177.0(7) . . . . ?
C8 C9 C10 C11 1.7(12) . . . . ?
N20 C10 C11 C14 -0.5(7) . . . . ?
C9 C10 C11 C14 -179.3(7) . . . . ?
N20 C10 C11 C12 116.6(7) . . . . ?
C9 C10 C11 C12 -62.1(9) . . . . ?
N20 C10 C11 C13 -117.0(6) . . . . ?
C9 C10 C11 C13 64.3(9) . . . . ?
C12 C11 C14 C15 60.8(10) . . . . ?
C10 C11 C14 C15 179.6(8) . . . . ?
C13 C11 C14 C15 -63.2(10) . . . . ?
C12 C11 C14 C19 -119.0(6) . . . . ?
C10 C11 C14 C19 -0.2(7) . . . . ?
C13 C11 C14 C19 117.1(6) . . . . ?
C19 C14 C15 C16 -0.3(11) . . . . ?
C11 C14 C15 C16 179.9(7) . . . . ?
C14 C15 C16 C17 0.0(12) . . . . ?
C15 C16 C17 C18 0.5(12) . . . . ?
C16 C17 C18 C19 -0.6(11) . . . . ?
C17 C18 C19 C14 0.3(11) . . . . ?
C17 C18 C19 N20 179.2(7) . . . . ?
C15 C14 C19 C18 0.1(11) . . . . ?
C11 C14 C19 C18 179.9(6) . . . . ?
C15 C14 C19 N20 -179.0(6) . . . . ?
C11 C14 C19 N20 0.8(7) . . . . ?
C9 C10 N20 C19 180.0(6) . . . . ?
C11 C10 N20 C19 1.1(8) . . . . ?
C9 C10 N20 C21 -1.5(11) . . . . ?
C11 C10 N20 C21 179.6(6) . . . . ?
C18 C19 N20 C10 179.7(7) . . . . ?
C14 C19 N20 C10 -1.2(8) . . . . ?
C18 C19 N20 C21 1.1(11) . . . . ?
C14 C19 N20 C21 -179.8(6) . . . . ?
C6 C5 C22 C23 -1.0(10) . . . . ?
C4 C5 C22 C23 -179.9(7) . . . . ?
C5 C22 C23 C24 0.9(11) . . . . ?
C22 C23 C24 C25 -0.4(11) . . . . ?
C23 C24 C25 C6 0.1(11) . . . . ?
C5 C6 C25 C24 -0.2(10) . . . . ?
C7 C6 C25 C24 178.9(7) . . . . ?

_refine_diff_density_max         1.353
_refine_diff_density_min         -1.458
_refine_diff_density_rms         0.169


_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: Ethanol'
####################################################################### 
# 
# 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_VS-KC-SPNO2-H3PO4
_database_code_depnum_ccdc_archive 'CCDC 1824261'
_audit_update_record             
;
2018-02-15 deposited with the CCDC.
2018-04-06 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2016/4
_shelx_SHELXL_version_number     2016/4
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         
'4(C19 H19 N2 O3), 2(H3 O4 P), 4(H2 O4 P), 4(C2 H3 N), H2 O'
_chemical_formula_sum            'C84 H104 N12 O37 P6'
_chemical_formula_weight         2059.61

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
P P 0.1023 0.0942 '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'

_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.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   12.6562(3)
_cell_length_b                   13.9654(7)
_cell_length_c                   28.3803(12)
_cell_angle_alpha                83.572(4)
_cell_angle_beta                 79.127(3)
_cell_angle_gamma                78.777(3)
_cell_volume                     4817.2(4)
_cell_formula_units_Z            2
_cell_measurement_temperature    297(2)
_cell_measurement_reflns_used    11865
_cell_measurement_theta_min      2.9210
_cell_measurement_theta_max      25.2550

_exptl_crystal_description       plate
_exptl_crystal_colour            'yellow orange'
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.420
_exptl_crystal_F_000             2156
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.400
_exptl_crystal_size_mid          0.300
_exptl_crystal_size_min          0.100
_exptl_absorpt_coefficient_mu    0.205
_shelx_estimated_absorpt_T_min   0.923
_shelx_estimated_absorpt_T_max   0.980
_exptl_absorpt_correction_T_min  0.86616
_exptl_absorpt_correction_T_max  1.00000
_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_absorpt_special_details   ?
_diffrn_ambient_temperature      297(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'Rigaku UltraX 18 rotating anode'
_diffrn_radiation_monochromator  'Xenocs Fox3D mirror'
_diffrn_measurement_device_type  'MAR345 image plate'
_diffrn_measurement_method       '194 images, ΔΦ 1.5° '
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            17346
_diffrn_reflns_av_unetI/netI     0.0612
_diffrn_reflns_av_R_equivalents  ?
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_limit_l_max       34
_diffrn_reflns_theta_min         2.932
_diffrn_reflns_theta_max         25.279
_diffrn_reflns_theta_full        25.000
_diffrn_measured_fraction_theta_max 0.990
_diffrn_measured_fraction_theta_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.990
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.990
_diffrn_reflns_point_group_measured_fraction_full 0.993
_reflns_number_total             17346
_reflns_number_gt                12878
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 _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.
;

_computing_data_collection       MAR
_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_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_structure_solution    'SHELXT (Sheldrick, 2015)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'MERCURY (Macrae et al., 2008)'
_computing_publication_material  
;
'MERCURY (Macrae et al., 2008), Platon (Spek, 2009)'
;

_refine_special_details          'Refined as a 2-component twin.,Twin'
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0654P)²+1.2082P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         17346
_refine_ls_number_parameters     1293
_refine_ls_number_restraints     4
_refine_ls_R_factor_all          0.0726
_refine_ls_R_factor_gt           0.0471
_refine_ls_wR_factor_ref         0.1288
_refine_ls_wR_factor_gt          0.1149
_refine_ls_goodness_of_fit_ref   1.005
_refine_ls_restrained_S_all      1.005
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

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
O1A O 0.59767(13) 1.06711(13) 0.06565(7) 0.0236(4) Uani 1 1 d . . . . .
H1A H 0.588781 1.125654 0.069469 0.035 Uiso 1 1 calc R U . . .
C2A C 0.5021(2) 1.04295(19) 0.06373(9) 0.0200(5) Uani 1 1 d . . . . .
C3A C 0.4070(2) 1.11331(19) 0.06296(9) 0.0230(6) Uani 1 1 d . . . . .
H3A H 0.410471 1.179075 0.063508 0.028 Uiso 1 1 calc R U . . .
C4A C 0.3094(2) 1.08736(19) 0.06141(10) 0.0240(6) Uani 1 1 d . . . . .
H4A H 0.246599 1.134735 0.061250 0.029 Uiso 1 1 calc R U . . .
C5A C 0.3050(2) 0.98882(19) 0.06007(9) 0.0221(6) Uani 1 1 d . . . . .
C6A C 0.39679(19) 0.91689(19) 0.06034(9) 0.0200(5) Uani 1 1 d . . . . .
H6A H 0.391749 0.851663 0.059186 0.024 Uiso 1 1 calc R U . . .
C7A C 0.49755(19) 0.94230(18) 0.06237(9) 0.0177(5) Uani 1 1 d . . . . .
C8A C 0.5896(2) 0.86237(19) 0.06339(9) 0.0199(5) Uani 1 1 d . . . . .
H8A H 0.573786 0.799692 0.064856 0.024 Uiso 1 1 calc R U . . .
C9A C 0.69547(19) 0.86754(19) 0.06249(9) 0.0207(6) Uani 1 1 d . . . . .
H9A H 0.714498 0.928763 0.061921 0.025 Uiso 1 1 calc R U . . .
C10A C 0.77949(19) 0.78253(19) 0.06236(9) 0.0204(6) Uani 1 1 d . . . . .
C11A C 0.76881(19) 0.67528(18) 0.06690(10) 0.0206(6) Uani 1 1 d . . . . .
C12A C 0.7056(2) 0.6492(2) 0.11721(10) 0.0277(6) Uani 1 1 d . . . . .
H12A H 0.630706 0.681340 0.119629 0.042 Uiso 1 1 calc R U . . .
H12B H 0.737931 0.670418 0.141324 0.042 Uiso 1 1 calc R U . . .
H12C H 0.708851 0.579618 0.122002 0.042 Uiso 1 1 calc R U . . .
C13A C 0.7175(2) 0.6465(2) 0.02673(11) 0.0277(6) Uani 1 1 d . . . . .
H13A H 0.752339 0.671498 -0.003939 0.042 Uiso 1 1 calc R U . . .
H13B H 0.640798 0.673547 0.031435 0.042 Uiso 1 1 calc R U . . .
H13C H 0.727185 0.576428 0.027635 0.042 Uiso 1 1 calc R U . . .
C14A C 0.8872(2) 0.62630(19) 0.06298(9) 0.0210(6) Uani 1 1 d . . . . .
C15A C 0.9352(2) 0.52875(19) 0.06300(10) 0.0252(6) Uani 1 1 d . . . . .
H15A H 0.892864 0.480194 0.066019 0.030 Uiso 1 1 calc R U . . .
C16A C 1.0485(2) 0.5048(2) 0.05837(10) 0.0276(6) Uani 1 1 d . . . . .
H16A H 1.081975 0.439381 0.057941 0.033 Uiso 1 1 calc R U . . .
C17A C 1.1122(2) 0.5761(2) 0.05441(10) 0.0289(6) Uani 1 1 d . . . . .
H17A H 1.187746 0.557666 0.051346 0.035 Uiso 1 1 calc R U . . .
C18A C 1.0657(2) 0.6748(2) 0.05491(10) 0.0281(6) Uani 1 1 d . . . . .
H18A H 1.107891 0.723235 0.052686 0.034 Uiso 1 1 calc R U . . .
C19A C 0.9526(2) 0.69701(19) 0.05891(10) 0.0219(6) Uani 1 1 d . . . . .
N20A N 0.88341(17) 0.79018(16) 0.05911(8) 0.0234(5) Uani 1 1 d . . . . .
C21A C 0.9258(2) 0.8819(2) 0.05630(13) 0.0382(8) Uani 1 1 d . . . . .
H21A H 1.000833 0.867249 0.060695 0.057 Uiso 1 1 calc R U . . .
H21B H 0.883415 0.921925 0.081016 0.057 Uiso 1 1 calc R U . . .
H21C H 0.920965 0.916406 0.025348 0.057 Uiso 1 1 calc R U . . .
N22A N 0.20192(18) 0.95985(18) 0.05829(9) 0.0320(6) Uani 1 1 d . . . . .
O23A O 0.19798(17) 0.87318(16) 0.05900(11) 0.0569(7) Uani 1 1 d . . . . .
O24A O 0.12041(18) 1.02286(17) 0.05694(12) 0.0723(9) Uani 1 1 d . . . . .
O1B O 0.39262(13) -0.04633(13) 0.43980(7) 0.0229(4) Uani 1 1 d . . . . .
H1B H 0.399887 -0.106135 0.440909 0.034 Uiso 1 1 calc R U . . .
C2B C 0.48960(19) -0.02106(18) 0.43950(9) 0.0182(5) Uani 1 1 d . . . . .
C3B C 0.5802(2) -0.09171(18) 0.44879(9) 0.0204(5) Uani 1 1 d . . . . .
H3B H 0.573265 -0.157215 0.454956 0.024 Uiso 1 1 calc R U . . .
C4B C 0.6786(2) -0.06488(19) 0.44883(9) 0.0227(6) Uani 1 1 d . . . . .
H4B H 0.738049 -0.111442 0.455820 0.027 Uiso 1 1 calc R U . . .
C5B C 0.6885(2) 0.03277(19) 0.43828(10) 0.0225(6) Uani 1 1 d . . . . .
C6B C 0.60179(19) 0.10407(19) 0.42871(9) 0.0202(5) Uani 1 1 d . . . . .
H6B H 0.611244 0.168787 0.421387 0.024 Uiso 1 1 calc R U . . .
C7B C 0.49908(19) 0.07887(18) 0.43002(9) 0.0168(5) Uani 1 1 d . . . . .
C8B C 0.40864(19) 0.15915(18) 0.42443(9) 0.0189(5) Uani 1 1 d . . . . .
H8B H 0.426644 0.221017 0.416114 0.023 Uiso 1 1 calc R U . . .
C9B C 0.30124(19) 0.15376(18) 0.42998(9) 0.0189(5) Uani 1 1 d . . . . .
H9B H 0.281723 0.092103 0.434552 0.023 Uiso 1 1 calc R U . . .
C10B C 0.21590(19) 0.23802(18) 0.42920(9) 0.0184(5) Uani 1 1 d . . . . .
C11B C 0.22422(19) 0.34557(18) 0.42634(9) 0.0189(5) Uani 1 1 d . . . . .
C12B C 0.2806(2) 0.37887(19) 0.37582(10) 0.0238(6) Uani 1 1 d . . . . .
H12D H 0.242050 0.364932 0.352071 0.036 Uiso 1 1 calc R U . . .
H12E H 0.354735 0.344427 0.370013 0.036 Uiso 1 1 calc R U . . .
H12F H 0.280312 0.447992 0.373922 0.036 Uiso 1 1 calc R U . . .
C13B C 0.2798(2) 0.3690(2) 0.46616(10) 0.0253(6) Uani 1 1 d . . . . .
H13D H 0.356852 0.344085 0.459124 0.038 Uiso 1 1 calc R U . . .
H13E H 0.249294 0.338982 0.496461 0.038 Uiso 1 1 calc R U . . .
H13F H 0.268114 0.438656 0.467824 0.038 Uiso 1 1 calc R U . . .
C14B C 0.10478(19) 0.39228(19) 0.43295(9) 0.0208(6) Uani 1 1 d . . . . .
C15B C 0.0541(2) 0.48977(19) 0.43407(10) 0.0251(6) Uani 1 1 d . . . . .
H15B H 0.094957 0.539282 0.431469 0.030 Uiso 1 1 calc R U . . .
C16B C -0.0586(2) 0.5115(2) 0.43913(10) 0.0298(7) Uani 1 1 d . . . . .
H16B H -0.093563 0.576443 0.440294 0.036 Uiso 1 1 calc R U . . .
C17B C -0.1207(2) 0.4386(2) 0.44251(11) 0.0309(7) Uani 1 1 d . . . . .
H17B H -0.196311 0.455775 0.445768 0.037 Uiso 1 1 calc R U . . .
C18B C -0.0721(2) 0.3405(2) 0.44114(10) 0.0285(6) Uani 1 1 d . . . . .
H18B H -0.112861 0.290952 0.443318 0.034 Uiso 1 1 calc R U . . .
C19B C 0.04086(19) 0.32114(19) 0.43631(9) 0.0210(6) Uani 1 1 d . . . . .
N20B N 0.11254(16) 0.22848(15) 0.43360(8) 0.0210(5) Uani 1 1 d . . . . .
C21B C 0.0710(2) 0.1367(2) 0.43602(12) 0.0338(7) Uani 1 1 d . . . . .
H21D H 0.003131 0.149386 0.424038 0.051 Uiso 1 1 calc R U . . .
H21E H 0.059290 0.109699 0.468823 0.051 Uiso 1 1 calc R U . . .
H21F H 0.123282 0.090924 0.416798 0.051 Uiso 1 1 calc R U . . .
N22B N 0.79251(18) 0.06213(18) 0.43887(10) 0.0329(6) Uani 1 1 d . . . . .
O23B O 0.81139(16) 0.13921(16) 0.41718(9) 0.0440(6) Uani 1 1 d . . . . .
O24B O 0.85762(18) 0.00699(18) 0.46134(11) 0.0628(8) Uani 1 1 d . . . . .
O1C O 0.59737(13) 1.13697(12) 0.29834(7) 0.0214(4) Uani 1 1 d . . . . .
H1C H 0.590675 1.195420 0.289437 0.032 Uiso 1 1 calc R U . . .
C2C C 0.5005(2) 1.10851(18) 0.30361(9) 0.0184(5) Uani 1 1 d . . . . .
C3C C 0.4055(2) 1.17651(18) 0.29834(9) 0.0198(5) Uani 1 1 d . . . . .
H3C H 0.409363 1.242645 0.291985 0.024 Uiso 1 1 calc R U . . .
C4C C 0.3069(2) 1.14674(19) 0.30242(9) 0.0219(6) Uani 1 1 d . . . . .
H4C H 0.244157 1.191973 0.298475 0.026 Uiso 1 1 calc R U . . .
C5C C 0.3024(2) 1.04808(19) 0.31254(9) 0.0210(6) Uani 1 1 d . . . . .
C6C C 0.3939(2) 0.97970(19) 0.31868(9) 0.0211(6) Uani 1 1 d . . . . .
H6C H 0.387891 0.914203 0.326157 0.025 Uiso 1 1 calc R U . . .
C7C C 0.49577(19) 1.00774(18) 0.31379(9) 0.0178(5) Uani 1 1 d . . . . .
C8C C 0.5887(2) 0.92969(18) 0.31857(9) 0.0209(6) Uani 1 1 d . . . . .
H8C H 0.572428 0.866862 0.324586 0.025 Uiso 1 1 calc R U . . .
C9C C 0.6945(2) 0.93524(18) 0.31555(9) 0.0203(5) Uani 1 1 d . . . . .
H9C H 0.714123 0.996775 0.312101 0.024 Uiso 1 1 calc R U . . .
C10C C 0.7786(2) 0.85029(18) 0.31741(9) 0.0194(5) Uani 1 1 d . . . . .
C11C C 0.76836(19) 0.74267(18) 0.32089(9) 0.0190(5) Uani 1 1 d . . . . .
C12C C 0.7189(2) 0.71677(19) 0.27926(10) 0.0239(6) Uani 1 1 d . . . . .
H12G H 0.756808 0.741300 0.249143 0.036 Uiso 1 1 calc R U . . .
H12H H 0.642906 0.745959 0.282926 0.036 Uiso 1 1 calc R U . . .
H12I H 0.726284 0.646946 0.279811 0.036 Uiso 1 1 calc R U . . .
C13C C 0.7058(2) 0.71222(19) 0.37062(9) 0.0219(6) Uani 1 1 d . . . . .
H13G H 0.630822 0.744471 0.373690 0.033 Uiso 1 1 calc R U . . .
H13H H 0.738417 0.730633 0.395376 0.033 Uiso 1 1 calc R U . . .
H13I H 0.709091 0.642578 0.373786 0.033 Uiso 1 1 calc R U . . .
C14C C 0.8869(2) 0.69366(19) 0.31703(9) 0.0219(6) Uani 1 1 d . . . . .
C15C C 0.9347(2) 0.5961(2) 0.31618(10) 0.0285(6) Uani 1 1 d . . . . .
H15C H 0.892549 0.547834 0.317913 0.034 Uiso 1 1 calc R U . . .
C16C C 1.0474(2) 0.5720(2) 0.31267(11) 0.0349(7) Uani 1 1 d . . . . .
H16C H 1.081083 0.506640 0.311868 0.042 Uiso 1 1 calc R U . . .
C17C C 1.1110(2) 0.6438(2) 0.31034(11) 0.0362(7) Uani 1 1 d . . . . .
H17C H 1.186307 0.625576 0.308227 0.043 Uiso 1 1 calc R U . . .
C18C C 1.0640(2) 0.7417(2) 0.31109(11) 0.0319(7) Uani 1 1 d . . . . .
H18C H 1.105875 0.790200 0.309526 0.038 Uiso 1 1 calc R U . . .
C19C C 0.9517(2) 0.76398(19) 0.31430(10) 0.0235(6) Uani 1 1 d . . . . .
N20C N 0.88207(17) 0.85758(16) 0.31515(8) 0.0248(5) Uani 1 1 d . . . . .
C21C C 0.9253(2) 0.9481(2) 0.31342(13) 0.0402(8) Uani 1 1 d . . . . .
H21G H 0.935695 0.976754 0.280896 0.060 Uiso 1 1 calc R U . . .
H21H H 0.994089 0.933587 0.324661 0.060 Uiso 1 1 calc R U . . .
H21I H 0.874586 0.993220 0.333573 0.060 Uiso 1 1 calc R U . . .
N22C N 0.19858(18) 1.01525(17) 0.31658(9) 0.0289(5) Uani 1 1 d . . . . .
O23C O 0.18711(15) 0.93610(15) 0.33859(8) 0.0390(5) Uani 1 1 d . . . . .
O24C O 0.12588(17) 1.06891(17) 0.29796(10) 0.0513(7) Uani 1 1 d . . . . .
O1D O 0.36944(13) -0.04465(12) 0.18304(7) 0.0224(4) Uani 1 1 d . . . . .
H1D H 0.377566 -0.104469 0.183768 0.034 Uiso 1 1 calc R U . . .
C2D C 0.46404(19) -0.01884(18) 0.18492(9) 0.0181(5) Uani 1 1 d . . . . .
C3D C 0.5596(2) -0.08844(18) 0.18776(9) 0.0208(6) Uani 1 1 d . . . . .
H3D H 0.557598 -0.154711 0.188002 0.025 Uiso 1 1 calc R U . . .
C4D C 0.6559(2) -0.05930(19) 0.19018(9) 0.0222(6) Uani 1 1 d . . . . .
H4D H 0.718916 -0.105537 0.192314 0.027 Uiso 1 1 calc R U . . .
C5D C 0.65838(19) 0.03973(19) 0.18942(9) 0.0206(6) Uani 1 1 d . . . . .
C6D C 0.56692(19) 0.11056(18) 0.18531(9) 0.0189(5) Uani 1 1 d . . . . .
H6D H 0.571375 0.176544 0.183858 0.023 Uiso 1 1 calc R U . . .
C7D C 0.46754(19) 0.08257(17) 0.18334(8) 0.0152(5) Uani 1 1 d . . . . .
C8D C 0.37403(19) 0.16031(18) 0.18138(9) 0.0180(5) Uani 1 1 d . . . . .
H8D H 0.388940 0.223622 0.177616 0.022 Uiso 1 1 calc R U . . .
C9D C 0.26809(19) 0.15333(18) 0.18428(9) 0.0189(5) Uani 1 1 d . . . . .
H9D H 0.249976 0.091387 0.186374 0.023 Uiso 1 1 calc R U . . .
C10D C 0.18257(19) 0.23681(18) 0.18429(9) 0.0180(5) Uani 1 1 d . . . . .
C11D C 0.19257(19) 0.34447(17) 0.17883(9) 0.0173(5) Uani 1 1 d . . . . .
C12D C 0.2542(2) 0.36790(19) 0.12801(9) 0.0215(6) Uani 1 1 d . . . . .
H12J H 0.224716 0.340533 0.104859 0.032 Uiso 1 1 calc R U . . .
H12K H 0.330349 0.340188 0.126222 0.032 Uiso 1 1 calc R U . . .
H12L H 0.246059 0.437598 0.121239 0.032 Uiso 1 1 calc R U . . .
C13D C 0.2440(2) 0.37493(19) 0.21837(10) 0.0231(6) Uani 1 1 d . . . . .
H13J H 0.320207 0.346412 0.214250 0.035 Uiso 1 1 calc R U . . .
H13K H 0.207859 0.352468 0.249318 0.035 Uiso 1 1 calc R U . . .
H13L H 0.236004 0.444984 0.216272 0.035 Uiso 1 1 calc R U . . .
C14D C 0.07410(19) 0.39296(18) 0.18320(9) 0.0190(5) Uani 1 1 d . . . . .
C15D C 0.0261(2) 0.49057(19) 0.18450(9) 0.0234(6) Uani 1 1 d . . . . .
H15D H 0.068572 0.538954 0.181794 0.028 Uiso 1 1 calc R U . . .
C16D C -0.0870(2) 0.5146(2) 0.18995(10) 0.0298(7) Uani 1 1 d . . . . .
H16D H -0.120743 0.579914 0.191268 0.036 Uiso 1 1 calc R U . . .
C17D C -0.1505(2) 0.4426(2) 0.19345(10) 0.0318(7) Uani 1 1 d . . . . .
H17D H -0.226040 0.460700 0.196720 0.038 Uiso 1 1 calc R U . . .
C18D C -0.1036(2) 0.3442(2) 0.19219(10) 0.0281(6) Uani 1 1 d . . . . .
H18D H -0.145687 0.295695 0.194277 0.034 Uiso 1 1 calc R U . . .
C19D C 0.0090(2) 0.32231(19) 0.18766(9) 0.0217(6) Uani 1 1 d . . . . .
N20D N 0.07904(16) 0.22870(15) 0.18753(8) 0.0205(5) Uani 1 1 d . . . . .
C21D C 0.0377(2) 0.1370(2) 0.19029(12) 0.0327(7) Uani 1 1 d . . . . .
H21J H -0.040588 0.150939 0.193499 0.049 Uiso 1 1 calc R U . . .
H21K H 0.058161 0.095683 0.217671 0.049 Uiso 1 1 calc R U . . .
H21L H 0.068241 0.104257 0.161509 0.049 Uiso 1 1 calc R U . . .
N22D N 0.75852(17) 0.07032(17) 0.19459(9) 0.0299(6) Uani 1 1 d . . . . .
O23D O 0.76167(16) 0.15756(15) 0.19156(9) 0.0440(6) Uani 1 1 d . . . . .
O24D O 0.83629(17) 0.00691(16) 0.20338(11) 0.0578(7) Uani 1 1 d . . . . .
P1E P 0.58333(5) 0.33221(5) 0.04895(2) 0.01951(15) Uani 1 1 d . . . . .
O2E O 0.46547(14) 0.37789(14) 0.04107(7) 0.0272(4) Uani 1 1 d . . . . .
H2E H 0.451339 0.434970 0.047999 0.041 Uiso 1 1 calc R U . . .
O3E O 0.63511(13) 0.41121(13) 0.06624(7) 0.0233(4) Uani 1 1 d . . . . .
H3E H 0.590945 0.440370 0.087200 0.035 Uiso 1 1 calc R U . . .
O4E O 0.58469(16) 0.24199(13) 0.08217(7) 0.0304(5) Uani 1 1 d . . . . .
O5E O 0.65252(15) 0.30640(13) -0.00049(6) 0.0266(4) Uani 1 1 d . . . . .
H5E H 0.639937 0.352109 -0.020627 0.040 Uiso 1 1 calc R U . . .
P1F P 0.40837(5) 0.57807(5) 0.11283(2) 0.01707(15) Uani 1 1 d . . . . .
O2F O 0.43381(14) 0.68474(12) 0.10465(6) 0.0220(4) Uani 1 1 d . . . . .
H2F H 0.414869 0.711393 0.129966 0.033 Uiso 1 1 calc R U . . .
O3F O 0.38522(13) 0.55323(12) 0.06590(6) 0.0208(4) Uani 1 1 d . . . . .
O4F O 0.50074(14) 0.50720(13) 0.13122(6) 0.0232(4) Uani 1 1 d . . . . .
O5F O 0.30061(13) 0.58250(13) 0.15081(6) 0.0226(4) Uani 1 1 d . . . . .
H5F H 0.312967 0.591671 0.177135 0.034 Uiso 1 1 calc R U . . .
P1G P 0.53890(5) 0.41153(5) 0.25313(2) 0.01779(15) Uani 1 1 d . . . . .
O2G O 0.55562(17) 0.37699(13) 0.20129(7) 0.0305(5) Uani 1 1 d . . . . .
H2G H 0.530998 0.422376 0.183221 0.046 Uiso 1 1 calc R U . . .
O3G O 0.57996(14) 0.32374(12) 0.28509(6) 0.0220(4) Uani 1 1 d . . . . .
O4G O 0.59337(13) 0.49833(12) 0.25370(6) 0.0200(4) Uani 1 1 d . . . . .
O5G O 0.41262(13) 0.44039(13) 0.27098(7) 0.0238(4) Uani 1 1 d . . . . .
H5G H 0.389897 0.493984 0.258029 0.036 Uiso 1 1 calc R U . . .
P1H P 0.38922(5) 0.70740(5) 0.23037(2) 0.01869(15) Uani 1 1 d . . . . .
O2H O 0.34109(13) 0.61566(12) 0.23311(6) 0.0203(4) Uani 1 1 d . . . . .
O3H O 0.37897(14) 0.77139(12) 0.18409(6) 0.0227(4) Uani 1 1 d . . . . .
O4H O 0.33045(15) 0.77382(14) 0.27206(7) 0.0303(5) Uani 1 1 d . . . . .
H4H H 0.362097 0.759003 0.295232 0.046 Uiso 1 1 calc R U . . .
O5H O 0.51171(14) 0.68075(13) 0.23603(8) 0.0273(4) Uani 1 1 d . . . . .
H5H H 0.528759 0.621215 0.240863 0.041 Uiso 1 1 calc R U . . .
P1I P 0.57158(5) 0.46841(5) 0.37875(2) 0.01848(15) Uani 1 1 d . . . . .
O2I O 0.56431(14) 0.35815(12) 0.37521(6) 0.0220(4) Uani 1 1 d . . . . .
H2I H 0.568724 0.348083 0.346932 0.033 Uiso 1 1 calc R U . . .
O3I O 0.66043(14) 0.49621(13) 0.33555(6) 0.0246(4) Uani 1 1 d . . . . .
H3I H 0.637590 0.497921 0.310224 0.037 Uiso 1 1 calc R U . . .
O4I O 0.46335(14) 0.53442(13) 0.37535(6) 0.0243(4) Uani 1 1 d . . . . .
O5I O 0.61218(14) 0.47267(13) 0.42500(6) 0.0224(4) Uani 1 1 d . . . . .
P1J P 0.40618(5) 0.67492(5) 0.46997(2) 0.01894(15) Uani 1 1 d . . . . .
O2J O 0.35259(14) 0.59849(12) 0.45200(7) 0.0227(4) Uani 1 1 d . . . . .
H2J H 0.392426 0.575350 0.428181 0.034 Uiso 1 1 calc R U . . .
O3J O 0.52969(14) 0.63332(14) 0.46863(7) 0.0276(4) Uani 1 1 d . . . . .
H3J H 0.545860 0.581989 0.455341 0.041 Uiso 1 1 calc R U . . .
O4J O 0.39047(15) 0.77182(13) 0.44157(7) 0.0278(4) Uani 1 1 d . . . . .
O5J O 0.35192(15) 0.68871(13) 0.52287(6) 0.0271(4) Uani 1 1 d D . . . .
H5J H 0.363802 0.636646 0.539114 0.041 Uiso 1 1 calc DR U . . .
O1V O 0.42657(19) 0.73209(11) 0.34629(6) 0.0405(5) Uani 1 1 d D . . . .
H1V H 0.436(2) 0.67209(13) 0.34815(15) 0.049 Uiso 1 1 d D U . . .
H2V H 0.409(2) 0.7464(3) 0.37429(8) 0.049 Uiso 1 1 d D U . . .
N1W N 1.0549(2) 0.2530(2) 0.06984(12) 0.0528(8) Uani 1 1 d . . . . .
C2W C 0.9693(3) 0.2399(2) 0.07030(12) 0.0413(8) Uani 1 1 d . . . . .
C3W C 0.8599(3) 0.2230(4) 0.07097(16) 0.0851(16) Uani 1 1 d . . . . .
H3WA H 0.827193 0.267023 0.047094 0.128 Uiso 1 1 calc R U . . .
H3WB H 0.816750 0.234119 0.102181 0.128 Uiso 1 1 calc R U . . .
H3WC H 0.862963 0.156659 0.064095 0.128 Uiso 1 1 calc R U . . .
N1X N -0.0842(3) 0.7765(2) 0.17345(12) 0.0570(8) Uani 1 1 d . . . . .
C2X C 0.0027(3) 0.7815(2) 0.17527(12) 0.0429(8) Uani 1 1 d . . . . .
C3X C 0.1151(3) 0.7885(4) 0.17730(16) 0.0735(13) Uani 1 1 d . . . . .
H3XA H 0.161705 0.767499 0.148145 0.110 Uiso 1 1 calc R U . . .
H3XB H 0.138295 0.747512 0.204271 0.110 Uiso 1 1 calc R U . . .
H3XC H 0.119343 0.855184 0.180812 0.110 Uiso 1 1 calc R U . . .
N1Y N 1.0458(3) 0.2969(3) 0.31790(12) 0.0659(10) Uani 1 1 d . . . . .
C2Y C 0.9565(3) 0.2935(3) 0.31884(12) 0.0469(9) Uani 1 1 d . . . . .
C3Y C 0.8431(3) 0.2884(3) 0.31979(16) 0.0739(13) Uani 1 1 d . . . . .
H3YA H 0.808925 0.346446 0.303159 0.111 Uiso 1 1 calc R U . . .
H3YB H 0.806303 0.283504 0.352564 0.111 Uiso 1 1 calc R U . . .
H3YC H 0.838829 0.231973 0.304283 0.111 Uiso 1 1 calc R U . . .
N1Z N -0.0761(2) 0.7708(2) 0.44314(12) 0.0553(8) Uani 1 1 d . . . . .
C2Z C 0.0140(3) 0.7744(2) 0.43882(12) 0.0429(8) Uani 1 1 d . . . . .
C3Z C 0.1294(3) 0.7774(3) 0.43417(16) 0.0700(13) Uani 1 1 d . . . . .
H3ZA H 0.164290 0.720765 0.451516 0.105 Uiso 1 1 calc R U . . .
H3ZB H 0.137981 0.835512 0.447109 0.105 Uiso 1 1 calc R U . . .
H3ZC H 0.162361 0.777887 0.400795 0.105 Uiso 1 1 calc R U . . .


_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
O1A C2A 1.329(3) . ?
O1A H1A 0.8200 . ?
C2A C3A 1.400(3) . ?
C2A C7A 1.423(3) . ?
C3A C4A 1.363(4) . ?
C3A H3A 0.9300 . ?
C4A C5A 1.393(4) . ?
C4A H4A 0.9300 . ?
C5A C6A 1.380(3) . ?
C5A N22A 1.451(3) . ?
C6A C7A 1.401(3) . ?
C6A H6A 0.9300 . ?
C7A C8A 1.451(3) . ?
C8A C9A 1.351(3) . ?
C8A H8A 0.9300 . ?
C9A C10A 1.431(3) . ?
C9A H9A 0.9300 . ?
C10A N20A 1.325(3) . ?
C10A C11A 1.519(3) . ?
C11A C14A 1.511(3) . ?
C11A C13A 1.539(3) . ?
C11A C12A 1.542(4) . ?
C12A H12A 0.9600 . ?
C12A H12B 0.9600 . ?
C12A H12C 0.9600 . ?
C13A H13A 0.9600 . ?
C13A H13B 0.9600 . ?
C13A H13C 0.9600 . ?
C14A C15A 1.379(4) . ?
C14A C19A 1.388(4) . ?
C15A C16A 1.392(4) . ?
C15A H15A 0.9300 . ?
C16A C17A 1.381(4) . ?
C16A H16A 0.9300 . ?
C17A C18A 1.390(4) . ?
C17A H17A 0.9300 . ?
C18A C19A 1.391(3) . ?
C18A H18A 0.9300 . ?
C19A N20A 1.420(3) . ?
N20A C21A 1.471(3) . ?
C21A H21A 0.9600 . ?
C21A H21B 0.9600 . ?
C21A H21C 0.9600 . ?
N22A O23A 1.219(3) . ?
N22A O24A 1.222(3) . ?
O1B C2B 1.340(3) . ?
O1B H1B 0.8200 . ?
C2B C3B 1.405(3) . ?
C2B C7B 1.415(3) . ?
C3B C4B 1.369(3) . ?
C3B H3B 0.9300 . ?
C4B C5B 1.388(4) . ?
C4B H4B 0.9300 . ?
C5B C6B 1.377(3) . ?
C5B N22B 1.457(3) . ?
C6B C7B 1.404(3) . ?
C6B H6B 0.9300 . ?
C7B C8B 1.457(3) . ?
C8B C9B 1.354(3) . ?
C8B H8B 0.9300 . ?
C9B C10B 1.435(3) . ?
C9B H9B 0.9300 . ?
C10B N20B 1.322(3) . ?
C10B C11B 1.518(3) . ?
C11B C14B 1.511(3) . ?
C11B C13B 1.534(3) . ?
C11B C12B 1.541(4) . ?
C12B H12D 0.9600 . ?
C12B H12E 0.9600 . ?
C12B H12F 0.9600 . ?
C13B H13D 0.9600 . ?
C13B H13E 0.9600 . ?
C13B H13F 0.9600 . ?
C14B C19B 1.383(4) . ?
C14B C15B 1.389(4) . ?
C15B C16B 1.382(4) . ?
C15B H15B 0.9300 . ?
C16B C17B 1.386(4) . ?
C16B H16B 0.9300 . ?
C17B C18B 1.391(4) . ?
C17B H17B 0.9300 . ?
C18B C19B 1.386(3) . ?
C18B H18B 0.9300 . ?
C19B N20B 1.429(3) . ?
N20B C21B 1.468(3) . ?
C21B H21D 0.9600 . ?
C21B H21E 0.9600 . ?
C21B H21F 0.9600 . ?
N22B O23B 1.221(3) . ?
N22B O24B 1.233(3) . ?
O1C C2C 1.338(3) . ?
O1C H1C 0.8200 . ?
C2C C3C 1.401(3) . ?
C2C C7C 1.415(3) . ?
C3C C4C 1.371(3) . ?
C3C H3C 0.9300 . ?
C4C C5C 1.386(4) . ?
C4C H4C 0.9300 . ?
C5C C6C 1.375(3) . ?
C5C N22C 1.455(3) . ?
C6C C7C 1.397(3) . ?
C6C H6C 0.9300 . ?
C7C C8C 1.455(3) . ?
C8C C9C 1.342(3) . ?
C8C H8C 0.9300 . ?
C9C C10C 1.435(3) . ?
C9C H9C 0.9300 . ?
C10C N20C 1.323(3) . ?
C10C C11C 1.524(3) . ?
C11C C14C 1.512(3) . ?
C11C C13C 1.541(3) . ?
C11C C12C 1.543(3) . ?
C12C H12G 0.9600 . ?
C12C H12H 0.9600 . ?
C12C H12I 0.9600 . ?
C13C H13G 0.9600 . ?
C13C H13H 0.9600 . ?
C13C H13I 0.9600 . ?
C14C C15C 1.380(4) . ?
C14C C19C 1.384(4) . ?
C15C C16C 1.387(4) . ?
C15C H15C 0.9300 . ?
C16C C17C 1.391(4) . ?
C16C H16C 0.9300 . ?
C17C C18C 1.382(4) . ?
C17C H17C 0.9300 . ?
C18C C19C 1.383(4) . ?
C18C H18C 0.9300 . ?
C19C N20C 1.427(3) . ?
N20C C21C 1.465(3) . ?
C21C H21G 0.9600 . ?
C21C H21H 0.9600 . ?
C21C H21I 0.9600 . ?
N22C O23C 1.227(3) . ?
N22C O24C 1.230(3) . ?
O1D C2D 1.328(3) . ?
O1D H1D 0.8200 . ?
C2D C3D 1.406(3) . ?
C2D C7D 1.421(3) . ?
C3D C4D 1.374(3) . ?
C3D H3D 0.9300 . ?
C4D C5D 1.387(4) . ?
C4D H4D 0.9300 . ?
C5D C6D 1.383(3) . ?
C5D N22D 1.451(3) . ?
C6D C7D 1.400(3) . ?
C6D H6D 0.9300 . ?
C7D C8D 1.447(3) . ?
C8D C9D 1.350(3) . ?
C8D H8D 0.9300 . ?
C9D C10D 1.428(3) . ?
C9D H9D 0.9300 . ?
C10D N20D 1.322(3) . ?
C10D C11D 1.522(3) . ?
C11D C14D 1.509(3) . ?
C11D C13D 1.534(3) . ?
C11D C12D 1.538(3) . ?
C12D H12J 0.9600 . ?
C12D H12K 0.9600 . ?
C12D H12L 0.9600 . ?
C13D H13J 0.9600 . ?
C13D H13K 0.9600 . ?
C13D H13L 0.9600 . ?
C14D C15D 1.382(3) . ?
C14D C19D 1.385(4) . ?
C15D C16D 1.388(4) . ?
C15D H15D 0.9300 . ?
C16D C17D 1.389(4) . ?
C16D H16D 0.9300 . ?
C17D C18D 1.388(4) . ?
C17D H17D 0.9300 . ?
C18D C19D 1.383(3) . ?
C18D H18D 0.9300 . ?
C19D N20D 1.430(3) . ?
N20D C21D 1.464(3) . ?
C21D H21J 0.9600 . ?
C21D H21K 0.9600 . ?
C21D H21L 0.9600 . ?
N22D O23D 1.220(3) . ?
N22D O24D 1.232(3) . ?
P1E O4E 1.4859(19) . ?
P1E O5E 1.5469(18) . ?
P1E O2E 1.5510(18) . ?
P1E O3E 1.5528(18) . ?
O2E H2E 0.8200 . ?
O3E H3E 0.8200 . ?
O5E H5E 0.8200 . ?
P1F O3F 1.5069(18) . ?
P1F O4F 1.5109(18) . ?
P1F O5F 1.5662(18) . ?
P1F O2F 1.5678(18) . ?
O2F H2F 0.8200 . ?
O5F H5F 0.8200 . ?
P1G O3G 1.5090(18) . ?
P1G O4G 1.5095(18) . ?
P1G O2G 1.5633(19) . ?
P1G O5G 1.5694(18) . ?
O2G H2G 0.8200 . ?
O5G H5G 0.8200 . ?
P1H O2H 1.5106(18) . ?
P1H O3H 1.5154(19) . ?
P1H O5H 1.5568(18) . ?
P1H O4H 1.5681(18) . ?
O4H H4H 0.8200 . ?
O5H H5H 0.8200 . ?
P1I O4I 1.5079(18) . ?
P1I O5I 1.5080(18) . ?
P1I O3I 1.5691(18) . ?
P1I O2I 1.5756(18) . ?
O2I H2I 0.8200 . ?
O3I H3I 0.8200 . ?
P1J O4J 1.4938(19) . ?
P1J O5J 1.5450(18) . ?
P1J O2J 1.5471(18) . ?
P1J O3J 1.5529(18) . ?
O2J H2J 0.8200 . ?
O3J H3J 0.8200 . ?
O5J H5J 0.8200 . ?
O1V H1V 0.82000(13) . ?
O1V H2V 0.82000(12) . ?
N1W C2W 1.130(4) . ?
C2W C3W 1.446(5) . ?
C3W H3WA 0.9600 . ?
C3W H3WB 0.9600 . ?
C3W H3WC 0.9600 . ?
N1X C2X 1.127(4) . ?
C2X C3X 1.457(5) . ?
C3X H3XA 0.9600 . ?
C3X H3XB 0.9600 . ?
C3X H3XC 0.9600 . ?
N1Y C2Y 1.134(4) . ?
C2Y C3Y 1.446(5) . ?
C3Y H3YA 0.9600 . ?
C3Y H3YB 0.9600 . ?
C3Y H3YC 0.9600 . ?
N1Z C2Z 1.135(4) . ?
C2Z C3Z 1.449(5) . ?
C3Z H3ZA 0.9600 . ?
C3Z H3ZB 0.9600 . ?
C3Z H3ZC 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
C2A O1A H1A 109.5 . . ?
O1A C2A C3A 122.0(2) . . ?
O1A C2A C7A 118.4(2) . . ?
C3A C2A C7A 119.6(2) . . ?
C4A C3A C2A 121.3(2) . . ?
C4A C3A H3A 119.3 . . ?
C2A C3A H3A 119.3 . . ?
C3A C4A C5A 119.0(2) . . ?
C3A C4A H4A 120.5 . . ?
C5A C4A H4A 120.5 . . ?
C6A C5A C4A 121.8(2) . . ?
C6A C5A N22A 118.4(2) . . ?
C4A C5A N22A 119.8(2) . . ?
C5A C6A C7A 119.9(2) . . ?
C5A C6A H6A 120.1 . . ?
C7A C6A H6A 120.1 . . ?
C6A C7A C2A 118.4(2) . . ?
C6A C7A C8A 116.5(2) . . ?
C2A C7A C8A 125.1(2) . . ?
C9A C8A C7A 128.1(2) . . ?
C9A C8A H8A 115.9 . . ?
C7A C8A H8A 115.9 . . ?
C8A C9A C10A 122.6(2) . . ?
C8A C9A H9A 118.7 . . ?
C10A C9A H9A 118.7 . . ?
N20A C10A C9A 121.2(2) . . ?
N20A C10A C11A 109.9(2) . . ?
C9A C10A C11A 128.9(2) . . ?
C14A C11A C10A 100.97(19) . . ?
C14A C11A C13A 110.6(2) . . ?
C10A C11A C13A 113.8(2) . . ?
C14A C11A C12A 109.9(2) . . ?
C10A C11A C12A 109.4(2) . . ?
C13A C11A C12A 111.6(2) . . ?
C11A C12A H12A 109.5 . . ?
C11A C12A H12B 109.5 . . ?
H12A C12A H12B 109.5 . . ?
C11A C12A H12C 109.5 . . ?
H12A C12A H12C 109.5 . . ?
H12B C12A H12C 109.5 . . ?
C11A C13A H13A 109.5 . . ?
C11A C13A H13B 109.5 . . ?
H13A C13A H13B 109.5 . . ?
C11A C13A H13C 109.5 . . ?
H13A C13A H13C 109.5 . . ?
H13B C13A H13C 109.5 . . ?
C15A C14A C19A 119.5(2) . . ?
C15A C14A C11A 131.0(2) . . ?
C19A C14A C11A 109.5(2) . . ?
C14A C15A C16A 118.3(3) . . ?
C14A C15A H15A 120.8 . . ?
C16A C15A H15A 120.8 . . ?
C17A C16A C15A 121.5(3) . . ?
C17A C16A H16A 119.3 . . ?
C15A C16A H16A 119.3 . . ?
C16A C17A C18A 121.3(2) . . ?
C16A C17A H17A 119.4 . . ?
C18A C17A H17A 119.4 . . ?
C17A C18A C19A 116.2(3) . . ?
C17A C18A H18A 121.9 . . ?
C19A C18A H18A 121.9 . . ?
C14A C19A C18A 123.2(2) . . ?
C14A C19A N20A 107.9(2) . . ?
C18A C19A N20A 128.9(2) . . ?
C10A N20A C19A 111.7(2) . . ?
C10A N20A C21A 126.0(2) . . ?
C19A N20A C21A 122.3(2) . . ?
N20A C21A H21A 109.5 . . ?
N20A C21A H21B 109.5 . . ?
H21A C21A H21B 109.5 . . ?
N20A C21A H21C 109.5 . . ?
H21A C21A H21C 109.5 . . ?
H21B C21A H21C 109.5 . . ?
O23A N22A O24A 121.4(2) . . ?
O23A N22A C5A 119.3(2) . . ?
O24A N22A C5A 119.2(2) . . ?
C2B O1B H1B 109.5 . . ?
O1B C2B C3B 121.0(2) . . ?
O1B C2B C7B 118.6(2) . . ?
C3B C2B C7B 120.3(2) . . ?
C4B C3B C2B 120.5(2) . . ?
C4B C3B H3B 119.7 . . ?
C2B C3B H3B 119.7 . . ?
C3B C4B C5B 119.1(2) . . ?
C3B C4B H4B 120.5 . . ?
C5B C4B H4B 120.5 . . ?
C6B C5B C4B 122.1(2) . . ?
C6B C5B N22B 118.4(2) . . ?
C4B C5B N22B 119.4(2) . . ?
C5B C6B C7B 119.9(2) . . ?
C5B C6B H6B 120.1 . . ?
C7B C6B H6B 120.1 . . ?
C6B C7B C2B 118.1(2) . . ?
C6B C7B C8B 116.9(2) . . ?
C2B C7B C8B 125.0(2) . . ?
C9B C8B C7B 127.3(2) . . ?
C9B C8B H8B 116.4 . . ?
C7B C8B H8B 116.4 . . ?
C8B C9B C10B 123.6(2) . . ?
C8B C9B H9B 118.2 . . ?
C10B C9B H9B 118.2 . . ?
N20B C10B C9B 121.1(2) . . ?
N20B C10B C11B 110.1(2) . . ?
C9B C10B C11B 128.8(2) . . ?
C14B C11B C10B 100.80(19) . . ?
C14B C11B C13B 111.6(2) . . ?
C10B C11B C13B 112.4(2) . . ?
C14B C11B C12B 108.8(2) . . ?
C10B C11B C12B 110.6(2) . . ?
C13B C11B C12B 112.1(2) . . ?
C11B C12B H12D 109.5 . . ?
C11B C12B H12E 109.5 . . ?
H12D C12B H12E 109.5 . . ?
C11B C12B H12F 109.5 . . ?
H12D C12B H12F 109.5 . . ?
H12E C12B H12F 109.5 . . ?
C11B C13B H13D 109.5 . . ?
C11B C13B H13E 109.5 . . ?
H13D C13B H13E 109.5 . . ?
C11B C13B H13F 109.5 . . ?
H13D C13B H13F 109.5 . . ?
H13E C13B H13F 109.5 . . ?
C19B C14B C15B 118.8(2) . . ?
C19B C14B C11B 109.9(2) . . ?
C15B C14B C11B 131.2(2) . . ?
C16B C15B C14B 118.4(3) . . ?
C16B C15B H15B 120.8 . . ?
C14B C15B H15B 120.8 . . ?
C15B C16B C17B 121.5(3) . . ?
C15B C16B H16B 119.2 . . ?
C17B C16B H16B 119.2 . . ?
C16B C17B C18B 121.4(3) . . ?
C16B C17B H17B 119.3 . . ?
C18B C17B H17B 119.3 . . ?
C19B C18B C17B 115.7(3) . . ?
C19B C18B H18B 122.1 . . ?
C17B C18B H18B 122.1 . . ?
C14B C19B C18B 124.2(2) . . ?
C14B C19B N20B 107.5(2) . . ?
C18B C19B N20B 128.3(2) . . ?
C10B N20B C19B 111.6(2) . . ?
C10B N20B C21B 126.7(2) . . ?
C19B N20B C21B 121.7(2) . . ?
N20B C21B H21D 109.5 . . ?
N20B C21B H21E 109.5 . . ?
H21D C21B H21E 109.5 . . ?
N20B C21B H21F 109.5 . . ?
H21D C21B H21F 109.5 . . ?
H21E C21B H21F 109.5 . . ?
O23B N22B O24B 123.2(2) . . ?
O23B N22B C5B 119.0(2) . . ?
O24B N22B C5B 117.8(2) . . ?
C2C O1C H1C 109.5 . . ?
O1C C2C C3C 121.0(2) . . ?
O1C C2C C7C 118.8(2) . . ?
C3C C2C C7C 120.2(2) . . ?
C4C C3C C2C 120.8(2) . . ?
C4C C3C H3C 119.6 . . ?
C2C C3C H3C 119.6 . . ?
C3C C4C C5C 118.8(2) . . ?
C3C C4C H4C 120.6 . . ?
C5C C4C H4C 120.6 . . ?
C6C C5C C4C 121.8(2) . . ?
C6C C5C N22C 118.7(2) . . ?
C4C C5C N22C 119.5(2) . . ?
C5C C6C C7C 120.6(2) . . ?
C5C C6C H6C 119.7 . . ?
C7C C6C H6C 119.7 . . ?
C6C C7C C2C 117.7(2) . . ?
C6C C7C C8C 116.6(2) . . ?
C2C C7C C8C 125.6(2) . . ?
C9C C8C C7C 129.4(2) . . ?
C9C C8C H8C 115.3 . . ?
C7C C8C H8C 115.3 . . ?
C8C C9C C10C 122.8(2) . . ?
C8C C9C H9C 118.6 . . ?
C10C C9C H9C 118.6 . . ?
N20C C10C C9C 121.7(2) . . ?
N20C C10C C11C 109.6(2) . . ?
C9C C10C C11C 128.7(2) . . ?
C14C C11C C10C 101.1(2) . . ?
C14C C11C C13C 109.0(2) . . ?
C10C C11C C13C 110.7(2) . . ?
C14C C11C C12C 110.3(2) . . ?
C10C C11C C12C 112.8(2) . . ?
C13C C11C C12C 112.3(2) . . ?
C11C C12C H12G 109.5 . . ?
C11C C12C H12H 109.5 . . ?
H12G C12C H12H 109.5 . . ?
C11C C12C H12I 109.5 . . ?
H12G C12C H12I 109.5 . . ?
H12H C12C H12I 109.5 . . ?
C11C C13C H13G 109.5 . . ?
C11C C13C H13H 109.5 . . ?
H13G C13C H13H 109.5 . . ?
C11C C13C H13I 109.5 . . ?
H13G C13C H13I 109.5 . . ?
H13H C13C H13I 109.5 . . ?
C15C C14C C19C 119.6(2) . . ?
C15C C14C C11C 130.8(2) . . ?
C19C C14C C11C 109.5(2) . . ?
C14C C15C C16C 118.2(3) . . ?
C14C C15C H15C 120.9 . . ?
C16C C15C H15C 120.9 . . ?
C15C C16C C17C 121.2(3) . . ?
C15C C16C H16C 119.4 . . ?
C17C C16C H16C 119.4 . . ?
C18C C17C C16C 121.1(3) . . ?
C18C C17C H17C 119.5 . . ?
C16C C17C H17C 119.5 . . ?
C17C C18C C19C 116.6(3) . . ?
C17C C18C H18C 121.7 . . ?
C19C C18C H18C 121.7 . . ?
C18C C19C C14C 123.2(3) . . ?
C18C C19C N20C 128.9(3) . . ?
C14C C19C N20C 107.9(2) . . ?
C10C N20C C19C 111.7(2) . . ?
C10C N20C C21C 126.6(2) . . ?
C19C N20C C21C 121.7(2) . . ?
N20C C21C H21G 109.5 . . ?
N20C C21C H21H 109.5 . . ?
H21G C21C H21H 109.5 . . ?
N20C C21C H21I 109.5 . . ?
H21G C21C H21I 109.5 . . ?
H21H C21C H21I 109.5 . . ?
O23C N22C O24C 123.1(2) . . ?
O23C N22C C5C 118.8(2) . . ?
O24C N22C C5C 118.1(2) . . ?
C2D O1D H1D 109.5 . . ?
O1D C2D C3D 122.0(2) . . ?
O1D C2D C7D 118.2(2) . . ?
C3D C2D C7D 119.8(2) . . ?
C4D C3D C2D 120.5(2) . . ?
C4D C3D H3D 119.8 . . ?
C2D C3D H3D 119.8 . . ?
C3D C4D C5D 119.4(2) . . ?
C3D C4D H4D 120.3 . . ?
C5D C4D H4D 120.3 . . ?
C6D C5D C4D 121.9(2) . . ?
C6D C5D N22D 118.7(2) . . ?
C4D C5D N22D 119.4(2) . . ?
C5D C6D C7D 119.7(2) . . ?
C5D C6D H6D 120.1 . . ?
C7D C6D H6D 120.1 . . ?
C6D C7D C2D 118.6(2) . . ?
C6D C7D C8D 116.8(2) . . ?
C2D C7D C8D 124.6(2) . . ?
C9D C8D C7D 128.7(2) . . ?
C9D C8D H8D 115.6 . . ?
C7D C8D H8D 115.6 . . ?
C8D C9D C10D 122.9(2) . . ?
C8D C9D H9D 118.5 . . ?
C10D C9D H9D 118.5 . . ?
N20D C10D C9D 122.2(2) . . ?
N20D C10D C11D 109.7(2) . . ?
C9D C10D C11D 128.1(2) . . ?
C14D C11D C10D 101.13(19) . . ?
C14D C11D C13D 110.2(2) . . ?
C10D C11D C13D 113.7(2) . . ?
C14D C11D C12D 110.1(2) . . ?
C10D C11D C12D 108.6(2) . . ?
C13D C11D C12D 112.6(2) . . ?
C11D C12D H12J 109.5 . . ?
C11D C12D H12K 109.5 . . ?
H12J C12D H12K 109.5 . . ?
C11D C12D H12L 109.5 . . ?
H12J C12D H12L 109.5 . . ?
H12K C12D H12L 109.5 . . ?
C11D C13D H13J 109.5 . . ?
C11D C13D H13K 109.5 . . ?
H13J C13D H13K 109.5 . . ?
C11D C13D H13L 109.5 . . ?
H13J C13D H13L 109.5 . . ?
H13K C13D H13L 109.5 . . ?
C15D C14D C19D 119.7(2) . . ?
C15D C14D C11D 130.6(2) . . ?
C19D C14D C11D 109.7(2) . . ?
C14D C15D C16D 118.3(3) . . ?
C14D C15D H15D 120.8 . . ?
C16D C15D H15D 120.8 . . ?
C15D C16D C17D 120.9(3) . . ?
C15D C16D H16D 119.5 . . ?
C17D C16D H16D 119.5 . . ?
C18D C17D C16D 121.5(3) . . ?
C18D C17D H17D 119.3 . . ?
C16D C17D H17D 119.3 . . ?
C19D C18D C17D 116.3(3) . . ?
C19D C18D H18D 121.9 . . ?
C17D C18D H18D 121.9 . . ?
C18D C19D C14D 123.3(2) . . ?
C18D C19D N20D 129.0(2) . . ?
C14D C19D N20D 107.7(2) . . ?
C10D N20D C19D 111.6(2) . . ?
C10D N20D C21D 125.9(2) . . ?
C19D N20D C21D 122.5(2) . . ?
N20D C21D H21J 109.5 . . ?
N20D C21D H21K 109.5 . . ?
H21J C21D H21K 109.5 . . ?
N20D C21D H21L 109.5 . . ?
H21J C21D H21L 109.5 . . ?
H21K C21D H21L 109.5 . . ?
O23D N22D O24D 122.4(2) . . ?
O23D N22D C5D 119.0(2) . . ?
O24D N22D C5D 118.5(2) . . ?
O4E P1E O5E 109.27(11) . . ?
O4E P1E O2E 111.37(11) . . ?
O5E P1E O2E 108.01(11) . . ?
O4E P1E O3E 113.18(11) . . ?
O5E P1E O3E 105.84(11) . . ?
O2E P1E O3E 108.91(10) . . ?
P1E O2E H2E 109.5 . . ?
P1E O3E H3E 109.5 . . ?
P1E O5E H5E 109.5 . . ?
O3F P1F O4F 113.61(10) . . ?
O3F P1F O5F 108.20(10) . . ?
O4F P1F O5F 110.50(10) . . ?
O3F P1F O2F 106.98(10) . . ?
O4F P1F O2F 111.00(10) . . ?
O5F P1F O2F 106.21(10) . . ?
P1F O2F H2F 109.5 . . ?
P1F O5F H5F 109.5 . . ?
O3G P1G O4G 113.68(10) . . ?
O3G P1G O2G 106.94(10) . . ?
O4G P1G O2G 111.60(11) . . ?
O3G P1G O5G 107.08(10) . . ?
O4G P1G O5G 109.68(10) . . ?
O2G P1G O5G 107.58(11) . . ?
P1G O2G H2G 109.5 . . ?
P1G O5G H5G 109.5 . . ?
O2H P1H O3H 113.06(10) . . ?
O2H P1H O5H 110.39(10) . . ?
O3H P1H O5H 109.38(11) . . ?
O2H P1H O4H 111.71(11) . . ?
O3H P1H O4H 105.72(10) . . ?
O5H P1H O4H 106.26(11) . . ?
P1H O4H H4H 109.5 . . ?
P1H O5H H5H 109.5 . . ?
O4I P1I O5I 113.67(10) . . ?
O4I P1I O3I 109.76(11) . . ?
O5I P1I O3I 108.44(10) . . ?
O4I P1I O2I 111.11(10) . . ?
O5I P1I O2I 106.77(10) . . ?
O3I P1I O2I 106.81(10) . . ?
P1I O2I H2I 109.5 . . ?
P1I O3I H3I 109.5 . . ?
O4J P1J O5J 108.78(10) . . ?
O4J P1J O2J 112.77(11) . . ?
O5J P1J O2J 107.15(11) . . ?
O4J P1J O3J 110.75(11) . . ?
O5J P1J O3J 108.39(11) . . ?
O2J P1J O3J 108.86(10) . . ?
P1J O2J H2J 109.5 . . ?
P1J O3J H3J 109.5 . . ?
P1J O5J H5J 109.5 . . ?
H1V O1V H2V 104.531(19) . . ?
N1W C2W C3W 179.9(5) . . ?
C2W C3W H3WA 109.5 . . ?
C2W C3W H3WB 109.5 . . ?
H3WA C3W H3WB 109.5 . . ?
C2W C3W H3WC 109.5 . . ?
H3WA C3W H3WC 109.5 . . ?
H3WB C3W H3WC 109.5 . . ?
N1X C2X C3X 179.6(5) . . ?
C2X C3X H3XA 109.5 . . ?
C2X C3X H3XB 109.5 . . ?
H3XA C3X H3XB 109.5 . . ?
C2X C3X H3XC 109.5 . . ?
H3XA C3X H3XC 109.5 . . ?
H3XB C3X H3XC 109.5 . . ?
N1Y C2Y C3Y 179.5(5) . . ?
C2Y C3Y H3YA 109.5 . . ?
C2Y C3Y H3YB 109.5 . . ?
H3YA C3Y H3YB 109.5 . . ?
C2Y C3Y H3YC 109.5 . . ?
H3YA C3Y H3YC 109.5 . . ?
H3YB C3Y H3YC 109.5 . . ?
N1Z C2Z C3Z 178.8(4) . . ?
C2Z C3Z H3ZA 109.5 . . ?
C2Z C3Z H3ZB 109.5 . . ?
H3ZA C3Z H3ZB 109.5 . . ?
C2Z C3Z H3ZC 109.5 . . ?
H3ZA C3Z H3ZC 109.5 . . ?
H3ZB C3Z H3ZC 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
O1A C2A C3A C4A -179.4(2) . . . . ?
C7A C2A C3A C4A 0.7(4) . . . . ?
C2A C3A C4A C5A -0.7(4) . . . . ?
C3A C4A C5A C6A 0.1(4) . . . . ?
C3A C4A C5A N22A -179.8(2) . . . . ?
C4A C5A C6A C7A 0.5(4) . . . . ?
N22A C5A C6A C7A -179.6(2) . . . . ?
C5A C6A C7A C2A -0.5(4) . . . . ?
C5A C6A C7A C8A 178.9(2) . . . . ?
O1A C2A C7A C6A -180.0(2) . . . . ?
C3A C2A C7A C6A -0.1(4) . . . . ?
O1A C2A C7A C8A 0.7(4) . . . . ?
C3A C2A C7A C8A -179.4(2) . . . . ?
C6A C7A C8A C9A 175.8(3) . . . . ?
C2A C7A C8A C9A -4.9(4) . . . . ?
C7A C8A C9A C10A -178.2(2) . . . . ?
C8A C9A C10A N20A 176.7(2) . . . . ?
C8A C9A C10A C11A -5.1(4) . . . . ?
N20A C10A C11A C14A -2.7(3) . . . . ?
C9A C10A C11A C14A 178.9(3) . . . . ?
N20A C10A C11A C13A -121.3(2) . . . . ?
C9A C10A C11A C13A 60.3(4) . . . . ?
N20A C10A C11A C12A 113.1(2) . . . . ?
C9A C10A C11A C12A -65.3(3) . . . . ?
C10A C11A C14A C15A -177.9(3) . . . . ?
C13A C11A C14A C15A -57.2(4) . . . . ?
C12A C11A C14A C15A 66.5(4) . . . . ?
C10A C11A C14A C19A 2.2(3) . . . . ?
C13A C11A C14A C19A 122.9(2) . . . . ?
C12A C11A C14A C19A -113.4(3) . . . . ?
C19A C14A C15A C16A -0.7(4) . . . . ?
C11A C14A C15A C16A 179.5(3) . . . . ?
C14A C15A C16A C17A 0.8(4) . . . . ?
C15A C16A C17A C18A 0.0(4) . . . . ?
C16A C17A C18A C19A -0.9(4) . . . . ?
C15A C14A C19A C18A -0.2(4) . . . . ?
C11A C14A C19A C18A 179.7(2) . . . . ?
C15A C14A C19A N20A 179.1(2) . . . . ?
C11A C14A C19A N20A -1.0(3) . . . . ?
C17A C18A C19A C14A 1.0(4) . . . . ?
C17A C18A C19A N20A -178.2(3) . . . . ?
C9A C10A N20A C19A -179.1(2) . . . . ?
C11A C10A N20A C19A 2.4(3) . . . . ?
C9A C10A N20A C21A 1.3(4) . . . . ?
C11A C10A N20A C21A -177.3(3) . . . . ?
C14A C19A N20A C10A -0.9(3) . . . . ?
C18A C19A N20A C10A 178.4(3) . . . . ?
C14A C19A N20A C21A 178.8(3) . . . . ?
C18A C19A N20A C21A -2.0(4) . . . . ?
C6A C5A N22A O23A 2.9(4) . . . . ?
C4A C5A N22A O23A -177.2(3) . . . . ?
C6A C5A N22A O24A -178.4(3) . . . . ?
C4A C5A N22A O24A 1.6(4) . . . . ?
O1B C2B C3B C4B -179.4(2) . . . . ?
C7B C2B C3B C4B 0.1(4) . . . . ?
C2B C3B C4B C5B -1.7(4) . . . . ?
C3B C4B C5B C6B 1.3(4) . . . . ?
C3B C4B C5B N22B 179.2(2) . . . . ?
C4B C5B C6B C7B 0.8(4) . . . . ?
N22B C5B C6B C7B -177.1(2) . . . . ?
C5B C6B C7B C2B -2.4(4) . . . . ?
C5B C6B C7B C8B 173.9(2) . . . . ?
O1B C2B C7B C6B -178.5(2) . . . . ?
C3B C2B C7B C6B 2.0(3) . . . . ?
O1B C2B C7B C8B 5.5(4) . . . . ?
C3B C2B C7B C8B -173.9(2) . . . . ?
C6B C7B C8B C9B -171.8(2) . . . . ?
C2B C7B C8B C9B 4.2(4) . . . . ?
C7B C8B C9B C10B 172.6(2) . . . . ?
C8B C9B C10B N20B 178.3(2) . . . . ?
C8B C9B C10B C11B -5.3(4) . . . . ?
N20B C10B C11B C14B 3.1(3) . . . . ?
C9B C10B C11B C14B -173.6(2) . . . . ?
N20B C10B C11B C13B 122.1(2) . . . . ?
C9B C10B C11B C13B -54.7(3) . . . . ?
N20B C10B C11B C12B -111.9(2) . . . . ?
C9B C10B C11B C12B 71.4(3) . . . . ?
C10B C11B C14B C19B -2.8(3) . . . . ?
C13B C11B C14B C19B -122.3(2) . . . . ?
C12B C11B C14B C19B 113.5(2) . . . . ?
C10B C11B C14B C15B -180.0(3) . . . . ?
C13B C11B C14B C15B 60.6(4) . . . . ?
C12B C11B C14B C15B -63.6(4) . . . . ?
C19B C14B C15B C16B 0.8(4) . . . . ?
C11B C14B C15B C16B 177.8(3) . . . . ?
C14B C15B C16B C17B -0.7(4) . . . . ?
C15B C16B C17B C18B 0.3(4) . . . . ?
C16B C17B C18B C19B 0.1(4) . . . . ?
C15B C14B C19B C18B -0.5(4) . . . . ?
C11B C14B C19B C18B -178.1(2) . . . . ?
C15B C14B C19B N20B 179.2(2) . . . . ?
C11B C14B C19B N20B 1.6(3) . . . . ?
C17B C18B C19B C14B 0.0(4) . . . . ?
C17B C18B C19B N20B -179.6(3) . . . . ?
C9B C10B N20B C19B 174.6(2) . . . . ?
C11B C10B N20B C19B -2.4(3) . . . . ?
C9B C10B N20B C21B -4.9(4) . . . . ?
C11B C10B N20B C21B 178.1(2) . . . . ?
C14B C19B N20B C10B 0.5(3) . . . . ?
C18B C19B N20B C10B -179.8(3) . . . . ?
C14B C19B N20B C21B -180.0(2) . . . . ?
C18B C19B N20B C21B -0.3(4) . . . . ?
C6B C5B N22B O23B -22.4(4) . . . . ?
C4B C5B N22B O23B 159.6(3) . . . . ?
C6B C5B N22B O24B 157.8(3) . . . . ?
C4B C5B N22B O24B -20.1(4) . . . . ?
O1C C2C C3C C4C 178.2(2) . . . . ?
C7C C2C C3C C4C -0.7(4) . . . . ?
C2C C3C C4C C5C 0.9(4) . . . . ?
C3C C4C C5C C6C 0.2(4) . . . . ?
C3C C4C C5C N22C -179.5(2) . . . . ?
C4C C5C C6C C7C -1.4(4) . . . . ?
N22C C5C C6C C7C 178.2(2) . . . . ?
C5C C6C C7C C2C 1.6(4) . . . . ?
C5C C6C C7C C8C -177.0(2) . . . . ?
O1C C2C C7C C6C -179.4(2) . . . . ?
C3C C2C C7C C6C -0.5(3) . . . . ?
O1C C2C C7C C8C -0.9(4) . . . . ?
C3C C2C C7C C8C 177.9(2) . . . . ?
C6C C7C C8C C9C 179.9(3) . . . . ?
C2C C7C C8C C9C 1.5(4) . . . . ?
C7C C8C C9C C10C -175.0(2) . . . . ?
C8C C9C C10C N20C -178.9(2) . . . . ?
C8C C9C C10C C11C 2.6(4) . . . . ?
N20C C10C C11C C14C -3.3(3) . . . . ?
C9C C10C C11C C14C 175.4(2) . . . . ?
N20C C10C C11C C13C 112.1(2) . . . . ?
C9C C10C C11C C13C -69.2(3) . . . . ?
N20C C10C C11C C12C -121.1(2) . . . . ?
C9C C10C C11C C12C 57.6(3) . . . . ?
C10C C11C C14C C15C -177.7(3) . . . . ?
C13C C11C C14C C15C 65.6(4) . . . . ?
C12C C11C C14C C15C -58.1(4) . . . . ?
C10C C11C C14C C19C 2.6(3) . . . . ?
C13C C11C C14C C19C -114.1(2) . . . . ?
C12C C11C C14C C19C 122.2(2) . . . . ?
C19C C14C C15C C16C 0.1(4) . . . . ?
C11C C14C C15C C16C -179.5(3) . . . . ?
C14C C15C C16C C17C 0.4(4) . . . . ?
C15C C16C C17C C18C -0.5(5) . . . . ?
C16C C17C C18C C19C 0.0(4) . . . . ?
C17C C18C C19C C14C 0.5(4) . . . . ?
C17C C18C C19C N20C -179.1(3) . . . . ?
C15C C14C C19C C18C -0.5(4) . . . . ?
C11C C14C C19C C18C 179.2(3) . . . . ?
C15C C14C C19C N20C 179.1(2) . . . . ?
C11C C14C C19C N20C -1.2(3) . . . . ?
C9C C10C N20C C19C -176.0(2) . . . . ?
C11C C10C N20C C19C 2.8(3) . . . . ?
C9C C10C N20C C21C 3.8(4) . . . . ?
C11C C10C N20C C21C -177.4(3) . . . . ?
C18C C19C N20C C10C 178.6(3) . . . . ?
C14C C19C N20C C10C -1.0(3) . . . . ?
C18C C19C N20C C21C -1.2(4) . . . . ?
C14C C19C N20C C21C 179.2(3) . . . . ?
C6C C5C N22C O23C 21.2(4) . . . . ?
C4C C5C N22C O23C -159.1(3) . . . . ?
C6C C5C N22C O24C -159.3(3) . . . . ?
C4C C5C N22C O24C 20.3(4) . . . . ?
O1D C2D C3D C4D -179.3(2) . . . . ?
C7D C2D C3D C4D 1.6(4) . . . . ?
C2D C3D C4D C5D -0.5(4) . . . . ?
C3D C4D C5D C6D -1.3(4) . . . . ?
C3D C4D C5D N22D 176.7(2) . . . . ?
C4D C5D C6D C7D 2.0(4) . . . . ?
N22D C5D C6D C7D -176.0(2) . . . . ?
C5D C6D C7D C2D -0.9(3) . . . . ?
C5D C6D C7D C8D 177.1(2) . . . . ?
O1D C2D C7D C6D 180.0(2) . . . . ?
C3D C2D C7D C6D -0.8(3) . . . . ?
O1D C2D C7D C8D 2.1(4) . . . . ?
C3D C2D C7D C8D -178.7(2) . . . . ?
C6D C7D C8D C9D -172.4(2) . . . . ?
C2D C7D C8D C9D 5.5(4) . . . . ?
C7D C8D C9D C10D 176.7(2) . . . . ?
C8D C9D C10D N20D -179.5(2) . . . . ?
C8D C9D C10D C11D 3.2(4) . . . . ?
N20D C10D C11D C14D 3.8(3) . . . . ?
C9D C10D C11D C14D -178.6(2) . . . . ?
N20D C10D C11D C13D 121.8(2) . . . . ?
C9D C10D C11D C13D -60.6(3) . . . . ?
N20D C10D C11D C12D -112.1(2) . . . . ?
C9D C10D C11D C12D 65.5(3) . . . . ?
C10D C11D C14D C15D 175.2(3) . . . . ?
C13D C11D C14D C15D 54.7(4) . . . . ?
C12D C11D C14D C15D -70.1(3) . . . . ?
C10D C11D C14D C19D -3.0(3) . . . . ?
C13D C11D C14D C19D -123.5(2) . . . . ?
C12D C11D C14D C19D 111.7(2) . . . . ?
C19D C14D C15D C16D -0.5(4) . . . . ?
C11D C14D C15D C16D -178.5(3) . . . . ?
C14D C15D C16D C17D -0.7(4) . . . . ?
C15D C16D C17D C18D 0.7(4) . . . . ?
C16D C17D C18D C19D 0.5(4) . . . . ?
C17D C18D C19D C14D -1.8(4) . . . . ?
C17D C18D C19D N20D 176.9(3) . . . . ?
C15D C14D C19D C18D 1.8(4) . . . . ?
C11D C14D C19D C18D -179.8(2) . . . . ?
C15D C14D C19D N20D -177.1(2) . . . . ?
C11D C14D C19D N20D 1.3(3) . . . . ?
C9D C10D N20D C19D 178.9(2) . . . . ?
C11D C10D N20D C19D -3.3(3) . . . . ?
C9D C10D N20D C21D -1.6(4) . . . . ?
C11D C10D N20D C21D 176.2(2) . . . . ?
C18D C19D N20D C10D -177.5(3) . . . . ?
C14D C19D N20D C10D 1.3(3) . . . . ?
C18D C19D N20D C21D 3.0(4) . . . . ?
C14D C19D N20D C21D -178.2(2) . . . . ?
C6D C5D N22D O23D -5.5(4) . . . . ?
C4D C5D N22D O23D 176.5(3) . . . . ?
C6D C5D N22D O24D 172.4(3) . . . . ?
C4D C5D N22D O24D -5.7(4) . . . . ?

_refine_diff_density_max         0.391
_refine_diff_density_min         -0.385
_refine_diff_density_rms         0.066


_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: Acetonitrile'
