# Electronic Supplementary Material (ESI) for ChemComm.
# This journal is © The Royal Society of Chemistry 2019

####################################################################### 
# 
# 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_2
_database_code_depnum_ccdc_archive 'CCDC 1920524'
loop_
_audit_author_name
_audit_author_address
'Israel carreira'
;Universidad de Burgos
Spain
;
_audit_update_record             
;
2019-06-03 deposited with the CCDC.	2019-07-29 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2016/6
_shelx_SHELXL_version_number     2016/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C20 H21 N4, Cl'
_chemical_formula_sum            'C20 H21 Cl N4'
_chemical_formula_weight         352.86

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/n'
_space_group_name_Hall           '-P 2yn'

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

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

_cell_length_a                   8.463(3)
_cell_length_b                   23.161(8)
_cell_length_c                   9.168(3)
_cell_angle_alpha                90
_cell_angle_beta                 104.664(7)
_cell_angle_gamma                90
_cell_volume                     1738.4(11)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    2014
_cell_measurement_theta_min      2.46
_cell_measurement_theta_max      25.78

_exptl_crystal_description       prism
_exptl_crystal_colour            orange
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.348
_exptl_crystal_F_000             744
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.100
_exptl_crystal_size_min          0.100
_exptl_absorpt_coefficient_mu    0.230
_shelx_estimated_absorpt_T_min   0.955
_shelx_estimated_absorpt_T_max   0.977
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'sealed tube'
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            19796
_diffrn_reflns_av_unetI/netI     0.1308
_diffrn_reflns_av_R_equivalents  0.1022
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -30
_diffrn_reflns_limit_k_max       30
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         1.758
_diffrn_reflns_theta_max         28.261
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.932
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.932
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.932
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             4016
_reflns_number_gt                2198
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0415P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         4016
_refine_ls_number_parameters     240
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1150
_refine_ls_R_factor_gt           0.0543
_refine_ls_wR_factor_ref         0.1086
_refine_ls_wR_factor_gt          0.0960
_refine_ls_goodness_of_fit_ref   0.874
_refine_ls_restrained_S_all      0.874
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.6772(3) 0.22288(11) 0.2153(3) 0.0314(7) Uani 1 1 d . . . . .
H1 H 0.659001 0.222613 0.108722 0.038 Uiso 1 1 calc R U . . .
C2 C 0.7723(3) 0.26117(11) 0.3104(3) 0.0303(7) Uani 1 1 d . . . . .
H2 H 0.832116 0.292236 0.282825 0.036 Uiso 1 1 calc R U . . .
C3 C 0.7660(3) 0.24630(11) 0.4572(3) 0.0274(6) Uani 1 1 d . . . . .
H3 H 0.820128 0.265804 0.547152 0.033 Uiso 1 1 calc R U . . .
C4 C 0.6672(3) 0.19837(10) 0.4478(3) 0.0226(6) Uani 1 1 d . . . . .
C5 C 0.6231(3) 0.16379(10) 0.5610(3) 0.0207(6) Uani 1 1 d . . . . .
C6 C 0.6761(3) 0.16524(10) 0.7203(3) 0.0216(6) Uani 1 1 d . . . . .
C7 C 0.7925(3) 0.20793(11) 0.8108(3) 0.0277(6) Uani 1 1 d . . . . .
H7A H 0.883964 0.213715 0.763056 0.033 Uiso 1 1 calc R U . . .
H7B H 0.838432 0.191957 0.912903 0.033 Uiso 1 1 calc R U . . .
C8 C 0.7146(3) 0.26587(11) 0.8251(3) 0.0387(8) Uani 1 1 d . . . . .
H8A H 0.679474 0.283928 0.725457 0.058 Uiso 1 1 calc R U . . .
H8B H 0.794252 0.290877 0.892484 0.058 Uiso 1 1 calc R U . . .
H8C H 0.619811 0.260269 0.866631 0.058 Uiso 1 1 calc R U . . .
C9 C 0.5991(3) 0.11998(10) 0.7731(3) 0.0225(6) Uani 1 1 d . . . . .
C10 C 0.6177(3) 0.10198(12) 0.9337(3) 0.0357(7) Uani 1 1 d . . . . .
H10A H 0.717984 0.118756 0.997255 0.053 Uiso 1 1 calc R U . . .
H10B H 0.623715 0.059782 0.940784 0.053 Uiso 1 1 calc R U . . .
H10C H 0.523559 0.115638 0.967962 0.053 Uiso 1 1 calc R U . . .
C11 C 0.4984(3) 0.09128(10) 0.6483(3) 0.0212(6) Uani 1 1 d . . . . .
C12 C 0.4002(3) 0.04367(11) 0.6469(3) 0.0233(6) Uani 1 1 d . . . . .
H12 H 0.395855 0.027882 0.741451 0.028 Uiso 1 1 calc R U . . .
C13 C 0.2007(3) -0.02775(11) 0.5189(3) 0.0238(6) Uani 1 1 d . . . . .
C14 C 0.1741(3) -0.05437(11) 0.6450(3) 0.0278(6) Uani 1 1 d . . . . .
H14 H 0.234754 -0.042426 0.742212 0.033 Uiso 1 1 calc R U . . .
C15 C 0.0595(3) -0.09861(11) 0.6319(3) 0.0311(7) Uani 1 1 d . . . . .
H15 H 0.044076 -0.116556 0.720475 0.037 Uiso 1 1 calc R U . . .
C16 C -0.0313(3) -0.11668(11) 0.4936(3) 0.0333(7) Uani 1 1 d . . . . .
H16 H -0.109444 -0.146666 0.486651 0.040 Uiso 1 1 calc R U . . .
C17 C -0.0084(3) -0.09090(10) 0.3636(3) 0.0276(6) Uani 1 1 d . . . . .
C18 C -0.0794(3) -0.09692(12) 0.2064(3) 0.0349(7) Uani 1 1 d . . . . .
H18 H -0.162576 -0.123519 0.160450 0.042 Uiso 1 1 calc R U . . .
C19 C -0.0081(3) -0.05840(11) 0.1344(3) 0.0343(7) Uani 1 1 d . . . . .
H19 H -0.034583 -0.053054 0.028198 0.041 Uiso 1 1 calc R U . . .
C20 C 0.1097(3) -0.04657(10) 0.3784(3) 0.0229(6) Uani 1 1 d . . . . .
N1 N 0.6123(3) 0.18519(9) 0.2966(2) 0.0269(5) Uani 1 1 d . . . . .
N2 N 0.5158(2) 0.11960(9) 0.5209(2) 0.0216(5) Uani 1 1 d . . . . .
N3 N 0.3117(2) 0.01832(9) 0.5240(2) 0.0224(5) Uani 1 1 d . . . . .
N4 N 0.1088(3) -0.02777(9) 0.2365(2) 0.0274(5) Uani 1 1 d . . . . .
Cl01 Cl 0.35723(8) 0.07343(3) 0.20129(7) 0.0326(2) Uani 1 1 d . . . . .
H2A H 0.466(3) 0.1080(11) 0.419(3) 0.039 Uiso 1 1 d . U . . .
H4 H 0.164(3) -0.0007(11) 0.211(3) 0.039 Uiso 1 1 d . U . . .
H3A H 0.314(3) 0.0337(11) 0.431(3) 0.039 Uiso 1 1 d . U . . .
H1A H 0.553(3) 0.1538(11) 0.261(3) 0.039 Uiso 1 1 d . U . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 N1 1.351(3) . ?
C1 C2 1.356(3) . ?
C1 H1 0.9500 . ?
C2 C3 1.403(3) . ?
C2 H2 0.9500 . ?
C3 C4 1.379(3) . ?
C3 H3 0.9500 . ?
C4 N1 1.380(3) . ?
C4 C5 1.433(3) . ?
C5 N2 1.356(3) . ?
C5 C6 1.416(3) . ?
C6 C9 1.385(3) . ?
C6 C7 1.491(3) . ?
C7 C8 1.515(3) . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C8 H8A 0.9800 . ?
C8 H8B 0.9800 . ?
C8 H8C 0.9800 . ?
C9 C11 1.408(3) . ?
C9 C10 1.499(3) . ?
C10 H10A 0.9800 . ?
C10 H10B 0.9800 . ?
C10 H10C 0.9800 . ?
C11 C12 1.379(3) . ?
C11 N2 1.379(3) . ?
C12 N3 1.322(3) . ?
C12 H12 0.9500 . ?
C13 C14 1.378(3) . ?
C13 C20 1.392(3) . ?
C13 N3 1.414(3) . ?
C14 C15 1.395(3) . ?
C14 H14 0.9500 . ?
C15 C16 1.371(4) . ?
C15 H15 0.9500 . ?
C16 C17 1.390(3) . ?
C16 H16 0.9500 . ?
C17 C20 1.416(3) . ?
C17 C18 1.421(4) . ?
C18 C19 1.340(3) . ?
C18 H18 0.9500 . ?
C19 N4 1.375(3) . ?
C19 H19 0.9500 . ?
C20 N4 1.370(3) . ?
N1 H1A 0.90(2) . ?
N2 H2A 0.96(2) . ?
N3 H3A 0.93(2) . ?
N4 H4 0.85(2) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N1 C1 C2 109.0(2) . . ?
N1 C1 H1 125.5 . . ?
C2 C1 H1 125.5 . . ?
C1 C2 C3 107.2(2) . . ?
C1 C2 H2 126.4 . . ?
C3 C2 H2 126.4 . . ?
C4 C3 C2 107.9(2) . . ?
C4 C3 H3 126.0 . . ?
C2 C3 H3 126.0 . . ?
C3 C4 N1 106.6(2) . . ?
C3 C4 C5 132.0(2) . . ?
N1 C4 C5 121.4(2) . . ?
N2 C5 C6 108.2(2) . . ?
N2 C5 C4 120.4(2) . . ?
C6 C5 C4 131.4(2) . . ?
C9 C6 C5 106.8(2) . . ?
C9 C6 C7 127.6(2) . . ?
C5 C6 C7 125.6(2) . . ?
C6 C7 C8 113.3(2) . . ?
C6 C7 H7A 108.9 . . ?
C8 C7 H7A 108.9 . . ?
C6 C7 H7B 108.9 . . ?
C8 C7 H7B 108.9 . . ?
H7A C7 H7B 107.7 . . ?
C7 C8 H8A 109.5 . . ?
C7 C8 H8B 109.5 . . ?
H8A C8 H8B 109.5 . . ?
C7 C8 H8C 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
C6 C9 C11 108.3(2) . . ?
C6 C9 C10 127.8(2) . . ?
C11 C9 C10 123.9(2) . . ?
C9 C10 H10A 109.5 . . ?
C9 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
C9 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
C12 C11 N2 124.4(2) . . ?
C12 C11 C9 128.6(2) . . ?
N2 C11 C9 106.9(2) . . ?
N3 C12 C11 125.0(2) . . ?
N3 C12 H12 117.5 . . ?
C11 C12 H12 117.5 . . ?
C14 C13 C20 117.8(2) . . ?
C14 C13 N3 123.9(2) . . ?
C20 C13 N3 118.3(2) . . ?
C13 C14 C15 120.9(3) . . ?
C13 C14 H14 119.5 . . ?
C15 C14 H14 119.5 . . ?
C16 C15 C14 121.2(3) . . ?
C16 C15 H15 119.4 . . ?
C14 C15 H15 119.4 . . ?
C15 C16 C17 119.7(3) . . ?
C15 C16 H16 120.2 . . ?
C17 C16 H16 120.2 . . ?
C16 C17 C20 118.5(2) . . ?
C16 C17 C18 135.5(3) . . ?
C20 C17 C18 106.0(2) . . ?
C19 C18 C17 107.9(2) . . ?
C19 C18 H18 126.1 . . ?
C17 C18 H18 126.1 . . ?
C18 C19 N4 110.1(2) . . ?
C18 C19 H19 124.9 . . ?
N4 C19 H19 124.9 . . ?
N4 C20 C13 130.4(2) . . ?
N4 C20 C17 107.8(2) . . ?
C13 C20 C17 121.9(2) . . ?
C1 N1 C4 109.3(2) . . ?
C1 N1 H1A 126.2(17) . . ?
C4 N1 H1A 124.0(17) . . ?
C5 N2 C11 109.7(2) . . ?
C5 N2 H2A 125.2(15) . . ?
C11 N2 H2A 124.9(15) . . ?
C12 N3 C13 126.3(2) . . ?
C12 N3 H3A 118.2(16) . . ?
C13 N3 H3A 115.3(16) . . ?
C20 N4 C19 108.2(2) . . ?
C20 N4 H4 128.9(18) . . ?
C19 N4 H4 122.8(18) . . ?

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 C3 0.1(3) . . . . ?
C1 C2 C3 C4 0.6(3) . . . . ?
C2 C3 C4 N1 -1.1(3) . . . . ?
C2 C3 C4 C5 177.2(2) . . . . ?
C3 C4 C5 N2 176.9(2) . . . . ?
N1 C4 C5 N2 -5.0(3) . . . . ?
C3 C4 C5 C6 -5.2(4) . . . . ?
N1 C4 C5 C6 172.9(2) . . . . ?
N2 C5 C6 C9 1.0(3) . . . . ?
C4 C5 C6 C9 -177.1(2) . . . . ?
N2 C5 C6 C7 -178.9(2) . . . . ?
C4 C5 C6 C7 3.0(4) . . . . ?
C9 C6 C7 C8 -101.5(3) . . . . ?
C5 C6 C7 C8 78.4(3) . . . . ?
C5 C6 C9 C11 -0.6(3) . . . . ?
C7 C6 C9 C11 179.3(2) . . . . ?
C5 C6 C9 C10 178.2(2) . . . . ?
C7 C6 C9 C10 -1.8(4) . . . . ?
C6 C9 C11 C12 179.5(2) . . . . ?
C10 C9 C11 C12 0.6(4) . . . . ?
C6 C9 C11 N2 0.0(3) . . . . ?
C10 C9 C11 N2 -178.9(2) . . . . ?
N2 C11 C12 N3 1.0(4) . . . . ?
C9 C11 C12 N3 -178.4(2) . . . . ?
C20 C13 C14 C15 -0.2(4) . . . . ?
N3 C13 C14 C15 178.3(2) . . . . ?
C13 C14 C15 C16 -0.6(4) . . . . ?
C14 C15 C16 C17 0.5(4) . . . . ?
C15 C16 C17 C20 0.3(4) . . . . ?
C15 C16 C17 C18 -178.4(3) . . . . ?
C16 C17 C18 C19 178.5(3) . . . . ?
C20 C17 C18 C19 -0.4(3) . . . . ?
C17 C18 C19 N4 1.0(3) . . . . ?
C14 C13 C20 N4 178.9(2) . . . . ?
N3 C13 C20 N4 0.4(4) . . . . ?
C14 C13 C20 C17 1.0(3) . . . . ?
N3 C13 C20 C17 -177.5(2) . . . . ?
C16 C17 C20 N4 -179.5(2) . . . . ?
C18 C17 C20 N4 -0.4(3) . . . . ?
C16 C17 C20 C13 -1.1(4) . . . . ?
C18 C17 C20 C13 178.0(2) . . . . ?
C2 C1 N1 C4 -0.8(3) . . . . ?
C3 C4 N1 C1 1.1(3) . . . . ?
C5 C4 N1 C1 -177.4(2) . . . . ?
C6 C5 N2 C11 -1.0(3) . . . . ?
C4 C5 N2 C11 177.3(2) . . . . ?
C12 C11 N2 C5 -178.9(2) . . . . ?
C9 C11 N2 C5 0.6(3) . . . . ?
C11 C12 N3 C13 -175.0(2) . . . . ?
C14 C13 N3 C12 -2.6(4) . . . . ?
C20 C13 N3 C12 175.9(2) . . . . ?
C13 C20 N4 C19 -177.2(2) . . . . ?
C17 C20 N4 C19 1.0(3) . . . . ?
C18 C19 N4 C20 -1.3(3) . . . . ?

_refine_diff_density_max         0.396
_refine_diff_density_min         -0.397
_refine_diff_density_rms         0.060

