# Electronic Supplementary Material (ESI) for RSC Advances.
# This journal is © The Royal Society of Chemistry 2021

####################################################################### 
# 
# 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. 
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#######################################################################

data_CPMD10a_19m_mb6_isa3_0s
_database_code_depnum_ccdc_archive 'CCDC 2087921'
loop_
_audit_author_name
_audit_author_address
'Manuel Fernandes'
;University of the Witwatersrand
South Africa
;
_audit_update_record             
;
2021-06-03 deposited with the CCDC.	2021-07-07 downloaded from the CCDC.
;
_audit_creation_date             2021-05-26
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6272)
;
_shelx_SHELXL_version_number     2017/1
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C17 H25 N3'
_chemical_formula_sum            'C17 H25 N3'
_chemical_formula_weight         271.40
_chemical_melting_point          398-400
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'

_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/c 1'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   9.7065(8)
_cell_length_b                   18.7394(15)
_cell_length_c                   8.5024(7)
_cell_angle_alpha                90
_cell_angle_beta                 99.072(2)
_cell_angle_gamma                90
_cell_volume                     1527.2(2)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    2164
_cell_measurement_temperature    173.15
_cell_measurement_theta_max      26.96
_cell_measurement_theta_min      2.39
_shelx_estimated_absorpt_T_max   0.992
_shelx_estimated_absorpt_T_min   0.975
_exptl_absorpt_coefficient_mu    0.071
_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    1.180
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             592
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
2.00 -1.00 1.00 0.1110
-2.00 1.00 0.00 0.1730
-3.00 -1.00 2.00 0.0980
1.00 0.00 -2.00 0.1050
0.00 1.00 0.00 0.0540
0.00 -1.00 0.00 0.0430
0.00 -3.00 -1.00 0.0700
1.00 2.00 1.00 0.1120
-1.00 -2.00 -1.00 0.1450
-2.00 -3.00 0.00 0.1080
2.00 3.00 0.00 0.1370

_exptl_crystal_size_max          0.366
_exptl_crystal_size_mid          0.343
_exptl_crystal_size_min          0.108
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0590
_diffrn_reflns_av_unetI/netI     0.0869
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       25
_diffrn_reflns_limit_k_min       -25
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_number            12390
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.470
_diffrn_reflns_theta_min         2.125
_diffrn_ambient_temperature      173.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.996
_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_source_current           40.0
_diffrn_source_power             2.0
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2121
_reflns_number_total             3843
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT v8.34A (Bruker, 2013)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT v8.34A (Bruker, 2013)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL  (Sheldrick, 2008)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         0.172
_refine_diff_density_min         -0.206
_refine_diff_density_rms         0.039
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.825
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     191
_refine_ls_number_reflns         3843
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0883
_refine_ls_R_factor_gt           0.0396
_refine_ls_restrained_S_all      0.825
_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)+(0.0337P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0727
_refine_ls_wR_factor_ref         0.0817
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C8(H8A,H8B)
2.b Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C4(H4), C5(H5)
2.c Idealised Me refined as rotating group:
 C11(H11A,H11B,H11C), C12(H12A,H12B,H12C), C13(H13A,H13B,H13C), C15(H15A,H15B,
 H15C), C16(H16A,H16B,H16C), C17(H17A,H17B,H17C)
;
_atom_sites_solution_hydrogens   mixed
_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
N1 N 0.44882(11) 0.39135(6) 0.48134(13) 0.0243(3) Uani 1 1 d . . . . .
H1 H 0.5276(15) 0.4159(7) 0.5217(16) 0.037(4) Uiso 1 1 d . . . . .
N2 N 0.20033(10) 0.40983(5) 0.25396(12) 0.0208(2) Uani 1 1 d . . . . .
N3 N 0.26665(10) 0.53058(6) 0.35451(11) 0.0214(2) Uani 1 1 d . . . . .
C1 C 0.44501(13) 0.36726(7) 0.32472(16) 0.0231(3) Uani 1 1 d . . . . .
C2 C 0.56176(14) 0.33524(7) 0.27737(17) 0.0301(3) Uani 1 1 d . . . . .
H2 H 0.646124 0.331749 0.350687 0.036 Uiso 1 1 calc R U . . .
C3 C 0.55579(15) 0.30865(7) 0.12530(18) 0.0344(4) Uani 1 1 d . . . . .
H3 H 0.636119 0.286959 0.095050 0.041 Uiso 1 1 calc R U . . .
C4 C 0.43430(15) 0.31316(7) 0.01615(17) 0.0330(4) Uani 1 1 d . . . . .
H4 H 0.430564 0.294091 -0.087963 0.040 Uiso 1 1 calc R U . . .
C5 C 0.31841(14) 0.34570(7) 0.06020(16) 0.0275(3) Uani 1 1 d . . . . .
H5 H 0.235051 0.349510 -0.014653 0.033 Uiso 1 1 calc R U . . .
C6 C 0.32266(13) 0.37287(6) 0.21279(15) 0.0219(3) Uani 1 1 d . . . . .
C7 C 0.11931(13) 0.36255(7) 0.35260(15) 0.0240(3) Uani 1 1 d . . . . .
C8 C 0.21179(13) 0.36084(7) 0.51917(15) 0.0238(3) Uani 1 1 d . . . . .
H8A H 0.154206 0.367975 0.604175 0.029 Uiso 1 1 calc R U . . .
H8B H 0.260834 0.314523 0.536829 0.029 Uiso 1 1 calc R U . . .
C9 C 0.31708(13) 0.42214(6) 0.51909(14) 0.0213(3) Uani 1 1 d . . . . .
C10 C 0.25704(12) 0.46382(7) 0.37038(14) 0.0198(3) Uani 1 1 d . . . . .
C11 C 0.09264(15) 0.28910(7) 0.27843(17) 0.0355(4) Uani 1 1 d . . . . .
H11A H 0.181907 0.265343 0.274086 0.053 Uiso 1 1 calc R U . . .
H11B H 0.040811 0.293987 0.170326 0.053 Uiso 1 1 calc R U . . .
H11C H 0.037986 0.260578 0.343009 0.053 Uiso 1 1 calc R U . . .
C12 C -0.01874(14) 0.39938(8) 0.36132(17) 0.0325(3) Uani 1 1 d . . . . .
H12A H -0.072017 0.371204 0.428017 0.049 Uiso 1 1 calc R U . . .
H12B H -0.072198 0.403677 0.253902 0.049 Uiso 1 1 calc R U . . .
H12C H -0.001028 0.447022 0.407651 0.049 Uiso 1 1 calc R U . . .
C13 C 0.34506(14) 0.46368(7) 0.67327(14) 0.0279(3) Uani 1 1 d . . . . .
H13A H 0.377688 0.431035 0.761341 0.042 Uiso 1 1 calc R U . . .
H13B H 0.258955 0.487072 0.692462 0.042 Uiso 1 1 calc R U . . .
H13C H 0.416687 0.499854 0.665952 0.042 Uiso 1 1 calc R U . . .
C14 C 0.21290(13) 0.56904(7) 0.20342(14) 0.0229(3) Uani 1 1 d . . . . .
C15 C 0.27942(14) 0.54148(7) 0.06375(15) 0.0293(3) Uani 1 1 d . . . . .
H15A H 0.244421 0.493424 0.034814 0.044 Uiso 1 1 calc R U . . .
H15B H 0.381014 0.539873 0.094543 0.044 Uiso 1 1 calc R U . . .
H15C H 0.255492 0.573455 -0.027677 0.044 Uiso 1 1 calc R U . . .
C16 C 0.25200(15) 0.64723(7) 0.23407(16) 0.0335(4) Uani 1 1 d . . . . .
H16A H 0.353766 0.651774 0.257130 0.050 Uiso 1 1 calc R U . . .
H16B H 0.211184 0.664596 0.325231 0.050 Uiso 1 1 calc R U . . .
H16C H 0.216153 0.675545 0.139541 0.050 Uiso 1 1 calc R U . . .
C17 C 0.05428(13) 0.56271(8) 0.16690(16) 0.0308(3) Uani 1 1 d . . . . .
H17A H 0.028298 0.512591 0.147166 0.046 Uiso 1 1 calc R U . . .
H17B H 0.019216 0.591118 0.072263 0.046 Uiso 1 1 calc R U . . .
H17C H 0.013486 0.580350 0.257839 0.046 Uiso 1 1 calc R 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
N1 H1 0.911(14) . ?
N1 C1 1.4010(16) . ?
N1 C9 1.4834(15) . ?
N2 C6 1.4640(16) . ?
N2 C7 1.5215(15) . ?
N2 C10 1.4610(15) . ?
N3 C10 1.2633(15) . ?
N3 C14 1.4934(15) . ?
C1 C2 1.3966(17) . ?
C1 C6 1.4038(18) . ?
C2 H2 0.9500 . ?
C2 C3 1.3783(19) . ?
C3 H3 0.9500 . ?
C3 C4 1.383(2) . ?
C4 H4 0.9500 . ?
C4 C5 1.3821(18) . ?
C5 H5 0.9500 . ?
C5 C6 1.3882(17) . ?
C7 C8 1.5529(17) . ?
C7 C11 1.5191(17) . ?
C7 C12 1.5195(18) . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C8 C9 1.5375(17) . ?
C9 C10 1.5219(17) . ?
C9 C13 1.5119(17) . ?
C11 H11A 0.9800 . ?
C11 H11B 0.9800 . ?
C11 H11C 0.9800 . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12C 0.9800 . ?
C13 H13A 0.9800 . ?
C13 H13B 0.9800 . ?
C13 H13C 0.9800 . ?
C14 C15 1.5283(18) . ?
C14 C16 1.5257(17) . ?
C14 C17 1.5265(18) . ?
C15 H15A 0.9800 . ?
C15 H15B 0.9800 . ?
C15 H15C 0.9800 . ?
C16 H16A 0.9800 . ?
C16 H16B 0.9800 . ?
C16 H16C 0.9800 . ?
C17 H17A 0.9800 . ?
C17 H17B 0.9800 . ?
C17 H17C 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1 N1 H1 114.5(9) . . ?
C1 N1 C9 115.88(10) . . ?
C9 N1 H1 115.0(9) . . ?
C6 N2 C7 111.44(9) . . ?
C10 N2 C6 104.86(9) . . ?
C10 N2 C7 101.66(9) . . ?
C10 N3 C14 123.23(11) . . ?
N1 C1 C6 120.86(11) . . ?
C2 C1 N1 120.76(12) . . ?
C2 C1 C6 118.35(12) . . ?
C1 C2 H2 119.7 . . ?
C3 C2 C1 120.65(13) . . ?
C3 C2 H2 119.7 . . ?
C2 C3 H3 119.6 . . ?
C2 C3 C4 120.83(13) . . ?
C4 C3 H3 119.6 . . ?
C3 C4 H4 120.4 . . ?
C5 C4 C3 119.29(13) . . ?
C5 C4 H4 120.4 . . ?
C4 C5 H5 119.7 . . ?
C4 C5 C6 120.63(13) . . ?
C6 C5 H5 119.7 . . ?
C1 C6 N2 120.31(11) . . ?
C5 C6 N2 119.42(11) . . ?
C5 C6 C1 120.23(12) . . ?
N2 C7 C8 103.89(9) . . ?
C11 C7 N2 111.58(10) . . ?
C11 C7 C8 113.34(11) . . ?
C11 C7 C12 109.75(11) . . ?
C12 C7 N2 107.38(10) . . ?
C12 C7 C8 110.63(10) . . ?
C7 C8 H8A 110.6 . . ?
C7 C8 H8B 110.6 . . ?
H8A C8 H8B 108.7 . . ?
C9 C8 C7 105.84(10) . . ?
C9 C8 H8A 110.6 . . ?
C9 C8 H8B 110.6 . . ?
N1 C9 C8 107.77(10) . . ?
N1 C9 C10 104.49(9) . . ?
N1 C9 C13 110.17(10) . . ?
C10 C9 C8 102.49(10) . . ?
C13 C9 C8 114.38(10) . . ?
C13 C9 C10 116.68(11) . . ?
N2 C10 C9 105.15(10) . . ?
N3 C10 N2 129.77(11) . . ?
N3 C10 C9 124.88(11) . . ?
C7 C11 H11A 109.5 . . ?
C7 C11 H11B 109.5 . . ?
C7 C11 H11C 109.5 . . ?
H11A C11 H11B 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
C7 C12 H12A 109.5 . . ?
C7 C12 H12B 109.5 . . ?
C7 C12 H12C 109.5 . . ?
H12A C12 H12B 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C9 C13 H13A 109.5 . . ?
C9 C13 H13B 109.5 . . ?
C9 C13 H13C 109.5 . . ?
H13A C13 H13B 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
N3 C14 C15 111.85(10) . . ?
N3 C14 C16 105.83(10) . . ?
N3 C14 C17 109.99(10) . . ?
C16 C14 C15 109.46(11) . . ?
C16 C14 C17 108.97(11) . . ?
C17 C14 C15 110.60(11) . . ?
C14 C15 H15A 109.5 . . ?
C14 C15 H15B 109.5 . . ?
C14 C15 H15C 109.5 . . ?
H15A C15 H15B 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
C14 C16 H16A 109.5 . . ?
C14 C16 H16B 109.5 . . ?
C14 C16 H16C 109.5 . . ?
H16A C16 H16B 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
C14 C17 H17A 109.5 . . ?
C14 C17 H17B 109.5 . . ?
C14 C17 H17C 109.5 . . ?
H17A C17 H17B 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
N1 C1 C2 C3 177.02(12) . . . . ?
N1 C1 C6 N2 5.45(18) . . . . ?
N1 C1 C6 C5 -176.92(11) . . . . ?
N1 C9 C10 N2 75.38(11) . . . . ?
N1 C9 C10 N3 -100.03(14) . . . . ?
N2 C7 C8 C9 14.98(12) . . . . ?
C1 N1 C9 C8 70.11(13) . . . . ?
C1 N1 C9 C10 -38.39(14) . . . . ?
C1 N1 C9 C13 -164.47(10) . . . . ?
C1 C2 C3 C4 0.1(2) . . . . ?
C2 C1 C6 N2 -176.31(11) . . . . ?
C2 C1 C6 C5 1.32(18) . . . . ?
C2 C3 C4 C5 0.9(2) . . . . ?
C3 C4 C5 C6 -0.8(2) . . . . ?
C4 C5 C6 N2 177.34(11) . . . . ?
C4 C5 C6 C1 -0.32(19) . . . . ?
C6 N2 C7 C8 73.72(12) . . . . ?
C6 N2 C7 C11 -48.74(14) . . . . ?
C6 N2 C7 C12 -169.05(10) . . . . ?
C6 N2 C10 N3 105.82(14) . . . . ?
C6 N2 C10 C9 -69.29(11) . . . . ?
C6 C1 C2 C3 -1.22(19) . . . . ?
C7 N2 C6 C1 -79.51(13) . . . . ?
C7 N2 C6 C5 102.84(13) . . . . ?
C7 N2 C10 N3 -138.02(13) . . . . ?
C7 N2 C10 C9 46.88(11) . . . . ?
C7 C8 C9 N1 -97.61(11) . . . . ?
C7 C8 C9 C10 12.26(12) . . . . ?
C7 C8 C9 C13 139.52(11) . . . . ?
C8 C9 C10 N2 -36.96(11) . . . . ?
C8 C9 C10 N3 147.63(12) . . . . ?
C9 N1 C1 C2 -177.95(11) . . . . ?
C9 N1 C1 C6 0.24(17) . . . . ?
C10 N2 C6 C1 29.69(14) . . . . ?
C10 N2 C6 C5 -147.96(11) . . . . ?
C10 N2 C7 C8 -37.53(11) . . . . ?
C10 N2 C7 C11 -159.99(10) . . . . ?
C10 N2 C7 C12 79.70(11) . . . . ?
C10 N3 C14 C15 -58.27(15) . . . . ?
C10 N3 C14 C16 -177.40(11) . . . . ?
C10 N3 C14 C17 65.04(15) . . . . ?
C11 C7 C8 C9 136.27(11) . . . . ?
C12 C7 C8 C9 -99.97(12) . . . . ?
C13 C9 C10 N2 -162.73(10) . . . . ?
C13 C9 C10 N3 21.86(18) . . . . ?
C14 N3 C10 N2 2.4(2) . . . . ?
C14 N3 C10 C9 176.60(11) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: Ethyl-acetate'
####################################################################### 
# 
# 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_CPMD10e_20m_mb6_cm1_dimed_0f
_database_code_depnum_ccdc_archive 'CCDC 2087922'
loop_
_audit_author_name
_audit_author_address
'Manuel Fernandes'
;University of the Witwatersrand
South Africa
;
_audit_update_record             
;
2021-06-03 deposited with the CCDC.	2021-07-07 downloaded from the CCDC.
;
_audit_creation_date             2020-09-15
_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 H29 N3'
_chemical_formula_sum            'C19 H29 N3'
_chemical_formula_weight         299.45
_chemical_melting_point          394-396
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'

_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                   12.5443(4)
_cell_length_b                   10.8032(3)
_cell_length_c                   13.1304(4)
_cell_angle_alpha                90
_cell_angle_beta                 90.6124(19)
_cell_angle_gamma                90
_cell_volume                     1779.31(9)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    5384
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      26.74
_cell_measurement_theta_min      2.26
_shelx_estimated_absorpt_T_max   0.987
_shelx_estimated_absorpt_T_min   0.966
_exptl_absorpt_coefficient_mu    0.066
_exptl_absorpt_correction_T_max  0.8621
_exptl_absorpt_correction_T_min  0.8278
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.0541 before and 0.0489 after correction. The Ratio of minimum to maximum transmission is 0.9602. The λ/2 correction factor is Not present.'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.118
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       shard
_exptl_crystal_F_000             656
_exptl_crystal_size_max          0.526
_exptl_crystal_size_mid          0.295
_exptl_crystal_size_min          0.197
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0405
_diffrn_reflns_av_unetI/netI     0.0291
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            28352
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.000
_diffrn_reflns_theta_min         2.233
_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                3186
_reflns_number_total             4297
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT v8.34A (Bruker, 2013)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT v8.34A (Bruker, 2013)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.229
_refine_diff_density_min         -0.186
_refine_diff_density_rms         0.038
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.055
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     211
_refine_ls_number_reflns         4297
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0617
_refine_ls_R_factor_gt           0.0421
_refine_ls_restrained_S_all      1.055
_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)+(0.0471P)²+0.3284P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0994
_refine_ls_wR_factor_ref         0.1092
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C10(H10A,H10B)
2.b Aromatic/amide H refined with riding coordinates:
 C2(H2), C5(H5)
2.c Idealised Me refined as rotating group:
 C7(H7A,H7B,H7C), C8(H8A,H8B,H8C), C13(H13A,H13B,H13C), C14(H14A,H14B,H14C),
 C15(H15A,H15B,H15C), C17(H17A,H17B,H17C), C18(H18A,H18B,H18C), C19(H19A,H19B,
 H19C)
;
_atom_sites_solution_hydrogens   mixed
_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 0.65744(9) 0.35463(10) 0.57927(8) 0.0229(2) Uani 1 1 d . . . . .
C2 C 0.62870(9) 0.23066(11) 0.56572(9) 0.0260(3) Uani 1 1 d . . . . .
H2 H 0.558058 0.205541 0.580905 0.031 Uiso 1 1 calc R . . . .
C3 C 0.70059(10) 0.14340(11) 0.53070(9) 0.0273(3) Uani 1 1 d . . . . .
C4 C 0.80583(10) 0.17952(11) 0.51062(9) 0.0294(3) Uani 1 1 d . . . . .
C5 C 0.83308(9) 0.30341(11) 0.52011(9) 0.0278(3) Uani 1 1 d . . . . .
H5 H 0.903586 0.328593 0.504445 0.033 Uiso 1 1 calc R . . . .
C6 C 0.76018(9) 0.39165(11) 0.55186(8) 0.0238(2) Uani 1 1 d . . . . .
C7 C 0.66569(11) 0.01116(12) 0.51498(11) 0.0382(3) Uani 1 1 d . . . . .
H7A H 0.709629 -0.043624 0.557587 0.057 Uiso 1 1 calc GR . . . .
H7B H 0.674048 -0.011404 0.443221 0.057 Uiso 1 1 calc GR . . . .
H7C H 0.590700 0.002544 0.533930 0.057 Uiso 1 1 calc GR . . . .
C8 C 0.88830(11) 0.08601(13) 0.47922(12) 0.0431(4) Uani 1 1 d . . . . .
H8A H 0.864474 0.044297 0.416731 0.065 Uiso 1 1 calc GR . . . .
H8B H 0.897927 0.024732 0.533581 0.065 Uiso 1 1 calc GR . . . .
H8C H 0.956126 0.128165 0.466934 0.065 Uiso 1 1 calc GR . . . .
C9 C 0.81888(9) 0.56941(11) 0.65715(9) 0.0283(3) Uani 1 1 d . . . . .
C10 C 0.71055(9) 0.57349(12) 0.71329(9) 0.0300(3) Uani 1 1 d . . . . .
H10A H 0.703703 0.501864 0.759796 0.036 Uiso 1 1 calc R . . . .
H10B H 0.704172 0.650656 0.753430 0.036 Uiso 1 1 calc R . . . .
C11 C 0.62430(9) 0.56855(11) 0.62854(8) 0.0238(2) Uani 1 1 d . . . . .
C12 C 0.68950(9) 0.58800(10) 0.53212(8) 0.0223(2) Uani 1 1 d . . . . .
C13 C 0.90147(11) 0.48659(14) 0.70784(11) 0.0409(3) Uani 1 1 d . . . . .
H13A H 0.871272 0.403878 0.717861 0.061 Uiso 1 1 calc GR . . . .
H13B H 0.922152 0.521730 0.773969 0.061 Uiso 1 1 calc GR . . . .
H13C H 0.964347 0.480684 0.664448 0.061 Uiso 1 1 calc GR . . . .
C14 C 0.86362(11) 0.69948(13) 0.64559(10) 0.0382(3) Uani 1 1 d . . . . .
H14A H 0.929519 0.696196 0.606274 0.057 Uiso 1 1 calc GR . . . .
H14B H 0.878815 0.734350 0.713101 0.057 Uiso 1 1 calc GR . . . .
H14C H 0.811332 0.751670 0.609964 0.057 Uiso 1 1 calc GR . . . .
C15 C 0.53218(10) 0.65609(12) 0.64480(10) 0.0305(3) Uani 1 1 d . . . . .
H15A H 0.479245 0.644988 0.590127 0.046 Uiso 1 1 calc GR . . . .
H15B H 0.558246 0.741596 0.644235 0.046 Uiso 1 1 calc GR . . . .
H15C H 0.499263 0.638484 0.710583 0.046 Uiso 1 1 calc GR . . . .
C16 C 0.72011(10) 0.65324(11) 0.35796(9) 0.0276(3) Uani 1 1 d . . . . .
C17 C 0.82476(11) 0.72195(13) 0.37731(11) 0.0383(3) Uani 1 1 d . . . . .
H17A H 0.809996 0.801517 0.410113 0.057 Uiso 1 1 calc GR . . . .
H17B H 0.860532 0.736369 0.312390 0.057 Uiso 1 1 calc GR . . . .
H17C H 0.870915 0.672062 0.421843 0.057 Uiso 1 1 calc GR . . . .
C18 C 0.65055(11) 0.72816(13) 0.28400(10) 0.0375(3) Uani 1 1 d . . . . .
H18A H 0.583734 0.683670 0.270840 0.056 Uiso 1 1 calc GR . . . .
H18B H 0.688529 0.739661 0.219851 0.056 Uiso 1 1 calc GR . . . .
H18C H 0.634846 0.809143 0.313942 0.056 Uiso 1 1 calc GR . . . .
C19 C 0.74235(12) 0.52602(12) 0.31257(10) 0.0375(3) Uani 1 1 d . . . . .
H19A H 0.789297 0.479347 0.358709 0.056 Uiso 1 1 calc GR . . . .
H19B H 0.777002 0.535802 0.246515 0.056 Uiso 1 1 calc GR . . . .
H19C H 0.675048 0.481143 0.303318 0.056 Uiso 1 1 calc GR . . . .
N1 N 0.58489(8) 0.43962(9) 0.62059(7) 0.0245(2) Uani 1 1 d . . . . .
N2 N 0.78963(7) 0.52278(9) 0.55125(7) 0.0245(2) Uani 1 1 d . . . . .
N3 N 0.65636(7) 0.64238(9) 0.45306(7) 0.0243(2) Uani 1 1 d . . . . .
H1 H 0.5182(12) 0.4299(14) 0.5968(11) 0.044(4) Uiso 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 1.3978(16) . ?
C1 C6 1.4002(16) . ?
C1 N1 1.4058(14) . ?
C2 H2 0.9500 . ?
C2 C3 1.3865(16) . ?
C3 C4 1.4043(17) . ?
C3 C7 1.5078(17) . ?
C4 C5 1.3866(17) . ?
C4 C8 1.5065(17) . ?
C5 H5 0.9500 . ?
C5 C6 1.3882(16) . ?
C6 N2 1.4640(15) . ?
C7 H7A 0.9800 . ?
C7 H7B 0.9800 . ?
C7 H7C 0.9800 . ?
C8 H8A 0.9800 . ?
C8 H8B 0.9800 . ?
C8 H8C 0.9800 . ?
C9 C10 1.5535(17) . ?
C9 C13 1.5174(17) . ?
C9 C14 1.5213(18) . ?
C9 N2 1.5202(15) . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C10 C11 1.5447(16) . ?
C11 C12 1.5291(16) . ?
C11 C15 1.5101(15) . ?
C11 N1 1.4813(15) . ?
C12 N2 1.4595(14) . ?
C12 N3 1.2595(15) . ?
C13 H13A 0.9800 . ?
C13 H13B 0.9800 . ?
C13 H13C 0.9800 . ?
C14 H14A 0.9800 . ?
C14 H14B 0.9800 . ?
C14 H14C 0.9800 . ?
C15 H15A 0.9800 . ?
C15 H15B 0.9800 . ?
C15 H15C 0.9800 . ?
C16 C17 1.5270(18) . ?
C16 C18 1.5302(17) . ?
C16 C19 1.5250(17) . ?
C16 N3 1.4948(15) . ?
C17 H17A 0.9800 . ?
C17 H17B 0.9800 . ?
C17 H17C 0.9800 . ?
C18 H18A 0.9800 . ?
C18 H18B 0.9800 . ?
C18 H18C 0.9800 . ?
C19 H19A 0.9800 . ?
C19 H19B 0.9800 . ?
C19 H19C 0.9800 . ?
N1 H1 0.896(16) . ?

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 C6 118.54(10) . . ?
C2 C1 N1 120.51(10) . . ?
C6 C1 N1 120.94(10) . . ?
C1 C2 H2 119.1 . . ?
C3 C2 C1 121.73(11) . . ?
C3 C2 H2 119.1 . . ?
C2 C3 C4 119.31(11) . . ?
C2 C3 C7 120.05(11) . . ?
C4 C3 C7 120.65(11) . . ?
C3 C4 C8 120.98(12) . . ?
C5 C4 C3 118.86(11) . . ?
C5 C4 C8 120.17(12) . . ?
C4 C5 H5 119.1 . . ?
C4 C5 C6 121.83(11) . . ?
C6 C5 H5 119.1 . . ?
C1 C6 N2 120.72(10) . . ?
C5 C6 C1 119.48(11) . . ?
C5 C6 N2 119.72(10) . . ?
C3 C7 H7A 109.5 . . ?
C3 C7 H7B 109.5 . . ?
C3 C7 H7C 109.5 . . ?
H7A C7 H7B 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
C4 C8 H8A 109.5 . . ?
C4 C8 H8B 109.5 . . ?
C4 C8 H8C 109.5 . . ?
H8A C8 H8B 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
C13 C9 C10 113.90(11) . . ?
C13 C9 C14 109.72(11) . . ?
C13 C9 N2 111.28(10) . . ?
C14 C9 C10 110.28(10) . . ?
N2 C9 C10 103.87(9) . . ?
N2 C9 C14 107.49(10) . . ?
C9 C10 H10A 110.6 . . ?
C9 C10 H10B 110.6 . . ?
H10A C10 H10B 108.8 . . ?
C11 C10 C9 105.47(9) . . ?
C11 C10 H10A 110.6 . . ?
C11 C10 H10B 110.6 . . ?
C12 C11 C10 102.41(9) . . ?
C15 C11 C10 114.06(10) . . ?
C15 C11 C12 116.61(10) . . ?
N1 C11 C10 108.29(9) . . ?
N1 C11 C12 104.59(9) . . ?
N1 C11 C15 110.09(9) . . ?
N2 C12 C11 104.96(9) . . ?
N3 C12 C11 124.87(10) . . ?
N3 C12 N2 130.01(10) . . ?
C9 C13 H13A 109.5 . . ?
C9 C13 H13B 109.5 . . ?
C9 C13 H13C 109.5 . . ?
H13A C13 H13B 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
C9 C14 H14A 109.5 . . ?
C9 C14 H14B 109.5 . . ?
C9 C14 H14C 109.5 . . ?
H14A C14 H14B 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C11 C15 H15A 109.5 . . ?
C11 C15 H15B 109.5 . . ?
C11 C15 H15C 109.5 . . ?
H15A C15 H15B 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
C17 C16 C18 109.38(11) . . ?
C19 C16 C17 110.04(11) . . ?
C19 C16 C18 109.52(11) . . ?
N3 C16 C17 111.46(10) . . ?
N3 C16 C18 105.38(10) . . ?
N3 C16 C19 110.94(10) . . ?
C16 C17 H17A 109.5 . . ?
C16 C17 H17B 109.5 . . ?
C16 C17 H17C 109.5 . . ?
H17A C17 H17B 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
C16 C18 H18A 109.5 . . ?
C16 C18 H18B 109.5 . . ?
C16 C18 H18C 109.5 . . ?
H18A C18 H18B 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
C16 C19 H19A 109.5 . . ?
C16 C19 H19B 109.5 . . ?
C16 C19 H19C 109.5 . . ?
H19A C19 H19B 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
C1 N1 C11 115.11(9) . . ?
C1 N1 H1 113.3(10) . . ?
C11 N1 H1 116.4(10) . . ?
C6 N2 C9 111.96(9) . . ?
C12 N2 C6 104.56(8) . . ?
C12 N2 C9 101.32(8) . . ?
C12 N3 C16 123.39(10) . . ?

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 1.60(17) . . . . ?
C1 C2 C3 C7 -178.68(11) . . . . ?
C1 C6 N2 C9 81.52(12) . . . . ?
C1 C6 N2 C12 -27.35(13) . . . . ?
C2 C1 C6 C5 -5.20(16) . . . . ?
C2 C1 C6 N2 171.58(10) . . . . ?
C2 C1 N1 C11 -178.54(10) . . . . ?
C2 C3 C4 C5 -4.14(17) . . . . ?
C2 C3 C4 C8 175.88(12) . . . . ?
C3 C4 C5 C6 2.03(18) . . . . ?
C4 C5 C6 C1 2.70(17) . . . . ?
C4 C5 C6 N2 -174.10(10) . . . . ?
C5 C6 N2 C9 -101.71(12) . . . . ?
C5 C6 N2 C12 149.42(10) . . . . ?
C6 C1 C2 C3 3.10(16) . . . . ?
C6 C1 N1 C11 2.18(15) . . . . ?
C7 C3 C4 C5 176.14(11) . . . . ?
C7 C3 C4 C8 -3.84(18) . . . . ?
C8 C4 C5 C6 -177.99(12) . . . . ?
C9 C10 C11 C12 -10.77(12) . . . . ?
C9 C10 C11 C15 -137.68(11) . . . . ?
C9 C10 C11 N1 99.38(11) . . . . ?
C10 C9 N2 C6 -71.43(11) . . . . ?
C10 C9 N2 C12 39.50(11) . . . . ?
C10 C11 C12 N2 36.58(11) . . . . ?
C10 C11 C12 N3 -147.70(11) . . . . ?
C10 C11 N1 C1 -70.72(12) . . . . ?
C11 C12 N2 C6 68.70(10) . . . . ?
C11 C12 N2 C9 -47.79(10) . . . . ?
C11 C12 N3 C16 -176.30(10) . . . . ?
C12 C11 N1 C1 37.95(12) . . . . ?
C13 C9 C10 C11 -138.25(11) . . . . ?
C13 C9 N2 C6 51.54(13) . . . . ?
C13 C9 N2 C12 162.46(10) . . . . ?
C14 C9 C10 C11 97.88(11) . . . . ?
C14 C9 N2 C6 171.70(9) . . . . ?
C14 C9 N2 C12 -77.38(11) . . . . ?
C15 C11 C12 N2 161.83(9) . . . . ?
C15 C11 C12 N3 -22.45(16) . . . . ?
C15 C11 N1 C1 163.97(9) . . . . ?
C17 C16 N3 C12 -60.09(15) . . . . ?
C18 C16 N3 C12 -178.65(11) . . . . ?
C19 C16 N3 C12 62.91(15) . . . . ?
N1 C1 C2 C3 -176.19(10) . . . . ?
N1 C1 C6 C5 174.09(10) . . . . ?
N1 C1 C6 N2 -9.13(16) . . . . ?
N1 C11 C12 N2 -76.33(10) . . . . ?
N1 C11 C12 N3 99.39(12) . . . . ?
N2 C9 C10 C11 -17.03(12) . . . . ?
N2 C12 N3 C16 -1.70(19) . . . . ?
N3 C12 N2 C6 -106.71(13) . . . . ?
N3 C12 N2 C9 136.80(12) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: Ethyl-Acetate'
####################################################################### 
# 
# 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_CPMD11f_20m_mb4_cm2_dicl_0f
_database_code_depnum_ccdc_archive 'CCDC 2087923'
loop_
_audit_author_name
_audit_author_address
'Manuel Fernandes'
;University of the Witwatersrand
South Africa
;
_audit_update_record             
;
2021-06-03 deposited with the CCDC.	2021-07-07 downloaded from the CCDC.
;
_audit_creation_date             2020-09-11
_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         'C18 H27 Cl2 N3'
_chemical_formula_sum            'C18 H27 Cl2 N3'
_chemical_formula_weight         356.32
_chemical_absolute_configuration ?
_chemical_melting_point          417-419
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'
Cl Cl 0.1484 0.1585 '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'

_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      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'

_cell_length_a                   8.1778(2)
_cell_length_b                   10.8600(3)
_cell_length_c                   21.2146(6)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1884.09(9)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    7681
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      23.09
_cell_measurement_theta_min      2.67
_shelx_estimated_absorpt_T_max   0.935
_shelx_estimated_absorpt_T_min   0.912
_exptl_absorpt_coefficient_mu    0.348
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_correction_T_min  0.7059
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.0556 before and 0.0520 after correction. The Ratio of minimum to maximum transmission is 0.9466. The λ/2 correction factor is Not present.'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.256
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       blocky
_exptl_crystal_F_000             760
_exptl_crystal_size_max          0.269
_exptl_crystal_size_mid          0.256
_exptl_crystal_size_min          0.196
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0462
_diffrn_reflns_av_unetI/netI     0.0307
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_number            36147
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.998
_diffrn_reflns_theta_min         1.920
_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         0.751
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     1.000
_reflns_number_gt                3983
_reflns_number_total             4542
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT v8.34A (Bruker, 2013)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT v8.34A (Bruker, 2013)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.194
_refine_diff_density_min         -0.164
_refine_diff_density_rms         0.037
_refine_ls_abs_structure_details 
;
 Flack x determined using 1581 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.03(2)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.069
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     223
_refine_ls_number_reflns         4542
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0372
_refine_ls_R_factor_gt           0.0298
_refine_ls_restrained_S_all      1.069
_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)+(0.0347P)²+0.0736P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0665
_refine_ls_wR_factor_ref         0.0692
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C14(H14A,H14B)
2.b Aromatic/amide H refined with riding coordinates:
 C2(H2), C5(H5)
2.c Idealised Me refined as rotating group:
 C9(H9A,H9B,H9C), C10(H10A,H10B,H10C), C12(H12A,H12B,H12C), C13(H13A,H13B,
 H13C), C16(H16A,H16B,H16C), C17(H17A,H17B,H17C), C18(H18A,H18B,H18C)
;
_atom_sites_solution_hydrogens   mixed
_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 0.6427(3) 0.27969(18) 0.54040(9) 0.0219(4) Uani 1 1 d . . . . .
C2 C 0.5907(3) 0.38043(18) 0.50562(9) 0.0230(4) Uani 1 1 d . . . . .
H2 H 0.521016 0.368934 0.470263 0.028 Uiso 1 1 calc R . . . .
C3 C 0.6405(3) 0.49838(17) 0.52252(9) 0.0228(4) Uani 1 1 d . . . . .
C4 C 0.7427(3) 0.51512(17) 0.57371(9) 0.0225(4) Uani 1 1 d . . . . .
C5 C 0.7931(3) 0.41507(17) 0.60895(9) 0.0218(4) Uani 1 1 d . . . . .
H5 H 0.862757 0.427554 0.644205 0.026 Uiso 1 1 calc R . . . .
C6 C 0.7432(2) 0.29620(17) 0.59354(9) 0.0199(4) Uani 1 1 d . . . . .
C7 C 0.7262(2) 0.09206(17) 0.62251(9) 0.0197(4) Uani 1 1 d . . . . .
C8 C 0.5859(3) 0.07021(18) 0.57592(9) 0.0229(4) Uani 1 1 d . . . . .
C9 C 0.5876(3) -0.05761(18) 0.54627(11) 0.0345(5) Uani 1 1 d . . . . .
H9A H 0.506441 -0.061236 0.512343 0.052 Uiso 1 1 calc GR . . . .
H9B H 0.561092 -0.119285 0.578401 0.052 Uiso 1 1 calc GR . . . .
H9C H 0.696490 -0.074513 0.528994 0.052 Uiso 1 1 calc GR . . . .
C10 C 0.4236(3) 0.0928(2) 0.61043(11) 0.0352(5) Uani 1 1 d . . . . .
H10A H 0.424223 0.175397 0.628998 0.053 Uiso 1 1 calc GR . . . .
H10B H 0.410155 0.031310 0.643852 0.053 Uiso 1 1 calc GR . . . .
H10C H 0.332851 0.086007 0.580460 0.053 Uiso 1 1 calc GR . . . .
C11 C 0.8837(2) -0.00936(18) 0.71253(9) 0.0217(4) Uani 1 1 d . . . . .
C12 C 1.0550(3) 0.0263(2) 0.68895(10) 0.0309(5) Uani 1 1 d . . . . .
H12A H 1.083680 -0.024569 0.652438 0.046 Uiso 1 1 calc GR . . . .
H12B H 1.134962 0.012958 0.722657 0.046 Uiso 1 1 calc GR . . . .
H12C H 1.055494 0.113336 0.676703 0.046 Uiso 1 1 calc GR . . . .
C13 C 0.8884(3) -0.14446(18) 0.73297(10) 0.0336(5) Uani 1 1 d . . . . .
H13A H 0.776910 -0.173159 0.741399 0.050 Uiso 1 1 calc GR . . . .
H13B H 0.954452 -0.152411 0.771296 0.050 Uiso 1 1 calc GR . . . .
H13C H 0.936835 -0.194324 0.699296 0.050 Uiso 1 1 calc GR . . . .
C14 C 0.8374(3) 0.08045(17) 0.76608(9) 0.0221(4) Uani 1 1 d . . . . .
H14A H 0.935243 0.087474 0.793316 0.027 Uiso 1 1 calc R . . . .
H14B H 0.822318 0.161996 0.746047 0.027 Uiso 1 1 calc R . . . .
C15 C 0.6904(3) 0.0625(2) 0.81085(10) 0.0312(5) Uani 1 1 d . . . . .
C16 C 0.5316(3) 0.0370(3) 0.77587(12) 0.0547(8) Uani 1 1 d . . . . .
H16A H 0.511851 0.102620 0.745078 0.082 Uiso 1 1 calc GR . . . .
H16B H 0.440897 0.034179 0.806028 0.082 Uiso 1 1 calc GR . . . .
H16C H 0.539720 -0.042201 0.753966 0.082 Uiso 1 1 calc GR . . . .
C17 C 0.6711(4) 0.1840(3) 0.84689(12) 0.0519(7) Uani 1 1 d . . . . .
H17A H 0.773775 0.203812 0.868435 0.078 Uiso 1 1 calc GR . . . .
H17B H 0.583282 0.175764 0.878036 0.078 Uiso 1 1 calc GR . . . .
H17C H 0.643878 0.250070 0.817225 0.078 Uiso 1 1 calc GR . . . .
C18 C 0.7228(4) -0.0376(3) 0.86073(12) 0.0552(8) Uani 1 1 d . . . . .
H18A H 0.719221 -0.118883 0.840719 0.083 Uiso 1 1 calc GR . . . .
H18B H 0.638958 -0.033016 0.893644 0.083 Uiso 1 1 calc GR . . . .
H18C H 0.830878 -0.024588 0.879550 0.083 Uiso 1 1 calc GR . . . .
Cl1 Cl 0.57100(8) 0.62334(5) 0.47915(2) 0.03513(15) Uani 1 1 d . . . . .
Cl2 Cl 0.81010(7) 0.66112(4) 0.59533(2) 0.03079(13) Uani 1 1 d . . . . .
N1 N 0.6085(2) 0.15865(16) 0.52425(8) 0.0257(4) Uani 1 1 d . . . . .
H1 H 0.538(3) 0.149(2) 0.4980(11) 0.035(7) Uiso 1 1 d . . . . .
N2 N 0.7972(2) 0.19825(14) 0.63067(7) 0.0210(4) Uani 1 1 d . . . . .
N3 N 0.7656(2) -0.00497(16) 0.65933(8) 0.0216(4) Uani 1 1 d . . . . .
H3 H 0.711(3) -0.073(2) 0.6511(10) 0.027(6) Uiso 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 1.386(3) . ?
C1 C6 1.407(3) . ?
C1 N1 1.387(3) . ?
C2 H2 0.9500 . ?
C2 C3 1.391(3) . ?
C3 C4 1.382(3) . ?
C3 Cl1 1.7354(19) . ?
C4 C5 1.382(3) . ?
C4 Cl2 1.7403(19) . ?
C5 H5 0.9500 . ?
C5 C6 1.393(3) . ?
C6 N2 1.396(2) . ?
C7 C8 1.533(3) . ?
C7 N2 1.303(2) . ?
C7 N3 1.351(2) . ?
C8 C9 1.524(3) . ?
C8 C10 1.535(3) . ?
C8 N1 1.469(3) . ?
C9 H9A 0.9800 . ?
C9 H9B 0.9800 . ?
C9 H9C 0.9800 . ?
C10 H10A 0.9800 . ?
C10 H10B 0.9800 . ?
C10 H10C 0.9800 . ?
C11 C12 1.537(3) . ?
C11 C13 1.530(3) . ?
C11 C14 1.544(3) . ?
C11 N3 1.486(2) . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12C 0.9800 . ?
C13 H13A 0.9800 . ?
C13 H13B 0.9800 . ?
C13 H13C 0.9800 . ?
C14 H14A 0.9900 . ?
C14 H14B 0.9900 . ?
C14 C15 1.544(3) . ?
C15 C16 1.521(3) . ?
C15 C17 1.533(3) . ?
C15 C18 1.540(3) . ?
C16 H16A 0.9800 . ?
C16 H16B 0.9800 . ?
C16 H16C 0.9800 . ?
C17 H17A 0.9800 . ?
C17 H17B 0.9800 . ?
C17 H17C 0.9800 . ?
C18 H18A 0.9800 . ?
C18 H18B 0.9800 . ?
C18 H18C 0.9800 . ?
N1 H1 0.81(2) . ?
N3 H3 0.88(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
C2 C1 C6 120.34(17) . . ?
C2 C1 N1 123.70(18) . . ?
N1 C1 C6 115.88(17) . . ?
C1 C2 H2 120.0 . . ?
C1 C2 C3 119.96(18) . . ?
C3 C2 H2 120.0 . . ?
C2 C3 Cl1 119.16(16) . . ?
C4 C3 C2 120.06(18) . . ?
C4 C3 Cl1 120.78(15) . . ?
C3 C4 Cl2 121.23(15) . . ?
C5 C4 C3 120.13(17) . . ?
C5 C4 Cl2 118.63(15) . . ?
C4 C5 H5 119.5 . . ?
C4 C5 C6 120.96(18) . . ?
C6 C5 H5 119.5 . . ?
C5 C6 C1 118.52(17) . . ?
C5 C6 N2 118.77(17) . . ?
N2 C6 C1 122.70(16) . . ?
N2 C7 C8 123.81(16) . . ?
N2 C7 N3 120.50(18) . . ?
N3 C7 C8 115.50(16) . . ?
C7 C8 C10 108.35(16) . . ?
C9 C8 C7 113.59(17) . . ?
C9 C8 C10 110.50(19) . . ?
N1 C8 C7 106.59(16) . . ?
N1 C8 C9 106.64(16) . . ?
N1 C8 C10 111.13(17) . . ?
C8 C9 H9A 109.5 . . ?
C8 C9 H9B 109.5 . . ?
C8 C9 H9C 109.5 . . ?
H9A C9 H9B 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
C8 C10 H10A 109.5 . . ?
C8 C10 H10B 109.5 . . ?
C8 C10 H10C 109.5 . . ?
H10A C10 H10B 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
C12 C11 C14 107.68(17) . . ?
C13 C11 C12 108.13(18) . . ?
C13 C11 C14 113.77(17) . . ?
N3 C11 C12 109.70(16) . . ?
N3 C11 C13 105.20(16) . . ?
N3 C11 C14 112.26(16) . . ?
C11 C12 H12A 109.5 . . ?
C11 C12 H12B 109.5 . . ?
C11 C12 H12C 109.5 . . ?
H12A C12 H12B 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C11 C13 H13A 109.5 . . ?
C11 C13 H13B 109.5 . . ?
C11 C13 H13C 109.5 . . ?
H13A C13 H13B 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
C11 C14 H14A 106.2 . . ?
C11 C14 H14B 106.2 . . ?
H14A C14 H14B 106.4 . . ?
C15 C14 C11 124.32(17) . . ?
C15 C14 H14A 106.2 . . ?
C15 C14 H14B 106.2 . . ?
C16 C15 C14 112.79(18) . . ?
C16 C15 C17 108.2(2) . . ?
C16 C15 C18 110.7(2) . . ?
C17 C15 C14 106.18(19) . . ?
C17 C15 C18 106.42(19) . . ?
C18 C15 C14 112.2(2) . . ?
C15 C16 H16A 109.5 . . ?
C15 C16 H16B 109.5 . . ?
C15 C16 H16C 109.5 . . ?
H16A C16 H16B 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
C15 C17 H17A 109.5 . . ?
C15 C17 H17B 109.5 . . ?
C15 C17 H17C 109.5 . . ?
H17A C17 H17B 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
C15 C18 H18A 109.5 . . ?
C15 C18 H18B 109.5 . . ?
C15 C18 H18C 109.5 . . ?
H18A C18 H18B 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
C1 N1 C8 117.43(16) . . ?
C1 N1 H1 115.7(17) . . ?
C8 N1 H1 110.1(18) . . ?
C7 N2 C6 117.29(16) . . ?
C7 N3 C11 128.25(18) . . ?
C7 N3 H3 114.7(14) . . ?
C11 N3 H3 117.0(14) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C1 C2 C3 C4 0.4(3) . . . . ?
C1 C2 C3 Cl1 -178.86(16) . . . . ?
C1 C6 N2 C7 -13.4(3) . . . . ?
C2 C1 C6 C5 -2.1(3) . . . . ?
C2 C1 C6 N2 179.14(18) . . . . ?
C2 C1 N1 C8 -146.9(2) . . . . ?
C2 C3 C4 C5 -1.2(3) . . . . ?
C2 C3 C4 Cl2 178.91(16) . . . . ?
C3 C4 C5 C6 0.4(3) . . . . ?
C4 C5 C6 C1 1.3(3) . . . . ?
C4 C5 C6 N2 -179.90(18) . . . . ?
C5 C6 N2 C7 167.86(19) . . . . ?
C6 C1 C2 C3 1.3(3) . . . . ?
C6 C1 N1 C8 36.5(3) . . . . ?
C7 C8 N1 C1 -46.3(2) . . . . ?
C8 C7 N2 C6 -1.4(3) . . . . ?
C8 C7 N3 C11 -173.74(18) . . . . ?
C9 C8 N1 C1 -167.91(18) . . . . ?
C10 C8 N1 C1 71.6(2) . . . . ?
C11 C14 C15 C16 -50.6(3) . . . . ?
C11 C14 C15 C17 -169.0(2) . . . . ?
C11 C14 C15 C18 75.2(3) . . . . ?
C12 C11 C14 C15 -168.12(19) . . . . ?
C12 C11 N3 C7 -59.4(3) . . . . ?
C13 C11 C14 C15 -48.3(3) . . . . ?
C13 C11 N3 C7 -175.48(19) . . . . ?
C14 C11 N3 C7 60.3(3) . . . . ?
Cl1 C3 C4 C5 178.04(16) . . . . ?
Cl1 C3 C4 Cl2 -1.8(2) . . . . ?
Cl2 C4 C5 C6 -179.75(16) . . . . ?
N1 C1 C2 C3 -175.20(19) . . . . ?
N1 C1 C6 C5 174.66(18) . . . . ?
N1 C1 C6 N2 -4.1(3) . . . . ?
N2 C7 C8 C9 146.4(2) . . . . ?
N2 C7 C8 C10 -90.4(2) . . . . ?
N2 C7 C8 N1 29.3(3) . . . . ?
N2 C7 N3 C11 1.4(3) . . . . ?
N3 C7 C8 C9 -38.6(2) . . . . ?
N3 C7 C8 C10 84.6(2) . . . . ?
N3 C7 C8 N1 -155.74(17) . . . . ?
N3 C7 N2 C6 -176.11(17) . . . . ?
N3 C11 C14 C15 71.0(2) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: Ethyl-Acetate'
####################################################################### 
# 
# 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_CPMD11g_20m_mb5_cm1_dicl_0f
_database_code_depnum_ccdc_archive 'CCDC 2087924'
loop_
_audit_author_name
_audit_author_address
'Manuel Fernandes'
;University of the Witwatersrand
South Africa
;
_audit_update_record             
;
2021-06-03 deposited with the CCDC.	2021-07-07 downloaded from the CCDC.
;
_audit_creation_date             2020-09-12
_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         'C14 H19 Cl2 N3'
_chemical_formula_sum            'C14 H19 Cl2 N3'
_chemical_formula_weight         300.22
_chemical_absolute_configuration ?
_chemical_melting_point          430-432
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'
Cl Cl 0.1484 0.1585 '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'

_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      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'

_cell_length_a                   8.4799(2)
_cell_length_b                   11.2725(3)
_cell_length_c                   16.0259(5)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1531.91(7)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    7855
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      26.28
_cell_measurement_theta_min      2.21
_shelx_estimated_absorpt_T_max   0.947
_shelx_estimated_absorpt_T_min   0.848
_exptl_absorpt_coefficient_mu    0.415
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_correction_T_min  0.6914
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.0469 before and 0.0415 after correction. The Ratio of minimum to maximum transmission is 0.9272. The λ/2 correction factor is Not present.'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.302
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             632
_exptl_crystal_size_max          0.411
_exptl_crystal_size_mid          0.321
_exptl_crystal_size_min          0.134
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0299
_diffrn_reflns_av_unetI/netI     0.0247
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            20413
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.308
_diffrn_reflns_theta_min         2.209
_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         0.747
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     1.000
_reflns_number_gt                3505
_reflns_number_total             3823
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT v8.34A (Bruker, 2013)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT v8.34A (Bruker, 2013)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.173
_refine_diff_density_min         -0.159
_refine_diff_density_rms         0.035
_refine_ls_abs_structure_details 
;
 Flack x determined using 1416 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.029(18)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.045
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     185
_refine_ls_number_reflns         3823
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0311
_refine_ls_R_factor_gt           0.0269
_refine_ls_restrained_S_all      1.045
_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)+(0.0341P)²+0.1018P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0618
_refine_ls_wR_factor_ref         0.0638
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C3(H3), C6(H6)
2.b Idealised Me refined as rotating group:
 C9(H9A,H9B,H9C), C10(H10A,H10B,H10C), C12(H12A,H12B,H12C), C13(H13A,H13B,
 H13C), C14(H14A,H14B,H14C)
;
_atom_sites_solution_hydrogens   mixed
_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 0.1434(2) 0.17930(16) 0.61029(10) 0.0202(3) Uani 1 1 d . . . . .
C2 C 0.0409(2) 0.21559(15) 0.54608(10) 0.0214(3) Uani 1 1 d . . . . .
C3 C -0.0131(2) 0.13329(15) 0.48820(11) 0.0244(4) Uani 1 1 d . . . . .
H3 H -0.082221 0.157686 0.444804 0.029 Uiso 1 1 calc R . . . .
C4 C 0.0337(2) 0.01531(16) 0.49365(11) 0.0244(4) Uani 1 1 d . . . . .
C5 C 0.1358(2) -0.02099(15) 0.55622(11) 0.0230(4) Uani 1 1 d . . . . .
C6 C 0.1910(2) 0.06105(15) 0.61395(11) 0.0230(4) Uani 1 1 d . . . . .
H6 H 0.261989 0.036291 0.656390 0.028 Uiso 1 1 calc R . . . .
C7 C 0.1417(2) 0.36308(16) 0.67320(11) 0.0216(4) Uani 1 1 d . . . . .
C8 C -0.0030(2) 0.40103(16) 0.62227(12) 0.0267(4) Uani 1 1 d . . . . .
C9 C -0.1497(2) 0.3668(2) 0.67199(14) 0.0412(5) Uani 1 1 d . . . . .
H9A H -0.244264 0.386272 0.639598 0.062 Uiso 1 1 calc GR . . . .
H9B H -0.151237 0.410710 0.724765 0.062 Uiso 1 1 calc GR . . . .
H9C H -0.147833 0.281434 0.683534 0.062 Uiso 1 1 calc GR . . . .
C10 C -0.0046(3) 0.53281(18) 0.60042(15) 0.0461(6) Uani 1 1 d . . . . .
H10A H 0.098351 0.555726 0.577841 0.069 Uiso 1 1 calc GR . . . .
H10B H -0.026746 0.579305 0.650746 0.069 Uiso 1 1 calc GR . . . .
H10C H -0.086560 0.548013 0.558629 0.069 Uiso 1 1 calc GR . . . .
C11 C 0.3076(2) 0.42096(16) 0.79832(10) 0.0250(4) Uani 1 1 d . . . . .
C12 C 0.4685(2) 0.38446(18) 0.76411(13) 0.0319(4) Uani 1 1 d . . . . .
H12A H 0.457083 0.312460 0.730378 0.048 Uiso 1 1 calc GR . . . .
H12B H 0.540672 0.368976 0.810598 0.048 Uiso 1 1 calc GR . . . .
H12C H 0.510895 0.448527 0.729403 0.048 Uiso 1 1 calc GR . . . .
C13 C 0.3213(3) 0.53901(19) 0.84445(14) 0.0403(5) Uani 1 1 d . . . . .
H13A H 0.364568 0.599205 0.806715 0.061 Uiso 1 1 calc GR . . . .
H13B H 0.391532 0.529619 0.892578 0.061 Uiso 1 1 calc GR . . . .
H13C H 0.216773 0.563981 0.863654 0.061 Uiso 1 1 calc GR . . . .
C14 C 0.2437(3) 0.3258(2) 0.85678(13) 0.0388(5) Uani 1 1 d . . . . .
H14A H 0.138753 0.349102 0.876539 0.058 Uiso 1 1 calc GR . . . .
H14B H 0.314774 0.316964 0.904573 0.058 Uiso 1 1 calc GR . . . .
H14C H 0.236308 0.250243 0.826821 0.058 Uiso 1 1 calc GR . . . .
Cl1 Cl 0.19792(6) -0.16737(4) 0.56386(3) 0.03244(12) Uani 1 1 d . . . . .
Cl2 Cl -0.03929(6) -0.08639(4) 0.42219(3) 0.03725(13) Uani 1 1 d . . . . .
N1 N 0.20568(18) 0.25875(13) 0.66885(9) 0.0231(3) Uani 1 1 d . . . . .
N2 N 0.0054(2) 0.33570(14) 0.54269(10) 0.0264(3) Uani 1 1 d . . . . .
H2 H -0.068(3) 0.3534(18) 0.5113(14) 0.033(6) Uiso 1 1 d . . . . .
N3 N 0.19444(19) 0.44257(14) 0.72953(10) 0.0244(3) Uani 1 1 d . . . . .
H3A H 0.151(3) 0.502(2) 0.7289(12) 0.025(6) Uiso 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 1.408(2) . ?
C1 C6 1.394(2) . ?
C1 N1 1.401(2) . ?
C2 C3 1.390(2) . ?
C2 N2 1.388(2) . ?
C3 H3 0.9500 . ?
C3 C4 1.391(2) . ?
C4 C5 1.387(2) . ?
C4 Cl2 1.7346(18) . ?
C5 C6 1.389(2) . ?
C5 Cl1 1.7363(17) . ?
C6 H6 0.9500 . ?
C7 C8 1.535(2) . ?
C7 N1 1.297(2) . ?
C7 N3 1.348(2) . ?
C8 C9 1.527(3) . ?
C8 C10 1.526(3) . ?
C8 N2 1.474(2) . ?
C9 H9A 0.9800 . ?
C9 H9B 0.9800 . ?
C9 H9C 0.9800 . ?
C10 H10A 0.9800 . ?
C10 H10B 0.9800 . ?
C10 H10C 0.9800 . ?
C11 C12 1.527(3) . ?
C11 C13 1.527(3) . ?
C11 C14 1.524(3) . ?
C11 N3 1.482(2) . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12C 0.9800 . ?
C13 H13A 0.9800 . ?
C13 H13B 0.9800 . ?
C13 H13C 0.9800 . ?
C14 H14A 0.9800 . ?
C14 H14B 0.9800 . ?
C14 H14C 0.9800 . ?
N2 H2 0.82(2) . ?
N3 H3A 0.77(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
C6 C1 C2 119.17(16) . . ?
C6 C1 N1 118.30(15) . . ?
N1 C1 C2 122.46(16) . . ?
C3 C2 C1 119.84(15) . . ?
N2 C2 C1 116.48(15) . . ?
N2 C2 C3 123.61(15) . . ?
C2 C3 H3 119.9 . . ?
C2 C3 C4 120.15(15) . . ?
C4 C3 H3 119.9 . . ?
C3 C4 Cl2 119.26(13) . . ?
C5 C4 C3 120.40(16) . . ?
C5 C4 Cl2 120.34(14) . . ?
C4 C5 C6 119.70(16) . . ?
C4 C5 Cl1 121.39(14) . . ?
C6 C5 Cl1 118.91(13) . . ?
C1 C6 H6 119.6 . . ?
C5 C6 C1 120.73(16) . . ?
C5 C6 H6 119.6 . . ?
N1 C7 C8 123.97(16) . . ?
N1 C7 N3 119.98(16) . . ?
N3 C7 C8 115.86(15) . . ?
C9 C8 C7 107.66(16) . . ?
C10 C8 C7 113.61(16) . . ?
C10 C8 C9 111.01(18) . . ?
N2 C8 C7 106.37(14) . . ?
N2 C8 C9 111.40(16) . . ?
N2 C8 C10 106.74(16) . . ?
C8 C9 H9A 109.5 . . ?
C8 C9 H9B 109.5 . . ?
C8 C9 H9C 109.5 . . ?
H9A C9 H9B 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
C8 C10 H10A 109.5 . . ?
C8 C10 H10B 109.5 . . ?
C8 C10 H10C 109.5 . . ?
H10A C10 H10B 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
C12 C11 C13 109.91(17) . . ?
C14 C11 C12 110.43(17) . . ?
C14 C11 C13 110.06(16) . . ?
N3 C11 C12 110.84(14) . . ?
N3 C11 C13 105.45(15) . . ?
N3 C11 C14 110.04(16) . . ?
C11 C12 H12A 109.5 . . ?
C11 C12 H12B 109.5 . . ?
C11 C12 H12C 109.5 . . ?
H12A C12 H12B 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C11 C13 H13A 109.5 . . ?
C11 C13 H13B 109.5 . . ?
C11 C13 H13C 109.5 . . ?
H13A C13 H13B 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
C11 C14 H14A 109.5 . . ?
C11 C14 H14B 109.5 . . ?
C11 C14 H14C 109.5 . . ?
H14A C14 H14B 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C7 N1 C1 117.26(15) . . ?
C2 N2 C8 117.64(14) . . ?
C2 N2 H2 115.0(15) . . ?
C8 N2 H2 111.8(15) . . ?
C7 N3 C11 127.14(16) . . ?
C7 N3 H3A 114.4(16) . . ?
C11 N3 H3A 117.8(16) . . ?

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 0.1(3) . . . . ?
C1 C2 N2 C8 -33.1(2) . . . . ?
C2 C1 C6 C5 -1.4(3) . . . . ?
C2 C1 N1 C7 13.8(2) . . . . ?
C2 C3 C4 C5 -0.7(3) . . . . ?
C2 C3 C4 Cl2 178.42(14) . . . . ?
C3 C2 N2 C8 149.84(17) . . . . ?
C3 C4 C5 C6 0.3(3) . . . . ?
C3 C4 C5 Cl1 -179.30(14) . . . . ?
C4 C5 C6 C1 0.7(3) . . . . ?
C6 C1 C2 C3 1.0(2) . . . . ?
C6 C1 C2 N2 -176.19(16) . . . . ?
C6 C1 N1 C7 -169.15(16) . . . . ?
C7 C8 N2 C2 45.4(2) . . . . ?
C8 C7 N1 C1 3.9(3) . . . . ?
C8 C7 N3 C11 166.01(16) . . . . ?
C9 C8 N2 C2 -71.7(2) . . . . ?
C10 C8 N2 C2 167.01(16) . . . . ?
C12 C11 N3 C7 63.0(2) . . . . ?
C13 C11 N3 C7 -178.06(18) . . . . ?
C14 C11 N3 C7 -59.4(2) . . . . ?
Cl1 C5 C6 C1 -179.65(13) . . . . ?
Cl2 C4 C5 C6 -178.81(14) . . . . ?
Cl2 C4 C5 Cl1 1.6(2) . . . . ?
N1 C1 C2 C3 177.96(16) . . . . ?
N1 C1 C2 N2 0.8(2) . . . . ?
N1 C1 C6 C5 -178.49(16) . . . . ?
N1 C7 C8 C9 87.9(2) . . . . ?
N1 C7 C8 C10 -148.79(19) . . . . ?
N1 C7 C8 N2 -31.7(2) . . . . ?
N1 C7 N3 C11 -9.2(3) . . . . ?
N2 C2 C3 C4 176.99(17) . . . . ?
N3 C7 C8 C9 -87.1(2) . . . . ?
N3 C7 C8 C10 36.3(2) . . . . ?
N3 C7 C8 N2 153.39(15) . . . . ?
N3 C7 N1 C1 178.66(16) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'


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

_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: Ethyl-Acetate'
