# Electronic Supplementary Material (ESI) for Green Chemistry.
# This journal is © The Royal Society of Chemistry 2017

####################################################################### 
# 
# 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_RJ-17
_database_code_depnum_ccdc_archive 'CCDC 1425946'
_audit_update_record             
;
2016-10-18 deposited with the CCDC.
2017-02-06 downloaded from the CCDC.
;
_audit_creation_date             2015-09-19
_audit_creation_method           
;
  Olex2 1.2-ac2
  (compiled 2012.03.27 svn.r2268, GUI svn.r4156)
;
_chemical_formula_moiety         'C23 H21 Cl N2'
_chemical_formula_sum            'C23 H21 Cl N2'
_chemical_formula_weight         360.89
_chemical_oxdiff_formula         C23H21ClN2
loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
_atom_type_scat_dispersion_source
H 0.00000 0.00000 'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
C 0.00347 0.00161 'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
Cl 0.14873 0.16029 'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
N 0.00653 0.00323 'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'

_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_id
_space_group_symop_operation_xyz
1 x,y,z
2 -x,-y,-z

_cell_length_a                   6.0657(4)
_cell_length_b                   11.6494(10)
_cell_length_c                   14.2527(12)
_cell_angle_alpha                104.148(7)
_cell_angle_beta                 102.007(6)
_cell_angle_gamma                92.918(6)
_cell_volume                     949.69(14)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    2096
_cell_measurement_temperature    296.9(6)
_cell_measurement_theta_max      27.2570
_cell_measurement_theta_min      3.9000
_exptl_absorpt_coefficient_mu    0.210
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.96440
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.2619
_exptl_crystal_description       block
_exptl_crystal_F_000             380.4239
_exptl_crystal_size_max          0.23
_exptl_crystal_size_mid          0.23
_exptl_crystal_size_min          0.21
_diffrn_reflns_av_R_equivalents  0.0241
_diffrn_reflns_av_unetI/netI     0.0430
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            6931
_diffrn_reflns_theta_full        28.721783
_diffrn_reflns_theta_max         28.72
_diffrn_reflns_theta_min         3.03
_diffrn_ambient_temperature      296.9(6)
_diffrn_detector_area_resol_mean 8.0640
_diffrn_measured_fraction_theta_full 0.9987
_diffrn_measured_fraction_theta_max 0.8620
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega  -38.00   13.00   1.0000    6.2100
omega____ theta____ kappa____ phi______ frames
    -      -20.2184  -77.0000  120.0000 51

#__ type_ start__ end____ width___ exp.time_
  2 omega  -10.00   17.00   1.0000    6.2100
omega____ theta____ kappa____ phi______ frames
    -      -20.2184  -99.0000    0.0000 27

#__ type_ start__ end____ width___ exp.time_
  3 omega  -48.00   46.00   1.0000    6.2100
omega____ theta____ kappa____ phi______ frames
    -       22.4059  -57.0000 -150.0000 94

#__ type_ start__ end____ width___ exp.time_
  4 omega    0.00   89.00   1.0000    6.2100
omega____ theta____ kappa____ phi______ frames
    -       22.4059   57.0000    0.0000 89

#__ type_ start__ end____ width___ exp.time_
  5 omega  -30.00   -3.00   1.0000    6.2100
omega____ theta____ kappa____ phi______ frames
    -       22.4059  -57.0000   60.0000 27

#__ type_ start__ end____ width___ exp.time_
  6 omega   66.00  100.00   1.0000    6.2100
omega____ theta____ kappa____ phi______ frames
    -       22.4059  178.0000 -180.0000 34

#__ type_ start__ end____ width___ exp.time_
  7 omega  -45.00   32.00   1.0000    6.2100
omega____ theta____ kappa____ phi______ frames
    -       22.4059  -37.0000   90.0000 77
;
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      -0.0008045000
_diffrn_orient_matrix_UB_12      -0.0454527000
_diffrn_orient_matrix_UB_13      -0.0435234000
_diffrn_orient_matrix_UB_21      -0.0116673000
_diffrn_orient_matrix_UB_22      -0.0437928000
_diffrn_orient_matrix_UB_23      0.0260592000
_diffrn_orient_matrix_UB_31      -0.1196766000
_diffrn_orient_matrix_UB_32      -0.0022334000
_diffrn_orient_matrix_UB_33      -0.0143051000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.7107
_diffrn_source                   'Enhance (Mo) X-ray Source'
_reflns_Friedel_coverage         0.0
_reflns_limit_h_max              7
_reflns_limit_h_min              -8
_reflns_limit_k_max              14
_reflns_limit_k_min              -15
_reflns_limit_l_max              19
_reflns_limit_l_min              0
_reflns_number_gt                2999
_reflns_number_total             4235
_reflns_odcompleteness_completeness 99.87
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_reflns_threshold_expression     I>=2u(I)
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_molecular_graphics    
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_publication_material  
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_structure_refinement  
;
olex2.refine (L.J. Bourhis, O.V. Dolomanov, R.J. Gildea, J.A.K. Howard,
H. Puschmann, in preparation, 2011)
;
_computing_structure_solution    'J. Appl. Cryst. (2007) 40, 786-790'
_refine_diff_density_max         0.374788
_refine_diff_density_min         -0.348616
_refine_diff_density_rms         0.066045
_refine_ls_d_res_high            0.739486
_refine_ls_d_res_low             6.728731
_refine_ls_goodness_of_fit_ref   1.047577
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_constraints    37
_refine_ls_number_parameters     236
_refine_ls_number_reflns         4235
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.084562
_refine_ls_R_factor_gt           0.056699
_refine_ls_restrained_S_all      1.047577
_refine_ls_shift/su_max          0.0003
_refine_ls_shift/su_mean         0.0001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0515P)²+0.2247P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_ref         0.138382
_atom_sites_solution_primary     iterative
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_refinement_flags_posn
Cl18 Cl 0.39289(12) 0.13805(6) 0.97942(5) 0.0700(2) Uani 1.000000 .
N1 N 0.1708(3) 0.62233(15) 0.81714(12) 0.0435(4) Uani 1.000000 .
N5 N 0.3148(3) 0.63868(17) 0.63524(14) 0.0600(5) Uani 1.000000 .
H5 H 0.2458(3) 0.60664(17) 0.57449(14) 0.0721(6) Uiso 1.000000 R
C2 C 0.3520(3) 0.56916(17) 0.81848(14) 0.0387(4) Uani 1.000000 .
C12 C 0.3615(3) 0.46154(17) 0.85697(14) 0.0389(4) Uani 1.000000 .
C19 C 0.5306(3) 0.46458(18) 0.62794(14) 0.0419(5) Uani 1.000000 .
C11 C 0.1502(3) 0.72214(17) 0.77779(15) 0.0417(5) Uani 1.000000 .
C15 C 0.3777(4) 0.26170(18) 0.93168(15) 0.0480(5) Uani 1.000000 .
C3 C 0.5538(3) 0.61789(18) 0.78856(14) 0.0419(5) Uani 1.000000 .
H3a H 0.5817(3) 0.70302(18) 0.81866(14) 0.0502(5) Uiso 1.000000 R
H3b H 0.6860(3) 0.58215(18) 0.81470(14) 0.0502(5) Uiso 1.000000 R
C6 C 0.2218(3) 0.73168(19) 0.69275(16) 0.0480(5) Uani 1.000000 .
C4 C 0.5254(3) 0.59544(18) 0.67633(15) 0.0441(5) Uani 1.000000 .
H4 H 0.6518(3) 0.64091(18) 0.66392(15) 0.0530(6) Uiso 1.000000 R
C10 C 0.0300(3) 0.81112(18) 0.82162(17) 0.0479(5) Uani 1.000000 .
H10 H -0.0197(3) 0.80390(18) 0.87760(17) 0.0575(6) Uiso 1.000000 R
C20 C 0.7371(4) 0.4168(2) 0.64050(17) 0.0519(5) Uani 1.000000 .
H20 H 0.8700(4) 0.4672(2) 0.67122(17) 0.0623(6) Uiso 1.000000 R
C13 C 0.1997(3) 0.43224(19) 0.90602(16) 0.0487(5) Uani 1.000000 .
H13 H 0.0836(3) 0.48039(19) 0.91368(16) 0.0584(6) Uiso 1.000000 R
C9 C -0.0190(4) 0.90918(19) 0.78631(18) 0.0534(6) Uani 1.000000 .
C16 C 0.5378(4) 0.2873(2) 0.88309(18) 0.0582(6) Uani 1.000000 .
H16 H 0.6516(4) 0.2379(2) 0.87458(18) 0.0698(7) Uiso 1.000000 R
C21 C 0.7477(4) 0.2961(2) 0.60813(18) 0.0592(6) Uani 1.000000 .
H21 H 0.8867(4) 0.2655(2) 0.61854(18) 0.0711(7) Uiso 1.000000 R
C17 C 0.5305(4) 0.3867(2) 0.84664(17) 0.0553(6) Uani 1.000000 .
H17 H 0.6415(4) 0.4039(2) 0.81439(17) 0.0664(7) Uiso 1.000000 R
C24 C 0.3390(4) 0.3887(2) 0.57704(17) 0.0548(6) Uani 1.000000 .
H24 H 0.2002(4) 0.4191(2) 0.56462(17) 0.0657(7) Uiso 1.000000 R
C8 C 0.0596(4) 0.9209(2) 0.70378(18) 0.0600(6) Uani 1.000000 .
C14 C 0.2070(4) 0.3338(2) 0.94350(17) 0.0534(5) Uani 1.000000 .
H14 H 0.0977(4) 0.3162(2) 0.97647(17) 0.0641(7) Uiso 1.000000 R
C7 C 0.1777(4) 0.8324(2) 0.65932(18) 0.0614(6) Uani 1.000000 .
H7 H 0.2300(4) 0.8409(2) 0.60427(18) 0.0737(7) Uiso 1.000000 R
C22 C 0.5551(4) 0.2215(2) 0.5609(2) 0.0673(7) Uani 1.000000 .
H22 H 0.5619(4) 0.1399(2) 0.5402(2) 0.0808(8) Uiso 1.000000 R
C23 C 0.3504(4) 0.2676(2) 0.5440(2) 0.0702(7) Uani 1.000000 .
H23 H 0.2192(4) 0.2172(2) 0.5103(2) 0.0842(9) Uiso 1.000000 R
C26 C -0.1607(5) 0.9984(2) 0.8352(2) 0.0772(8) Uani 1.000000 .
H26a H -0.3089(11) 0.9901(12) 0.7926(7) 0.1159(12) Uiso 1.000000 G
H26b H -0.174(3) 0.9842(11) 0.8975(7) 0.1159(12) Uiso 1.000000 G
H26c H -0.0892(17) 1.0776(2) 0.8466(13) 0.1159(12) Uiso 1.000000 G
C25 C 0.0192(6) 1.0278(3) 0.6620(3) 0.0976(11) Uani 1.000000 .
H25a H -0.1402(7) 1.0273(11) 0.6360(16) 0.1464(16) Uiso 1.000000 G
H25b H 0.074(4) 1.0995(3) 0.7138(5) 0.1464(16) Uiso 1.000000 G
H25c H 0.098(3) 1.0242(11) 0.6098(12) 0.1464(16) Uiso 1.000000 G


loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Cl18 C15 1.736(2) .
N1 C2 1.288(2) .
N1 C11 1.409(2) .
N5 H5 0.8600 .
N5 C6 1.408(3) .
N5 C4 1.459(3) .
C2 C12 1.485(3) .
C2 C3 1.506(3) .
C12 C13 1.391(3) .
C12 C17 1.387(3) .
C19 C4 1.517(3) .
C19 C20 1.392(3) .
C19 C24 1.374(3) .
C11 C6 1.397(3) .
C11 C10 1.395(3) .
C15 C16 1.365(3) .
C15 C14 1.378(3) .
C3 H3a 0.9700 .
C3 H3b 0.9700 .
C3 C4 1.527(3) .
C6 C7 1.388(3) .
C4 H4 0.9800 .
C10 H10 0.9300 .
C10 C9 1.378(3) .
C20 H20 0.9300 .
C20 C21 1.378(3) .
C13 H13 0.9300 .
C13 C14 1.377(3) .
C9 C8 1.391(3) .
C9 C26 1.513(3) .
C16 H16 0.9300 .
C16 C17 1.379(3) .
C21 H21 0.9300 .
C21 C22 1.362(3) .
C17 H17 0.9300 .
C24 H24 0.9300 .
C24 C23 1.384(3) .
C8 C7 1.386(3) .
C8 C25 1.516(3) .
C14 H14 0.9300 .
C7 H7 0.9300 .
C22 H22 0.9300 .
C22 C23 1.377(4) .
C23 H23 0.9300 .
C26 H26a 0.9600 .
C26 H26b 0.9600 .
C26 H26c 0.9600 .
C25 H25a 0.9600 .
C25 H25b 0.9600 .
C25 H25c 0.9600 .

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
C11 N1 C2 119.70(16) . .
C6 N5 H5 119.23(11) . .
C4 N5 H5 119.23(11) . .
C4 N5 C6 121.53(17) . .
C12 C2 N1 117.56(16) . .
C3 C2 N1 121.66(18) . .
C3 C2 C12 120.66(16) . .
C13 C12 C2 120.77(17) . .
C17 C12 C2 122.12(17) . .
C17 C12 C13 117.12(19) . .
C20 C19 C4 118.69(18) . .
C24 C19 C4 123.20(18) . .
C24 C19 C20 118.0(2) . .
C6 C11 N1 124.27(18) . .
C10 C11 N1 116.97(18) . .
C10 C11 C6 118.44(19) . .
C16 C15 Cl18 119.32(17) . .
C14 C15 Cl18 120.33(17) . .
C14 C15 C16 120.4(2) . .
H3a C3 C2 108.78(11) . .
H3b C3 C2 108.78(11) . .
H3b C3 H3a 107.7 . .
C4 C3 C2 113.88(16) . .
C4 C3 H3a 108.78(11) . .
C4 C3 H3b 108.78(10) . .
C11 C6 N5 122.49(19) . .
C7 C6 N5 119.4(2) . .
C7 C6 C11 117.8(2) . .
C19 C4 N5 111.67(17) . .
C3 C4 N5 109.01(16) . .
C3 C4 C19 110.97(16) . .
H4 C4 N5 108.37(11) . .
H4 C4 C19 108.37(10) . .
H4 C4 C3 108.37(10) . .
H10 C10 C11 118.27(12) . .
C9 C10 C11 123.5(2) . .
C9 C10 H10 118.27(14) . .
H20 C20 C19 119.48(13) . .
C21 C20 C19 121.0(2) . .
C21 C20 H20 119.48(14) . .
H13 C13 C12 119.13(12) . .
C14 C13 C12 121.73(19) . .
C14 C13 H13 119.13(12) . .
C8 C9 C10 118.1(2) . .
C26 C9 C10 120.1(2) . .
C26 C9 C8 121.8(2) . .
H16 C16 C15 120.04(13) . .
C17 C16 C15 119.9(2) . .
C17 C16 H16 120.04(13) . .
H21 C21 C20 119.90(14) . .
C22 C21 C20 120.2(2) . .
C22 C21 H21 119.90(14) . .
C16 C17 C12 121.5(2) . .
H17 C17 C12 119.24(12) . .
H17 C17 C16 119.24(13) . .
H24 C24 C19 119.62(13) . .
C23 C24 C19 120.8(2) . .
C23 C24 H24 119.62(14) . .
C7 C8 C9 118.8(2) . .
C25 C8 C9 121.5(2) . .
C25 C8 C7 119.7(2) . .
C13 C14 C15 119.4(2) . .
H14 C14 C15 120.32(13) . .
H14 C14 C13 120.32(12) . .
C8 C7 C6 123.4(2) . .
H7 C7 C6 118.31(14) . .
H7 C7 C8 118.31(14) . .
H22 C22 C21 120.18(15) . .
C23 C22 C21 119.6(2) . .
C23 C22 H22 120.18(15) . .
C22 C23 C24 120.3(2) . .
H23 C23 C24 119.86(14) . .
H23 C23 C22 119.86(15) . .
H26a C26 C9 109.5 . .
H26b C26 C9 109.5 . .
H26b C26 H26a 109.5 . .
H26c C26 C9 109.5 . .
H26c C26 H26a 109.5 . .
H26c C26 H26b 109.5 . .
H25a C25 C8 109.5 . .
H25b C25 C8 109.5 . .
H25b C25 H25a 109.5 . .
H25c C25 C8 109.5 . .
H25c C25 H25a 109.5 . .
H25c C25 H25b 109.5 . .

_chemical_name_systematic        RJ-17
