# Electronic Supplementary Material (ESI) for RSC Advances.
# This journal is © The Royal Society of Chemistry 2017

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

data_comp2O
_database_code_depnum_ccdc_archive 'CCDC 1543227'
_audit_update_record             
;
2017-04-10 deposited with the CCDC.
2017-05-29 downloaded from the CCDC.
;

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

_audit_creation_method           'SHELXL-2014/7 and enCIFer'
_shelx_SHELXL_version_number     2014/7
_audit_creation_date             '10 February 2017'

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

_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C21 H22 N O2, H O4 S'
_chemical_formula_sum            'C21 H23 N O6 S'
_chemical_formula_weight         417.46

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

_cell_length_a                   19.606(9)
_cell_length_b                   11.969(5)
_cell_length_c                   8.053(4)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1889.7(14)
_cell_formula_units_Z            4
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    2530
_cell_measurement_theta_min      3.48
_cell_measurement_theta_max      26.73

_exptl_crystal_description       needle
_exptl_crystal_colour            brown
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.467
_exptl_crystal_F_000             880
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.150
_exptl_crystal_size_mid          0.020
_exptl_crystal_size_min          0.010
_exptl_absorpt_coefficient_mu    0.212
_shelx_estimated_absorpt_T_min   0.969
_shelx_estimated_absorpt_T_max   0.998
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.969
_exptl_absorpt_correction_T_max  0.999
_exptl_absorpt_process_details   
; 
'SADABS V2012/1 (Bruker AXS Inc.)' 
;


_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_measurement_device_type  'Bruker X8 Kappa CCD APEX II'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            16423
_diffrn_reflns_av_unetI/netI     0.1711
_diffrn_reflns_av_R_equivalents  0.1918
_diffrn_reflns_limit_h_min       -23
_diffrn_reflns_limit_h_max       23
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_theta_min         3.690
_diffrn_reflns_theta_max         25.018
_diffrn_reflns_theta_full        25.018
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measured_fraction_theta_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.927
_diffrn_reflns_point_group_measured_fraction_full 0.927


_reflns_number_total             3089
_reflns_number_gt                1838
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.730
_reflns_Friedel_fraction_max     0.849
_reflns_Friedel_fraction_full    0.849

_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       'APEX2 (Bruker AXS Inc., 2012)'
_computing_cell_refinement       'SAINT (Bruker AXS Inc., 2012)'
_computing_data_reduction        'SAINT (Bruker AXS Inc., 2012)'
_computing_structure_solution    'SHELXS (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'DIAMOND (Brandenburg, 2009)'
_computing_publication_material  'SHELXTL (Sheldrick, 2014)'


_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)+(0.0280P)²] 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_abs_structure_details 
;
 Flack x determined using 600 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.06(15)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         3089
_refine_ls_number_parameters     270
_refine_ls_number_restraints     3
_refine_ls_R_factor_all          0.1450
_refine_ls_R_factor_gt           0.0644
_refine_ls_wR_factor_ref         0.1196
_refine_ls_wR_factor_gt          0.0995
_refine_ls_goodness_of_fit_ref   0.999
_refine_ls_restrained_S_all      0.999
_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 0.7332(3) 0.5082(4) -0.0674(7) 0.0281(14) Uani 1 1 d D . . . .
H1 H 0.6873(14) 0.509(6) -0.104(9) 0.042 Uiso 1 1 d D U . . .
O2 O 0.7148(3) 0.7039(4) 0.6544(6) 0.0220(14) Uani 1 1 d . . . . .
N1 N 0.5970(3) 0.8345(5) 1.1268(7) 0.0221(17) Uani 1 1 d . . . . .
C1 C 0.7393(4) 0.5494(6) 0.0882(10) 0.0220(19) Uani 1 1 d . . . . .
C2 C 0.8048(4) 0.5712(7) 0.1470(10) 0.028(2) Uani 1 1 d . . . . .
H2 H 0.8430 0.5546 0.0787 0.033 Uiso 1 1 calc R U . . .
C3 C 0.8151(4) 0.6161(6) 0.3015(10) 0.024(2) Uani 1 1 d . . . . .
C4 C 0.7589(4) 0.6393(6) 0.4003(9) 0.0175(19) Uani 1 1 d . . . . .
C5 C 0.6927(4) 0.6129(6) 0.3444(10) 0.020(2) Uani 1 1 d . . . . .
H5 H 0.6545 0.6258 0.4144 0.024 Uiso 1 1 calc R U . . .
C6 C 0.6834(4) 0.5684(6) 0.1889(10) 0.022(2) Uani 1 1 d . . . . .
H6 H 0.6388 0.5507 0.1508 0.027 Uiso 1 1 calc R U . . .
C7 C 0.8854(4) 0.6304(9) 0.3760(13) 0.055(3) Uani 1 1 d . . . . .
H7A H 0.8975 0.5614 0.4369 0.066 Uiso 1 1 calc R U . . .
H7B H 0.9187 0.6396 0.2847 0.066 Uiso 1 1 calc R U . . .
C8 C 0.8919(4) 0.7263(7) 0.4901(11) 0.037(2) Uani 1 1 d . . . . .
H8A H 0.8955 0.7957 0.4239 0.045 Uiso 1 1 calc R U . . .
H8B H 0.9346 0.7181 0.5545 0.045 Uiso 1 1 calc R U . . .
C9 C 0.8332(4) 0.7376(6) 0.6091(9) 0.019(2) Uani 1 1 d . . . . .
C10 C 0.7712(4) 0.6928(6) 0.5578(10) 0.021(2) Uani 1 1 d . . . . .
C11 C 0.8364(4) 0.7920(6) 0.7589(10) 0.023(2) Uani 1 1 d . . . . .
H11 H 0.8787 0.8222 0.7948 0.028 Uiso 1 1 calc R U . . .
C12 C 0.7792(4) 0.8042(6) 0.8593(10) 0.0184(19) Uani 1 1 d . . . . .
C13 C 0.7165(4) 0.7595(6) 0.8038(9) 0.019(2) Uani 1 1 d . . . . .
C14 C 0.6566(4) 0.7690(6) 0.8871(10) 0.021(2) Uani 1 1 d . . . . .
H14 H 0.6159 0.7381 0.8427 0.025 Uiso 1 1 calc R U . . .
C15 C 0.6558(4) 0.8257(6) 1.0408(9) 0.022(2) Uani 1 1 d . . . . .
C16 C 0.7187(4) 0.8699(6) 1.1021(10) 0.023(2) Uani 1 1 d . . . . .
H16 H 0.7192 0.9073 1.2062 0.027 Uiso 1 1 calc R U . . .
C17 C 0.7784(4) 0.8598(6) 1.0147(10) 0.024(2) Uani 1 1 d . . . . .
H17 H 0.8194 0.8902 1.0585 0.028 Uiso 1 1 calc R U . . .
C18 C 0.5883(4) 0.9091(6) 1.2699(9) 0.025(2) Uani 1 1 d . . . . .
H18A H 0.5430 0.9454 1.2624 0.030 Uiso 1 1 calc R U . . .
H18B H 0.6233 0.9686 1.2647 0.030 Uiso 1 1 calc R U . . .
C19 C 0.5938(4) 0.8500(6) 1.4356(9) 0.030(2) Uani 1 1 d . . . . .
H19A H 0.5638 0.7845 1.4360 0.044 Uiso 1 1 calc R U . . .
H19B H 0.5802 0.9011 1.5247 0.044 Uiso 1 1 calc R U . . .
H19C H 0.6411 0.8260 1.4534 0.044 Uiso 1 1 calc R U . . .
C20 C 0.5346(4) 0.7784(5) 1.0750(9) 0.023(2) Uani 1 1 d . . . . .
H20A H 0.5064 0.7626 1.1741 0.027 Uiso 1 1 calc R U . . .
H20B H 0.5465 0.7060 1.0230 0.027 Uiso 1 1 calc R U . . .
C21 C 0.4931(4) 0.8472(7) 0.9527(10) 0.034(2) Uani 1 1 d . . . . .
H21A H 0.4847 0.9216 0.9994 0.051 Uiso 1 1 calc R U . . .
H21B H 0.4495 0.8100 0.9315 0.051 Uiso 1 1 calc R U . . .
H21C H 0.5184 0.8545 0.8482 0.051 Uiso 1 1 calc R U . . .
S1 S 0.54786(9) 0.51624(14) -0.2780(3) 0.0242(5) Uani 1 1 d . . . . .
O3 O 0.6033(3) 0.4998(4) -0.1583(6) 0.0329(15) Uani 1 1 d . . . . .
O4 O 0.4846(3) 0.4522(4) -0.2059(6) 0.0328(15) Uani 1 1 d D . . . .
H4 H 0.470(4) 0.491(6) -0.109(6) 0.049 Uiso 1 1 d D U . . .
O5 O 0.5604(3) 0.4582(4) -0.4356(6) 0.0243(13) Uani 1 1 d . . . . .
O6 O 0.5289(3) 0.6317(3) -0.2964(8) 0.0336(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 C1 1.352(9) . ?
O1 H1 0.948(14) . ?
O2 C10 1.359(9) . ?
O2 C13 1.376(8) . ?
N1 C15 1.349(10) . ?
N1 C20 1.456(9) . ?
N1 C18 1.468(9) . ?
C1 C6 1.382(10) . ?
C1 C2 1.392(11) . ?
C2 C3 1.371(10) . ?
C2 H2 0.9500 . ?
C3 C4 1.386(10) . ?
C3 C7 1.513(11) . ?
C4 C5 1.410(10) . ?
C4 C10 1.441(10) . ?
C5 C6 1.373(10) . ?
C5 H5 0.9500 . ?
C6 H6 0.9500 . ?
C7 C8 1.476(11) . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C8 C9 1.504(11) . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C9 C11 1.373(10) . ?
C9 C10 1.391(10) . ?
C11 C12 1.389(10) . ?
C11 H11 0.9500 . ?
C12 C13 1.413(9) . ?
C12 C17 1.418(11) . ?
C13 C14 1.359(10) . ?
C14 C15 1.411(10) . ?
C14 H14 0.9500 . ?
C15 C16 1.431(11) . ?
C16 C17 1.370(10) . ?
C16 H16 0.9500 . ?
C17 H17 0.9500 . ?
C18 C19 1.515(10) . ?
C18 H18A 0.9900 . ?
C18 H18B 0.9900 . ?
C19 H19A 0.9800 . ?
C19 H19B 0.9800 . ?
C19 H19C 0.9800 . ?
C20 C21 1.520(10) . ?
C20 H20A 0.9900 . ?
C20 H20B 0.9900 . ?
C21 H21A 0.9800 . ?
C21 H21B 0.9800 . ?
C21 H21C 0.9800 . ?
S1 O6 1.439(4) . ?
S1 O3 1.466(5) . ?
S1 O5 1.467(5) . ?
S1 O4 1.570(5) . ?
O4 H4 0.951(14) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1 O1 H1 112(5) . . ?
C10 O2 C13 121.8(7) . . ?
C15 N1 C20 122.3(6) . . ?
C15 N1 C18 123.3(6) . . ?
C20 N1 C18 114.1(6) . . ?
O1 C1 C6 122.3(7) . . ?
O1 C1 C2 117.7(7) . . ?
C6 C1 C2 120.0(8) . . ?
C3 C2 C1 121.2(8) . . ?
C3 C2 H2 119.4 . . ?
C1 C2 H2 119.4 . . ?
C2 C3 C4 118.9(8) . . ?
C2 C3 C7 122.6(8) . . ?
C4 C3 C7 118.3(8) . . ?
C3 C4 C5 120.2(8) . . ?
C3 C4 C10 117.5(7) . . ?
C5 C4 C10 122.3(7) . . ?
C6 C5 C4 120.0(7) . . ?
C6 C5 H5 120.0 . . ?
C4 C5 H5 120.0 . . ?
C5 C6 C1 119.6(8) . . ?
C5 C6 H6 120.2 . . ?
C1 C6 H6 120.2 . . ?
C8 C7 C3 114.4(8) . . ?
C8 C7 H7A 108.6 . . ?
C3 C7 H7A 108.6 . . ?
C8 C7 H7B 108.6 . . ?
C3 C7 H7B 108.6 . . ?
H7A C7 H7B 107.6 . . ?
C7 C8 C9 113.6(7) . . ?
C7 C8 H8A 108.8 . . ?
C9 C8 H8A 108.8 . . ?
C7 C8 H8B 108.8 . . ?
C9 C8 H8B 108.8 . . ?
H8A C8 H8B 107.7 . . ?
C11 C9 C10 118.9(7) . . ?
C11 C9 C8 124.6(8) . . ?
C10 C9 C8 116.4(7) . . ?
O2 C10 C9 120.3(7) . . ?
O2 C10 C4 114.3(7) . . ?
C9 C10 C4 125.4(7) . . ?
C9 C11 C12 121.6(8) . . ?
C9 C11 H11 119.2 . . ?
C12 C11 H11 119.2 . . ?
C11 C12 C13 118.5(7) . . ?
C11 C12 C17 124.9(8) . . ?
C13 C12 C17 116.5(7) . . ?
C14 C13 O2 116.8(7) . . ?
C14 C13 C12 124.4(7) . . ?
O2 C13 C12 118.8(7) . . ?
C13 C14 C15 118.8(7) . . ?
C13 C14 H14 120.6 . . ?
C15 C14 H14 120.6 . . ?
N1 C15 C14 119.8(8) . . ?
N1 C15 C16 122.1(7) . . ?
C14 C15 C16 118.1(8) . . ?
C17 C16 C15 121.7(7) . . ?
C17 C16 H16 119.1 . . ?
C15 C16 H16 119.1 . . ?
C16 C17 C12 120.3(8) . . ?
C16 C17 H17 119.8 . . ?
C12 C17 H17 119.8 . . ?
N1 C18 C19 113.5(5) . . ?
N1 C18 H18A 108.9 . . ?
C19 C18 H18A 108.9 . . ?
N1 C18 H18B 108.9 . . ?
C19 C18 H18B 108.9 . . ?
H18A C18 H18B 107.7 . . ?
C18 C19 H19A 109.5 . . ?
C18 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
C18 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
N1 C20 C21 112.7(6) . . ?
N1 C20 H20A 109.1 . . ?
C21 C20 H20A 109.1 . . ?
N1 C20 H20B 109.1 . . ?
C21 C20 H20B 109.1 . . ?
H20A C20 H20B 107.8 . . ?
C20 C21 H21A 109.5 . . ?
C20 C21 H21B 109.5 . . ?
H21A C21 H21B 109.5 . . ?
C20 C21 H21C 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
O6 S1 O3 112.8(3) . . ?
O6 S1 O5 114.1(3) . . ?
O3 S1 O5 112.3(3) . . ?
O6 S1 O4 107.6(3) . . ?
O3 S1 O4 106.1(3) . . ?
O5 S1 O4 102.8(3) . . ?
S1 O4 H4 107(5) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O1 C1 C2 C3 178.0(7) . . . . ?
C6 C1 C2 C3 -2.9(11) . . . . ?
C1 C2 C3 C4 0.4(11) . . . . ?
C1 C2 C3 C7 173.9(8) . . . . ?
C2 C3 C4 C5 2.4(11) . . . . ?
C7 C3 C4 C5 -171.3(7) . . . . ?
C2 C3 C4 C10 -176.3(7) . . . . ?
C7 C3 C4 C10 9.9(10) . . . . ?
C3 C4 C5 C6 -2.8(10) . . . . ?
C10 C4 C5 C6 175.9(7) . . . . ?
C4 C5 C6 C1 0.2(10) . . . . ?
O1 C1 C6 C5 -178.4(6) . . . . ?
C2 C1 C6 C5 2.6(10) . . . . ?
C2 C3 C7 C8 149.5(8) . . . . ?
C4 C3 C7 C8 -37.0(12) . . . . ?
C3 C7 C8 C9 43.9(12) . . . . ?
C7 C8 C9 C11 156.8(8) . . . . ?
C7 C8 C9 C10 -25.8(11) . . . . ?
C13 O2 C10 C9 0.4(10) . . . . ?
C13 O2 C10 C4 -175.7(6) . . . . ?
C11 C9 C10 O2 0.5(11) . . . . ?
C8 C9 C10 O2 -177.0(6) . . . . ?
C11 C9 C10 C4 176.2(7) . . . . ?
C8 C9 C10 C4 -1.3(11) . . . . ?
C3 C4 C10 O2 -174.3(6) . . . . ?
C5 C4 C10 O2 7.0(10) . . . . ?
C3 C4 C10 C9 9.8(11) . . . . ?
C5 C4 C10 C9 -168.9(7) . . . . ?
C10 C9 C11 C12 -0.6(11) . . . . ?
C8 C9 C11 C12 176.8(7) . . . . ?
C9 C11 C12 C13 -0.3(10) . . . . ?
C9 C11 C12 C17 -179.6(6) . . . . ?
C10 O2 C13 C14 177.6(6) . . . . ?
C10 O2 C13 C12 -1.3(9) . . . . ?
C11 C12 C13 C14 -177.6(7) . . . . ?
C17 C12 C13 C14 1.7(10) . . . . ?
C11 C12 C13 O2 1.2(10) . . . . ?
C17 C12 C13 O2 -179.5(6) . . . . ?
O2 C13 C14 C15 -179.8(6) . . . . ?
C12 C13 C14 C15 -1.0(11) . . . . ?
C20 N1 C15 C14 5.9(10) . . . . ?
C18 N1 C15 C14 -167.9(6) . . . . ?
C20 N1 C15 C16 -172.5(6) . . . . ?
C18 N1 C15 C16 13.7(10) . . . . ?
C13 C14 C15 N1 -178.9(7) . . . . ?
C13 C14 C15 C16 -0.4(10) . . . . ?
N1 C15 C16 C17 179.4(7) . . . . ?
C14 C15 C16 C17 1.0(11) . . . . ?
C15 C16 C17 C12 -0.2(11) . . . . ?
C11 C12 C17 C16 178.2(7) . . . . ?
C13 C12 C17 C16 -1.1(10) . . . . ?
C15 N1 C18 C19 -100.2(8) . . . . ?
C20 N1 C18 C19 85.5(8) . . . . ?
C15 N1 C20 C21 -87.1(8) . . . . ?
C18 N1 C20 C21 87.2(8) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
O1 H1 O3 0.948(14) 1.707(17) 2.652(8) 175(7) .
O4 H4 O5 0.951(14) 1.636(19) 2.582(7) 172(8) 2_665

_refine_diff_density_max         0.421
_refine_diff_density_min         -0.307
_refine_diff_density_rms         0.070

####################################################################### 
# 
# 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_comp1
_database_code_depnum_ccdc_archive 'CCDC 1543226'
_audit_update_record             
;
2017-04-10 deposited with the CCDC.
2017-05-29 downloaded from the CCDC.
;

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

_audit_creation_method           'SHELXL-2014/7 and enCIFer'
_shelx_SHELXL_version_number     2014/7
_audit_creation_date             '23 January 2017'

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


_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C21 H22 N O, B F4'
_chemical_formula_sum            'C21 H22 B F4 N O'
_chemical_formula_weight         391.20

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'
B B 0.0013 0.0007 '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'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_H-M_alt        'C 2/c'
_space_group_name_Hall           '-C 2yc'

_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'
'-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                   17.6076(16)
_cell_length_b                   17.9505(12)
_cell_length_c                   14.4826(13)
_cell_angle_alpha                90
_cell_angle_beta                 125.893(3)
_cell_angle_gamma                90
_cell_volume                     3708.2(5)
_cell_formula_units_Z            8
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    3573
_cell_measurement_theta_min      2.86
_cell_measurement_theta_max      26.37

_exptl_crystal_description       prism
_exptl_crystal_colour            brown
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.401
_exptl_crystal_F_000             1632
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.120
_exptl_crystal_size_min          0.100
_exptl_absorpt_coefficient_mu    0.112
_shelx_estimated_absorpt_T_min   0.978
_shelx_estimated_absorpt_T_max   0.989
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.834
_exptl_absorpt_correction_T_max  0.862
_exptl_absorpt_process_details   
; 
'SADABS V2012/1 (Bruker AXS Inc.)' 
;


_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_measurement_device_type  'Bruker X8 Kappa CCD APEX II'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            19043
_diffrn_reflns_av_unetI/netI     0.0399
_diffrn_reflns_av_R_equivalents  0.0462
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         3.649
_diffrn_reflns_theta_max         26.372
_diffrn_reflns_theta_full        25.242
_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             3784
_reflns_number_gt                2538
_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_cell_refinement       'SAINT (Bruker AXS Inc., 2012)'
_computing_data_reduction        'SAINT (Bruker AXS Inc., 2012)'
_computing_structure_solution    'SHELXS (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'DIAMOND (Brandenburg, 2009)'
_computing_publication_material  'SHELXTL (Sheldrick, 2014)'


_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)+(0.0478P)²+4.0538P] 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         3784
_refine_ls_number_parameters     256
_refine_ls_number_restraints     18
_refine_ls_R_factor_all          0.0831
_refine_ls_R_factor_gt           0.0495
_refine_ls_wR_factor_ref         0.1277
_refine_ls_wR_factor_gt          0.1112
_refine_ls_goodness_of_fit_ref   1.032
_refine_ls_restrained_S_all      1.041
_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 0.03482(10) 0.00746(7) 0.66835(11) 0.0261(3) Uani 1 1 d . . . . .
N1 N 0.32015(12) -0.09139(9) 0.98572(14) 0.0290(4) Uani 1 1 d . . . . .
C1 C 0.4854(2) -0.1021(2) 1.0549(3) 0.0888(12) Uani 1 1 d . U . . .
H1A H 0.4752 -0.1531 1.0260 0.133 Uiso 1 1 calc R U . . .
H1B H 0.5499 -0.0969 1.1233 0.133 Uiso 1 1 calc R U . . .
H1C H 0.4749 -0.0672 0.9964 0.133 Uiso 1 1 calc R U . . .
C2 C 0.41892(15) -0.08519(12) 1.08403(19) 0.0367(5) Uani 1 1 d . . . . .
H2A H 0.4309 -0.1199 1.1443 0.044 Uiso 1 1 calc R U . . .
H2B H 0.4308 -0.0340 1.1151 0.044 Uiso 1 1 calc R U . . .
C3 C 0.28074(16) -0.16696(11) 0.96072(18) 0.0322(5) Uani 1 1 d . . . . .
H3A H 0.2153 -0.1642 0.9367 0.039 Uiso 1 1 calc R U . . .
H3B H 0.3170 -0.1971 1.0314 0.039 Uiso 1 1 calc R U . . .
C4 C 0.28155(18) -0.20624(13) 0.8682(2) 0.0465(6) Uani 1 1 d . . . . .
H4A H 0.2455 -0.1770 0.7977 0.070 Uiso 1 1 calc R U . . .
H4B H 0.2534 -0.2558 0.8545 0.070 Uiso 1 1 calc R U . . .
H4C H 0.3463 -0.2113 0.8927 0.070 Uiso 1 1 calc R U . . .
C5 C 0.26871(14) -0.03311(11) 0.92053(17) 0.0269(5) Uani 1 1 d . . . . .
C6 C 0.30749(15) 0.04146(11) 0.94853(18) 0.0308(5) Uani 1 1 d . . . . .
H6 H 0.3705 0.0489 1.0126 0.037 Uiso 1 1 calc R U . . .
C7 C 0.25551(16) 0.10065(11) 0.88499(18) 0.0329(5) Uani 1 1 d . . . . .
H7 H 0.2828 0.1489 0.9065 0.039 Uiso 1 1 calc R U . . .
C8 C 0.16144(15) 0.09311(11) 0.78711(18) 0.0285(5) Uani 1 1 d . . . . .
C9 C 0.12522(14) 0.01888(10) 0.76110(16) 0.0254(4) Uani 1 1 d . . . . .
C10 C 0.17491(14) -0.04193(11) 0.82400(17) 0.0267(4) Uani 1 1 d . . . . .
H10 H 0.1468 -0.0899 0.8032 0.032 Uiso 1 1 calc R U . . .
C11 C 0.10485(15) 0.15009(11) 0.71462(18) 0.0312(5) Uani 1 1 d . . . . .
H11 H 0.1277 0.1998 0.7319 0.037 Uiso 1 1 calc R U . . .
C12 C 0.01504(15) 0.13606(11) 0.61679(18) 0.0296(5) Uani 1 1 d . . . . .
C13 C -0.01820(15) 0.06392(10) 0.59688(16) 0.0263(4) Uani 1 1 d . . . . .
C14 C -0.11082(15) 0.04193(11) 0.50052(17) 0.0275(5) Uani 1 1 d . . . . .
C15 C -0.17647(16) 0.09886(11) 0.43603(18) 0.0303(5) Uani 1 1 d . . . . .
C16 C -0.14954(16) 0.17906(11) 0.47312(19) 0.0373(5) Uani 1 1 d . . . . .
H16A H -0.1637 0.1916 0.5281 0.045 Uiso 1 1 calc R U . . .
H16B H -0.1879 0.2119 0.4060 0.045 Uiso 1 1 calc R U . . .
C17 C -0.04625(16) 0.19408(11) 0.52810(19) 0.0359(5) Uani 1 1 d . . . . .
H17A H -0.0350 0.1940 0.4687 0.043 Uiso 1 1 calc R U . . .
H17B H -0.0295 0.2439 0.5642 0.043 Uiso 1 1 calc R U . . .
C18 C -0.13660(15) -0.03320(11) 0.47189(17) 0.0292(5) Uani 1 1 d . . . . .
H18 H -0.0926 -0.0716 0.5158 0.035 Uiso 1 1 calc R U . . .
C19 C -0.22630(15) -0.05074(12) 0.37949(18) 0.0324(5) Uani 1 1 d . . . . .
H19 H -0.2438 -0.1014 0.3592 0.039 Uiso 1 1 calc R U . . .
C20 C -0.29094(16) 0.00530(12) 0.31613(18) 0.0351(5) Uani 1 1 d . . . . .
H20 H -0.3525 -0.0072 0.2527 0.042 Uiso 1 1 calc R U . . .
C21 C -0.26624(16) 0.07919(12) 0.34475(18) 0.0353(5) Uani 1 1 d . . . . .
H21 H -0.3114 0.1170 0.3013 0.042 Uiso 1 1 calc R U . . .
F1 F -0.03739(16) -0.17612(12) 0.6545(2) 0.1137(9) Uani 1 1 d . U . . .
F2 F -0.06897(11) -0.26224(9) 0.73807(15) 0.0706(5) Uani 1 1 d . . . . .
B1 B 0.0000 -0.2184(2) 0.7500 0.0395(9) Uani 1 2 d S T P . .
F3 F 0.42064(11) 0.19782(8) 0.19085(16) 0.0721(5) Uani 1 1 d . . . . .
F4 F 0.50369(12) 0.11052(12) 0.17629(16) 0.0945(7) Uani 1 1 d . U . . .
B2 B 0.5000 0.15417(19) 0.2500 0.0359(8) Uani 1 2 d S T 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 C13 1.355(2) . ?
O1 C9 1.369(2) . ?
N1 C5 1.343(3) . ?
N1 C3 1.469(3) . ?
N1 C2 1.470(3) . ?
C1 C2 1.489(4) . ?
C1 H1A 0.9800 . ?
C1 H1B 0.9800 . ?
C1 H1C 0.9800 . ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
C3 C4 1.522(3) . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C4 H4A 0.9800 . ?
C4 H4B 0.9800 . ?
C4 H4C 0.9800 . ?
C5 C10 1.414(3) . ?
C5 C6 1.448(3) . ?
C6 C7 1.351(3) . ?
C6 H6 0.9500 . ?
C7 C8 1.421(3) . ?
C7 H7 0.9500 . ?
C8 C11 1.384(3) . ?
C8 C9 1.429(3) . ?
C9 C10 1.361(3) . ?
C10 H10 0.9500 . ?
C11 C12 1.394(3) . ?
C11 H11 0.9500 . ?
C12 C13 1.380(3) . ?
C12 C17 1.508(3) . ?
C13 C14 1.447(3) . ?
C14 C18 1.406(3) . ?
C14 C15 1.410(3) . ?
C15 C21 1.386(3) . ?
C15 C16 1.512(3) . ?
C16 C17 1.522(3) . ?
C16 H16A 0.9900 . ?
C16 H16B 0.9900 . ?
C17 H17A 0.9900 . ?
C17 H17B 0.9900 . ?
C18 C19 1.381(3) . ?
C18 H18 0.9500 . ?
C19 C20 1.387(3) . ?
C19 H19 0.9500 . ?
C20 C21 1.382(3) . ?
C20 H20 0.9500 . ?
C21 H21 0.9500 . ?
F1 B1 1.361(3) . ?
F2 B1 1.370(3) . ?
B1 F1 1.361(3) 2_556 ?
B1 F2 1.370(3) 2_556 ?
F3 B2 1.377(2) . ?
F4 B2 1.356(2) . ?
B2 F4 1.356(2) 2_655 ?
B2 F3 1.377(2) 2_655 ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C13 O1 C9 121.43(15) . . ?
C5 N1 C3 121.31(17) . . ?
C5 N1 C2 123.31(17) . . ?
C3 N1 C2 115.36(16) . . ?
C2 C1 H1A 109.5 . . ?
C2 C1 H1B 109.5 . . ?
H1A C1 H1B 109.5 . . ?
C2 C1 H1C 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
N1 C2 C1 113.0(2) . . ?
N1 C2 H2A 109.0 . . ?
C1 C2 H2A 109.0 . . ?
N1 C2 H2B 109.0 . . ?
C1 C2 H2B 109.0 . . ?
H2A C2 H2B 107.8 . . ?
N1 C3 C4 113.45(18) . . ?
N1 C3 H3A 108.9 . . ?
C4 C3 H3A 108.9 . . ?
N1 C3 H3B 108.9 . . ?
C4 C3 H3B 108.9 . . ?
H3A C3 H3B 107.7 . . ?
C3 C4 H4A 109.5 . . ?
C3 C4 H4B 109.5 . . ?
H4A C4 H4B 109.5 . . ?
C3 C4 H4C 109.5 . . ?
H4A C4 H4C 109.5 . . ?
H4B C4 H4C 109.5 . . ?
N1 C5 C10 121.55(18) . . ?
N1 C5 C6 120.68(19) . . ?
C10 C5 C6 117.76(18) . . ?
C7 C6 C5 121.1(2) . . ?
C7 C6 H6 119.5 . . ?
C5 C6 H6 119.5 . . ?
C6 C7 C8 122.18(19) . . ?
C6 C7 H7 118.9 . . ?
C8 C7 H7 118.9 . . ?
C11 C8 C7 125.90(19) . . ?
C11 C8 C9 118.53(19) . . ?
C7 C8 C9 115.52(18) . . ?
C10 C9 O1 117.27(17) . . ?
C10 C9 C8 123.98(19) . . ?
O1 C9 C8 118.74(17) . . ?
C9 C10 C5 119.46(18) . . ?
C9 C10 H10 120.3 . . ?
C5 C10 H10 120.3 . . ?
C8 C11 C12 121.37(18) . . ?
C8 C11 H11 119.3 . . ?
C12 C11 H11 119.3 . . ?
C13 C12 C11 118.11(18) . . ?
C13 C12 C17 117.78(19) . . ?
C11 C12 C17 124.03(18) . . ?
O1 C13 C12 121.62(19) . . ?
O1 C13 C14 114.50(17) . . ?
C12 C13 C14 123.88(18) . . ?
C18 C14 C15 120.2(2) . . ?
C18 C14 C13 122.18(18) . . ?
C15 C14 C13 117.64(18) . . ?
C21 C15 C14 118.75(19) . . ?
C21 C15 C16 121.74(19) . . ?
C14 C15 C16 119.4(2) . . ?
C15 C16 C17 112.59(18) . . ?
C15 C16 H16A 109.1 . . ?
C17 C16 H16A 109.1 . . ?
C15 C16 H16B 109.1 . . ?
C17 C16 H16B 109.1 . . ?
H16A C16 H16B 107.8 . . ?
C12 C17 C16 111.24(17) . . ?
C12 C17 H17A 109.4 . . ?
C16 C17 H17A 109.4 . . ?
C12 C17 H17B 109.4 . . ?
C16 C17 H17B 109.4 . . ?
H17A C17 H17B 108.0 . . ?
C19 C18 C14 119.52(19) . . ?
C19 C18 H18 120.2 . . ?
C14 C18 H18 120.2 . . ?
C18 C19 C20 120.3(2) . . ?
C18 C19 H19 119.9 . . ?
C20 C19 H19 119.9 . . ?
C21 C20 C19 120.4(2) . . ?
C21 C20 H20 119.8 . . ?
C19 C20 H20 119.8 . . ?
C20 C21 C15 120.9(2) . . ?
C20 C21 H21 119.6 . . ?
C15 C21 H21 119.6 . . ?
F1 B1 F1 112.2(3) 2_556 . ?
F1 B1 F2 108.27(11) 2_556 . ?
F1 B1 F2 109.08(13) . . ?
F1 B1 F2 109.08(13) 2_556 2_556 ?
F1 B1 F2 108.26(11) . 2_556 ?
F2 B1 F2 109.9(3) . 2_556 ?
F4 B2 F4 109.4(3) 2_655 . ?
F4 B2 F3 109.79(11) 2_655 2_655 ?
F4 B2 F3 108.60(11) . 2_655 ?
F4 B2 F3 108.60(11) 2_655 . ?
F4 B2 F3 109.79(11) . . ?
F3 B2 F3 110.7(3) 2_655 . ?

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
C5 N1 C2 C1 -94.7(3) . . . . ?
C3 N1 C2 C1 83.9(3) . . . . ?
C5 N1 C3 C4 81.6(2) . . . . ?
C2 N1 C3 C4 -97.0(2) . . . . ?
C3 N1 C5 C10 -1.0(3) . . . . ?
C2 N1 C5 C10 177.52(18) . . . . ?
C3 N1 C5 C6 177.84(18) . . . . ?
C2 N1 C5 C6 -3.6(3) . . . . ?
N1 C5 C6 C7 -178.41(19) . . . . ?
C10 C5 C6 C7 0.5(3) . . . . ?
C5 C6 C7 C8 -1.1(3) . . . . ?
C6 C7 C8 C11 -176.9(2) . . . . ?
C6 C7 C8 C9 0.6(3) . . . . ?
C13 O1 C9 C10 -176.06(16) . . . . ?
C13 O1 C9 C8 4.7(3) . . . . ?
C11 C8 C9 C10 178.15(19) . . . . ?
C7 C8 C9 C10 0.4(3) . . . . ?
C11 C8 C9 O1 -2.7(3) . . . . ?
C7 C8 C9 O1 179.59(17) . . . . ?
O1 C9 C10 C5 179.84(16) . . . . ?
C8 C9 C10 C5 -1.0(3) . . . . ?
N1 C5 C10 C9 179.38(18) . . . . ?
C6 C5 C10 C9 0.5(3) . . . . ?
C7 C8 C11 C12 176.2(2) . . . . ?
C9 C8 C11 C12 -1.3(3) . . . . ?
C8 C11 C12 C13 3.3(3) . . . . ?
C8 C11 C12 C17 -173.41(19) . . . . ?
C9 O1 C13 C12 -2.7(3) . . . . ?
C9 O1 C13 C14 177.60(16) . . . . ?
C11 C12 C13 O1 -1.3(3) . . . . ?
C17 C12 C13 O1 175.59(17) . . . . ?
C11 C12 C13 C14 178.31(18) . . . . ?
C17 C12 C13 C14 -4.8(3) . . . . ?
O1 C13 C14 C18 -11.7(3) . . . . ?
C12 C13 C14 C18 168.66(19) . . . . ?
O1 C13 C14 C15 167.12(16) . . . . ?
C12 C13 C14 C15 -12.6(3) . . . . ?
C18 C14 C15 C21 0.1(3) . . . . ?
C13 C14 C15 C21 -178.68(18) . . . . ?
C18 C14 C15 C16 175.71(18) . . . . ?
C13 C14 C15 C16 -3.1(3) . . . . ?
C21 C15 C16 C17 -151.03(19) . . . . ?
C14 C15 C16 C17 33.5(3) . . . . ?
C13 C12 C17 C16 35.1(3) . . . . ?
C11 C12 C17 C16 -148.2(2) . . . . ?
C15 C16 C17 C12 -48.0(2) . . . . ?
C15 C14 C18 C19 0.7(3) . . . . ?
C13 C14 C18 C19 179.45(18) . . . . ?
C14 C18 C19 C20 -0.8(3) . . . . ?
C18 C19 C20 C21 0.0(3) . . . . ?
C19 C20 C21 C15 0.8(3) . . . . ?
C14 C15 C21 C20 -0.9(3) . . . . ?
C16 C15 C21 C20 -176.35(19) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
C2 H2A F2 0.99 2.51 3.459(3) 159.9 8_546
C3 H3A F1 0.99 2.60 3.576(3) 169.0 2_556
C3 H3B F2 0.99 2.55 3.506(3) 163.4 8_546
C6 H6 F4 0.95 2.41 3.315(3) 158.4 1_556

_refine_diff_density_max         0.351
_refine_diff_density_min         -0.389
_refine_diff_density_rms         0.045

####################################################################### 
# 
# 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_comp2M
_database_code_depnum_ccdc_archive 'CCDC 1543228'
_audit_update_record             
;
2017-04-10 deposited with the CCDC.
2017-05-29 downloaded from the CCDC.
;


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

_audit_creation_method           'SHELXL-2014/7 and enCIFer'
_shelx_SHELXL_version_number     2014/7
_audit_creation_date             '10 February 2017'

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

_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C21 H22 N O2, H O4 S'
_chemical_formula_sum            'C21 H23 N O6 S'
_chemical_formula_weight         417.46

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      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                   11.3956(7)
_cell_length_b                   14.0481(9)
_cell_length_c                   13.0280(8)
_cell_angle_alpha                90
_cell_angle_beta                 114.240(3)
_cell_angle_gamma                90
_cell_volume                     1901.7(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    9991
_cell_measurement_theta_min      2.47
_cell_measurement_theta_max      29.01

_exptl_crystal_description       block
_exptl_crystal_colour            brown
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.458
_exptl_crystal_F_000             880
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.350
_exptl_crystal_size_mid          0.170
_exptl_crystal_size_min          0.070
_exptl_absorpt_coefficient_mu    0.211
_shelx_estimated_absorpt_T_min   0.930
_shelx_estimated_absorpt_T_max   0.985
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.929
_exptl_absorpt_correction_T_max  0.981
_exptl_absorpt_process_details   
; 
'SADABS V2012/1 (Bruker AXS Inc.)' 
;


_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_measurement_device_type  'Bruker X8 Kappa CCD APEX II'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            50030
_diffrn_reflns_av_unetI/netI     0.0170
_diffrn_reflns_av_R_equivalents  0.0348
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         3.724
_diffrn_reflns_theta_max         25.678
_diffrn_reflns_theta_full        25.242
_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             3570
_reflns_number_gt                3021
_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       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_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)+(0.0438P)²+1.0668P] 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         3570
_refine_ls_number_parameters     270
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.0422
_refine_ls_R_factor_gt           0.0334
_refine_ls_wR_factor_ref         0.0931
_refine_ls_wR_factor_gt          0.0870
_refine_ls_goodness_of_fit_ref   1.066
_refine_ls_restrained_S_all      1.067
_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 -0.03658(11) 0.63098(10) -0.08469(10) 0.0316(3) Uani 1 1 d D . . . .
H1 H -0.010(2) 0.6263(16) -0.1428(14) 0.047 Uiso 1 1 d D U . . .
O2 O 0.36732(10) 0.63292(8) 0.42163(9) 0.0179(2) Uani 1 1 d . . . . .
N1 N 0.50908(12) 0.66561(10) 0.81795(11) 0.0202(3) Uani 1 1 d . . . . .
C1 C 0.06826(15) 0.62853(12) 0.01498(14) 0.0222(4) Uani 1 1 d . . . . .
C2 C 0.04832(15) 0.61552(12) 0.11302(14) 0.0231(4) Uani 1 1 d . . . . .
H2 H -0.0365 0.6081 0.1086 0.028 Uiso 1 1 calc R U . . .
C3 C 0.15213(15) 0.61345(11) 0.21604(14) 0.0204(3) Uani 1 1 d . . . . .
H3 H 0.1387 0.6048 0.2827 0.024 Uiso 1 1 calc R U . . .
C4 C 0.27792(15) 0.62407(11) 0.22310(13) 0.0175(3) Uani 1 1 d . . . . .
C5 C 0.29774(15) 0.63758(11) 0.12375(13) 0.0186(3) Uani 1 1 d . . . . .
C6 C 0.19239(16) 0.63939(11) 0.02101(14) 0.0216(3) Uani 1 1 d . . . . .
H6 H 0.2049 0.6481 -0.0461 0.026 Uiso 1 1 calc R U . . .
C7 C 0.43274(15) 0.65262(12) 0.13340(13) 0.0221(4) Uani 1 1 d . . . . .
H7A H 0.4564 0.7205 0.1494 0.026 Uiso 1 1 calc R U . . .
H7B H 0.4367 0.6362 0.0610 0.026 Uiso 1 1 calc R U . . .
C8 C 0.52832(15) 0.59135(12) 0.22692(13) 0.0204(3) Uani 1 1 d . . . . .
H8A H 0.5131 0.5234 0.2056 0.024 Uiso 1 1 calc R U . . .
H8B H 0.6171 0.6075 0.2374 0.024 Uiso 1 1 calc R U . . .
C9 C 0.51390(15) 0.60748(11) 0.33546(13) 0.0179(3) Uani 1 1 d . . . . .
C10 C 0.39028(15) 0.62163(11) 0.32823(13) 0.0172(3) Uani 1 1 d . . . . .
C11 C 0.61516(15) 0.60572(11) 0.44100(14) 0.0199(3) Uani 1 1 d . . . . .
H11 H 0.7001 0.5947 0.4474 0.024 Uiso 1 1 calc R U . . .
C12 C 0.59407(15) 0.61992(11) 0.53792(13) 0.0183(3) Uani 1 1 d . . . . .
C13 C 0.46639(14) 0.63294(10) 0.52700(13) 0.0173(3) Uani 1 1 d . . . . .
C14 C 0.43432(14) 0.64719(11) 0.61653(13) 0.0183(3) Uani 1 1 d . . . . .
H14 H 0.3469 0.6538 0.6051 0.022 Uiso 1 1 calc R U . . .
C15 C 0.53396(15) 0.65188(11) 0.72604(13) 0.0183(3) Uani 1 1 d . . . . .
C16 C 0.66452(15) 0.64007(12) 0.73876(14) 0.0213(3) Uani 1 1 d . . . . .
H16 H 0.7326 0.6438 0.8117 0.026 Uiso 1 1 calc R U . . .
C17 C 0.69239(15) 0.62371(12) 0.64882(14) 0.0212(3) Uani 1 1 d . . . . .
H17 H 0.7795 0.6146 0.6601 0.025 Uiso 1 1 calc R U . . .
C18 C 0.37791(15) 0.65839(12) 0.81161(14) 0.0211(3) Uani 1 1 d . . . . .
H18A H 0.3808 0.6253 0.8797 0.025 Uiso 1 1 calc R U . . .
H18B H 0.3255 0.6192 0.7454 0.025 Uiso 1 1 calc R U . . .
C19 C 0.31326(19) 0.75380(14) 0.80236(18) 0.0382(5) Uani 1 1 d . . . . .
H19A H 0.3628 0.7922 0.8689 0.057 Uiso 1 1 calc R U . . .
H19B H 0.2259 0.7443 0.7975 0.057 Uiso 1 1 calc R U . . .
H19C H 0.3090 0.7868 0.7347 0.057 Uiso 1 1 calc R U . . .
C20 C 0.61073(16) 0.68423(12) 0.93067(13) 0.0232(4) Uani 1 1 d . . . . .
H20A H 0.5752 0.7248 0.9732 0.028 Uiso 1 1 calc R U . . .
H20B H 0.6814 0.7199 0.9226 0.028 Uiso 1 1 calc R U . . .
C21 C 0.66496(17) 0.59394(13) 0.99725(14) 0.0276(4) Uani 1 1 d . . . . .
H21A H 0.5946 0.5560 1.0009 0.041 Uiso 1 1 calc R U . . .
H21B H 0.7259 0.6106 1.0737 0.041 Uiso 1 1 calc R U . . .
H21C H 0.7094 0.5569 0.9602 0.041 Uiso 1 1 calc R U . . .
S1 S 0.04324(4) 0.54833(3) -0.33870(3) 0.02176(13) Uani 1 1 d . . . . .
O3 O 0.01939(12) 0.61950(9) -0.26901(10) 0.0307(3) Uani 1 1 d . . . . .
O4 O 0.08806(13) 0.60860(9) -0.41765(11) 0.0314(3) Uani 1 1 d D . . . .
H4 H 0.079(2) 0.5707(14) -0.4795(13) 0.047 Uiso 1 1 d D U . . .
O5 O -0.07636(12) 0.50114(10) -0.41375(10) 0.0324(3) Uani 1 1 d . . . . .
O6 O 0.14339(14) 0.48314(10) -0.27745(13) 0.0457(4) 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 C1 1.357(2) . ?
O1 H1 0.928(10) . ?
O2 C10 1.3548(18) . ?
O2 C13 1.3734(19) . ?
N1 C15 1.353(2) . ?
N1 C18 1.466(2) . ?
N1 C20 1.473(2) . ?
C1 C6 1.393(2) . ?
C1 C2 1.398(2) . ?
C2 C3 1.378(2) . ?
C2 H2 0.9500 . ?
C3 C4 1.406(2) . ?
C3 H3 0.9500 . ?
C4 C5 1.415(2) . ?
C4 C10 1.441(2) . ?
C5 C6 1.383(2) . ?
C5 C7 1.506(2) . ?
C6 H6 0.9500 . ?
C7 C8 1.524(2) . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C8 C9 1.506(2) . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C9 C11 1.386(2) . ?
C9 C10 1.387(2) . ?
C11 C12 1.393(2) . ?
C11 H11 0.9500 . ?
C12 C13 1.415(2) . ?
C12 C17 1.420(2) . ?
C13 C14 1.373(2) . ?
C14 C15 1.414(2) . ?
C14 H14 0.9500 . ?
C15 C16 1.437(2) . ?
C16 C17 1.354(2) . ?
C16 H16 0.9500 . ?
C17 H17 0.9500 . ?
C18 C19 1.510(2) . ?
C18 H18A 0.9900 . ?
C18 H18B 0.9900 . ?
C19 H19A 0.9800 . ?
C19 H19B 0.9800 . ?
C19 H19C 0.9800 . ?
C20 C21 1.518(2) . ?
C20 H20A 0.9900 . ?
C20 H20B 0.9900 . ?
C21 H21A 0.9800 . ?
C21 H21B 0.9800 . ?
C21 H21C 0.9800 . ?
S1 O6 1.4249(14) . ?
S1 O3 1.4493(13) . ?
S1 O5 1.4692(13) . ?
S1 O4 1.5706(12) . ?
O4 H4 0.936(10) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1 O1 H1 108.9(14) . . ?
C10 O2 C13 121.01(12) . . ?
C15 N1 C18 121.30(13) . . ?
C15 N1 C20 122.88(13) . . ?
C18 N1 C20 115.76(12) . . ?
O1 C1 C6 121.75(15) . . ?
O1 C1 C2 117.91(14) . . ?
C6 C1 C2 120.34(15) . . ?
C3 C2 C1 119.75(15) . . ?
C3 C2 H2 120.1 . . ?
C1 C2 H2 120.1 . . ?
C2 C3 C4 120.40(15) . . ?
C2 C3 H3 119.8 . . ?
C4 C3 H3 119.8 . . ?
C3 C4 C5 119.71(14) . . ?
C3 C4 C10 122.94(14) . . ?
C5 C4 C10 117.35(14) . . ?
C6 C5 C4 119.11(14) . . ?
C6 C5 C7 121.94(14) . . ?
C4 C5 C7 118.92(14) . . ?
C5 C6 C1 120.69(15) . . ?
C5 C6 H6 119.7 . . ?
C1 C6 H6 119.7 . . ?
C5 C7 C8 110.97(13) . . ?
C5 C7 H7A 109.4 . . ?
C8 C7 H7A 109.4 . . ?
C5 C7 H7B 109.4 . . ?
C8 C7 H7B 109.4 . . ?
H7A C7 H7B 108.0 . . ?
C9 C8 C7 110.36(13) . . ?
C9 C8 H8A 109.6 . . ?
C7 C8 H8A 109.6 . . ?
C9 C8 H8B 109.6 . . ?
C7 C8 H8B 109.6 . . ?
H8A C8 H8B 108.1 . . ?
C11 C9 C10 118.60(14) . . ?
C11 C9 C8 124.16(14) . . ?
C10 C9 C8 117.20(14) . . ?
O2 C10 C9 121.40(14) . . ?
O2 C10 C4 115.28(13) . . ?
C9 C10 C4 123.32(14) . . ?
C9 C11 C12 120.90(14) . . ?
C9 C11 H11 119.5 . . ?
C12 C11 H11 119.5 . . ?
C11 C12 C13 118.71(14) . . ?
C11 C12 C17 124.74(14) . . ?
C13 C12 C17 116.54(14) . . ?
C14 C13 O2 116.94(13) . . ?
C14 C13 C12 123.72(15) . . ?
O2 C13 C12 119.33(14) . . ?
C13 C14 C15 118.73(14) . . ?
C13 C14 H14 120.6 . . ?
C15 C14 H14 120.6 . . ?
N1 C15 C14 121.77(14) . . ?
N1 C15 C16 119.84(14) . . ?
C14 C15 C16 118.38(14) . . ?
C17 C16 C15 121.30(15) . . ?
C17 C16 H16 119.4 . . ?
C15 C16 H16 119.4 . . ?
C16 C17 C12 121.30(15) . . ?
C16 C17 H17 119.3 . . ?
C12 C17 H17 119.3 . . ?
N1 C18 C19 113.31(14) . . ?
N1 C18 H18A 108.9 . . ?
C19 C18 H18A 108.9 . . ?
N1 C18 H18B 108.9 . . ?
C19 C18 H18B 108.9 . . ?
H18A C18 H18B 107.7 . . ?
C18 C19 H19A 109.5 . . ?
C18 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
C18 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
N1 C20 C21 112.99(14) . . ?
N1 C20 H20A 109.0 . . ?
C21 C20 H20A 109.0 . . ?
N1 C20 H20B 109.0 . . ?
C21 C20 H20B 109.0 . . ?
H20A C20 H20B 107.8 . . ?
C20 C21 H21A 109.5 . . ?
C20 C21 H21B 109.5 . . ?
H21A C21 H21B 109.5 . . ?
C20 C21 H21C 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
O6 S1 O3 113.93(8) . . ?
O6 S1 O5 113.17(9) . . ?
O3 S1 O5 111.53(7) . . ?
O6 S1 O4 108.19(8) . . ?
O3 S1 O4 103.50(7) . . ?
O5 S1 O4 105.64(7) . . ?
S1 O4 H4 108.0(14) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O1 C1 C2 C3 -179.43(15) . . . . ?
C6 C1 C2 C3 0.0(2) . . . . ?
C1 C2 C3 C4 -0.2(2) . . . . ?
C2 C3 C4 C5 0.4(2) . . . . ?
C2 C3 C4 C10 -179.39(15) . . . . ?
C3 C4 C5 C6 -0.5(2) . . . . ?
C10 C4 C5 C6 179.35(14) . . . . ?
C3 C4 C5 C7 177.65(14) . . . . ?
C10 C4 C5 C7 -2.5(2) . . . . ?
C4 C5 C6 C1 0.3(2) . . . . ?
C7 C5 C6 C1 -177.77(15) . . . . ?
O1 C1 C6 C5 179.35(15) . . . . ?
C2 C1 C6 C5 -0.1(2) . . . . ?
C6 C5 C7 C8 -144.62(15) . . . . ?
C4 C5 C7 C8 37.31(19) . . . . ?
C5 C7 C8 C9 -53.03(17) . . . . ?
C7 C8 C9 C11 -145.43(15) . . . . ?
C7 C8 C9 C10 36.89(19) . . . . ?
C13 O2 C10 C9 1.5(2) . . . . ?
C13 O2 C10 C4 -179.33(13) . . . . ?
C11 C9 C10 O2 -0.5(2) . . . . ?
C8 C9 C10 O2 177.34(13) . . . . ?
C11 C9 C10 C4 -179.55(14) . . . . ?
C8 C9 C10 C4 -1.7(2) . . . . ?
C3 C4 C10 O2 -16.3(2) . . . . ?
C5 C4 C10 O2 163.93(13) . . . . ?
C3 C4 C10 C9 162.88(15) . . . . ?
C5 C4 C10 C9 -16.9(2) . . . . ?
C10 C9 C11 C12 -1.4(2) . . . . ?
C8 C9 C11 C12 -179.05(14) . . . . ?
C9 C11 C12 C13 2.2(2) . . . . ?
C9 C11 C12 C17 -176.93(15) . . . . ?
C10 O2 C13 C14 178.44(13) . . . . ?
C10 O2 C13 C12 -0.7(2) . . . . ?
C11 C12 C13 C14 179.80(15) . . . . ?
C17 C12 C13 C14 -1.0(2) . . . . ?
C11 C12 C13 O2 -1.1(2) . . . . ?
C17 C12 C13 O2 178.05(13) . . . . ?
O2 C13 C14 C15 -177.27(13) . . . . ?
C12 C13 C14 C15 1.8(2) . . . . ?
C18 N1 C15 C14 11.7(2) . . . . ?
C20 N1 C15 C14 -171.15(14) . . . . ?
C18 N1 C15 C16 -167.28(14) . . . . ?
C20 N1 C15 C16 9.9(2) . . . . ?
C13 C14 C15 N1 -179.89(14) . . . . ?
C13 C14 C15 C16 -0.9(2) . . . . ?
N1 C15 C16 C17 178.24(15) . . . . ?
C14 C15 C16 C17 -0.8(2) . . . . ?
C15 C16 C17 C12 1.6(2) . . . . ?
C11 C12 C17 C16 178.39(16) . . . . ?
C13 C12 C17 C16 -0.7(2) . . . . ?
C15 N1 C18 C19 -99.02(18) . . . . ?
C20 N1 C18 C19 83.62(18) . . . . ?
C15 N1 C20 C21 -89.30(18) . . . . ?
C18 N1 C20 C21 88.01(17) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
O1 H1 O3 0.928(10) 1.809(10) 2.7308(17) 172(2) .
O4 H4 O5 0.936(10) 1.708(10) 2.6417(17) 175(2) 3_564

_refine_diff_density_max         0.243
_refine_diff_density_min         -0.436
_refine_diff_density_rms         0.048

