# Electronic Supplementary Material (ESI) for RSC Advances.
# This journal is © The Royal Society of Chemistry 2016

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

data_sme
_database_code_depnum_ccdc_archive 'CCDC 1456040'
_audit_update_record             
;
2016-02-26 deposited with the CCDC.
2016-09-05 downloaded from the CCDC.
;
#==================================================================
_audit_creation_date             2016-02-04
_audit_creation_method           

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

# SUBMISSION DETAILS
;
Olex2 1.2-beta
(compiled 2015.11.10 svn.r3248 for OlexSys, GUI svn.r5133)
;
_shelxl_version_number           2014/6

#==========================================================================
# CHEMICAL DATA
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C18 H14 B F2 N O S'
_chemical_formula_sum            'C18 H14 B F2 N O S'
_chemical_formula_weight         341.17
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
B B 0.0013 0.0007 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
#==========================================================================

# CRYSTAL DATA 
_space_group_crystal_system      orthorhombic
_space_group_IT_number           61
_space_group_name_H-M_alt        'P b c a'
_space_group_name_Hall           '-P 2ac 2ab'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'x, -y-1/2, z-1/2'
'-x-1/2, y-1/2, z'

_cell_length_a                   10.661(2)
_cell_length_b                   11.234(2)
_cell_length_c                   25.712(5)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     3079.5(11)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    5933
_cell_measurement_temperature    110.15
_cell_measurement_theta_max      27.129
_cell_measurement_theta_min      2.483
_shelx_estimated_absorpt_T_max   0.976
_shelx_estimated_absorpt_T_min   0.916
_exptl_absorpt_coefficient_mu    0.236
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6639
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
#==========================================================================

# Experimental data 
;
SADABS-2014/3 (Bruker,2014/3) was used for absorption correction.
wR2(int) was 0.1455 before and 0.0572 after correction.
The Ratio of minimum to maximum transmission is 0.8904.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.472
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1408
_exptl_crystal_size_max          0.38
_exptl_crystal_size_mid          0.127
_exptl_crystal_size_min          0.104
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0895
_diffrn_reflns_av_unetI/netI     0.0451
_diffrn_reflns_Laue_measured_fraction_full 0.978
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       30
_diffrn_reflns_limit_l_min       -30
_diffrn_reflns_number            27275
_diffrn_reflns_point_group_measured_fraction_full 0.978
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         24.998
_diffrn_reflns_theta_min         2.482
_diffrn_ambient_temperature      110.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.978
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_special_details          ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2104
_reflns_number_total             2721
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT v8.34A (Bruker, 2013)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT v8.34A (Bruker, 2013)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.277
_refine_diff_density_min         -0.304
_refine_diff_density_rms         0.056
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.060
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     218
_refine_ls_number_reflns         2721
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0675
_refine_ls_R_factor_gt           0.0458
_refine_ls_restrained_S_all      1.060
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0248P)²+3.1531P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0822
_refine_ls_wR_factor_ref         0.0915
#==========================================================================

# Refinement data 
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C7(H7), C8(H8), C9(H9), C10(H10), C11(H11), C14(H14),
 C15(H15), C16(H16), C17(H17)
2.b Idealised Me refined as rotating group:
 C18(H18A,H18B,H18C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
#==========================================================================

# ATOMIC COORDINATES AND DISPLACEMENT PARAMETERS
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_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 0.26976(6) 0.41313(6) 0.73867(2) 0.02442(18) Uani 1 1 d . . . . .
F1 F 0.06983(13) 0.44458(14) 0.56621(6) 0.0340(4) Uani 1 1 d . . . . .
F2 F 0.09312(14) 0.32376(13) 0.63627(6) 0.0334(4) Uani 1 1 d . . . . .
O1 O 0.24976(15) 0.32961(14) 0.57410(6) 0.0184(4) Uani 1 1 d . . . . .
N1 N 0.21683(17) 0.50070(17) 0.63262(7) 0.0139(4) Uani 1 1 d . . . . .
C1 C 0.3655(2) 0.3694(2) 0.56531(9) 0.0151(5) Uani 1 1 d . . . . .
C2 C 0.4429(2) 0.3006(2) 0.53260(9) 0.0172(5) Uani 1 1 d . . . . .
H2 H 0.4108 0.2305 0.5168 0.021 Uiso 1 1 calc R . . . .
C3 C 0.5629(2) 0.3343(2) 0.52365(9) 0.0182(6) Uani 1 1 d . . . . .
H3 H 0.6136 0.2873 0.5013 0.022 Uiso 1 1 calc R . . . .
C4 C 0.6151(2) 0.4377(2) 0.54674(9) 0.0154(5) Uani 1 1 d . . . . .
C5 C 0.5390(2) 0.5100(2) 0.57895(8) 0.0135(5) Uani 1 1 d . . . . .
C6 C 0.4114(2) 0.4728(2) 0.58866(8) 0.0126(5) Uani 1 1 d . . . . .
C7 C 0.7410(2) 0.4709(2) 0.53780(9) 0.0203(6) Uani 1 1 d . . . . .
H7 H 0.7923 0.4222 0.5164 0.024 Uiso 1 1 calc R . . . .
C8 C 0.7903(2) 0.5710(2) 0.55921(9) 0.0216(6) Uani 1 1 d . . . . .
H8 H 0.8758 0.5908 0.5535 0.026 Uiso 1 1 calc R . . . .
C9 C 0.7143(2) 0.6447(2) 0.58972(9) 0.0176(6) Uani 1 1 d . . . . .
H9 H 0.7481 0.7157 0.6040 0.021 Uiso 1 1 calc R . . . .
C10 C 0.5914(2) 0.6154(2) 0.59926(9) 0.0157(5) Uani 1 1 d . . . . .
H10 H 0.5410 0.6669 0.6198 0.019 Uiso 1 1 calc R . . . .
C11 C 0.3324(2) 0.5329(2) 0.62434(9) 0.0137(5) Uani 1 1 d . . . . .
H11 H 0.3649 0.5992 0.6429 0.016 Uiso 1 1 calc R . . . .
C12 C 0.1456(2) 0.5616(2) 0.67271(9) 0.0151(5) Uani 1 1 d . . . . .
C13 C 0.1634(2) 0.5289(2) 0.72474(9) 0.0171(6) Uani 1 1 d . . . . .
C14 C 0.0936(2) 0.5894(2) 0.76210(10) 0.0225(6) Uani 1 1 d . . . . .
H14 H 0.1038 0.5698 0.7978 0.027 Uiso 1 1 calc R . . . .
C15 C 0.0100(2) 0.6776(2) 0.74811(10) 0.0236(6) Uani 1 1 d . . . . .
H15 H -0.0368 0.7178 0.7742 0.028 Uiso 1 1 calc R . . . .
C16 C -0.0063(2) 0.7076(2) 0.69661(10) 0.0232(6) Uani 1 1 d . . . . .
H16 H -0.0639 0.7684 0.6872 0.028 Uiso 1 1 calc R . . . .
C17 C 0.0618(2) 0.6488(2) 0.65874(10) 0.0197(6) Uani 1 1 d . . . . .
H17 H 0.0506 0.6686 0.6231 0.024 Uiso 1 1 calc R . . . .
C18 C 0.3013(2) 0.4335(2) 0.80672(9) 0.0266(6) Uani 1 1 d . . . . .
H18A H 0.3275 0.5159 0.8130 0.040 Uiso 1 1 calc GR . . . .
H18B H 0.3683 0.3792 0.8175 0.040 Uiso 1 1 calc GR . . . .
H18C H 0.2252 0.4166 0.8268 0.040 Uiso 1 1 calc GR . . . .
B1 B 0.1531(3) 0.3974(3) 0.60136(11) 0.0200(7) Uani 1 1 d . . . . .

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

# MOLECULAR GEOMETRY 
_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 C13 1.762(2) . ?
S1 C18 1.796(3) . ?
F1 B1 1.373(3) . ?
F2 B1 1.378(3) . ?
O1 C1 1.332(3) . ?
O1 B1 1.460(3) . ?
N1 C11 1.301(3) . ?
N1 C12 1.452(3) . ?
N1 B1 1.566(3) . ?
C1 C2 1.409(3) . ?
C1 C6 1.396(3) . ?
C2 H2 0.9500 . ?
C2 C3 1.353(3) . ?
C3 H3 0.9500 . ?
C3 C4 1.419(3) . ?
C4 C5 1.416(3) . ?
C4 C7 1.412(3) . ?
C5 C6 1.445(3) . ?
C5 C10 1.409(3) . ?
C6 C11 1.418(3) . ?
C7 H7 0.9500 . ?
C7 C8 1.357(3) . ?
C8 H8 0.9500 . ?
C8 C9 1.399(3) . ?
C9 H9 0.9500 . ?
C9 C10 1.373(3) . ?
C10 H10 0.9500 . ?
C11 H11 0.9500 . ?
C12 C13 1.400(3) . ?
C12 C17 1.374(3) . ?
C13 C14 1.392(3) . ?
C14 H14 0.9500 . ?
C14 C15 1.381(3) . ?
C15 H15 0.9500 . ?
C15 C16 1.377(4) . ?
C16 H16 0.9500 . ?
C16 C17 1.382(3) . ?
C17 H17 0.9500 . ?
C18 H18A 0.9800 . ?
C18 H18B 0.9800 . ?
C18 H18C 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
C13 S1 C18 102.95(12) . . ?
C1 O1 B1 124.05(19) . . ?
C11 N1 C12 118.70(19) . . ?
C11 N1 B1 122.2(2) . . ?
C12 N1 B1 119.11(18) . . ?
O1 C1 C2 117.4(2) . . ?
O1 C1 C6 122.1(2) . . ?
C6 C1 C2 120.5(2) . . ?
C1 C2 H2 119.9 . . ?
C3 C2 C1 120.1(2) . . ?
C3 C2 H2 119.9 . . ?
C2 C3 H3 119.0 . . ?
C2 C3 C4 121.9(2) . . ?
C4 C3 H3 119.0 . . ?
C5 C4 C3 119.3(2) . . ?
C7 C4 C3 121.4(2) . . ?
C7 C4 C5 119.3(2) . . ?
C4 C5 C6 118.3(2) . . ?
C10 C5 C4 118.1(2) . . ?
C10 C5 C6 123.5(2) . . ?
C1 C6 C5 119.8(2) . . ?
C1 C6 C11 117.8(2) . . ?
C11 C6 C5 122.2(2) . . ?
C4 C7 H7 119.3 . . ?
C8 C7 C4 121.3(2) . . ?
C8 C7 H7 119.3 . . ?
C7 C8 H8 120.2 . . ?
C7 C8 C9 119.6(2) . . ?
C9 C8 H8 120.2 . . ?
C8 C9 H9 119.6 . . ?
C10 C9 C8 120.7(2) . . ?
C10 C9 H9 119.6 . . ?
C5 C10 H10 119.6 . . ?
C9 C10 C5 120.9(2) . . ?
C9 C10 H10 119.6 . . ?
N1 C11 C6 122.4(2) . . ?
N1 C11 H11 118.8 . . ?
C6 C11 H11 118.8 . . ?
C13 C12 N1 118.9(2) . . ?
C17 C12 N1 119.4(2) . . ?
C17 C12 C13 121.7(2) . . ?
C12 C13 S1 118.38(18) . . ?
C14 C13 S1 124.34(19) . . ?
C14 C13 C12 117.3(2) . . ?
C13 C14 H14 119.5 . . ?
C15 C14 C13 121.1(2) . . ?
C15 C14 H14 119.5 . . ?
C14 C15 H15 119.8 . . ?
C16 C15 C14 120.5(2) . . ?
C16 C15 H15 119.8 . . ?
C15 C16 H16 120.2 . . ?
C15 C16 C17 119.6(2) . . ?
C17 C16 H16 120.2 . . ?
C12 C17 C16 119.9(2) . . ?
C12 C17 H17 120.1 . . ?
C16 C17 H17 120.1 . . ?
S1 C18 H18A 109.5 . . ?
S1 C18 H18B 109.5 . . ?
S1 C18 H18C 109.5 . . ?
H18A C18 H18B 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
F1 B1 F2 111.1(2) . . ?
F1 B1 O1 110.0(2) . . ?
F1 B1 N1 109.4(2) . . ?
F2 B1 O1 109.1(2) . . ?
F2 B1 N1 108.2(2) . . ?
O1 B1 N1 109.08(19) . . ?

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
S1 C13 C14 C15 -178.56(19) . . . . ?
O1 C1 C2 C3 -177.7(2) . . . . ?
O1 C1 C6 C5 178.2(2) . . . . ?
O1 C1 C6 C11 2.6(3) . . . . ?
N1 C12 C13 S1 -1.2(3) . . . . ?
N1 C12 C13 C14 179.9(2) . . . . ?
N1 C12 C17 C16 -179.8(2) . . . . ?
C1 O1 B1 F1 102.4(2) . . . . ?
C1 O1 B1 F2 -135.6(2) . . . . ?
C1 O1 B1 N1 -17.6(3) . . . . ?
C1 C2 C3 C4 0.5(4) . . . . ?
C1 C6 C11 N1 -5.6(3) . . . . ?
C2 C1 C6 C5 0.4(3) . . . . ?
C2 C1 C6 C11 -175.1(2) . . . . ?
C2 C3 C4 C5 -1.8(3) . . . . ?
C2 C3 C4 C7 178.9(2) . . . . ?
C3 C4 C5 C6 2.3(3) . . . . ?
C3 C4 C5 C10 -176.8(2) . . . . ?
C3 C4 C7 C8 178.9(2) . . . . ?
C4 C5 C6 C1 -1.6(3) . . . . ?
C4 C5 C6 C11 173.7(2) . . . . ?
C4 C5 C10 C9 -2.5(3) . . . . ?
C4 C7 C8 C9 -1.6(4) . . . . ?
C5 C4 C7 C8 -0.4(3) . . . . ?
C5 C6 C11 N1 179.0(2) . . . . ?
C6 C1 C2 C3 0.2(3) . . . . ?
C6 C5 C10 C9 178.4(2) . . . . ?
C7 C4 C5 C6 -178.4(2) . . . . ?
C7 C4 C5 C10 2.4(3) . . . . ?
C7 C8 C9 C10 1.6(4) . . . . ?
C8 C9 C10 C5 0.5(3) . . . . ?
C10 C5 C6 C1 177.4(2) . . . . ?
C10 C5 C6 C11 -7.2(3) . . . . ?
C11 N1 C12 C13 -80.1(3) . . . . ?
C11 N1 C12 C17 100.5(3) . . . . ?
C11 N1 B1 F1 -106.0(2) . . . . ?
C11 N1 B1 F2 132.9(2) . . . . ?
C11 N1 B1 O1 14.3(3) . . . . ?
C12 N1 C11 C6 175.3(2) . . . . ?
C12 N1 B1 F1 74.9(3) . . . . ?
C12 N1 B1 F2 -46.2(3) . . . . ?
C12 N1 B1 O1 -164.76(19) . . . . ?
C12 C13 C14 C15 0.3(3) . . . . ?
C13 C12 C17 C16 0.8(4) . . . . ?
C13 C14 C15 C16 0.0(4) . . . . ?
C14 C15 C16 C17 0.1(4) . . . . ?
C15 C16 C17 C12 -0.5(4) . . . . ?
C17 C12 C13 S1 178.22(18) . . . . ?
C17 C12 C13 C14 -0.7(3) . . . . ?
C18 S1 C13 C12 162.10(19) . . . . ?
C18 S1 C13 C14 -19.0(2) . . . . ?
B1 O1 C1 C2 -171.8(2) . . . . ?
B1 O1 C1 C6 10.4(3) . . . . ?
B1 N1 C11 C6 -3.8(3) . . . . ?
B1 N1 C12 C13 99.0(3) . . . . ?
B1 N1 C12 C17 -80.4(3) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
# End of CIF  ============================================================
####################################################################### 
# 
# 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_papaecu
_database_code_depnum_ccdc_archive 'CCDC 1456041'
_audit_update_record             
;
2016-02-26 deposited with the CCDC.
2016-09-05 downloaded from the CCDC.
;
#==================================================================




_audit_creation_date             2015-11-24
_audit_creation_method           

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

# SUBMISSION DETAILS
;
Olex2 1.2-beta
(compiled 2015.11.10 svn.r3248 for OlexSys, GUI svn.r5133)
;
_shelxl_version_number           2014-3

#==========================================================================
# CHEMICAL DATA
_chemical_name_common            ?
_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         'C23 H18 N4 O'
_chemical_formula_sum            'C23 H18 N4 O'
_chemical_formula_weight         366.41
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
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'

_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.
;
#==========================================================================

# CRYSTAL DATA 
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_H-M_alt        'C 1 2/c 1'
_space_group_name_Hall           '-C 2yc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z-1/2'

_cell_length_a                   21.2631(7)
_cell_length_b                   14.0448(4)
_cell_length_c                   16.2080(9)
_cell_angle_alpha                90
_cell_angle_beta                 129.2990(10)
_cell_angle_gamma                90
_cell_volume                     3745.7(3)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    9973
_cell_measurement_temperature    110.15
_cell_measurement_theta_max      62.344
_cell_measurement_theta_min      4.138
_shelx_estimated_absorpt_T_max   0.891
_shelx_estimated_absorpt_T_min   0.743
_exptl_absorpt_coefficient_mu    0.657
_exptl_absorpt_correction_T_max  0.7519
_exptl_absorpt_correction_T_min  0.5521
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
#==========================================================================

# Experimental data 
;
SADABS-2014/3 (Bruker,2014/3) was used for absorption correction.
wR2(int) was 0.1508 before and 0.0461 after correction.
The Ratio of minimum to maximum transmission is 0.7343.
The λ/2 correction factor is Not present.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.300
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1536
_exptl_crystal_size_max          0.48
_exptl_crystal_size_mid          0.35
_exptl_crystal_size_min          0.18
_exptl_special_details           
;
 ?
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0331
_diffrn_reflns_av_unetI/netI     0.0195
_diffrn_reflns_Laue_measured_fraction_full 0.801
_diffrn_reflns_Laue_measured_fraction_max 0.958
_diffrn_reflns_limit_h_max       23
_diffrn_reflns_limit_h_min       -24
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            26351
_diffrn_reflns_point_group_measured_fraction_full 0.801
_diffrn_reflns_point_group_measured_fraction_max 0.958
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         60.588
_diffrn_reflns_theta_min         4.138
_diffrn_ambient_temperature      110.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.801
_diffrn_measured_fraction_theta_max 0.958
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_source                   ?
_diffrn_special_details          ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2597
_reflns_number_total             2722
#==========================================================================

# Refinement data 
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT v8.34A (Bruker, 2013)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT v8.34A (Bruker, 2013)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    ?
_refine_diff_density_max         0.173
_refine_diff_density_min         -0.269
_refine_diff_density_rms         0.040
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.063
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     254
_refine_ls_number_reflns         2722
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0353
_refine_ls_R_factor_gt           0.0341
_refine_ls_restrained_S_all      1.063
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0503P)²+1.9442P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0878
_refine_ls_wR_factor_ref         0.0889
_refine_special_details          
;
 ?
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C22(H22A,H22B)
2.b Aromatic/amide H refined with riding coordinates:
 C7(H7), C8(H8), C9(H9), C10(H10), C11(H11), C12(H12), C13(H13), C14(H14),
 C16(H16), C17(H17), C18(H18), C19(H19), C20(H20)
2.c Idealised Me refined as rotating group:
 C23(H23A,H23B,H23C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
#==========================================================================

# ATOMIC COORDINATES AND DISPLACEMENT PARAMETERS 
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_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 0.60843(6) 0.51885(6) 0.49261(7) 0.0281(2) Uani 1 1 d . . . . .
N1 N 0.62022(6) 0.37871(7) 0.42939(8) 0.0231(2) Uani 1 1 d . . . . .
N2 N 0.64311(6) 0.13061(7) 0.52286(8) 0.0217(2) Uani 1 1 d . . . . .
N3 N 0.61283(7) -0.02262(7) 0.49246(9) 0.0289(3) Uani 1 1 d . . . . .
N4 N 0.60394(8) 0.47751(8) 0.69699(9) 0.0359(3) Uani 1 1 d . . . . .
C1 C 0.62845(7) 0.28290(8) 0.43542(9) 0.0213(3) Uani 1 1 d . . . . .
C2 C 0.63364(7) 0.23201(8) 0.51360(9) 0.0213(3) Uani 1 1 d . . . . .
C3 C 0.62936(7) 0.27919(9) 0.58609(9) 0.0219(3) Uani 1 1 d . . . . .
C4 C 0.62054(7) 0.37776(8) 0.57774(9) 0.0230(3) Uani 1 1 d . . . . .
C5 C 0.61664(7) 0.42393(8) 0.49744(9) 0.0228(3) Uani 1 1 d . . . . .
C6 C 0.62777(7) 0.24073(8) 0.35018(10) 0.0218(3) Uani 1 1 d . . . . .
C7 C 0.58889(7) 0.29240(8) 0.25568(9) 0.0240(3) Uani 1 1 d . . . . .
H7 H 0.5643 0.3518 0.2481 0.029 Uiso 1 1 calc R . . . .
C8 C 0.58564(8) 0.25846(9) 0.17277(10) 0.0271(3) Uani 1 1 d . . . . .
H8 H 0.5591 0.2946 0.1091 0.033 Uiso 1 1 calc R . . . .
C9 C 0.62115(8) 0.17172(9) 0.18251(10) 0.0283(3) Uani 1 1 d . . . . .
H9 H 0.6180 0.1477 0.1252 0.034 Uiso 1 1 calc R . . . .
C10 C 0.66119(8) 0.12052(9) 0.27641(10) 0.0281(3) Uani 1 1 d . . . . .
H10 H 0.6864 0.0617 0.2837 0.034 Uiso 1 1 calc R . . . .
C11 C 0.66495(8) 0.15411(9) 0.36002(10) 0.0252(3) Uani 1 1 d . . . . .
H11 H 0.6928 0.1183 0.4241 0.030 Uiso 1 1 calc R . . . .
C12 C 0.58433(8) 0.06441(8) 0.46113(10) 0.0246(3) Uani 1 1 d . . . . .
H12 H 0.5294 0.0791 0.4026 0.030 Uiso 1 1 calc R . . . .
C13 C 0.69346(8) -0.01169(9) 0.57782(10) 0.0274(3) Uani 1 1 d . . . . .
H13 H 0.7304 -0.0627 0.6171 0.033 Uiso 1 1 calc R . . . .
C14 C 0.71349(8) 0.08185(9) 0.59872(10) 0.0265(3) Uani 1 1 d . . . . .
H14 H 0.7653 0.1081 0.6541 0.032 Uiso 1 1 calc R . . . .
C15 C 0.63285(8) 0.22620(8) 0.66865(9) 0.0229(3) Uani 1 1 d . . . . .
C16 C 0.57052(8) 0.16482(8) 0.63979(10) 0.0261(3) Uani 1 1 d . . . . .
H16 H 0.5260 0.1545 0.5666 0.031 Uiso 1 1 calc R . . . .
C17 C 0.57325(9) 0.11877(9) 0.71735(11) 0.0323(3) Uani 1 1 d . . . . .
H17 H 0.5300 0.0779 0.6971 0.039 Uiso 1 1 calc R . . . .
C18 C 0.63803(9) 0.13164(10) 0.82352(11) 0.0363(3) Uani 1 1 d . . . . .
H18 H 0.6397 0.0995 0.8764 0.044 Uiso 1 1 calc R . . . .
C19 C 0.70056(9) 0.19138(11) 0.85281(11) 0.0392(4) Uani 1 1 d . . . . .
H19 H 0.7456 0.2000 0.9261 0.047 Uiso 1 1 calc R . . . .
C20 C 0.69816(8) 0.23904(10) 0.77590(10) 0.0325(3) Uani 1 1 d . . . . .
H20 H 0.7413 0.2805 0.7967 0.039 Uiso 1 1 calc R . . . .
C21 C 0.61201(8) 0.43272(9) 0.64489(10) 0.0260(3) Uani 1 1 d . . . . .
C22 C 0.60168(9) 0.56789(9) 0.40837(11) 0.0313(3) Uani 1 1 d . . . . .
H22A H 0.5614 0.5357 0.3391 0.038 Uiso 1 1 calc R . . . .
H22B H 0.6548 0.5686 0.4238 0.038 Uiso 1 1 calc R . . . .
C23 C 0.57458(9) 0.66784(9) 0.40519(13) 0.0387(4) Uani 1 1 d . . . . .
H23A H 0.5735 0.7055 0.3534 0.058 Uiso 1 1 calc GR . . . .
H23B H 0.6126 0.6968 0.4760 0.058 Uiso 1 1 calc GR . . . .
H23C H 0.5200 0.6662 0.3841 0.058 Uiso 1 1 calc GR . . . .

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

# MOLECULAR GEOMETRY 
_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 C5 1.3404(15) . ?
O1 C22 1.4528(15) . ?
N1 C1 1.3524(16) . ?
N1 C5 1.3161(15) . ?
N2 C2 1.4327(16) . ?
N2 C12 1.3578(16) . ?
N2 C14 1.3746(16) . ?
N3 C12 1.3151(17) . ?
N3 C13 1.3683(18) . ?
N4 C21 1.1496(17) . ?
C1 C2 1.3970(16) . ?
C1 C6 1.4947(16) . ?
C2 C3 1.4012(17) . ?
C3 C4 1.3920(17) . ?
C3 C15 1.4913(16) . ?
C4 C5 1.4087(17) . ?
C4 C21 1.4365(17) . ?
C6 C7 1.3973(17) . ?
C6 C11 1.4038(18) . ?
C7 H7 0.9500 . ?
C7 C8 1.3857(17) . ?
C8 H8 0.9500 . ?
C8 C9 1.3885(19) . ?
C9 H9 0.9500 . ?
C9 C10 1.3844(19) . ?
C10 H10 0.9500 . ?
C10 C11 1.3887(18) . ?
C11 H11 0.9500 . ?
C12 H12 0.9500 . ?
C13 H13 0.9500 . ?
C13 C14 1.3561(18) . ?
C14 H14 0.9500 . ?
C15 C16 1.3905(18) . ?
C15 C20 1.3874(18) . ?
C16 H16 0.9500 . ?
C16 C17 1.3819(18) . ?
C17 H17 0.9500 . ?
C17 C18 1.374(2) . ?
C18 H18 0.9500 . ?
C18 C19 1.377(2) . ?
C19 H19 0.9500 . ?
C19 C20 1.3871(19) . ?
C20 H20 0.9500 . ?
C22 H22A 0.9900 . ?
C22 H22B 0.9900 . ?
C22 C23 1.5058(19) . ?
C23 H23A 0.9800 . ?
C23 H23B 0.9800 . ?
C23 H23C 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
C5 O1 C22 117.27(9) . . ?
C5 N1 C1 119.54(10) . . ?
C12 N2 C2 126.93(10) . . ?
C12 N2 C14 106.88(10) . . ?
C14 N2 C2 126.16(10) . . ?
C12 N3 C13 105.19(10) . . ?
N1 C1 C2 120.46(10) . . ?
N1 C1 C6 113.73(10) . . ?
C2 C1 C6 125.77(10) . . ?
C1 C2 N2 121.92(10) . . ?
C1 C2 C3 120.58(11) . . ?
C3 C2 N2 117.49(10) . . ?
C2 C3 C15 121.57(11) . . ?
C4 C3 C2 117.72(11) . . ?
C4 C3 C15 120.71(10) . . ?
C3 C4 C5 118.23(11) . . ?
C3 C4 C21 122.32(11) . . ?
C5 C4 C21 119.39(11) . . ?
O1 C5 C4 116.18(10) . . ?
N1 C5 O1 120.37(10) . . ?
N1 C5 C4 123.46(11) . . ?
C7 C6 C1 117.39(10) . . ?
C7 C6 C11 118.31(11) . . ?
C11 C6 C1 124.28(11) . . ?
C6 C7 H7 119.5 . . ?
C8 C7 C6 121.06(11) . . ?
C8 C7 H7 119.5 . . ?
C7 C8 H8 119.9 . . ?
C7 C8 C9 120.13(11) . . ?
C9 C8 H8 119.9 . . ?
C8 C9 H9 120.3 . . ?
C10 C9 C8 119.49(11) . . ?
C10 C9 H9 120.3 . . ?
C9 C10 H10 119.6 . . ?
C9 C10 C11 120.77(12) . . ?
C11 C10 H10 119.6 . . ?
C6 C11 H11 119.9 . . ?
C10 C11 C6 120.22(12) . . ?
C10 C11 H11 119.9 . . ?
N2 C12 H12 124.2 . . ?
N3 C12 N2 111.59(11) . . ?
N3 C12 H12 124.2 . . ?
N3 C13 H13 124.6 . . ?
C14 C13 N3 110.82(11) . . ?
C14 C13 H13 124.6 . . ?
N2 C14 H14 127.2 . . ?
C13 C14 N2 105.52(11) . . ?
C13 C14 H14 127.2 . . ?
C16 C15 C3 120.83(11) . . ?
C20 C15 C3 120.06(11) . . ?
C20 C15 C16 119.10(11) . . ?
C15 C16 H16 119.9 . . ?
C17 C16 C15 120.15(12) . . ?
C17 C16 H16 119.9 . . ?
C16 C17 H17 119.7 . . ?
C18 C17 C16 120.58(12) . . ?
C18 C17 H17 119.7 . . ?
C17 C18 H18 120.2 . . ?
C17 C18 C19 119.66(12) . . ?
C19 C18 H18 120.2 . . ?
C18 C19 H19 119.8 . . ?
C18 C19 C20 120.41(13) . . ?
C20 C19 H19 119.8 . . ?
C15 C20 H20 120.0 . . ?
C19 C20 C15 120.08(12) . . ?
C19 C20 H20 120.0 . . ?
N4 C21 C4 178.74(15) . . ?
O1 C22 H22A 110.5 . . ?
O1 C22 H22B 110.5 . . ?
O1 C22 C23 106.38(10) . . ?
H22A C22 H22B 108.6 . . ?
C23 C22 H22A 110.5 . . ?
C23 C22 H22B 110.5 . . ?
C22 C23 H23A 109.5 . . ?
C22 C23 H23B 109.5 . . ?
C22 C23 H23C 109.5 . . ?
H23A C23 H23B 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 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
N1 C1 C2 N2 -179.44(10) . . . . ?
N1 C1 C2 C3 0.82(17) . . . . ?
N1 C1 C6 C7 -24.31(15) . . . . ?
N1 C1 C6 C11 154.29(12) . . . . ?
N2 C2 C3 C4 179.71(10) . . . . ?
N2 C2 C3 C15 -1.16(16) . . . . ?
N3 C13 C14 N2 -0.79(14) . . . . ?
C1 N1 C5 O1 -179.96(10) . . . . ?
C1 N1 C5 C4 -0.31(17) . . . . ?
C1 C2 C3 C4 -0.54(16) . . . . ?
C1 C2 C3 C15 178.59(11) . . . . ?
C1 C6 C7 C8 179.87(10) . . . . ?
C1 C6 C11 C10 -179.94(11) . . . . ?
C2 N2 C12 N3 -178.43(10) . . . . ?
C2 N2 C14 C13 178.80(11) . . . . ?
C2 C1 C6 C7 153.23(12) . . . . ?
C2 C1 C6 C11 -28.17(18) . . . . ?
C2 C3 C4 C5 -0.12(16) . . . . ?
C2 C3 C4 C21 177.25(11) . . . . ?
C2 C3 C15 C16 -66.71(16) . . . . ?
C2 C3 C15 C20 114.42(14) . . . . ?
C3 C4 C5 O1 -179.77(10) . . . . ?
C3 C4 C5 N1 0.57(17) . . . . ?
C3 C15 C16 C17 -177.73(11) . . . . ?
C3 C15 C20 C19 178.56(12) . . . . ?
C4 C3 C15 C16 112.39(13) . . . . ?
C4 C3 C15 C20 -66.48(16) . . . . ?
C5 O1 C22 C23 167.57(11) . . . . ?
C5 N1 C1 C2 -0.39(16) . . . . ?
C5 N1 C1 C6 177.29(10) . . . . ?
C6 C1 C2 N2 3.18(18) . . . . ?
C6 C1 C2 C3 -176.56(11) . . . . ?
C6 C7 C8 C9 0.15(18) . . . . ?
C7 C6 C11 C10 -1.36(18) . . . . ?
C7 C8 C9 C10 -1.34(19) . . . . ?
C8 C9 C10 C11 1.16(19) . . . . ?
C9 C10 C11 C6 0.20(18) . . . . ?
C11 C6 C7 C8 1.19(18) . . . . ?
C12 N2 C2 C1 -77.86(15) . . . . ?
C12 N2 C2 C3 101.89(13) . . . . ?
C12 N2 C14 C13 0.65(12) . . . . ?
C12 N3 C13 C14 0.61(14) . . . . ?
C13 N3 C12 N2 -0.17(13) . . . . ?
C14 N2 C2 C1 104.36(14) . . . . ?
C14 N2 C2 C3 -75.89(15) . . . . ?
C14 N2 C12 N3 -0.30(13) . . . . ?
C15 C3 C4 C5 -179.26(11) . . . . ?
C15 C3 C4 C21 -1.88(17) . . . . ?
C15 C16 C17 C18 -1.17(19) . . . . ?
C16 C15 C20 C19 -0.3(2) . . . . ?
C16 C17 C18 C19 0.3(2) . . . . ?
C17 C18 C19 C20 0.5(2) . . . . ?
C18 C19 C20 C15 -0.5(2) . . . . ?
C20 C15 C16 C17 1.15(18) . . . . ?
C21 C4 C5 O1 2.78(16) . . . . ?
C21 C4 C5 N1 -176.89(11) . . . . ?
C22 O1 C5 N1 1.57(16) . . . . ?
C22 O1 C5 C4 -178.11(10) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
# End of CIF  ============================================================
