# Electronic Supplementary Material (ESI) for RSC Advances.
# This journal is © The Royal Society of Chemistry 2020

####################################################################### 
# 
# 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_cmpd_17A
_database_code_depnum_ccdc_archive 'CCDC 1970362'
loop_
_audit_author_name
_audit_author_address
'Manuel Fernandes'
;University of the Witwatersrand
South Africa
;
_audit_update_record             
;
2020-01-20 deposited with the CCDC.	2020-02-17 downloaded from the CCDC.
;
# 19m_mb3_cck_c1c_1pr_0s
_audit_creation_date             2019-12-04
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C19 H16 N4 O3'
_chemical_formula_sum            'C19 H16 N4 O3'
_chemical_formula_weight         348.36
_chemical_melting_point          461-463
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'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           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                   20.8879(15)
_cell_length_b                   7.2791(5)
_cell_length_c                   21.5015(15)
_cell_angle_alpha                90
_cell_angle_beta                 96.086(5)
_cell_angle_gamma                90
_cell_volume                     3250.8(4)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    1315
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      20.55
_cell_measurement_theta_min      2.59
_shelx_estimated_absorpt_T_max   0.994
_shelx_estimated_absorpt_T_min   0.952
_exptl_absorpt_coefficient_mu    0.100
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.424
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             1456
_exptl_crystal_size_max          0.495
_exptl_crystal_size_mid          0.086
_exptl_crystal_size_min          0.063
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.1096
_diffrn_reflns_av_unetI/netI     0.1327
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       24
_diffrn_reflns_limit_h_min       -24
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            10492
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        24.999
_diffrn_reflns_theta_max         24.999
_diffrn_reflns_theta_min         1.905
_diffrn_ambient_temperature      173.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_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_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1204
_reflns_number_total             2857
_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       'APEX2 Ver. 2013.10-0 (Bruker, 2013)'
_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, 2015b)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015a)'
_refine_diff_density_max         0.163
_refine_diff_density_min         -0.184
_refine_diff_density_rms         0.042
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.780
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     235
_refine_ls_number_reflns         2857
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1383
_refine_ls_R_factor_gt           0.0444
_refine_ls_restrained_S_all      0.780
_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)+(0.0238P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0686
_refine_ls_wR_factor_ref         0.0847
_refine_special_details          
;
The crystal was a thin needle with the cell volume being rather large.
Consequently the sample didn't scatter very strongly resulting in the
final Rint and Rsigma being 0.1096 and 0.1327. A cif check on the final 
refinements have the following C alert:
026_ALERT_3_C Ratio Observed / Unique Reflections (too) Low ..        42% Check

In the data collection, we selected the largest needle we had 
(0.063x0.086x0.495mm) and ran it with the following settings:
Dist: 4cm
Count time: 60s
Collection time: 14 hours
Collection Temperature: -100 degree C
Frame width: 0.5 degree
;

_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2.a Ternary CH refined with riding coordinates:
 C6(H6)
2.b Secondary CH2 refined with riding coordinates:
 C7(H7A,H7B), C8(H8A,H8B), C9(H9A,H9B), C10(H10A,H10B)
2.c Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C4(H4), C15(H15), C16(H16), C18(H18), C19(H19)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.42948(13) 0.1728(4) 0.53511(13) 0.0427(7) Uani 1 1 d . . . . .
C2 C 0.36348(12) 0.1438(4) 0.51683(14) 0.0536(8) Uani 1 1 d . . . . .
H2 H 0.335783 0.099575 0.545793 0.064 Uiso 1 1 calc R . . . .
C3 C 0.34042(14) 0.1811(4) 0.45633(14) 0.0633(9) Uani 1 1 d . . . . .
H3 H 0.296096 0.160837 0.443283 0.076 Uiso 1 1 calc R . . . .
C4 C 0.37973(14) 0.2476(4) 0.41334(13) 0.0556(9) Uani 1 1 d . . . . .
H4 H 0.362206 0.271359 0.371520 0.067 Uiso 1 1 calc R . . . .
C5 C 0.44352(15) 0.2792(4) 0.43090(13) 0.0495(8) Uani 1 1 d . . . . .
C6 C 0.54536(14) 0.3026(4) 0.38484(11) 0.0539(8) Uani 1 1 d . . . . .
H6 H 0.543014 0.167571 0.376400 0.065 Uiso 1 1 calc R . . . .
C7 C 0.55944(16) 0.3994(4) 0.32513(11) 0.0705(10) Uani 1 1 d . . . . .
H7A H 0.533186 0.342526 0.289183 0.085 Uiso 1 1 calc R . . . .
H7B H 0.546317 0.529767 0.327328 0.085 Uiso 1 1 calc R . . . .
C8 C 0.62974(16) 0.3910(4) 0.31388(12) 0.0717(10) Uani 1 1 d . . . . .
H8A H 0.642748 0.261495 0.308926 0.086 Uiso 1 1 calc R . . . .
H8B H 0.636239 0.457738 0.274921 0.086 Uiso 1 1 calc R . . . .
C9 C 0.67066(15) 0.4767(4) 0.36843(12) 0.0733(10) Uani 1 1 d . . . . .
H9A H 0.657114 0.605422 0.374011 0.088 Uiso 1 1 calc R . . . .
H9B H 0.716404 0.476894 0.360214 0.088 Uiso 1 1 calc R . . . .
C10 C 0.66288(14) 0.3666(4) 0.42748(12) 0.0621(9) Uani 1 1 d . . . . .
H10A H 0.684023 0.245803 0.424088 0.074 Uiso 1 1 calc R . . . .
H10B H 0.685776 0.431716 0.463668 0.074 Uiso 1 1 calc R . . . .
C11 C 0.59458(13) 0.3349(4) 0.44041(12) 0.0463(8) Uani 1 1 d . . . . .
C12 C 0.53032(12) 0.2616(3) 0.52206(11) 0.0365(7) Uani 1 1 d . . . . .
C13 C 0.52455(12) 0.2052(3) 0.58314(11) 0.0357(7) Uani 1 1 d . . . . .
C14 C 0.57503(12) 0.1986(3) 0.63610(11) 0.0353(7) Uani 1 1 d . . . . .
C15 C 0.63695(12) 0.2629(3) 0.63270(11) 0.0458(8) Uani 1 1 d . . . . .
H15 H 0.647909 0.315672 0.594827 0.055 Uiso 1 1 calc R . . . .
C16 C 0.68303(12) 0.2514(4) 0.68368(11) 0.0493(8) Uani 1 1 d . . . . .
H16 H 0.725301 0.296886 0.681147 0.059 Uiso 1 1 calc R . . . .
C17 C 0.66690(12) 0.1734(4) 0.73794(11) 0.0397(7) Uani 1 1 d . . . . .
C18 C 0.60613(13) 0.1115(4) 0.74359(11) 0.0452(8) Uani 1 1 d . . . . .
H18 H 0.595629 0.060068 0.781829 0.054 Uiso 1 1 calc R . . . .
C19 C 0.56024(12) 0.1250(4) 0.69272(11) 0.0442(8) Uani 1 1 d . . . . .
H19 H 0.517689 0.083347 0.696329 0.053 Uiso 1 1 calc R . . . .
N1 N 0.46329(10) 0.1516(3) 0.59091(9) 0.0426(6) Uani 1 1 d . . . . .
N2 N 0.46795(10) 0.2376(3) 0.49128(9) 0.0398(6) Uani 1 1 d . . . . .
N3 N 0.58499(11) 0.3141(3) 0.49835(9) 0.0450(6) Uani 1 1 d . . . . .
N4 N 0.71635(12) 0.1601(4) 0.79163(11) 0.0541(7) Uani 1 1 d . . . . .
O1 O 0.48104(10) 0.3671(3) 0.39362(8) 0.0591(6) Uani 1 1 d . . . . .
O2 O 0.76780(10) 0.2372(3) 0.78828(8) 0.0790(8) Uani 1 1 d . . . . .
O3 O 0.70333(9) 0.0723(3) 0.83796(8) 0.0621(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
C1 C2 1.409(3) . ?
C1 N1 1.335(3) . ?
C1 N2 1.385(3) . ?
C2 H2 0.9500 . ?
C2 C3 1.366(3) . ?
C3 H3 0.9500 . ?
C3 C4 1.387(4) . ?
C4 H4 0.9500 . ?
C4 C5 1.365(3) . ?
C5 N2 1.377(3) . ?
C5 O1 1.342(3) . ?
C6 H6 1.0000 . ?
C6 C7 1.520(3) . ?
C6 C11 1.510(3) . ?
C6 O1 1.454(3) . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C7 C8 1.515(3) . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C8 C9 1.511(3) . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C9 C10 1.525(3) . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C10 C11 1.500(4) . ?
C11 N3 1.291(3) . ?
C12 C13 1.393(3) . ?
C12 N2 1.408(3) . ?
C12 N3 1.354(3) . ?
C13 C14 1.468(3) . ?
C13 N1 1.365(3) . ?
C14 C15 1.385(3) . ?
C14 C19 1.394(3) . ?
C15 H15 0.9500 . ?
C15 C16 1.382(3) . ?
C16 H16 0.9500 . ?
C16 C17 1.371(3) . ?
C17 C18 1.364(3) . ?
C17 N4 1.468(3) . ?
C18 H18 0.9500 . ?
C18 C19 1.379(3) . ?
C19 H19 0.9500 . ?
N4 O2 1.221(3) . ?
N4 O3 1.238(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
N1 C1 C2 130.0(3) . . ?
N1 C1 N2 111.2(2) . . ?
N2 C1 C2 118.8(3) . . ?
C1 C2 H2 120.9 . . ?
C3 C2 C1 118.2(3) . . ?
C3 C2 H2 120.9 . . ?
C2 C3 H3 119.0 . . ?
C2 C3 C4 122.0(3) . . ?
C4 C3 H3 119.0 . . ?
C3 C4 H4 119.9 . . ?
C5 C4 C3 120.2(3) . . ?
C5 C4 H4 119.9 . . ?
C4 C5 N2 118.5(3) . . ?
O1 C5 C4 122.0(3) . . ?
O1 C5 N2 119.1(3) . . ?
C7 C6 H6 108.2 . . ?
C11 C6 H6 108.2 . . ?
C11 C6 C7 114.8(3) . . ?
O1 C6 H6 108.2 . . ?
O1 C6 C7 103.0(2) . . ?
O1 C6 C11 114.1(2) . . ?
C6 C7 H7A 108.9 . . ?
C6 C7 H7B 108.9 . . ?
H7A C7 H7B 107.8 . . ?
C8 C7 C6 113.2(2) . . ?
C8 C7 H7A 108.9 . . ?
C8 C7 H7B 108.9 . . ?
C7 C8 H8A 109.7 . . ?
C7 C8 H8B 109.7 . . ?
H8A C8 H8B 108.2 . . ?
C9 C8 C7 109.7(2) . . ?
C9 C8 H8A 109.7 . . ?
C9 C8 H8B 109.7 . . ?
C8 C9 H9A 109.8 . . ?
C8 C9 H9B 109.8 . . ?
C8 C9 C10 109.2(3) . . ?
H9A C9 H9B 108.3 . . ?
C10 C9 H9A 109.8 . . ?
C10 C9 H9B 109.8 . . ?
C9 C10 H10A 108.5 . . ?
C9 C10 H10B 108.5 . . ?
H10A C10 H10B 107.5 . . ?
C11 C10 C9 115.0(3) . . ?
C11 C10 H10A 108.5 . . ?
C11 C10 H10B 108.5 . . ?
C10 C11 C6 117.3(2) . . ?
N3 C11 C6 125.7(3) . . ?
N3 C11 C10 116.4(2) . . ?
C13 C12 N2 103.8(2) . . ?
N3 C12 C13 126.8(2) . . ?
N3 C12 N2 129.3(2) . . ?
C12 C13 C14 127.9(2) . . ?
N1 C13 C12 112.1(2) . . ?
N1 C13 C14 120.1(2) . . ?
C15 C14 C13 123.1(2) . . ?
C15 C14 C19 118.1(2) . . ?
C19 C14 C13 118.8(2) . . ?
C14 C15 H15 119.6 . . ?
C16 C15 C14 120.9(2) . . ?
C16 C15 H15 119.6 . . ?
C15 C16 H16 120.4 . . ?
C17 C16 C15 119.1(2) . . ?
C17 C16 H16 120.4 . . ?
C16 C17 N4 118.7(2) . . ?
C18 C17 C16 121.8(2) . . ?
C18 C17 N4 119.4(2) . . ?
C17 C18 H18 120.6 . . ?
C17 C18 C19 118.7(2) . . ?
C19 C18 H18 120.6 . . ?
C14 C19 H19 119.3 . . ?
C18 C19 C14 121.3(2) . . ?
C18 C19 H19 119.3 . . ?
C1 N1 C13 105.7(2) . . ?
C1 N2 C12 107.3(2) . . ?
C5 N2 C1 122.2(2) . . ?
C5 N2 C12 130.4(2) . . ?
C11 N3 C12 128.3(2) . . ?
O2 N4 C17 118.2(2) . . ?
O2 N4 O3 123.7(3) . . ?
O3 N4 C17 118.1(3) . . ?
C5 O1 C6 122.0(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
C1 C2 C3 C4 -0.7(4) . . . . ?
C2 C1 N1 C13 -177.7(3) . . . . ?
C2 C1 N2 C5 1.7(4) . . . . ?
C2 C1 N2 C12 177.5(2) . . . . ?
C2 C3 C4 C5 -0.4(5) . . . . ?
C3 C4 C5 N2 2.2(4) . . . . ?
C3 C4 C5 O1 -170.4(3) . . . . ?
C4 C5 N2 C1 -2.8(4) . . . . ?
C4 C5 N2 C12 -177.5(3) . . . . ?
C4 C5 O1 C6 -136.0(3) . . . . ?
C6 C7 C8 C9 -58.4(3) . . . . ?
C6 C11 N3 C12 -0.5(4) . . . . ?
C7 C6 C11 C10 -30.8(4) . . . . ?
C7 C6 C11 N3 158.9(3) . . . . ?
C7 C6 O1 C5 161.7(2) . . . . ?
C7 C8 C9 C10 62.3(3) . . . . ?
C8 C9 C10 C11 -51.8(3) . . . . ?
C9 C10 C11 C6 36.5(4) . . . . ?
C9 C10 C11 N3 -152.2(2) . . . . ?
C10 C11 N3 C12 -171.0(3) . . . . ?
C11 C6 C7 C8 41.7(3) . . . . ?
C11 C6 O1 C5 -73.3(3) . . . . ?
C12 C13 C14 C15 4.8(4) . . . . ?
C12 C13 C14 C19 -175.5(3) . . . . ?
C12 C13 N1 C1 0.1(3) . . . . ?
C13 C12 N2 C1 1.0(3) . . . . ?
C13 C12 N2 C5 176.3(2) . . . . ?
C13 C12 N3 C11 166.2(3) . . . . ?
C13 C14 C15 C16 -179.1(2) . . . . ?
C13 C14 C19 C18 178.5(2) . . . . ?
C14 C13 N1 C1 -179.8(2) . . . . ?
C14 C15 C16 C17 0.6(4) . . . . ?
C15 C14 C19 C18 -1.8(4) . . . . ?
C15 C16 C17 C18 -1.9(4) . . . . ?
C15 C16 C17 N4 179.4(2) . . . . ?
C16 C17 C18 C19 1.3(4) . . . . ?
C16 C17 N4 O2 8.0(4) . . . . ?
C16 C17 N4 O3 -172.5(2) . . . . ?
C17 C18 C19 C14 0.6(4) . . . . ?
C18 C17 N4 O2 -170.7(3) . . . . ?
C18 C17 N4 O3 8.8(4) . . . . ?
C19 C14 C15 C16 1.1(4) . . . . ?
N1 C1 C2 C3 178.2(3) . . . . ?
N1 C1 N2 C5 -176.7(2) . . . . ?
N1 C1 N2 C12 -1.0(3) . . . . ?
N1 C13 C14 C15 -175.3(3) . . . . ?
N1 C13 C14 C19 4.4(4) . . . . ?
N2 C1 C2 C3 0.1(4) . . . . ?
N2 C1 N1 C13 0.5(3) . . . . ?
N2 C5 O1 C6 51.5(3) . . . . ?
N2 C12 C13 C14 179.2(2) . . . . ?
N2 C12 C13 N1 -0.7(3) . . . . ?
N2 C12 N3 C11 -8.6(5) . . . . ?
N3 C12 C13 C14 3.4(4) . . . . ?
N3 C12 C13 N1 -176.5(2) . . . . ?
N3 C12 N2 C1 176.7(3) . . . . ?
N3 C12 N2 C5 -8.0(4) . . . . ?
N4 C17 C18 C19 180.0(2) . . . . ?
O1 C5 N2 C1 170.0(2) . . . . ?
O1 C5 N2 C12 -4.7(4) . . . . ?
O1 C6 C7 C8 166.3(2) . . . . ?
O1 C6 C11 C10 -149.3(2) . . . . ?
O1 C6 C11 N3 40.4(4) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'


###===========###
_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent: DCM'
####################################################################### 
# 
# 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_cmpd_17C
_database_code_depnum_ccdc_archive 'CCDC 1970363'
loop_
_audit_author_name
_audit_author_address
'Manuel Fernandes'
;University of the Witwatersrand
South Africa
;
_audit_update_record             
;
2020-01-20 deposited with the CCDC.	2020-02-17 downloaded from the CCDC.
;
#19m_mb4_cck_c4c_1pr_longcolles
# start Validation Reply Form
_vrf_PLAT026_cmpd_17C            
;
PROBLEM: Ratio Observed / Unique Reflections (too) Low ..        36% Check 
RESPONSE: The crystal was a small needle of size 0.046 0.053 0.188 and
didn't diffract well. The weak data also leads to the all the C alerts
including GOODF01_ALERT_2_C.
;
# end Validation Reply Form

_audit_creation_date             2019-09-14
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;

_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C20 H16 N4 O'
_chemical_formula_sum            'C20 H16 N4 O'
_chemical_formula_weight         328.37
_chemical_melting_point          403-405
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'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/n 1'
_space_group_name_Hall           '-P 2yn'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   12.0432(7)
_cell_length_b                   7.3016(4)
_cell_length_c                   18.3346(12)
_cell_angle_alpha                90
_cell_angle_beta                 96.116(4)
_cell_angle_gamma                90
_cell_volume                     1603.07(17)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    816
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      20.55
_cell_measurement_theta_min      2.23
_shelx_estimated_absorpt_T_max   0.996
_shelx_estimated_absorpt_T_min   0.984
_exptl_absorpt_coefficient_mu    0.088
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.361
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             688
_exptl_crystal_size_max          0.188
_exptl_crystal_size_mid          0.053
_exptl_crystal_size_min          0.046
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.1479
_diffrn_reflns_av_unetI/netI     0.2114
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            11067
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        24.990
_diffrn_reflns_theta_max         24.990
_diffrn_reflns_theta_min         1.933
_diffrn_ambient_temperature      173.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_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_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1032
_reflns_number_total             2831
_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       'APEX2 Ver. 2013.10-0 (Bruker, 2013)'
_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, 2015b)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015a)'
_refine_diff_density_max         0.171
_refine_diff_density_min         -0.181
_refine_diff_density_rms         0.044
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.716
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     226
_refine_ls_number_reflns         2831
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1629
_refine_ls_R_factor_gt           0.0410
_refine_ls_restrained_S_all      0.716
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0135P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0524
_refine_ls_wR_factor_ref         0.0687
_refine_special_details          
;
The crystal was a small needle (0.046x0.053x0.188 mm). Consequently the sample 
didn't scatter very strongly resulting in the Rint and Rsigma being 0.1479 
and 0.2114. A cif check on the final refinements have the following B alert:
026_ALERT_3_B Ratio Observed / Unique Reflections (too) Low ..        36% Check

In the data collection, we selected the largest needle we had and ran it with 
the following settings:
Dist: 4cm
Count time: 70s
Collection time: 12 hours
Collection Temperature: -100 degree C
Frame width: 0.5 degree
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2.a Ternary CH refined with riding coordinates:
 C6(H6)
2.b Secondary CH2 refined with riding coordinates:
 C7(H7A,H7B), C8(H8A,H8B), C9(H9A,H9B), C10(H10A,H10B)
2.c Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C4(H4), C15(H15), C16(H16), C17(H17), C19(H19)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.4787(3) 0.8520(4) 0.41290(16) 0.0292(8) Uani 1 1 d . . . . .
C2 C 0.3985(3) 0.9114(4) 0.35751(15) 0.0328(9) Uani 1 1 d . . . . .
H2 H 0.420216 0.963562 0.313727 0.039 Uiso 1 1 calc R . . . .
C3 C 0.2881(3) 0.8931(4) 0.36736(17) 0.0374(9) Uani 1 1 d . . . . .
H3 H 0.232614 0.934529 0.330335 0.045 Uiso 1 1 calc R . . . .
C4 C 0.2560(2) 0.8140(4) 0.43133(16) 0.0334(9) Uani 1 1 d . . . . .
H4 H 0.178854 0.801693 0.437119 0.040 Uiso 1 1 calc R . . . .
C5 C 0.3333(3) 0.7549(4) 0.48504(16) 0.0290(8) Uani 1 1 d . . . . .
C6 C 0.3568(2) 0.6984(4) 0.61793(15) 0.0328(9) Uani 1 1 d . . . . .
H6 H 0.358768 0.833965 0.625785 0.039 Uiso 1 1 calc R . . . .
C7 C 0.2736(2) 0.6148(4) 0.66518(14) 0.0370(9) Uani 1 1 d . . . . .
H7A H 0.206960 0.694671 0.663268 0.044 Uiso 1 1 calc R . . . .
H7B H 0.249308 0.494279 0.644458 0.044 Uiso 1 1 calc R . . . .
C8 C 0.3206(2) 0.5892(4) 0.74470(15) 0.0405(10) Uani 1 1 d . . . . .
H8A H 0.341310 0.709689 0.766914 0.049 Uiso 1 1 calc R . . . .
H8B H 0.263266 0.533354 0.772604 0.049 Uiso 1 1 calc R . . . .
C9 C 0.4221(2) 0.4671(4) 0.74866(16) 0.0453(10) Uani 1 1 d . . . . .
H9A H 0.401385 0.347109 0.726042 0.054 Uiso 1 1 calc R . . . .
H9B H 0.450780 0.446005 0.800605 0.054 Uiso 1 1 calc R . . . .
C10 C 0.5127(2) 0.5559(4) 0.70857(15) 0.0376(9) Uani 1 1 d . . . . .
H10A H 0.544671 0.660139 0.738307 0.045 Uiso 1 1 calc R . . . .
H10B H 0.573234 0.465637 0.705088 0.045 Uiso 1 1 calc R . . . .
C11 C 0.4737(2) 0.6250(4) 0.63184(16) 0.0270(8) Uani 1 1 d . . . . .
C12 C 0.5413(2) 0.7181(4) 0.52059(16) 0.0249(8) Uani 1 1 d . . . . .
C13 C 0.6288(3) 0.7698(4) 0.48062(16) 0.0262(8) Uani 1 1 d . . . . .
C14 C 0.7489(3) 0.7501(4) 0.49993(15) 0.0265(8) Uani 1 1 d . . . . .
C15 C 0.8205(2) 0.8163(4) 0.45113(16) 0.0331(9) Uani 1 1 d . . . . .
H15 H 0.789587 0.873748 0.407088 0.040 Uiso 1 1 calc R . . . .
C16 C 0.9355(2) 0.8008(4) 0.46503(16) 0.0376(9) Uani 1 1 d . . . . .
H16 H 0.982380 0.847604 0.430893 0.045 Uiso 1 1 calc R . . . .
C17 C 0.9818(2) 0.7168(4) 0.52894(15) 0.0367(9) Uani 1 1 d . . . . .
H17 H 1.060470 0.705605 0.539233 0.044 Uiso 1 1 calc R . . . .
C18 C 0.9113(3) 0.6496(4) 0.57749(15) 0.0291(8) Uani 1 1 d . . . . .
C19 C 0.7962(2) 0.6657(4) 0.56392(16) 0.0297(8) Uani 1 1 d . . . . .
H19 H 0.749658 0.619152 0.598285 0.036 Uiso 1 1 calc R . . . .
C20 C 0.9581(3) 0.5540(5) 0.64250(19) 0.0390(10) Uani 1 1 d . . . . .
N1 N 0.5900(2) 0.8513(3) 0.41535(12) 0.0291(7) Uani 1 1 d . . . . .
N2 N 0.4447(2) 0.7733(3) 0.47676(13) 0.0261(7) Uani 1 1 d . . . . .
N3 N 0.55106(19) 0.6381(3) 0.58857(13) 0.0285(7) Uani 1 1 d . . . . .
N4 N 0.9962(2) 0.4755(4) 0.69366(15) 0.0543(9) Uani 1 1 d . . . . .
O1 O 0.30450(15) 0.6604(3) 0.54335(10) 0.0330(6) 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
C1 C2 1.394(3) . ?
C1 N1 1.337(3) . ?
C1 N2 1.404(3) . ?
C2 H2 0.9500 . ?
C2 C3 1.368(4) . ?
C3 H3 0.9500 . ?
C3 C4 1.398(4) . ?
C4 H4 0.9500 . ?
C4 C5 1.352(3) . ?
C5 N2 1.373(3) . ?
C5 O1 1.348(3) . ?
C6 H6 1.0000 . ?
C6 C7 1.521(3) . ?
C6 C11 1.502(4) . ?
C6 O1 1.470(3) . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C7 C8 1.518(3) . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C8 C9 1.509(3) . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C9 C10 1.523(3) . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C10 C11 1.521(3) . ?
C11 N3 1.290(3) . ?
C12 C13 1.398(4) . ?
C12 N2 1.401(3) . ?
C12 N3 1.370(3) . ?
C13 C14 1.460(4) . ?
C13 N1 1.373(3) . ?
C14 C15 1.393(4) . ?
C14 C19 1.392(3) . ?
C15 H15 0.9500 . ?
C15 C16 1.386(4) . ?
C16 H16 0.9500 . ?
C16 C17 1.386(3) . ?
C17 H17 0.9500 . ?
C17 C18 1.384(4) . ?
C18 C19 1.386(4) . ?
C18 C20 1.443(4) . ?
C19 H19 0.9500 . ?
C20 N4 1.152(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 C1 N2 119.6(3) . . ?
N1 C1 C2 129.8(3) . . ?
N1 C1 N2 110.6(3) . . ?
C1 C2 H2 120.6 . . ?
C3 C2 C1 118.8(3) . . ?
C3 C2 H2 120.6 . . ?
C2 C3 H3 119.6 . . ?
C2 C3 C4 120.7(3) . . ?
C4 C3 H3 119.6 . . ?
C3 C4 H4 119.6 . . ?
C5 C4 C3 120.8(3) . . ?
C5 C4 H4 119.6 . . ?
C4 C5 N2 119.6(3) . . ?
O1 C5 C4 121.7(3) . . ?
O1 C5 N2 118.3(3) . . ?
C7 C6 H6 108.8 . . ?
C11 C6 H6 108.8 . . ?
C11 C6 C7 115.0(3) . . ?
O1 C6 H6 108.8 . . ?
O1 C6 C7 102.2(2) . . ?
O1 C6 C11 113.1(3) . . ?
C6 C7 H7A 108.9 . . ?
C6 C7 H7B 108.9 . . ?
H7A C7 H7B 107.7 . . ?
C8 C7 C6 113.3(2) . . ?
C8 C7 H7A 108.9 . . ?
C8 C7 H7B 108.9 . . ?
C7 C8 H8A 109.7 . . ?
C7 C8 H8B 109.7 . . ?
H8A C8 H8B 108.2 . . ?
C9 C8 C7 109.6(3) . . ?
C9 C8 H8A 109.7 . . ?
C9 C8 H8B 109.7 . . ?
C8 C9 H9A 109.6 . . ?
C8 C9 H9B 109.6 . . ?
C8 C9 C10 110.1(3) . . ?
H9A C9 H9B 108.2 . . ?
C10 C9 H9A 109.6 . . ?
C10 C9 H9B 109.6 . . ?
C9 C10 H10A 108.5 . . ?
C9 C10 H10B 108.5 . . ?
H10A C10 H10B 107.5 . . ?
C11 C10 C9 114.9(3) . . ?
C11 C10 H10A 108.5 . . ?
C11 C10 H10B 108.5 . . ?
C6 C11 C10 117.8(3) . . ?
N3 C11 C6 126.4(3) . . ?
N3 C11 C10 114.9(3) . . ?
C13 C12 N2 104.4(2) . . ?
N3 C12 C13 126.5(3) . . ?
N3 C12 N2 129.1(3) . . ?
C12 C13 C14 129.0(3) . . ?
N1 C13 C12 111.6(3) . . ?
N1 C13 C14 119.3(3) . . ?
C15 C14 C13 118.4(3) . . ?
C19 C14 C13 123.6(3) . . ?
C19 C14 C15 118.0(3) . . ?
C14 C15 H15 119.1 . . ?
C16 C15 C14 121.9(3) . . ?
C16 C15 H15 119.1 . . ?
C15 C16 H16 120.1 . . ?
C15 C16 C17 119.7(3) . . ?
C17 C16 H16 120.1 . . ?
C16 C17 H17 120.6 . . ?
C18 C17 C16 118.8(3) . . ?
C18 C17 H17 120.6 . . ?
C17 C18 C19 121.6(3) . . ?
C17 C18 C20 119.3(3) . . ?
C19 C18 C20 119.0(3) . . ?
C14 C19 H19 120.0 . . ?
C18 C19 C14 120.0(3) . . ?
C18 C19 H19 120.0 . . ?
N4 C20 C18 178.8(4) . . ?
C1 N1 C13 106.1(3) . . ?
C5 N2 C1 120.5(3) . . ?
C5 N2 C12 132.1(3) . . ?
C12 N2 C1 107.3(2) . . ?
C11 N3 C12 126.4(3) . . ?
C5 O1 C6 121.3(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
C1 C2 C3 C4 -0.9(5) . . . . ?
C2 C1 N1 C13 -176.9(3) . . . . ?
C2 C1 N2 C5 -0.1(4) . . . . ?
C2 C1 N2 C12 176.9(3) . . . . ?
C2 C3 C4 C5 0.4(5) . . . . ?
C3 C4 C5 N2 0.2(4) . . . . ?
C3 C4 C5 O1 -172.6(3) . . . . ?
C4 C5 N2 C1 -0.4(4) . . . . ?
C4 C5 N2 C12 -176.6(3) . . . . ?
C4 C5 O1 C6 -137.7(3) . . . . ?
C6 C7 C8 C9 -58.8(3) . . . . ?
C6 C11 N3 C12 -1.6(5) . . . . ?
C7 C6 C11 C10 -29.2(4) . . . . ?
C7 C6 C11 N3 161.7(3) . . . . ?
C7 C6 O1 C5 160.7(3) . . . . ?
C7 C8 C9 C10 61.8(3) . . . . ?
C8 C9 C10 C11 -49.4(4) . . . . ?
C9 C10 C11 C6 33.5(4) . . . . ?
C9 C10 C11 N3 -156.1(3) . . . . ?
C10 C11 N3 C12 -171.0(3) . . . . ?
C11 C6 C7 C8 41.8(4) . . . . ?
C11 C6 O1 C5 -75.1(4) . . . . ?
C12 C13 C14 C15 -178.7(3) . . . . ?
C12 C13 C14 C19 2.5(5) . . . . ?
C12 C13 N1 C1 -0.2(3) . . . . ?
C13 C12 N2 C1 0.9(3) . . . . ?
C13 C12 N2 C5 177.4(3) . . . . ?
C13 C12 N3 C11 164.5(3) . . . . ?
C13 C14 C15 C16 -179.2(3) . . . . ?
C13 C14 C19 C18 178.8(3) . . . . ?
C14 C13 N1 C1 -179.4(2) . . . . ?
C14 C15 C16 C17 0.2(5) . . . . ?
C15 C14 C19 C18 0.0(5) . . . . ?
C15 C16 C17 C18 0.2(5) . . . . ?
C16 C17 C18 C19 -0.5(5) . . . . ?
C16 C17 C18 C20 177.0(3) . . . . ?
C17 C18 C19 C14 0.4(5) . . . . ?
C19 C14 C15 C16 -0.3(5) . . . . ?
C20 C18 C19 C14 -177.1(3) . . . . ?
N1 C1 C2 C3 178.3(3) . . . . ?
N1 C1 N2 C5 -178.1(3) . . . . ?
N1 C1 N2 C12 -1.0(3) . . . . ?
N1 C13 C14 C15 0.4(4) . . . . ?
N1 C13 C14 C19 -178.4(3) . . . . ?
N2 C1 C2 C3 0.7(4) . . . . ?
N2 C1 N1 C13 0.8(3) . . . . ?
N2 C5 O1 C6 49.4(4) . . . . ?
N2 C12 C13 C14 178.7(3) . . . . ?
N2 C12 C13 N1 -0.4(3) . . . . ?
N2 C12 N3 C11 -12.7(5) . . . . ?
N3 C12 C13 C14 0.9(5) . . . . ?
N3 C12 C13 N1 -178.2(3) . . . . ?
N3 C12 N2 C1 178.5(3) . . . . ?
N3 C12 N2 C5 -4.9(5) . . . . ?
O1 C5 N2 C1 172.7(3) . . . . ?
O1 C5 N2 C12 -3.5(5) . . . . ?
O1 C6 C7 C8 164.7(2) . . . . ?
O1 C6 C11 C10 -146.0(3) . . . . ?
O1 C6 C11 N3 44.9(4) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'


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_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent: DCM'
