# Electronic Supplementary Material (ESI) for Physical Chemistry Chemical Physics.
# This journal is © the Owner Societies 2018

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

data_stu7092
_database_code_depnum_ccdc_archive 'CCDC 1817427'
_audit_update_record             
;
2018-08-14 deposited with the CCDC.
2018-08-17 downloaded from the CCDC.
;

_audit_creation_method           'APEX3 v2016.1-0'
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C19 H19 N4 O Si'
_chemical_formula_iupac          ?
_chemical_formula_weight         347.47
_chemical_absolute_configuration .

_chemical_melting_point          ?

_space_group_crystal_system      monoclinic
_space_group_name_H-M_alt        'C 1 m 1'
_space_group_name_Hall           'C -2y'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'x, -y, z'
'x+1/2, y+1/2, z'
'x+1/2, -y+1/2, z'

_cell_length_a                   9.6565(5)
_cell_length_b                   17.9910(9)
_cell_length_c                   5.8635(3)
_cell_angle_alpha                90
_cell_angle_beta                 113.819(2)
_cell_angle_gamma                90
_cell_volume                     931.90(8)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    1274
_cell_measurement_theta_min      4.08
_cell_measurement_theta_max      28.28
_cell_measurement_temperature    223.(2)

_exptl_crystal_description       needle
_exptl_crystal_colour            red
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.080
_exptl_crystal_size_min          0.030
_exptl_crystal_density_diffrn    1.238
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             366

_exptl_absorpt_coefficient_mu    0.140
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
Denzo (Otwinowski, Borek, Majewski & Minor, 2003)
;
_exptl_absorpt_correction_T_min  0.97
_exptl_absorpt_correction_T_max  1.00

_exptl_special_details           
;
;

_diffrn_ambient_temperature      223.(2)

_diffrn_source                   MoK\a
_diffrn_source_type              'rotating anode Nonius FR591'

_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_monochromator  'Montel mirror'

_diffrn_measurement_device_type  'Nonius KappaCCD APEXII'
_diffrn_measurement_method       'omega and phi scans'

_diffrn_detector_area_resol_mean ?

_diffrn_reflns_number            4397
_diffrn_reflns_av_R_equivalents  0.0597
_diffrn_reflns_av_unetI/netI     0.0397
_diffrn_reflns_theta_min         4.11
_diffrn_reflns_theta_max         28.58
_diffrn_reflns_theta_full        28.58
_diffrn_measured_fraction_theta_max 0.984
_diffrn_measured_fraction_theta_full 0.984
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_l_min       -7
_diffrn_reflns_limit_l_max       7

_refine_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.

The hydrogens at C6 atom were refined freely.

One phenyl is disordered over two positions. Several
restraints (SADI, SAME, ISOR and SIMU) were used in order to improve 
refinement stability.
;

_reflns_number_total             2193
_reflns_number_gt                1819
_reflns_threshold_expression     'I > 2σ(I)'

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_R_factor_all          0.0837
_refine_ls_R_factor_gt           0.0659
_refine_ls_wR_factor_gt          0.1423
_refine_ls_wR_factor_ref         0.1557
_refine_ls_goodness_of_fit_ref   1.063
_refine_ls_restrained_S_all      1.088
_refine_ls_number_reflns         2193
_refine_ls_number_parameters     185
_refine_ls_number_restraints     190
_refine_ls_number_constraints    ?
_refine_ls_hydrogen_treatment    mixed
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0479P)²+1.3019P] where P=(Fo²+2Fc²)/3'

_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?

_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         0.245
_refine_diff_density_min         -0.172
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_abs_structure_details 
;
Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   0.4(4)

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'
Si Si 0.0817 0.0704 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_computing_data_collection       
;
Collect (Nonius B.V., 1998)
;
_computing_cell_refinement       'Collect (Nonius B.V., 1998)'
_computing_data_reduction        'Denzo-SMN (Otwinowski & Minor, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'XP (Sheldrick, 2014)'
_computing_publication_material  'SHELXL-2014/7 (Sheldrick, 2014)'

loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_refinement_flags_posn
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O O1 0.9245(6) 1.0 0.8141(9) 0.0615(13) Uani d T P S 1.0 . .
N N2 0.7087(5) 0.9335(2) 0.2029(7) 0.0501(9) Uani d . . . 1.0 . .
C C1 0.8459(7) 1.0 0.5924(11) 0.0477(15) Uani d T P S 1.0 A .
C C2 0.6687(7) 1.0 0.0973(12) 0.0452(14) Uani d T P S 1.0 . .
C C3 0.5664(8) 1.0 -0.1622(12) 0.0508(15) Uani d TU P S 1.0 . .
C C4 0.4709(8) 1.0 -0.3732(13) 0.0572(17) Uani d TU P S 1.0 . .
Si Si1 0.3010(2) 1.0 -0.6712(3) 0.0549(5) Uani d TU P S 1.0 . .
C C5 0.3020(9) 0.9154(5) -0.8491(13) 0.092(2) Uani d U . . 1.0 . .
H H5A 0.3879 0.9169 -0.8949 0.138 Uiso calc U . R 1.0 . .
H H5B 0.3095 0.8718 -0.7471 0.138 Uiso calc U . R 1.0 . .
H H5C 0.209 0.913 -0.9987 0.138 Uiso calc U . R 1.0 . .
C C6 0.1397(9) 1.0 -0.5793(14) 0.071(2) Uani d TU P S 1.0 . .
H H6A 0.045(13) 1.0 -0.75(2) 0.106 Uiso d U P S 1.0 . .
H H6B 0.143(8) 1.038(4) -0.448(15) 0.106 Uiso d U . . 1.0 . .
N N1 0.7971(4) 0.9356(2) 0.4541(6) 0.0460(9) Uani d U . D 1.0 . .
C C11 0.8581(11) 0.8650(5) 0.5594(16) 0.052(3) Uani d U P D 0.784(9) A 1
C C12 0.8403(8) 0.8405(4) 0.7678(13) 0.065(2) Uani d U P D 0.784(9) A 1
H H12 0.7911 0.8701 0.8444 0.079 Uiso calc U P R 0.784(9) A 1
C C13 0.8970(12) 0.7706(5) 0.8626(18) 0.090(3) Uani d U P D 0.784(9) A 1
H H13 0.8827 0.7519 1.0012 0.108 Uiso calc U P R 0.784(9) A 1
C C14 0.9722(15) 0.7297(6) 0.757(2) 0.095(3) Uani d U P D 0.784(9) A 1
H H14 1.014 0.6837 0.8272 0.114 Uiso calc U P R 0.784(9) A 1
C C15 0.9883(13) 0.7541(5) 0.548(2) 0.100(3) Uani d U P D 0.784(9) A 1
H H15 1.0384 0.7244 0.4735 0.12 Uiso calc U P R 0.784(9) A 1
C C16 0.9305(10) 0.8231(5) 0.4469(16) 0.076(2) Uani d U P D 0.784(9) A 1
H H16 0.9411 0.8405 0.3036 0.092 Uiso calc U P R 0.784(9) A 1
C C11A 0.832(3) 0.8635(14) 0.586(7) 0.052(10) Uani d U P D 0.216(9) A 2
C C12A 0.968(3) 0.8449(13) 0.777(4) 0.076(8) Uani d U P D 0.216(9) A 2
H H12A 1.0408 0.882 0.8549 0.091 Uiso calc U P R 0.216(9) A 2
C C13A 0.998(3) 0.7721(13) 0.851(6) 0.071(8) Uani d U P D 0.216(9) A 2
H H13A 1.0911 0.7597 0.9808 0.085 Uiso calc U P R 0.216(9) A 2
C C14A 0.895(3) 0.7169(14) 0.739(6) 0.074(8) Uani d U P D 0.216(9) A 2
H H14A 0.9215 0.6666 0.7727 0.088 Uiso calc U P R 0.216(9) A 2
C C15A 0.752(3) 0.7366(14) 0.579(6) 0.097(11) Uani d U P D 0.216(9) A 2
H H15A 0.6736 0.7012 0.5284 0.117 Uiso calc U P R 0.216(9) A 2
C C16A 0.723(3) 0.8081(12) 0.490(5) 0.070(8) Uani d U P D 0.216(9) A 2
H H16A 0.6281 0.8197 0.363 0.084 Uiso calc U P R 0.216(9) A 2


_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_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
O1 C1 . 1.212(7) ?
N2 C2 . 1.331(5) ?
N2 N1 . 1.372(5) ?
C1 N1 2_575 1.383(5) ?
C1 N1 . 1.383(5) ?
C2 N2 2_575 1.331(5) ?
C2 C3 . 1.441(9) ?
C3 C4 . 1.208(9) ?
C4 Si1 . 1.851(7) ?
Si1 C6 . 1.843(8) ?
Si1 C5 . 1.848(8) ?
Si1 C5 2_575 1.848(8) ?
C5 H5A . 0.97 ?
C5 H5B . 0.97 ?
C5 H5C . 0.97 ?
C6 H6A . 1.06(12) ?
C6 H6B . 1.02(8) ?
N1 C11 . 1.431(8) ?
N1 C11A . 1.48(2) ?
C11 C16 . 1.365(14) ?
C11 C12 . 1.373(12) ?
C12 C13 . 1.395(10) ?
C12 H12 . 0.94 ?
C13 C14 . 1.349(11) ?
C13 H13 . 0.94 ?
C14 C15 . 1.365(12) ?
C14 H14 . 0.94 ?
C15 C16 . 1.392(10) ?
C15 H15 . 0.94 ?
C16 H16 . 0.94 ?
C11A C12A . 1.383(19) ?
C11A C16A . 1.39(2) ?
C12A C13A . 1.375(18) ?
C12A H12A . 0.94 ?
C13A C14A . 1.372(19) ?
C13A H13A . 0.94 ?
C14A C15A . 1.366(19) ?
C14A H14A . 0.94 ?
C15A C16A . 1.372(19) ?
C15A H15A . 0.94 ?
C16A H16A . 0.94 ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C2 N2 N1 . . 114.4(4) ?
O1 C1 N1 . 2_575 123.1(2) ?
O1 C1 N1 . . 123.1(2) ?
N1 C1 N1 2_575 . 113.8(5) ?
N2 C2 N2 2_575 . 128.0(6) ?
N2 C2 C3 2_575 . 116.0(3) ?
N2 C2 C3 . . 116.0(3) ?
C4 C3 C2 . . 174.6(8) ?
C3 C4 Si1 . . 170.1(7) ?
C6 Si1 C5 . . 111.3(3) ?
C6 Si1 C5 . 2_575 111.3(3) ?
C5 Si1 C5 . 2_575 111.0(6) ?
C6 Si1 C4 . . 104.8(3) ?
C5 Si1 C4 . . 109.2(3) ?
C5 Si1 C4 2_575 . 109.2(3) ?
Si1 C5 H5A . . 109.5 ?
Si1 C5 H5B . . 109.5 ?
H5A C5 H5B . . 109.5 ?
Si1 C5 H5C . . 109.5 ?
H5A C5 H5C . . 109.5 ?
H5B C5 H5C . . 109.5 ?
Si1 C6 H6A . . 103.(6) ?
Si1 C6 H6B . . 116.(4) ?
H6A C6 H6B . . 118.(6) ?
N2 N1 C1 . . 124.7(4) ?
N2 N1 C11 . . 114.1(5) ?
C1 N1 C11 . . 120.5(5) ?
N2 N1 C11A . . 116.7(14) ?
C1 N1 C11A . . 118.4(15) ?
C16 C11 C12 . . 121.7(7) ?
C16 C11 N1 . . 118.9(8) ?
C12 C11 N1 . . 119.4(9) ?
C11 C12 C13 . . 118.3(8) ?
C11 C12 H12 . . 120.9 ?
C13 C12 H12 . . 120.9 ?
C14 C13 C12 . . 120.4(8) ?
C14 C13 H13 . . 119.8 ?
C12 C13 H13 . . 119.8 ?
C13 C14 C15 . . 120.9(8) ?
C13 C14 H14 . . 119.5 ?
C15 C14 H14 . . 119.5 ?
C14 C15 C16 . . 119.9(9) ?
C14 C15 H15 . . 120.0 ?
C16 C15 H15 . . 120.0 ?
C11 C16 C15 . . 118.7(8) ?
C11 C16 H16 . . 120.6 ?
C15 C16 H16 . . 120.6 ?
C12A C11A C16A . . 118.3(19) ?
C12A C11A N1 . . 125.(2) ?
C16A C11A N1 . . 116.3(17) ?
C13A C12A C11A . . 120.(2) ?
C13A C12A H12A . . 120.2 ?
C11A C12A H12A . . 120.2 ?
C14A C13A C12A . . 121.(2) ?
C14A C13A H13A . . 119.3 ?
C12A C13A H13A . . 119.3 ?
C15A C14A C13A . . 119.(2) ?
C15A C14A H14A . . 120.7 ?
C13A C14A H14A . . 120.7 ?
C14A C15A C16A . . 120.(2) ?
C14A C15A H15A . . 120.0 ?
C16A C15A H15A . . 120.0 ?
C15A C16A C11A . . 121.(2) ?
C15A C16A H16A . . 119.6 ?
C11A C16A H16A . . 119.6 ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
N1 N2 C2 N2 . . . 2_575 2.9(10) ?
N1 N2 C2 C3 . . . . -175.4(6) ?
C2 N2 N1 C1 . . . . -1.3(8) ?
C2 N2 N1 C11 . . . . -171.3(7) ?
C2 N2 N1 C11A . . . . 174.(2) ?
O1 C1 N1 N2 . . . . -179.7(6) ?
N1 C1 N1 N2 2_575 . . . 0.1(9) ?
O1 C1 N1 C11 . . . . -10.3(10) ?
N1 C1 N1 C11 2_575 . . . 169.4(7) ?
O1 C1 N1 C11A . . . . 5.(2) ?
N1 C1 N1 C11A 2_575 . . . -175.(2) ?
N2 N1 C11 C16 . . . . 50.1(10) ?
C1 N1 C11 C16 . . . . -120.3(8) ?
N2 N1 C11 C12 . . . . -128.8(7) ?
C1 N1 C11 C12 . . . . 60.8(10) ?
C16 C11 C12 C13 . . . . -0.6(12) ?
N1 C11 C12 C13 . . . . 178.2(8) ?
C11 C12 C13 C14 . . . . 2.4(14) ?
C12 C13 C14 C15 . . . . -3.0(19) ?
C13 C14 C15 C16 . . . . 2.(2) ?
C12 C11 C16 C15 . . . . -0.5(15) ?
N1 C11 C16 C15 . . . . -179.3(8) ?
C14 C15 C16 C11 . . . . -0.1(17) ?
N2 N1 C11A C12A . . . . 142.(4) ?
C1 N1 C11A C12A . . . . -42.(5) ?
N2 N1 C11A C16A . . . . -30.(5) ?
C1 N1 C11A C16A . . . . 145.(3) ?
C16A C11A C12A C13A . . . . 5.(6) ?
N1 C11A C12A C13A . . . . -167.(4) ?
C11A C12A C13A C14A . . . . 0.(6) ?
C12A C13A C14A C15A . . . . -10.(6) ?
C13A C14A C15A C16A . . . . 14.(6) ?
C14A C15A C16A C11A . . . . -8.(6) ?
C12A C11A C16A C15A . . . . -1.(6) ?
N1 C11A C16A C15A . . . . 171.(3) ?


# start Validation Reply Form
_vrf_PLAT413_stu7092             
;
PROBLEM: Short Inter XH3 .. XHn     H5C      ..H12A             1.60 Ang.  
RESPONSE: This alert is generated becouse there is a large amount of disorder
in the structure. The phenyl substituent is very dinamic and was refined over 
two positions. Several restraints (SADI, SAME, ISOR and SIMU) were used in 
order to improve refinement stability. Moreover, the structure was refined as 
an inversion twin (TWIN, BASF). 
;
_vrf_PLAT391_stu7092             
;
PROBLEM: Deviating Methyl C6        H-C-H Bond Angle ....         84 Degree
RESPONSE: The methyl C6 was found on a special position (sof = 0.5). The 
hydrogens at this C6 atom were refined freely.  
;
# end Validation Reply Form

#=============================================================================
#  end of cif data for "stu7092" (compound 3) 
#=============================================================================
#=============================================================================
#  end of cif file
#=============================================================================

####################################################################### 
# 
# 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_stu7135
_database_code_depnum_ccdc_archive 'CCDC 1817428'
_audit_update_record             
;
2018-08-14 deposited with the CCDC.
2018-08-17 downloaded from the CCDC.
;

_audit_creation_method           'APEX3 v2016.1-0'
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C16 H11 N4 O'
_chemical_formula_iupac          ?
_chemical_formula_weight         275.29
_chemical_absolute_configuration .

_chemical_melting_point          ?

_space_group_crystal_system      orthorhombic
_space_group_name_H-M_alt        'P n a 21'
_space_group_name_Hall           'P 2c -2n'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, z+1/2'
'x+1/2, -y+1/2, z'
'-x+1/2, y+1/2, z+1/2'

_cell_length_a                   17.0182(6)
_cell_length_b                   20.5047(7)
_cell_length_c                   3.86780(10)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1349.68(7)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    1827
_cell_measurement_theta_min      0.88
_cell_measurement_theta_max      68.25
_cell_measurement_temperature    223.(2)

_exptl_crystal_description       needle
_exptl_crystal_colour            red
_exptl_crystal_size_max          0.230
_exptl_crystal_size_mid          0.040
_exptl_crystal_size_min          0.040
_exptl_crystal_density_diffrn    1.355
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             572

_exptl_absorpt_coefficient_mu    0.724
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
Denzo (Otwinowski, Borek, Majewski & Minor, 2003)
;
_exptl_absorpt_correction_T_min  0.85
_exptl_absorpt_correction_T_max  0.97

_exptl_special_details           
;
;

_diffrn_ambient_temperature      223.(2)

_diffrn_source                   CuK\a
_diffrn_source_type              'fine-focus sealed tube'

_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_monochromator  graphite

_diffrn_measurement_device_type  'Nonius KappaCCD APEXII'
_diffrn_measurement_method       'omega and phi scans'

_diffrn_detector_area_resol_mean ?

_diffrn_reflns_number            6206
_diffrn_reflns_av_R_equivalents  0.0450
_diffrn_reflns_av_unetI/netI     0.0372
_diffrn_reflns_theta_min         3.38
_diffrn_reflns_theta_max         67.19
_diffrn_reflns_theta_full        67.19
_diffrn_measured_fraction_theta_max 0.975
_diffrn_measured_fraction_theta_full 0.975
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_k_max       24
_diffrn_reflns_limit_l_min       -4
_diffrn_reflns_limit_l_max       4

_refine_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_number_total             2243
_reflns_number_gt                1979
_reflns_threshold_expression     'I > 2σ(I)'

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_R_factor_all          0.0472
_refine_ls_R_factor_gt           0.0401
_refine_ls_wR_factor_gt          0.0925
_refine_ls_wR_factor_ref         0.0974
_refine_ls_goodness_of_fit_ref   1.050
_refine_ls_restrained_S_all      1.050
_refine_ls_number_reflns         2243
_refine_ls_number_parameters     190
_refine_ls_number_restraints     1
_refine_ls_number_constraints    ?
_refine_ls_hydrogen_treatment    constr
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0434P)²+0.3597P] where P=(Fo²+2Fc²)/3'

_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?

_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         0.132
_refine_diff_density_min         -0.173
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_abs_structure_details 
;
Flack x determined using 710 quotients [(I+)-(I-)]/[(I+)+(I-)]
(Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.3(4)

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'

_computing_data_collection       
;
Collect (Nonius B.V., 1998)
;
_computing_cell_refinement       'Collect (Nonius B.V., 1998)'
_computing_data_reduction        'Denzo-SMN (Otwinowski & Minor, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXS-97 (Sheldrick, 1990)'
_computing_molecular_graphics    'XP (Sheldrick, 2014)'
_computing_publication_material  'SHELXL-2014/7 (Sheldrick, 2014)'

loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_refinement_flags_posn
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O O1 0.91980(12) 0.69042(9) 0.8797(7) 0.0458(6) Uani d . . . 1 . .
N N1 0.80708(13) 0.66333(11) 0.5912(7) 0.0349(6) Uani d . . . 1 . .
N N2 0.73783(13) 0.68068(11) 0.4356(8) 0.0372(6) Uani d . . . 1 . .
C C2 0.72888(16) 0.74489(13) 0.3933(9) 0.0332(7) Uani d . . . 1 . .
N N3 0.77928(13) 0.79222(11) 0.4721(7) 0.0355(6) Uani d . . . 1 . .
N N4 0.84734(13) 0.77127(11) 0.6238(7) 0.0330(6) Uani d . . . 1 . .
C C1 0.86295(17) 0.70702(13) 0.7116(8) 0.0335(7) Uani d . . . 1 . .
C C3 0.65706(17) 0.76641(14) 0.2340(9) 0.0368(7) Uani d . . . 1 . .
C C4 0.59912(18) 0.78602(15) 0.1044(10) 0.0458(8) Uani d . . . 1 . .
H H4 0.5528 0.8017 0.0008 0.055 Uiso calc U . R 1 . .
C C11 0.81685(17) 0.59425(13) 0.6540(8) 0.0361(7) Uani d . . . 1 . .
C C12 0.8851(2) 0.56345(14) 0.5529(10) 0.0452(8) Uani d . . . 1 . .
H H12 0.9261 0.5871 0.4488 0.054 Uiso calc U . R 1 . .
C C13 0.8921(2) 0.49686(16) 0.6077(11) 0.0555(10) Uani d . . . 1 . .
H H13 0.9382 0.475 0.5404 0.067 Uiso calc U . R 1 . .
C C14 0.8316(2) 0.46248(16) 0.7609(11) 0.0588(11) Uani d . . . 1 . .
H H14 0.8368 0.4174 0.7985 0.071 Uiso calc U . R 1 . .
C C15 0.7640(2) 0.49378(15) 0.8584(12) 0.0522(9) Uani d . . . 1 . .
H H15 0.7229 0.4701 0.961 0.063 Uiso calc U . R 1 . .
C C16 0.75611(19) 0.56023(15) 0.8061(9) 0.0432(8) Uani d . . . 1 . .
H H16 0.7099 0.5819 0.8734 0.052 Uiso calc U . R 1 . .
C C21 0.90095(17) 0.82270(13) 0.7186(8) 0.0325(7) Uani d . . . 1 . .
C C22 0.97970(17) 0.81654(14) 0.6417(10) 0.0383(7) Uani d . . . 1 . .
H H22 0.9987 0.7788 0.5323 0.046 Uiso calc U . R 1 . .
C C23 1.03038(19) 0.86683(14) 0.7279(10) 0.0445(8) Uani d . . . 1 . .
H H23 1.0843 0.8632 0.6776 0.053 Uiso calc U . R 1 . .
C C24 1.00203(19) 0.92205(14) 0.8870(10) 0.0445(8) Uani d . . . 1 . .
H H24 1.0368 0.9556 0.9509 0.053 Uiso calc U . R 1 . .
C C25 0.92278(19) 0.92838(14) 0.9529(9) 0.0427(8) Uani d . . . 1 . .
H H25 0.9036 0.967 1.0531 0.051 Uiso calc U . R 1 . .
C C26 0.87133(18) 0.87850(13) 0.8729(9) 0.0371(7) Uani d . . . 1 . .
H H26 0.8174 0.8823 0.9221 0.044 Uiso calc U . R 1 . .


_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_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
O1 C1 . 1.214(4) ?
N1 N2 . 1.370(3) ?
N1 C1 . 1.387(4) ?
N1 C11 . 1.447(4) ?
N2 C2 . 1.335(3) ?
C2 N3 . 1.330(3) ?
C2 C3 . 1.438(4) ?
N3 N4 . 1.368(3) ?
N4 C1 . 1.386(4) ?
N4 C21 . 1.442(3) ?
C3 C4 . 1.177(4) ?
C4 H4 . 0.94 ?
C11 C12 . 1.379(4) ?
C11 C16 . 1.379(4) ?
C12 C13 . 1.387(4) ?
C12 H12 . 0.94 ?
C13 C14 . 1.381(5) ?
C13 H13 . 0.94 ?
C14 C15 . 1.370(5) ?
C14 H14 . 0.94 ?
C15 C16 . 1.384(4) ?
C15 H15 . 0.94 ?
C16 H16 . 0.94 ?
C21 C22 . 1.379(4) ?
C21 C26 . 1.385(4) ?
C22 C23 . 1.385(4) ?
C22 H22 . 0.94 ?
C23 C24 . 1.376(5) ?
C23 H23 . 0.94 ?
C24 C25 . 1.379(4) ?
C24 H24 . 0.94 ?
C25 C26 . 1.381(4) ?
C25 H25 . 0.94 ?
C26 H26 . 0.94 ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
N2 N1 C1 . . 124.7(2) ?
N2 N1 C11 . . 115.3(2) ?
C1 N1 C11 . . 119.8(2) ?
C2 N2 N1 . . 114.1(2) ?
N3 C2 N2 . . 128.1(3) ?
N3 C2 C3 . . 115.0(2) ?
N2 C2 C3 . . 116.9(2) ?
C2 N3 N4 . . 114.5(2) ?
N3 N4 C1 . . 124.5(2) ?
N3 N4 C21 . . 114.5(2) ?
C1 N4 C21 . . 120.8(2) ?
O1 C1 N4 . . 123.4(3) ?
O1 C1 N1 . . 123.0(3) ?
N4 C1 N1 . . 113.6(2) ?
C4 C3 C2 . . 177.9(3) ?
C3 C4 H4 . . 180.0 ?
C12 C11 C16 . . 121.4(3) ?
C12 C11 N1 . . 119.8(3) ?
C16 C11 N1 . . 118.7(3) ?
C11 C12 C13 . . 118.7(3) ?
C11 C12 H12 . . 120.7 ?
C13 C12 H12 . . 120.7 ?
C14 C13 C12 . . 120.3(4) ?
C14 C13 H13 . . 119.9 ?
C12 C13 H13 . . 119.9 ?
C15 C14 C13 . . 120.3(3) ?
C15 C14 H14 . . 119.9 ?
C13 C14 H14 . . 119.9 ?
C14 C15 C16 . . 120.2(3) ?
C14 C15 H15 . . 119.9 ?
C16 C15 H15 . . 119.9 ?
C11 C16 C15 . . 119.2(3) ?
C11 C16 H16 . . 120.4 ?
C15 C16 H16 . . 120.4 ?
C22 C21 C26 . . 121.5(3) ?
C22 C21 N4 . . 119.5(3) ?
C26 C21 N4 . . 118.9(3) ?
C21 C22 C23 . . 119.0(3) ?
C21 C22 H22 . . 120.5 ?
C23 C22 H22 . . 120.5 ?
C24 C23 C22 . . 120.1(3) ?
C24 C23 H23 . . 119.9 ?
C22 C23 H23 . . 119.9 ?
C23 C24 C25 . . 120.2(3) ?
C23 C24 H24 . . 119.9 ?
C25 C24 H24 . . 119.9 ?
C24 C25 C26 . . 120.6(3) ?
C24 C25 H25 . . 119.7 ?
C26 C25 H25 . . 119.7 ?
C25 C26 C21 . . 118.5(3) ?
C25 C26 H26 . . 120.7 ?
C21 C26 H26 . . 120.7 ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
C1 N1 N2 C2 . . . . 2.7(4) ?
C11 N1 N2 C2 . . . . 177.4(3) ?
N1 N2 C2 N3 . . . . 2.5(5) ?
N1 N2 C2 C3 . . . . -179.5(3) ?
N2 C2 N3 N4 . . . . -2.0(5) ?
C3 C2 N3 N4 . . . . 179.9(3) ?
C2 N3 N4 C1 . . . . -3.7(4) ?
C2 N3 N4 C21 . . . . -178.2(3) ?
N3 N4 C1 O1 . . . . -171.7(3) ?
C21 N4 C1 O1 . . . . 2.5(5) ?
N3 N4 C1 N1 . . . . 7.9(4) ?
C21 N4 C1 N1 . . . . -177.9(3) ?
N2 N1 C1 O1 . . . . 172.2(3) ?
C11 N1 C1 O1 . . . . -2.3(5) ?
N2 N1 C1 N4 . . . . -7.4(4) ?
C11 N1 C1 N4 . . . . 178.1(3) ?
N2 N1 C11 C12 . . . . 130.2(3) ?
C1 N1 C11 C12 . . . . -54.8(4) ?
N2 N1 C11 C16 . . . . -47.9(4) ?
C1 N1 C11 C16 . . . . 127.1(3) ?
C16 C11 C12 C13 . . . . -0.2(5) ?
N1 C11 C12 C13 . . . . -178.3(3) ?
C11 C12 C13 C14 . . . . 0.0(6) ?
C12 C13 C14 C15 . . . . 0.3(6) ?
C13 C14 C15 C16 . . . . -0.4(6) ?
C12 C11 C16 C15 . . . . 0.1(5) ?
N1 C11 C16 C15 . . . . 178.2(3) ?
C14 C15 C16 C11 . . . . 0.2(6) ?
N3 N4 C21 C22 . . . . -134.5(3) ?
C1 N4 C21 C22 . . . . 50.8(4) ?
N3 N4 C21 C26 . . . . 42.9(4) ?
C1 N4 C21 C26 . . . . -131.8(3) ?
C26 C21 C22 C23 . . . . 1.4(5) ?
N4 C21 C22 C23 . . . . 178.7(3) ?
C21 C22 C23 C24 . . . . -0.2(5) ?
C22 C23 C24 C25 . . . . -1.8(5) ?
C23 C24 C25 C26 . . . . 2.6(5) ?
C24 C25 C26 C21 . . . . -1.4(5) ?
C22 C21 C26 C25 . . . . -0.6(5) ?
N4 C21 C26 C25 . . . . -178.0(3) ?

####################################################################### 
# 
# 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_stu7889
_database_code_depnum_ccdc_archive 'CCDC 1817430'
_audit_update_record             
;
2018-08-14 deposited with the CCDC.
2018-08-17 downloaded from the CCDC.
;

_audit_creation_method           'APEX3 v2016.1-0'
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C18 H11 N4 O'
_chemical_formula_iupac          ?
_chemical_formula_weight         299.31
_chemical_absolute_configuration .

_chemical_melting_point          ?

_space_group_crystal_system      monoclinic
_space_group_name_H-M_alt        'C 1 m 1'
_space_group_name_Hall           'C -2y'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'x, -y, z'
'x+1/2, y+1/2, z'
'x+1/2, -y+1/2, z'

_cell_length_a                   11.2700(8)
_cell_length_b                   16.9544(11)
_cell_length_c                   3.7589(2)
_cell_angle_alpha                90
_cell_angle_beta                 96.640(2)
_cell_angle_gamma                90
_cell_volume                     713.42(8)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    2760
_cell_measurement_theta_min      2.4014
_cell_measurement_theta_max      25.0736
_cell_measurement_temperature    104.(2)

_exptl_crystal_description       needle
_exptl_crystal_colour            red
_exptl_crystal_size_max          0.152
_exptl_crystal_size_mid          0.081
_exptl_crystal_size_min          0.040
_exptl_crystal_density_diffrn    1.393
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             310

_exptl_absorpt_coefficient_mu    0.091
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
Bruker AXS (2014). SADABS, Version 2014/5, Bruker AXS Inc., Madison, Wisconsin,
USA.
;
_exptl_absorpt_correction_T_min  0.99
_exptl_absorpt_correction_T_max  1.00

_exptl_special_details           
;
;

_diffrn_ambient_temperature      104.(2)

_diffrn_source                   'Mo ImS'
_diffrn_source_type              'micro focus tube'

_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_monochromator  'MX mirror'

_diffrn_measurement_device_type  'Bruker D8 Venture PHOTON 100 CMOS'
_diffrn_measurement_method       'omega and phi scans'

_diffrn_detector_area_resol_mean 10.4167

_diffrn_reflns_number            4586
_diffrn_reflns_av_R_equivalents  0.0336
_diffrn_reflns_av_unetI/netI     0.0292
_diffrn_reflns_theta_min         2.40
_diffrn_reflns_theta_max         25.02
_diffrn_reflns_theta_full        25.02
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measured_fraction_theta_full 0.994
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_l_min       -4
_diffrn_reflns_limit_l_max       4

_refine_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_number_total             1211
_reflns_number_gt                1127
_reflns_threshold_expression     'I > 2σ(I)'

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_R_factor_all          0.0315
_refine_ls_R_factor_gt           0.0267
_refine_ls_wR_factor_gt          0.0572
_refine_ls_wR_factor_ref         0.0592
_refine_ls_goodness_of_fit_ref   1.116
_refine_ls_restrained_S_all      1.115
_refine_ls_number_reflns         1211
_refine_ls_number_parameters     119
_refine_ls_number_restraints     2
_refine_ls_number_constraints    ?
_refine_ls_hydrogen_treatment    mixed
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0248P)²+0.1838P] where P=(Fo²+2Fc²)/3'

_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?

_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         0.117
_refine_diff_density_min         -0.134
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_extinction_coef       0.043(5)
_refine_ls_abs_structure_details 
;
Flack x determined using 480 quotients [(I+)-(I-)]/[(I+)+(I-)]
(Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -1.6(9)

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'

_computing_data_collection       
;
APEX2 v.2014.1-1 (Bruker AXS Inc., 2014)
;
_computing_cell_refinement       'SAINT V8.34A (Bruker AXS Inc., 2013)'
_computing_data_reduction        'SAINT V8.34A (Bruker AXS Inc., 2013)'
_computing_structure_solution    'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'XP (Sheldrick, 2014)'
_computing_publication_material  'SHELXL-2014/7 (Sheldrick, 2014)'

loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_refinement_flags_posn
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
N N1 0.68643(15) 0.43156(10) 0.3556(4) 0.0132(5) Uani d . . . 1 . .
N N2 0.57492(16) 0.42930(11) 0.4709(5) 0.0149(5) Uani d . . . 1 . .
O O1 0.83624(19) 0.5 0.1298(6) 0.0191(6) Uani d T P S 1 . .
C C1 0.7437(3) 0.5 0.2694(9) 0.0134(7) Uani d T P S 1 . .
C C2 0.5272(3) 0.5 0.5137(9) 0.0114(7) Uani d T P S 1 . .
C C3 0.4096(3) 0.5 0.6290(8) 0.0150(7) Uani d T P S 1 . .
C C4 0.3109(3) 0.5 0.7192(9) 0.0158(7) Uani d T P S 1 . .
C C5 0.1972(3) 0.5 0.8237(9) 0.0176(7) Uani d T P S 1 . .
C C6 0.0993(3) 0.5 0.9154(10) 0.0234(8) Uani d T P S 1 . .
H H6 0.018(5) 0.5 1.014(15) 0.063(15) Uiso d . P S 1 . .
C C11 0.73794(19) 0.35545(12) 0.3014(6) 0.0149(5) Uani d . . . 1 . .
C C12 0.8548(2) 0.33946(14) 0.4435(6) 0.0174(5) Uani d . . . 1 . .
H H12 0.903 0.3793 0.5646 0.021 Uiso calc U . R 1 . .
C C13 0.8997(2) 0.26428(15) 0.4054(7) 0.0203(6) Uani d . . . 1 . .
H H13 0.9795 0.2525 0.5005 0.024 Uiso calc U . R 1 . .
C C14 0.8289(2) 0.20602(14) 0.2292(7) 0.0219(6) Uani d . . . 1 . .
H H14 0.8602 0.1545 0.2058 0.026 Uiso calc U . R 1 . .
C C15 0.7127(2) 0.22297(14) 0.0874(6) 0.0198(6) Uani d . . . 1 . .
H H15 0.6645 0.183 -0.0338 0.024 Uiso calc U . R 1 . .
C C16 0.6664(2) 0.29797(13) 0.1219(6) 0.0156(5) Uani d . . . 1 . .
H H16 0.5869 0.3099 0.0242 0.019 Uiso calc U . R 1 . .


_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_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
N1 N2 . 1.377(2) ?
N1 C1 . 1.384(2) ?
N1 C11 . 1.439(3) ?
N2 C2 . 1.331(2) ?
O1 C1 . 1.220(4) ?
C1 N1 2_565 1.384(2) ?
C2 N2 2_565 1.331(2) ?
C2 C3 . 1.442(5) ?
C3 C4 . 1.199(4) ?
C4 C5 . 1.383(4) ?
C5 C6 . 1.193(5) ?
C6 H6 . 1.03(5) ?
C11 C16 . 1.389(3) ?
C11 C12 . 1.390(3) ?
C12 C13 . 1.385(3) ?
C12 H12 . 0.95 ?
C13 C14 . 1.388(4) ?
C13 H13 . 0.95 ?
C14 C15 . 1.386(3) ?
C14 H14 . 0.95 ?
C15 C16 . 1.386(3) ?
C15 H15 . 0.95 ?
C16 H16 . 0.95 ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
N2 N1 C1 . . 124.37(18) ?
N2 N1 C11 . . 114.68(16) ?
C1 N1 C11 . . 120.78(18) ?
C2 N2 N1 . . 114.2(2) ?
O1 C1 N1 . 2_565 123.05(13) ?
O1 C1 N1 . . 123.05(13) ?
N1 C1 N1 2_565 . 113.9(3) ?
N2 C2 N2 2_565 . 128.4(3) ?
N2 C2 C3 2_565 . 115.77(14) ?
N2 C2 C3 . . 115.77(14) ?
C4 C3 C2 . . 178.9(4) ?
C3 C4 C5 . . 179.9(3) ?
C6 C5 C4 . . 179.7(3) ?
C5 C6 H6 . . 176.(3) ?
C16 C11 C12 . . 121.41(19) ?
C16 C11 N1 . . 118.47(19) ?
C12 C11 N1 . . 120.04(19) ?
C13 C12 C11 . . 118.8(2) ?
C13 C12 H12 . . 120.6 ?
C11 C12 H12 . . 120.6 ?
C12 C13 C14 . . 120.5(2) ?
C12 C13 H13 . . 119.7 ?
C14 C13 H13 . . 119.7 ?
C15 C14 C13 . . 120.1(2) ?
C15 C14 H14 . . 120.0 ?
C13 C14 H14 . . 120.0 ?
C16 C15 C14 . . 120.2(2) ?
C16 C15 H15 . . 119.9 ?
C14 C15 H15 . . 119.9 ?
C15 C16 C11 . . 119.0(2) ?
C15 C16 H16 . . 120.5 ?
C11 C16 H16 . . 120.5 ?

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_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
C1 N1 N2 C2 . . . . -3.5(3) ?
C11 N1 N2 C2 . . . . -178.8(2) ?
N2 N1 C1 O1 . . . . -171.5(3) ?
C11 N1 C1 O1 . . . . 3.5(4) ?
N2 N1 C1 N1 . . . 2_565 8.4(4) ?
C11 N1 C1 N1 . . . 2_565 -176.56(17) ?
N1 N2 C2 N2 . . . 2_565 -2.4(4) ?
N1 N2 C2 C3 . . . . 179.1(2) ?
N2 N1 C11 C16 . . . . 44.9(3) ?
C1 N1 C11 C16 . . . . -130.5(3) ?
N2 N1 C11 C12 . . . . -131.74(19) ?
C1 N1 C11 C12 . . . . 52.8(3) ?
C16 C11 C12 C13 . . . . -0.3(3) ?
N1 C11 C12 C13 . . . . 176.2(2) ?
C11 C12 C13 C14 . . . . -0.2(3) ?
C12 C13 C14 C15 . . . . 0.5(4) ?
C13 C14 C15 C16 . . . . -0.2(3) ?
C14 C15 C16 C11 . . . . -0.3(3) ?
C12 C11 C16 C15 . . . . 0.6(3) ?
N1 C11 C16 C15 . . . . -176.04(18) ?


# start Validation Reply Form
_vrf_PLAT089_stu7889             
;
PROBLEM: Poor Data / Parameter Ratio (Zmax < 18) ........       5.55 Note  
RESPONSE: A full set of data was collected, however at the very high angle
some week data (dominated by noise) were omitted. A data cutoff (theta max
25.07) was done using the option SHEL 0.84  
;
# end Validation Reply Form

#=============================================================================
#  end of cif data for "stu7889" (compound 6) 
#=============================================================================
#=============================================================================
#  end of cif file
#=============================================================================

####################################################################### 
# 
# 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_stu8144
_database_code_depnum_ccdc_archive 'CCDC 1817429'
_audit_update_record             
;
2018-08-14 deposited with the CCDC.
2018-08-17 downloaded from the CCDC.
;

_audit_creation_method           'APEX3 v2016.1-0'
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C21 H19 N4 O Si'
_chemical_formula_iupac          ?
_chemical_formula_weight         371.49

_chemical_melting_point          ?

_space_group_crystal_system      monoclinic
_space_group_name_H-M_alt        'P 1 21/m 1'
_space_group_name_Hall           '-P 2yb'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z'
'-x, -y, -z'
'x, -y-1/2, z'

_cell_length_a                   5.9346(2)
_cell_length_b                   16.9487(6)
_cell_length_c                   10.0933(4)
_cell_angle_alpha                90
_cell_angle_beta                 99.999(2)
_cell_angle_gamma                90
_cell_volume                     999.80(6)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    7192
_cell_measurement_theta_min      2.3753
_cell_measurement_theta_max      27.4694
_cell_measurement_temperature    100.(2)

_exptl_crystal_description       prism
_exptl_crystal_colour            red
_exptl_crystal_size_max          0.216
_exptl_crystal_size_mid          0.212
_exptl_crystal_size_min          0.097
_exptl_crystal_density_diffrn    1.234
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             390

_exptl_absorpt_coefficient_mu    0.135
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
Bruker AXS (2014). SADABS, Version 2014/5, Bruker AXS Inc., Madison, Wisconsin,
USA.
;
_exptl_absorpt_correction_T_min  0.97
_exptl_absorpt_correction_T_max  0.99

_exptl_special_details           
;
;

_diffrn_ambient_temperature      100.(2)

_diffrn_source                   'Mo ImS'
_diffrn_source_type              'micro focus tube'

_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_monochromator  'MX mirror'

_diffrn_measurement_device_type  'Bruker D8 Venture PHOTON 100 CMOS'
_diffrn_measurement_method       'omega and phi scans'

_diffrn_detector_area_resol_mean 10.4167

_diffrn_reflns_number            17213
_diffrn_reflns_av_R_equivalents  0.0468
_diffrn_reflns_av_unetI/netI     0.0256
_diffrn_reflns_theta_min         2.38
_diffrn_reflns_theta_max         27.53
_diffrn_reflns_theta_full        27.53
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       13

_refine_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_number_total             2377
_reflns_number_gt                2046
_reflns_threshold_expression     'I > 2σ(I)'

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_R_factor_all          0.0476
_refine_ls_R_factor_gt           0.0385
_refine_ls_wR_factor_gt          0.0885
_refine_ls_wR_factor_ref         0.0930
_refine_ls_goodness_of_fit_ref   1.061
_refine_ls_restrained_S_all      1.061
_refine_ls_number_reflns         2377
_refine_ls_number_parameters     144
_refine_ls_number_restraints     0
_refine_ls_number_constraints    ?
_refine_ls_hydrogen_treatment    mixed
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0346P)²+0.6418P] where P=(Fo²+2Fc²)/3'

_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?

_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         0.311
_refine_diff_density_min         -0.310
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?

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'
Si Si 0.0817 0.0704 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_computing_data_collection       
;
APEX2 v.2014.1-1 (Bruker AXS Inc., 2014)
;
_computing_cell_refinement       'SAINT V8.34A (Bruker AXS Inc., 2013)'
_computing_data_reduction        'SAINT V8.34A (Bruker AXS Inc., 2013)'
_computing_structure_solution    'SHELXL-2014 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick, 2014)'
_computing_molecular_graphics    'XP (Sheldrick, 2014)'
_computing_publication_material  'SHELXL-2014 (Sheldrick, 2014)'

loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_refinement_flags_posn
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Si Si1 1.43224(9) 0.75 0.99475(5) 0.01414(14) Uani d T P S 1 . .
N N1 0.09865(18) 0.68135(6) 0.42115(12) 0.0137(2) Uani d . . . 1 . .
N N2 0.31686(18) 0.67904(7) 0.49326(12) 0.0146(2) Uani d . . . 1 . .
O O1 -0.2102(2) 0.75 0.31104(14) 0.0164(3) Uani d T P S 1 . .
C C1 -0.0215(3) 0.75 0.37903(19) 0.0134(4) Uani d T P S 1 . .
C C2 0.4071(3) 0.75 0.52525(19) 0.0130(4) Uani d T P S 1 . .
C C3 0.6318(3) 0.75 0.60643(19) 0.0141(4) Uani d T P S 1 . .
C C4 0.8167(3) 0.75 0.67689(19) 0.0137(4) Uani d T P S 1 . .
C C5 1.0238(3) 0.75 0.76378(19) 0.0140(4) Uani d T P S 1 . .
C C6 1.1999(3) 0.75 0.8448(2) 0.0156(4) Uani d T P S 1 . .
C C7 1.2712(4) 0.75 1.1367(2) 0.0293(5) Uani d T P S 1 . .
H H7A 1.374(5) 0.75 1.221(3) 0.041(8) Uiso d . P S 1 . .
H H7B 1.181(4) 0.7024(13) 1.128(2) 0.058(7) Uiso d . . . 1 . .
C C8 1.6055(3) 0.65919(9) 0.99170(16) 0.0257(3) Uani d . . . 1 . .
H H8A 1.6855 0.661 0.9146 0.039 Uiso calc U . R 1 . .
H H8B 1.5049 0.613 0.9838 0.039 Uiso calc U . R 1 . .
H H8C 1.7176 0.6556 1.0751 0.039 Uiso calc U . R 1 . .
C C11 0.0095(2) 0.60617(8) 0.36966(15) 0.0175(3) Uani d . . . 1 . .
C C12 -0.1960(2) 0.57850(8) 0.39917(16) 0.0213(3) Uani d . . . 1 . .
H H12 -0.2825 0.6096 0.4505 0.026 Uiso calc U . R 1 . .
C C13 -0.2730(3) 0.50452(9) 0.35233(19) 0.0307(4) Uani d . . . 1 . .
H H13 -0.4121 0.4843 0.3731 0.037 Uiso calc U . R 1 . .
C C14 -0.1485(3) 0.46017(10) 0.2757(2) 0.0374(5) Uani d . . . 1 . .
H H14 -0.2029 0.4098 0.2432 0.045 Uiso calc U . R 1 . .
C C15 0.0552(3) 0.48880(11) 0.2460(2) 0.0376(5) Uani d . . . 1 . .
H H15 0.1396 0.4582 0.1927 0.045 Uiso calc U . R 1 . .
C C16 0.1370(3) 0.56230(10) 0.29395(17) 0.0273(4) Uani d . . . 1 . .
H H16 0.2779 0.5819 0.275 0.033 Uiso calc U . R 1 . .


_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_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
Si1 C8 4_575 1.8541(15) ?
Si1 C8 . 1.8541(15) ?
Si1 C7 . 1.856(2) ?
Si1 C6 . 1.862(2) ?
N1 N2 . 1.3715(15) ?
N1 C1 . 1.3919(15) ?
N1 C11 . 1.4417(17) ?
N2 C2 . 1.3332(14) ?
O1 C1 . 1.208(2) ?
C1 N1 4_575 1.3919(15) ?
C2 N2 4_575 1.3332(14) ?
C2 C3 . 1.439(3) ?
C3 C4 . 1.200(3) ?
C4 C5 . 1.380(3) ?
C5 C6 . 1.210(3) ?
C7 H7A . 0.96(3) ?
C7 H7B . 0.96(2) ?
C8 H8A . 0.98 ?
C8 H8B . 0.98 ?
C8 H8C . 0.98 ?
C11 C16 . 1.382(2) ?
C11 C12 . 1.386(2) ?
C12 C13 . 1.389(2) ?
C12 H12 . 0.95 ?
C13 C14 . 1.381(3) ?
C13 H13 . 0.95 ?
C14 C15 . 1.382(3) ?
C14 H14 . 0.95 ?
C15 C16 . 1.393(2) ?
C15 H15 . 0.95 ?
C16 H16 . 0.95 ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C8 Si1 C8 4_575 . 112.21(11) ?
C8 Si1 C7 4_575 . 111.98(6) ?
C8 Si1 C7 . . 111.98(6) ?
C8 Si1 C6 4_575 . 108.72(6) ?
C8 Si1 C6 . . 108.72(6) ?
C7 Si1 C6 . . 102.69(10) ?
N2 N1 C1 . . 124.91(11) ?
N2 N1 C11 . . 114.82(10) ?
C1 N1 C11 . . 119.49(11) ?
C2 N2 N1 . . 113.91(11) ?
O1 C1 N1 . . 123.29(8) ?
O1 C1 N1 . 4_575 123.29(8) ?
N1 C1 N1 . 4_575 113.42(16) ?
N2 C2 N2 4_575 . 128.87(17) ?
N2 C2 C3 4_575 . 115.56(8) ?
N2 C2 C3 . . 115.56(8) ?
C4 C3 C2 . . 178.4(2) ?
C3 C4 C5 . . 177.0(2) ?
C6 C5 C4 . . 177.0(2) ?
C5 C6 Si1 . . 168.56(17) ?
Si1 C7 H7A . . 110.6(17) ?
Si1 C7 H7B . . 106.5(14) ?
H7A C7 H7B . . 109.7(16) ?
Si1 C8 H8A . . 109.5 ?
Si1 C8 H8B . . 109.5 ?
H8A C8 H8B . . 109.5 ?
Si1 C8 H8C . . 109.5 ?
H8A C8 H8C . . 109.5 ?
H8B C8 H8C . . 109.5 ?
C16 C11 C12 . . 121.55(14) ?
C16 C11 N1 . . 118.21(13) ?
C12 C11 N1 . . 120.21(13) ?
C11 C12 C13 . . 118.82(15) ?
C11 C12 H12 . . 120.6 ?
C13 C12 H12 . . 120.6 ?
C14 C13 C12 . . 120.35(16) ?
C14 C13 H13 . . 119.8 ?
C12 C13 H13 . . 119.8 ?
C13 C14 C15 . . 120.20(15) ?
C13 C14 H14 . . 119.9 ?
C15 C14 H14 . . 119.9 ?
C14 C15 C16 . . 120.26(16) ?
C14 C15 H15 . . 119.9 ?
C16 C15 H15 . . 119.9 ?
C11 C16 C15 . . 118.80(16) ?
C11 C16 H16 . . 120.6 ?
C15 C16 H16 . . 120.6 ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
C1 N1 N2 C2 . . . . 2.1(2) ?
C11 N1 N2 C2 . . . . 171.86(13) ?
N2 N1 C1 O1 . . . . 176.97(15) ?
C11 N1 C1 O1 . . . . 7.6(2) ?
N2 N1 C1 N1 . . . 4_575 -2.1(2) ?
C11 N1 C1 N1 . . . 4_575 -171.40(10) ?
N1 N2 C2 N2 . . . 4_575 -2.2(3) ?
N1 N2 C2 C3 . . . . 177.16(14) ?
C8 Si1 C6 C5 4_575 . . . -118.78(6) ?
C8 Si1 C6 C5 . . . . 118.78(6) ?
C7 Si1 C6 C5 . . . . 0.000(4) ?
N2 N1 C11 C16 . . . . -53.33(18) ?
C1 N1 C11 C16 . . . . 117.04(16) ?
N2 N1 C11 C12 . . . . 124.99(14) ?
C1 N1 C11 C12 . . . . -64.64(19) ?
C16 C11 C12 C13 . . . . 0.7(2) ?
N1 C11 C12 C13 . . . . -177.58(13) ?
C11 C12 C13 C14 . . . . -1.2(2) ?
C12 C13 C14 C15 . . . . 0.6(3) ?
C13 C14 C15 C16 . . . . 0.4(3) ?
C12 C11 C16 C15 . . . . 0.3(2) ?
N1 C11 C16 C15 . . . . 178.64(15) ?
C14 C15 C16 C11 . . . . -0.9(3) ?

