# Electronic Supplementary Material (ESI) for Green Chemistry.
# This journal is © The Royal Society of Chemistry 2015

####################################################################### 
# 
# 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_xrf09052013a
_database_code_depnum_ccdc_archive 'CCDC 963785'
_audit_update_record             
;
2013-09-30 deposited with the CCDC.
2015-05-20 downloaded from the CCDC.
;

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

# 5. CHEMICAL DATA

_chemical_name_systematic        
;
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C23 H14 Cl N O2'
# Ex: 'C12 H16 N2 O6, H2 O' and '(Cd 2+)3, (C6 N6 Cr 3-)2, 2(H2 O)'
_chemical_formula_structural     ?
_chemical_formula_sum            'C23 H14 Cl N O2'
_chemical_formula_iupac          ?
_chemical_formula_weight         371.80
_chemical_compound_source        'see text'

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'
O O 0.0106 0.0060 ' International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

# 6. CRYSTAL DATA

_symmetry_cell_setting           Triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_symmetry_Int_Tables_number      2

loop_
_symmetry_equiv_pos_site_id
_symmetry_equiv_pos_as_xyz
1 x,y,z
2 -x,-y,-z

_cell_length_a                   8.686(6)
_cell_length_b                   10.371(8)
_cell_length_c                   11.293(8)
_cell_angle_alpha                109.138(7)
_cell_angle_beta                 111.662(9)
_cell_angle_gamma                92.379(9)
_cell_volume                     877.8(11)
_cell_formula_units_Z            2
_cell_measurement_temperature    293
_cell_measurement_reflns_used    1214
_cell_measurement_theta_min      3.0
_cell_measurement_theta_max      25.4
_cell_special_details            
;
;

_exptl_crystal_description       Block
_exptl_crystal_colour            Colorless

_exptl_crystal_size_max          0.300
_exptl_crystal_size_mid          0.180
_exptl_crystal_size_min          0.160
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.407
_exptl_crystal_density_method    'Not Measured'
_exptl_crystal_F_000             384
_exptl_absorpt_coefficient_mu    0.236
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_process_details   'REQAB (Rigaku, 1998)'
_exptl_absorpt_correction_T_min  0.9326
_exptl_absorpt_correction_T_max  0.9632

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

# 7. EXPERIMENTAL DATA

_exptl_special_details           
;
;
_diffrn_ambient_temperature      293
_diffrn_source_power             0.0
_diffrn_source_voltage           50.0
_diffrn_source_current           0.6
_diffrn_radiation_wavelength     0.71075
_diffrn_radiation_type           'Mo K\a'
_diffrn_source                   MicroMax003_Mo
_diffrn_radiation_monochromator  Confocal
_diffrn_measurement_specimen_support Fiber
_diffrn_detector                 CCD
_diffrn_measurement_device       
;
AFC12 (Right): Kappa 3 circle
;
_diffrn_measurement_device_type  
;
Rigaku Saturn724+ (4x4 bin mode)
;
_diffrn_detector_area_resol_mean 28.5714
_diffrn_measurement_method       'profile data from ω-scans'

_diffrn_reflns_number            6884
_diffrn_reflns_av_R_equivalents  0.0397
_diffrn_reflns_av_sigmaI/netI    0.0641
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         3.01
_diffrn_reflns_theta_max         25.35
_reflns_number_total             3137
_reflns_number_gt                1706
_reflns_threshold_expression     >2sigma(I)
_diffrn_measured_fraction_theta_max 0.975
_diffrn_reflns_theta_full        25.35
_diffrn_measured_fraction_theta_full 0.975


_computing_data_collection       
;
CrystalClear-SM Expert 2.1 b24 (Rigaku, 2012)
;
_computing_cell_refinement       
;
CrystalClear-SM Expert 2.1 b24 (Rigaku, 2012)
;
_computing_data_reduction        
;
CrystalClear-SM Expert 2.1 b24 (Rigaku, 2012)
;
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'SHELXTL (Bruker, 1997)'
_computing_publication_material  'PLATON (Spek, 2003)'


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

# 8. REFINEMENT DATA

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0781P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         3137
_refine_ls_number_parameters     244
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0775
_refine_ls_R_factor_gt           0.0505
_refine_ls_wR_factor_ref         0.1463
_refine_ls_wR_factor_gt          0.1228
_refine_ls_goodness_of_fit_ref   0.914
_refine_ls_restrained_S_all      0.914
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         0.322
_refine_diff_density_min         -0.326

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

# 9. ATOMIC COORDINATES AND DISPLACEMENT PARAMETERS

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_thermal_displace_type
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_occupancy
_atom_site_U_iso_or_equiv
_atom_site_calc_flag
_atom_site_refinement_flags

_atom_site_disorder_assembly
_atom_site_disorder_group

Cl1 Cl Uani 1.42859 0.56507 1.22049 1.000 0.0654 . . . .
O1 O Uani 0.70199 0.31829 0.51306 1.000 0.0582 . . . .
O2 O Uani 0.94443 0.39127 0.68983 1.000 0.0573 . . . .
N1 N Uani 0.71968 -0.09520 0.45716 1.000 0.0430 . . . .
C1 C Uani 0.57442 0.21316 0.40480 1.000 0.0481 . . . .
C2 C Uani 0.44488 0.25701 0.32180 1.000 0.0647 . . . .
C3 C Uani 0.31697 0.15800 0.20992 1.000 0.0676 . . . .
C4 C Uani 0.31745 0.01906 0.18384 1.000 0.0610 . . . .
C5 C Uani 0.44749 -0.02200 0.27046 1.000 0.0510 . . . .
C6 C Uani 0.57880 0.07544 0.38339 1.000 0.0432 . . . .
C7 C Uani 0.71700 0.03806 0.48068 1.000 0.0386 . . . .
C8 C Uani 0.84009 0.14675 0.59733 1.000 0.0384 . . . .
C9 C Uani 0.83778 0.29245 0.60788 1.000 0.0457 . . . .
C10 C Uani 0.84705 -0.12882 0.54989 1.000 0.0407 . . . .
C11 C Uani 0.85016 -0.27174 0.52336 1.000 0.0526 . . . .
C12 C Uani 0.97151 -0.31234 0.61300 1.000 0.0534 . . . .
C13 C Uani 1.09702 -0.21500 0.73444 1.000 0.0488 . . . .
C14 C Uani 1.09507 -0.07702 0.76219 1.000 0.0454 . . . .
C15 C Uani 0.97111 -0.02901 0.67081 1.000 0.0392 . . . .
C16 C Uani 0.96526 0.11359 0.69573 1.000 0.0380 . . . .
C17 C Uani 1.08436 0.22160 0.82875 1.000 0.0387 . . . .
C18 C Uani 1.25423 0.25366 0.85856 1.000 0.0455 . . . .
C19 C Uani 1.35997 0.35638 0.97910 1.000 0.0489 . . . .
C20 C Uani 1.29753 0.42819 1.07178 1.000 0.0433 . . . .
C21 C Uani 1.13016 0.39575 1.04734 1.000 0.0457 . . . .
C22 C Uani 1.02455 0.29170 0.92470 1.000 0.0433 . . . .
C23 C Uani 1.23189 -0.26561 0.82960 1.000 0.0660 . . . .
H2 H Uiso 0.44362 0.35115 0.34069 1.000 0.0776 . . . .
H3 H Uiso 0.22955 0.18562 0.15159 1.000 0.0812 . . . .
H4 H Uiso 0.23072 -0.04708 0.10827 1.000 0.0732 . . . .
H5 H Uiso 0.44714 -0.11614 0.25297 1.000 0.0613 . . . .
H11 H Uiso 0.76858 -0.33814 0.44407 1.000 0.0631 . . . .
H12 H Uiso 0.97185 -0.40663 0.59382 1.000 0.0641 . . . .
H14 H Uiso 1.17675 -0.01248 0.84286 1.000 0.0544 . . . .
H18 H Uiso 1.29688 0.20494 0.79609 1.000 0.0546 . . . .
H19 H Uiso 1.47374 0.37742 0.99813 1.000 0.0587 . . . .
H21 H Uiso 1.08912 0.44260 1.11165 1.000 0.0548 . . . .
H22 H Uiso 0.91147 0.26881 0.90686 1.000 0.0519 . . . .
H23A H Uiso 1.21270 -0.36527 0.79270 1.000 0.0990 . . . .
H23B H Uiso 1.22777 -0.23423 0.91818 1.000 0.0990 . . . .
H23C H Uiso 1.34067 -0.22942 0.83825 1.000 0.0990 . . . .


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

# 10. MOLECULAR GEOMETRY

_geom_special_details            
;
 Bond distances, angles etc. have been calculated using the
 rounded fractional coordinates. All su's are estimated
 from the variances of the (full) variance-covariance matrix.
 The cell esds are taken into account in the estimation of
 distances, angles and torsion angles
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_1
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Cl1 C20 1.7387 . . yes
O1 C1 1.3917 . . yes
O1 C9 1.3754 . . yes
O2 C9 1.1964 . . yes
N1 C7 1.3219 . . yes
N1 C10 1.3633 . . yes
C1 C2 1.3765 . . no
C1 C6 1.3729 . . no
C2 C3 1.3796 . . no
C3 C4 1.3734 . . no
C4 C5 1.3826 . . no
C5 C6 1.3907 . . no
C6 C7 1.4637 . . no
C7 C8 1.4268 . . no
C8 C9 1.4778 . . no
C8 C16 1.3874 . . no
C10 C11 1.4162 . . no
C10 C15 1.4112 . . no
C11 C12 1.3571 . . no
C12 C13 1.4091 . . no
C13 C14 1.3631 . . no
C13 C23 1.5147 . . no
C14 C15 1.4259 . . no
C15 C16 1.4188 . . no
C16 C17 1.4949 . . no
C17 C18 1.3857 . . no
C17 C22 1.3795 . . no
C18 C19 1.3699 . . no
C19 C20 1.3732 . . no
C20 C21 1.3802 . . no
C21 C22 1.3871 . . no
C2 H2 0.9300 . . no
C3 H3 0.9300 . . no
C4 H4 0.9300 . . no
C5 H5 0.9300 . . no
C11 H11 0.9300 . . no
C12 H12 0.9300 . . no
C14 H14 0.9300 . . no
C18 H18 0.9300 . . no
C19 H19 0.9300 . . no
C21 H21 0.9300 . . no
C22 H22 0.9300 . . no
C23 H23A 0.9600 . . no
C23 H23B 0.9600 . . no
C23 H23C 0.9600 . . no

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_2
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1 O1 C9 122.81 . . . yes
C7 N1 C10 117.67 . . . yes
O1 C1 C2 115.44 . . . yes
O1 C1 C6 121.77 . . . yes
C2 C1 C6 122.79 . . . no
C1 C2 C3 118.43 . . . no
C2 C3 C4 120.65 . . . no
C3 C4 C5 119.68 . . . no
C4 C5 C6 120.94 . . . no
C1 C6 C5 117.48 . . . no
C1 C6 C7 119.22 . . . no
C5 C6 C7 123.27 . . . no
N1 C7 C6 118.17 . . . yes
N1 C7 C8 123.25 . . . yes
C6 C7 C8 118.57 . . . no
C7 C8 C9 119.52 . . . no
C7 C8 C16 119.46 . . . no
C9 C8 C16 120.94 . . . no
O1 C9 O2 116.01 . . . yes
O1 C9 C8 117.52 . . . yes
O2 C9 C8 126.46 . . . yes
N1 C10 C11 117.38 . . . yes
N1 C10 C15 123.29 . . . yes
C11 C10 C15 119.31 . . . no
C10 C11 C12 120.37 . . . no
C11 C12 C13 121.55 . . . no
C12 C13 C14 118.87 . . . no
C12 C13 C23 119.48 . . . no
C14 C13 C23 121.64 . . . no
C13 C14 C15 121.75 . . . no
C10 C15 C14 118.16 . . . no
C10 C15 C16 118.41 . . . no
C14 C15 C16 123.43 . . . no
C8 C16 C15 117.79 . . . no
C8 C16 C17 122.26 . . . no
C15 C16 C17 119.83 . . . no
C16 C17 C18 121.67 . . . no
C16 C17 C22 119.51 . . . no
C18 C17 C22 118.81 . . . no
C17 C18 C19 120.67 . . . no
C18 C19 C20 119.82 . . . no
Cl1 C20 C19 119.99 . . . yes
Cl1 C20 C21 119.01 . . . yes
C19 C20 C21 120.98 . . . no
C20 C21 C22 118.51 . . . no
C17 C22 C21 121.14 . . . no
C1 C2 H2 121.00 . . . no
C3 C2 H2 121.00 . . . no
C2 C3 H3 120.00 . . . no
C4 C3 H3 120.00 . . . no
C3 C4 H4 120.00 . . . no
C5 C4 H4 120.00 . . . no
C4 C5 H5 120.00 . . . no
C6 C5 H5 120.00 . . . no
C10 C11 H11 120.00 . . . no
C12 C11 H11 120.00 . . . no
C11 C12 H12 119.00 . . . no
C13 C12 H12 119.00 . . . no
C13 C14 H14 119.00 . . . no
C15 C14 H14 119.00 . . . no
C17 C18 H18 120.00 . . . no
C19 C18 H18 120.00 . . . no
C18 C19 H19 120.00 . . . no
C20 C19 H19 120.00 . . . no
C20 C21 H21 121.00 . . . no
C22 C21 H21 121.00 . . . no
C17 C22 H22 119.00 . . . no
C21 C22 H22 119.00 . . . no
C13 C23 H23A 109.00 . . . no
C13 C23 H23B 109.00 . . . no
C13 C23 H23C 109.00 . . . no
H23A C23 H23B 109.00 . . . no
H23A C23 H23C 109.00 . . . no
H23B C23 H23C 109.00 . . . no

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
C9 O1 C1 C2 177.97 . . . . no
C9 O1 C1 C6 -1.96 . . . . no
C1 O1 C9 C8 -3.93 . . . . no
C1 O1 C9 O2 174.79 . . . . no
C10 N1 C7 C8 0.05 . . . . no
C10 N1 C7 C6 -178.70 . . . . no
C7 N1 C10 C15 2.32 . . . . no
C7 N1 C10 C11 -179.37 . . . . no
O1 C1 C6 C7 3.02 . . . . no
C2 C1 C6 C5 1.61 . . . . no
C2 C1 C6 C7 -176.91 . . . . no
C6 C1 C2 C3 -2.13 . . . . no
O1 C1 C2 C3 177.94 . . . . no
O1 C1 C6 C5 -178.46 . . . . no
C1 C2 C3 C4 1.31 . . . . no
C2 C3 C4 C5 -0.07 . . . . no
C3 C4 C5 C6 -0.45 . . . . no
C4 C5 C6 C7 178.16 . . . . no
C4 C5 C6 C1 -0.29 . . . . no
C5 C6 C7 N1 2.32 . . . . no
C1 C6 C7 C8 1.95 . . . . no
C5 C6 C7 C8 -176.48 . . . . no
C1 C6 C7 N1 -179.25 . . . . no
N1 C7 C8 C16 -3.26 . . . . no
C6 C7 C8 C9 -7.75 . . . . no
C6 C7 C8 C16 175.48 . . . . no
N1 C7 C8 C9 173.51 . . . . no
C7 C8 C9 O1 8.74 . . . . no
C7 C8 C16 C17 -171.91 . . . . no
C9 C8 C16 C15 -172.74 . . . . no
C9 C8 C16 C17 11.36 . . . . no
C7 C8 C9 O2 -169.84 . . . . no
C16 C8 C9 O1 -174.54 . . . . no
C16 C8 C9 O2 6.89 . . . . no
C7 C8 C16 C15 3.99 . . . . no
N1 C10 C11 C12 -178.63 . . . . no
C15 C10 C11 C12 -0.25 . . . . no
N1 C10 C15 C14 178.04 . . . . no
N1 C10 C15 C16 -1.43 . . . . no
C11 C10 C15 C14 -0.24 . . . . no
C11 C10 C15 C16 -179.71 . . . . no
C10 C11 C12 C13 0.19 . . . . no
C11 C12 C13 C14 0.38 . . . . no
C11 C12 C13 C23 -178.69 . . . . no
C12 C13 C14 C15 -0.89 . . . . no
C23 C13 C14 C15 178.15 . . . . no
C13 C14 C15 C10 0.82 . . . . no
C13 C14 C15 C16 -179.74 . . . . no
C10 C15 C16 C8 -1.80 . . . . no
C10 C15 C16 C17 174.20 . . . . no
C14 C15 C16 C8 178.76 . . . . no
C14 C15 C16 C17 -5.24 . . . . no
C8 C16 C17 C18 -111.53 . . . . no
C8 C16 C17 C22 68.40 . . . . no
C15 C16 C17 C18 72.66 . . . . no
C15 C16 C17 C22 -107.42 . . . . no
C16 C17 C18 C19 177.72 . . . . no
C22 C17 C18 C19 -2.21 . . . . no
C16 C17 C22 C21 -177.86 . . . . no
C18 C17 C22 C21 2.07 . . . . no
C17 C18 C19 C20 0.22 . . . . no
C18 C19 C20 Cl1 -176.40 . . . . no
C18 C19 C20 C21 1.97 . . . . no
Cl1 C20 C21 C22 176.30 . . . . no
C19 C20 C21 C22 -2.08 . . . . no
C20 C21 C22 C17 0.04 . . . . no

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
#
#D   H   A   D - H  H...A   D...A    D - H...A  symm(A)
#
C21 H21 O2 0.9300 2.4600 3.3687 164.00 2_767 yes

# Loop Mechanism for Extra Tables(s)

#loop_
#_publ_manuscript_incl_extra_item
#'_geom_extra_tableA_col_1'
#'_geom_extra_tableA_col_2'
#'_geom_extra_tableA_col_3'
#'_geom_extra_table_head_A'
#'_geom_table_footnote_A'
#'_geom_extra_tableB_col_1'
#'_geom_extra_tableB_col_2'
#'_geom_extra_tableB_col_3'
#'_geom_extra_table_head_B'
#'_geom_table_footnote_B'


#
#loop_
#_geom_extra_tableA_col_1
#_geom_extra_tableA_col_2
#_geom_extra_tableA_col_3
# ? ? ?


#
#loop_
#_geom_extra_tableB_col_1
#_geom_extra_tableB_col_2
#_geom_extra_tableB_col_3
# ? ? ?


#
#_geom_table_footnote_A
#;
# ?
#;


#
#_geom_table_footnote_B
#;
# ?
#;


#
#_geom_table_footnote_A
#;
# ?
#;


#
#_geom_table_footnote_B
#;
# ?
#;


#===END
