# Electronic Supplementary Material (ESI) for Chemical Science.
# 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_jw616a
_database_code_depnum_ccdc_archive 'CCDC 1898982'
loop_
_audit_author_name
_audit_author_address
'Richard J. Staples'
;Michigan State University
United States of America
;
_audit_update_record             
;
2019-02-22 deposited with the CCDC.	2019-06-24 downloaded from the CCDC.
;
_audit_creation_date             2016-06-09
_audit_creation_method           
;
Olex2 1.2-alpha
(compiled 2016.02.24 svn.r3266 for OlexSys, GUI svn.r5155)
;
_shelxl_version_number           2014/6
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C15 H17 Cl N2'
_chemical_formula_sum            'C15 H17 Cl N2'
_chemical_formula_weight         260.75
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.3639 0.7018 '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'

_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                   10.1576(5)
_cell_length_b                   8.6724(5)
_cell_length_c                   15.2277(8)
_cell_angle_alpha                90
_cell_angle_beta                 97.993(3)
_cell_angle_gamma                90
_cell_volume                     1328.39(12)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    5359
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      71.96
_cell_measurement_theta_min      4.93
_shelx_estimated_absorpt_T_max   0.890
_shelx_estimated_absorpt_T_min   0.412
_exptl_absorpt_coefficient_mu    2.393
_exptl_absorpt_correction_T_max  0.7536
_exptl_absorpt_correction_T_min  0.5608
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'SADABS-2012/1 (Bruker,2012) was used for absorption correction. wR2(int) was 0.0654 before and 0.0368 after correction. The Ratio of minimum to maximum transmission is 0.7442. The λ/2 correction factor is 0.0015.'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.304
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             552
_exptl_crystal_recrystallization_method 'used as received'
_exptl_crystal_size_max          0.45
_exptl_crystal_size_mid          0.228
_exptl_crystal_size_min          0.05
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0251
_diffrn_reflns_av_unetI/netI     0.0260
_diffrn_reflns_Laue_measured_fraction_full 0.966
_diffrn_reflns_Laue_measured_fraction_max 0.947
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            7531
_diffrn_reflns_point_group_measured_fraction_full 0.966
_diffrn_reflns_point_group_measured_fraction_max 0.947
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         71.953
_diffrn_reflns_theta_min         4.934
_diffrn_ambient_temperature      173(2)
_diffrn_detector_area_resol_mean 8.36
_diffrn_measured_fraction_theta_full 0.966
_diffrn_measured_fraction_theta_max 0.947
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'ω and φ'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_source                   'sealed tube'
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2308
_reflns_number_total             2478
_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       'COSMO (BRUKER, V1.61, 2009)'
_computing_data_reduction        'SAINT v8.34A (Bruker, 2013)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_refine_diff_density_max         0.303
_refine_diff_density_min         -0.229
_refine_diff_density_rms         0.044
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.068
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     165
_refine_ls_number_reflns         2478
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0362
_refine_ls_R_factor_gt           0.0340
_refine_ls_restrained_S_all      1.068
_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)+(0.0465P)²+0.5436P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0910
_refine_ls_wR_factor_ref         0.0926
_refine_special_details          
'The structure was refined by Least Squares using version 2014/6 of XL (Sheldrick, 2008) incorporated in Olex2 (Dolomanov et al., 2009). All non-hydrogen atoms were refined anisotropically. Hydrogen atom positions were calculated geometrically and refined using the riding model, except for the Hydrogen atom on the nitrogen atom which was found by difference Fourier methods and refined isotropically.'
_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 Ternary CH refined with riding coordinates:
 C1(H1), C2(H2), C5(H5)
2.b Secondary CH2 refined with riding coordinates:
 C3(H3A,H3B), C4(H4A,H4B)
2.c Aromatic/amide H refined with riding coordinates:
 C9(H9), C10(H10), C11(H11), C12(H12)
2.d Idealised Me refined as rotating group:
 C13(H13A,H13B,H13C), C15(H15A,H15B,H15C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_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
Cl1 Cl 0.27201(4) 0.56436(5) 0.55167(2) 0.03275(14) Uani 1 1 d . . . . .
N1 N 0.22928(11) 0.99281(15) 0.44548(7) 0.0207(3) Uani 1 1 d . . . . .
N2 N 0.03795(15) 0.6186(2) 0.17179(10) 0.0443(4) Uani 1 1 d . . . . .
C1 C 0.19382(13) 0.83379(16) 0.46730(9) 0.0193(3) Uani 1 1 d . . . . .
H1 H 0.1403 0.8371 0.5176 0.023 Uiso 1 1 calc R . . . .
C2 C 0.31925(14) 0.73696(17) 0.49526(9) 0.0229(3) Uani 1 1 d . . . . .
H2 H 0.3813 0.7986 0.5384 0.027 Uiso 1 1 calc R . . . .
C3 C 0.39254(13) 0.69074(18) 0.41894(10) 0.0246(3) Uani 1 1 d . . . . .
H3A H 0.4650 0.6183 0.4409 0.029 Uiso 1 1 calc R . . . .
H3B H 0.4332 0.7834 0.3959 0.029 Uiso 1 1 calc R . . . .
C4 C 0.30022(13) 0.61475(17) 0.34395(9) 0.0222(3) Uani 1 1 d . . . . .
H4A H 0.2606 0.5203 0.3658 0.027 Uiso 1 1 calc R . . . .
H4B H 0.3507 0.5855 0.2954 0.027 Uiso 1 1 calc R . . . .
C5 C 0.19019(13) 0.73029(17) 0.30985(9) 0.0199(3) Uani 1 1 d . . . . .
H5 H 0.2346 0.8251 0.2907 0.024 Uiso 1 1 calc R . . . .
C6 C 0.10194(12) 0.78084(16) 0.38183(8) 0.0180(3) Uani 1 1 d . . . . .
C7 C 0.03823(13) 0.93380(16) 0.35207(9) 0.0198(3) Uani 1 1 d . . . . .
C8 C 0.11939(13) 1.05309(17) 0.39061(9) 0.0202(3) Uani 1 1 d . . . . .
C9 C 0.08810(15) 1.20638(18) 0.37072(10) 0.0254(3) Uani 1 1 d . . . . .
H9 H 0.1426 1.2875 0.3972 0.030 Uiso 1 1 calc R . . . .
C10 C -0.02561(16) 1.23785(19) 0.31069(10) 0.0300(3) Uani 1 1 d . . . . .
H10 H -0.0486 1.3419 0.2964 0.036 Uiso 1 1 calc R . . . .
C11 C -0.10549(15) 1.1204(2) 0.27158(10) 0.0302(3) Uani 1 1 d . . . . .
H11 H -0.1820 1.1445 0.2306 0.036 Uiso 1 1 calc R . . . .
C12 C -0.07398(14) 0.96621(18) 0.29217(10) 0.0249(3) Uani 1 1 d . . . . .
H12 H -0.1286 0.8852 0.2655 0.030 Uiso 1 1 calc R . . . .
C13 C 0.29696(16) 1.08899(19) 0.51620(11) 0.0303(3) Uani 1 1 d . . . . .
H13A H 0.2386 1.1054 0.5615 0.045 Uiso 1 1 calc GR . . . .
H13B H 0.3191 1.1887 0.4917 0.045 Uiso 1 1 calc GR . . . .
H13C H 0.3787 1.0376 0.5430 0.045 Uiso 1 1 calc GR . . . .
C14 C 0.10490(14) 0.66918(19) 0.23140(10) 0.0273(3) Uani 1 1 d . . . . .
C15 C 0.00270(13) 0.65608(17) 0.39938(10) 0.0236(3) Uani 1 1 d . . . . .
H15A H 0.0500 0.5589 0.4137 0.035 Uiso 1 1 calc GR . . . .
H15B H -0.0629 0.6421 0.3464 0.035 Uiso 1 1 calc GR . . . .
H15C H -0.0427 0.6872 0.4493 0.035 Uiso 1 1 calc GR . . . .


_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
Cl1 C2 1.8231(15) . ?
N1 C1 1.4748(19) . ?
N1 C8 1.3994(18) . ?
N1 C13 1.4568(18) . ?
N2 C14 1.143(2) . ?
C1 H1 1.0000 . ?
C1 C2 1.5358(19) . ?
C1 C6 1.5614(17) . ?
C2 H2 1.0000 . ?
C2 C3 1.519(2) . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C3 C4 1.5231(19) . ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?
C4 C5 1.5367(19) . ?
C5 H5 1.0000 . ?
C5 C6 1.5717(18) . ?
C5 C14 1.4734(19) . ?
C6 C7 1.5174(19) . ?
C6 C15 1.5275(19) . ?
C7 C8 1.400(2) . ?
C7 C12 1.3860(19) . ?
C8 C9 1.390(2) . ?
C9 H9 0.9500 . ?
C9 C10 1.397(2) . ?
C10 H10 0.9500 . ?
C10 C11 1.384(2) . ?
C11 H11 0.9500 . ?
C11 C12 1.400(2) . ?
C12 H12 0.9500 . ?
C13 H13A 0.9800 . ?
C13 H13B 0.9800 . ?
C13 H13C 0.9800 . ?
C15 H15A 0.9800 . ?
C15 H15B 0.9800 . ?
C15 H15C 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
C8 N1 C1 106.52(10) . . ?
C8 N1 C13 118.86(12) . . ?
C13 N1 C1 118.28(11) . . ?
N1 C1 H1 108.8 . . ?
N1 C1 C2 110.76(11) . . ?
N1 C1 C6 102.92(10) . . ?
C2 C1 H1 108.8 . . ?
C2 C1 C6 116.54(11) . . ?
C6 C1 H1 108.8 . . ?
Cl1 C2 H2 108.2 . . ?
C1 C2 Cl1 108.48(10) . . ?
C1 C2 H2 108.2 . . ?
C3 C2 Cl1 109.45(10) . . ?
C3 C2 C1 114.10(11) . . ?
C3 C2 H2 108.2 . . ?
C2 C3 H3A 109.3 . . ?
C2 C3 H3B 109.3 . . ?
C2 C3 C4 111.82(11) . . ?
H3A C3 H3B 107.9 . . ?
C4 C3 H3A 109.3 . . ?
C4 C3 H3B 109.3 . . ?
C3 C4 H4A 110.0 . . ?
C3 C4 H4B 110.0 . . ?
C3 C4 C5 108.32(12) . . ?
H4A C4 H4B 108.4 . . ?
C5 C4 H4A 110.0 . . ?
C5 C4 H4B 110.0 . . ?
C4 C5 H5 107.3 . . ?
C4 C5 C6 113.88(11) . . ?
C6 C5 H5 107.3 . . ?
C14 C5 C4 110.94(12) . . ?
C14 C5 H5 107.3 . . ?
C14 C5 C6 109.74(11) . . ?
C1 C6 C5 109.31(10) . . ?
C7 C6 C1 99.93(11) . . ?
C7 C6 C5 107.24(11) . . ?
C7 C6 C15 114.02(11) . . ?
C15 C6 C1 113.27(11) . . ?
C15 C6 C5 112.25(11) . . ?
C8 C7 C6 108.60(11) . . ?
C12 C7 C6 130.65(13) . . ?
C12 C7 C8 120.56(13) . . ?
N1 C8 C7 110.40(12) . . ?
C9 C8 N1 128.79(13) . . ?
C9 C8 C7 120.78(13) . . ?
C8 C9 H9 120.9 . . ?
C8 C9 C10 118.20(14) . . ?
C10 C9 H9 120.9 . . ?
C9 C10 H10 119.3 . . ?
C11 C10 C9 121.31(14) . . ?
C11 C10 H10 119.3 . . ?
C10 C11 H11 119.9 . . ?
C10 C11 C12 120.28(14) . . ?
C12 C11 H11 119.9 . . ?
C7 C12 C11 118.85(14) . . ?
C7 C12 H12 120.6 . . ?
C11 C12 H12 120.6 . . ?
N1 C13 H13A 109.5 . . ?
N1 C13 H13B 109.5 . . ?
N1 C13 H13C 109.5 . . ?
H13A C13 H13B 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
N2 C14 C5 178.23(19) . . ?
C6 C15 H15A 109.5 . . ?
C6 C15 H15B 109.5 . . ?
C6 C15 H15C 109.5 . . ?
H15A C15 H15B 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 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
Cl1 C2 C3 C4 69.91(13) . . . . ?
N1 C1 C2 Cl1 163.45(9) . . . . ?
N1 C1 C2 C3 -74.27(15) . . . . ?
N1 C1 C6 C5 80.54(13) . . . . ?
N1 C1 C6 C7 -31.80(12) . . . . ?
N1 C1 C6 C15 -153.48(11) . . . . ?
N1 C8 C9 C10 177.43(14) . . . . ?
C1 N1 C8 C7 -20.13(14) . . . . ?
C1 N1 C8 C9 161.67(14) . . . . ?
C1 C2 C3 C4 -51.85(17) . . . . ?
C1 C6 C7 C8 21.14(13) . . . . ?
C1 C6 C7 C12 -163.91(14) . . . . ?
C2 C1 C6 C5 -40.87(16) . . . . ?
C2 C1 C6 C7 -153.21(11) . . . . ?
C2 C1 C6 C15 85.11(14) . . . . ?
C2 C3 C4 C5 59.95(15) . . . . ?
C3 C4 C5 C6 -61.11(15) . . . . ?
C3 C4 C5 C14 174.49(12) . . . . ?
C4 C5 C6 C1 50.75(15) . . . . ?
C4 C5 C6 C7 158.22(11) . . . . ?
C4 C5 C6 C15 -75.81(14) . . . . ?
C5 C6 C7 C8 -92.80(13) . . . . ?
C5 C6 C7 C12 82.15(17) . . . . ?
C6 C1 C2 Cl1 -79.38(13) . . . . ?
C6 C1 C2 C3 42.91(17) . . . . ?
C6 C7 C8 N1 -1.81(15) . . . . ?
C6 C7 C8 C9 176.56(12) . . . . ?
C6 C7 C12 C11 -175.09(14) . . . . ?
C7 C8 C9 C10 -0.6(2) . . . . ?
C8 N1 C1 C2 157.98(11) . . . . ?
C8 N1 C1 C6 32.72(13) . . . . ?
C8 C7 C12 C11 -0.7(2) . . . . ?
C8 C9 C10 C11 -0.1(2) . . . . ?
C9 C10 C11 C12 0.5(2) . . . . ?
C10 C11 C12 C7 -0.1(2) . . . . ?
C12 C7 C8 N1 -177.36(12) . . . . ?
C12 C7 C8 C9 1.0(2) . . . . ?
C13 N1 C1 C2 -65.02(16) . . . . ?
C13 N1 C1 C6 169.72(12) . . . . ?
C13 N1 C8 C7 -156.83(13) . . . . ?
C13 N1 C8 C9 25.0(2) . . . . ?
C14 C5 C6 C1 175.79(12) . . . . ?
C14 C5 C6 C7 -76.74(14) . . . . ?
C14 C5 C6 C15 49.23(16) . . . . ?
C15 C6 C7 C8 142.28(12) . . . . ?
C15 C6 C7 C12 -42.8(2) . . . . ?

_olex2_diffrn_ambient_temperature_device 'Oxford Cryosystems'
_olex2_exptl_crystal_mounting_method 
'The crystal was mounted on a nylon loop with paratone oil'
_olex2_submission_original_sample_id SJT-05-809-Major
_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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_jw616b
_database_code_depnum_ccdc_archive 'CCDC 1898983'
loop_
_audit_author_name
_audit_author_address
'Richard J. Staples'
;Michigan State University
United States of America
;
_audit_update_record             
;
2019-02-22 deposited with the CCDC.	2019-06-24 downloaded from the CCDC.
;
_audit_creation_date             2016-06-15
_audit_creation_method           
;
Olex2 1.2-alpha
(compiled 2016.02.24 svn.r3266 for OlexSys, GUI svn.r5155)
;
_shelxl_version_number           2014/6
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C15 H17 Cl N2'
_chemical_formula_sum            'C15 H17 Cl N2'
_chemical_formula_weight         260.75
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
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      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   7.5795(6)
_cell_length_b                   8.9959(7)
_cell_length_c                   10.1131(8)
_cell_angle_alpha                94.1119(9)
_cell_angle_beta                 97.9337(9)
_cell_angle_gamma                104.1814(8)
_cell_volume                     658.13(9)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    5055
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      25.34
_cell_measurement_theta_min      2.35
_shelx_estimated_absorpt_T_max   0.968
_shelx_estimated_absorpt_T_min   0.926
_exptl_absorpt_coefficient_mu    0.274
_exptl_absorpt_correction_T_max  0.7452
_exptl_absorpt_correction_T_min  0.6957
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'SADABS-2014/5 (Bruker,2014/5) was used for absorption correction. wR2(int) was 0.0518 before and 0.0469 after correction. The Ratio of minimum to maximum transmission is 0.9336. The λ/2 correction factor is 0.00150.'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.316
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             276
_exptl_crystal_recrystallization_method 'used as received'
_exptl_crystal_size_max          0.287
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.119
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0331
_diffrn_reflns_av_unetI/netI     0.0289
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            10996
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.362
_diffrn_reflns_theta_min         2.046
_diffrn_ambient_temperature      173(2)
_diffrn_detector_area_resol_mean 8.36
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       ω
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'sealed tube'
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1970
_reflns_number_total             2413
_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       'COSMO (BRUKER, V1.61, 2009)'
_computing_data_reduction        'SAINT v8.34A (Bruker, 2013)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_refine_diff_density_max         0.258
_refine_diff_density_min         -0.297
_refine_diff_density_rms         0.048
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.041
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     165
_refine_ls_number_reflns         2413
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0524
_refine_ls_R_factor_gt           0.0422
_refine_ls_restrained_S_all      1.041
_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)+(0.0541P)²+0.3007P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1031
_refine_ls_wR_factor_ref         0.1120
_refine_special_details          
'The structure was refined by Least Squares using version 2014/6 of XL (Sheldrick, 2008) incorporated in Olex2 (Dolomanov et al., 2009). All non-hydrogen atoms were refined anisotropically. Hydrogen atom positions were calculated geometrically and refined using the riding model.'
_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 Ternary CH refined with riding coordinates:
 C1(H1), C2(H2), C5(H5)
2.b Secondary CH2 refined with riding coordinates:
 C3(H3A,H3B), C4(H4A,H4B)
2.c Aromatic/amide H refined with riding coordinates:
 C9(H9), C10(H10), C11(H11), C12(H12)
2.d Idealised Me refined as rotating group:
 C13(H13A,H13B,H13C), C15(H15A,H15B,H15C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_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
Cl1 Cl 0.29046(7) 0.71406(7) -0.02101(5) 0.0475(2) Uani 1 1 d . . . . .
N1 N 0.6767(2) 0.55201(17) 0.30537(16) 0.0276(4) Uani 1 1 d . . . . .
N2 N 0.8137(3) 1.0997(2) 0.42120(19) 0.0421(4) Uani 1 1 d . . . . .
C1 C 0.6496(2) 0.7079(2) 0.32634(18) 0.0261(4) Uani 1 1 d . . . . .
H1 H 0.6315 0.7269 0.4216 0.031 Uiso 1 1 calc R . . . .
C2 C 0.8183(3) 0.8328(2) 0.30245(19) 0.0291(4) Uani 1 1 d . . . . .
H2 H 0.9315 0.8060 0.3460 0.035 Uiso 1 1 calc R . . . .
C3 C 0.8317(3) 0.8424(2) 0.1532(2) 0.0344(5) Uani 1 1 d . . . . .
H3A H 0.9329 0.9325 0.1438 0.041 Uiso 1 1 calc R . . . .
H3B H 0.8610 0.7484 0.1154 0.041 Uiso 1 1 calc R . . . .
C4 C 0.6518(3) 0.8579(2) 0.0750(2) 0.0354(5) Uani 1 1 d . . . . .
H4A H 0.6215 0.9520 0.1116 0.043 Uiso 1 1 calc R . . . .
H4B H 0.6634 0.8660 -0.0207 0.043 Uiso 1 1 calc R . . . .
C5 C 0.5008(3) 0.7158(2) 0.08801(19) 0.0306(4) Uani 1 1 d . . . . .
H5 H 0.5414 0.6237 0.0561 0.037 Uiso 1 1 calc R . . . .
C6 C 0.4640(2) 0.6974(2) 0.23312(18) 0.0260(4) Uani 1 1 d . . . . .
C7 C 0.3665(2) 0.5301(2) 0.24130(18) 0.0271(4) Uani 1 1 d . . . . .
C8 C 0.4982(2) 0.4522(2) 0.28392(18) 0.0276(4) Uani 1 1 d . . . . .
C9 C 0.4469(3) 0.2970(2) 0.30177(19) 0.0322(4) Uani 1 1 d . . . . .
H9 H 0.5365 0.2442 0.3321 0.039 Uiso 1 1 calc R . . . .
C10 C 0.2611(3) 0.2210(2) 0.2741(2) 0.0357(5) Uani 1 1 d . . . . .
H10 H 0.2229 0.1152 0.2873 0.043 Uiso 1 1 calc R . . . .
C11 C 0.1301(3) 0.2963(2) 0.2275(2) 0.0372(5) Uani 1 1 d . . . . .
H11 H 0.0037 0.2414 0.2074 0.045 Uiso 1 1 calc R . . . .
C12 C 0.1824(3) 0.4523(2) 0.2100(2) 0.0335(5) Uani 1 1 d . . . . .
H12 H 0.0930 0.5042 0.1772 0.040 Uiso 1 1 calc R . . . .
C13 C 0.8131(3) 0.5137(2) 0.4035(2) 0.0369(5) Uani 1 1 d . . . . .
H13A H 0.7731 0.5147 0.4916 0.055 Uiso 1 1 calc GR . . . .
H13B H 0.9319 0.5898 0.4090 0.055 Uiso 1 1 calc GR . . . .
H13C H 0.8264 0.4108 0.3760 0.055 Uiso 1 1 calc GR . . . .
C14 C 0.8140(3) 0.9836(2) 0.36952(19) 0.0312(4) Uani 1 1 d . . . . .
C15 C 0.3650(3) 0.8131(2) 0.2860(2) 0.0356(5) Uani 1 1 d . . . . .
H15A H 0.2413 0.7934 0.2334 0.053 Uiso 1 1 calc GR . . . .
H15B H 0.4353 0.9182 0.2779 0.053 Uiso 1 1 calc GR . . . .
H15C H 0.3550 0.8019 0.3805 0.053 Uiso 1 1 calc GR . . . .


_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
Cl1 C5 1.8046(19) . ?
N1 C1 1.471(2) . ?
N1 C8 1.407(2) . ?
N1 C13 1.454(2) . ?
N2 C14 1.135(3) . ?
C1 H1 1.0000 . ?
C1 C2 1.541(3) . ?
C1 C6 1.560(2) . ?
C2 H2 1.0000 . ?
C2 C3 1.534(3) . ?
C2 C14 1.483(3) . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C3 C4 1.521(3) . ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?
C4 C5 1.520(3) . ?
C5 H5 1.0000 . ?
C5 C6 1.544(3) . ?
C6 C7 1.519(3) . ?
C6 C15 1.532(2) . ?
C7 C8 1.394(3) . ?
C7 C12 1.380(3) . ?
C8 C9 1.387(3) . ?
C9 H9 0.9500 . ?
C9 C10 1.386(3) . ?
C10 H10 0.9500 . ?
C10 C11 1.383(3) . ?
C11 H11 0.9500 . ?
C11 C12 1.393(3) . ?
C12 H12 0.9500 . ?
C13 H13A 0.9800 . ?
C13 H13B 0.9800 . ?
C13 H13C 0.9800 . ?
C15 H15A 0.9800 . ?
C15 H15B 0.9800 . ?
C15 H15C 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
C8 N1 C1 105.11(14) . . ?
C8 N1 C13 116.63(15) . . ?
C13 N1 C1 116.50(15) . . ?
N1 C1 H1 108.2 . . ?
N1 C1 C2 111.81(15) . . ?
N1 C1 C6 103.76(13) . . ?
C2 C1 H1 108.2 . . ?
C2 C1 C6 116.32(15) . . ?
C6 C1 H1 108.2 . . ?
C1 C2 H2 107.8 . . ?
C3 C2 C1 113.15(15) . . ?
C3 C2 H2 107.8 . . ?
C14 C2 C1 109.19(15) . . ?
C14 C2 H2 107.8 . . ?
C14 C2 C3 111.02(16) . . ?
C2 C3 H3A 109.4 . . ?
C2 C3 H3B 109.4 . . ?
H3A C3 H3B 108.0 . . ?
C4 C3 C2 111.10(16) . . ?
C4 C3 H3A 109.4 . . ?
C4 C3 H3B 109.4 . . ?
C3 C4 H4A 110.1 . . ?
C3 C4 H4B 110.1 . . ?
H4A C4 H4B 108.4 . . ?
C5 C4 C3 108.07(16) . . ?
C5 C4 H4A 110.1 . . ?
C5 C4 H4B 110.1 . . ?
Cl1 C5 H5 107.2 . . ?
C4 C5 Cl1 110.27(14) . . ?
C4 C5 H5 107.2 . . ?
C4 C5 C6 114.21(15) . . ?
C6 C5 Cl1 110.34(13) . . ?
C6 C5 H5 107.2 . . ?
C5 C6 C1 109.21(15) . . ?
C7 C6 C1 99.39(14) . . ?
C7 C6 C5 108.80(14) . . ?
C7 C6 C15 113.84(15) . . ?
C15 C6 C1 111.50(15) . . ?
C15 C6 C5 113.19(15) . . ?
C8 C7 C6 108.65(15) . . ?
C12 C7 C6 130.86(17) . . ?
C12 C7 C8 120.44(17) . . ?
C7 C8 N1 110.92(16) . . ?
C9 C8 N1 128.13(17) . . ?
C9 C8 C7 120.95(17) . . ?
C8 C9 H9 121.0 . . ?
C10 C9 C8 118.09(18) . . ?
C10 C9 H9 121.0 . . ?
C9 C10 H10 119.3 . . ?
C11 C10 C9 121.30(18) . . ?
C11 C10 H10 119.3 . . ?
C10 C11 H11 119.8 . . ?
C10 C11 C12 120.33(18) . . ?
C12 C11 H11 119.8 . . ?
C7 C12 C11 118.81(18) . . ?
C7 C12 H12 120.6 . . ?
C11 C12 H12 120.6 . . ?
N1 C13 H13A 109.5 . . ?
N1 C13 H13B 109.5 . . ?
N1 C13 H13C 109.5 . . ?
H13A C13 H13B 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
N2 C14 C2 178.9(2) . . ?
C6 C15 H15A 109.5 . . ?
C6 C15 H15B 109.5 . . ?
C6 C15 H15C 109.5 . . ?
H15A C15 H15B 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 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
Cl1 C5 C6 C1 -177.10(12) . . . . ?
Cl1 C5 C6 C7 75.37(16) . . . . ?
Cl1 C5 C6 C15 -52.25(18) . . . . ?
N1 C1 C2 C3 75.75(19) . . . . ?
N1 C1 C2 C14 -160.06(15) . . . . ?
N1 C1 C6 C5 -81.55(17) . . . . ?
N1 C1 C6 C7 32.25(17) . . . . ?
N1 C1 C6 C15 152.61(15) . . . . ?
N1 C8 C9 C10 -179.98(18) . . . . ?
C1 N1 C8 C7 21.88(19) . . . . ?
C1 N1 C8 C9 -157.25(19) . . . . ?
C1 C2 C3 C4 52.1(2) . . . . ?
C1 C6 C7 C8 -20.11(18) . . . . ?
C1 C6 C7 C12 162.4(2) . . . . ?
C2 C1 C6 C5 41.7(2) . . . . ?
C2 C1 C6 C7 155.48(15) . . . . ?
C2 C1 C6 C15 -84.16(19) . . . . ?
C2 C3 C4 C5 -60.8(2) . . . . ?
C3 C4 C5 Cl1 -172.15(13) . . . . ?
C3 C4 C5 C6 62.9(2) . . . . ?
C4 C5 C6 C1 -52.2(2) . . . . ?
C4 C5 C6 C7 -159.75(16) . . . . ?
C4 C5 C6 C15 72.6(2) . . . . ?
C5 C6 C7 C8 94.00(17) . . . . ?
C5 C6 C7 C12 -83.5(2) . . . . ?
C6 C1 C2 C3 -43.2(2) . . . . ?
C6 C1 C2 C14 81.00(19) . . . . ?
C6 C7 C8 N1 0.0(2) . . . . ?
C6 C7 C8 C9 179.21(17) . . . . ?
C6 C7 C12 C11 -179.95(19) . . . . ?
C7 C8 C9 C10 1.0(3) . . . . ?
C8 N1 C1 C2 -160.08(15) . . . . ?
C8 N1 C1 C6 -33.94(17) . . . . ?
C8 C7 C12 C11 2.8(3) . . . . ?
C8 C9 C10 C11 1.2(3) . . . . ?
C9 C10 C11 C12 -1.3(3) . . . . ?
C10 C11 C12 C7 -0.7(3) . . . . ?
C12 C7 C8 N1 177.80(17) . . . . ?
C12 C7 C8 C9 -3.0(3) . . . . ?
C13 N1 C1 C2 69.1(2) . . . . ?
C13 N1 C1 C6 -164.75(16) . . . . ?
C13 N1 C8 C7 152.62(16) . . . . ?
C13 N1 C8 C9 -26.5(3) . . . . ?
C14 C2 C3 C4 -71.1(2) . . . . ?
C15 C6 C7 C8 -138.75(17) . . . . ?
C15 C6 C7 C12 43.8(3) . . . . ?

_olex2_diffrn_ambient_temperature_device 'Oxford Cryosystems'
_olex2_exptl_crystal_mounting_method 
'The crystal was mounted on a nylon loop with paratone oil'
_olex2_submission_original_sample_id SJT-05-809-Minor
_olex2_submission_special_instructions 'No special instructions were received'
