# Electronic Supplementary Material (ESI) for RSC Advances.
# This journal is © The Royal Society of Chemistry 2016

####################################################################### 
# 
# 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_gp-2cl-1
_database_code_depnum_ccdc_archive 'CCDC 1483531'
_audit_update_record             
;
2016-06-05 deposited with the CCDC.
2016-11-02 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C22 H14 Cl O'
_chemical_formula_sum            'C22 H14 Cl O'
_chemical_formula_weight         329.78

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

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   'P 21/c'
_space_group_name_Hall           '-P 2ybc'
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   17.382(19)
_cell_length_b                   6.286(7)
_cell_length_c                   17.040(18)
_cell_angle_alpha                90.00
_cell_angle_beta                 117.003(18)
_cell_angle_gamma                90.00
_cell_volume                     1659(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    891
_cell_measurement_theta_min      3.96
_cell_measurement_theta_max      22.97

_exptl_crystal_description       Block
_exptl_crystal_colour            Colourless
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.12
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.321
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             684
_exptl_absorpt_coefficient_mu    0.234
_exptl_absorpt_correction_type   multi-Scan
_exptl_absorpt_correction_T_min  0.935
_exptl_absorpt_correction_T_max  0.972
_exptl_absorpt_process_details   multi-Scan

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            3748
_diffrn_reflns_av_R_equivalents  0.1027
_diffrn_reflns_av_sigmaI/netI    0.0785
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_k_min       -3
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         3.96
_diffrn_reflns_theta_max         25.25
_reflns_number_total             3010
_reflns_number_gt                1753
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_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)+(0.0500P)²+1.7000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         3010
_refine_ls_number_parameters     217
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0915
_refine_ls_R_factor_gt           0.0683
_refine_ls_wR_factor_ref         0.1664
_refine_ls_wR_factor_gt          0.1508
_refine_ls_goodness_of_fit_ref   1.016
_refine_ls_restrained_S_all      1.016
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Cl1 Cl 0.35811(8) 0.42205(16) 0.42806(8) 0.0803(4) Uani 1 1 d . . .
C8 C 0.27470(19) 0.8229(5) 0.4657(2) 0.0430(8) Uani 1 1 d . . .
H8 H 0.2704 0.6797 0.4861 0.052 Uiso 1 1 calc R . .
C17 C 0.2746(2) 0.8051(5) 0.3757(2) 0.0430(8) Uani 1 1 d . . .
C16 C 0.3548(2) 0.9322(5) 0.5364(2) 0.0466(8) Uani 1 1 d . . .
C22 C 0.3096(2) 0.6291(5) 0.3533(2) 0.0528(9) Uani 1 1 d . . .
C5 C 0.1093(2) 0.9386(6) 0.4146(2) 0.0493(9) Uani 1 1 d . . .
C18 C 0.2396(2) 0.9658(6) 0.3137(2) 0.0488(8) Uani 1 1 d . . .
H18 H 0.2167 1.0857 0.3274 0.059 Uiso 1 1 calc R . .
C11 C 0.3301(2) 1.1032(6) 0.5732(2) 0.0517(9) Uani 1 1 d . . .
C9 C 0.2367(2) 1.1137(6) 0.5271(2) 0.0538(9) Uani 1 1 d . . .
O1 O 0.19092(18) 1.2611(5) 0.5474(2) 0.0862(10) Uani 1 1 d . . .
C6 C 0.0588(2) 1.0984(6) 0.4270(2) 0.0568(10) Uani 1 1 d . . .
C10 C 0.2022(2) 0.9596(5) 0.4657(2) 0.0462(8) Uani 1 1 d . . .
C19 C 0.2380(2) 0.9512(7) 0.2304(2) 0.0628(10) Uani 1 1 d . . .
H19 H 0.2142 1.0603 0.1895 0.075 Uiso 1 1 calc R . .
C4 C 0.0678(2) 0.7746(7) 0.3550(2) 0.0641(11) Uani 1 1 d . . .
H4 H 0.1002 0.6678 0.3464 0.077 Uiso 1 1 calc R . .
C1 C -0.0310(3) 1.0903(8) 0.3808(3) 0.0734(12) Uani 1 1 d . . .
H1 H -0.0641 1.1946 0.3897 0.088 Uiso 1 1 calc R . .
C21 C 0.3087(3) 0.6120(7) 0.2704(3) 0.0635(11) Uani 1 1 d . . .
H21 H 0.3323 0.4936 0.2566 0.076 Uiso 1 1 calc R . .
C15 C 0.4421(2) 0.8901(6) 0.5651(2) 0.0582(10) Uani 1 1 d . . .
H15 H 0.4596 0.7793 0.5407 0.070 Uiso 1 1 calc R . .
C14 C 0.5029(3) 1.0174(8) 0.6312(3) 0.0680(11) Uani 1 1 d . . .
H14 H 0.5614 0.9911 0.6507 0.082 Uiso 1 1 calc R . .
C12 C 0.3908(3) 1.2283(7) 0.6395(3) 0.0685(11) Uani 1 1 d . . .
H12 H 0.3738 1.3399 0.6640 0.082 Uiso 1 1 calc R . .
C7 C 0.1021(3) 1.2798(7) 0.4879(3) 0.0822(13) Uani 1 1 d . . .
H7 H 0.0714 1.4021 0.4867 0.099 Uiso 1 1 calc R . .
C20 C 0.2721(3) 0.7736(8) 0.2101(3) 0.0695(12) Uani 1 1 d . . .
H20 H 0.2704 0.7628 0.1549 0.083 Uiso 1 1 calc R . .
C13 C 0.4776(3) 1.1826(8) 0.6683(3) 0.0730(12) Uani 1 1 d . . .
H13 H 0.5194 1.2638 0.7131 0.088 Uiso 1 1 calc R . .
C3 C -0.0225(3) 0.7704(8) 0.3083(3) 0.0837(14) Uani 1 1 d . . .
H3 H -0.0500 0.6616 0.2682 0.100 Uiso 1 1 calc R . .
C2 C -0.0707(3) 0.9275(9) 0.3217(3) 0.0885(15) Uani 1 1 d . . .
H2 H -0.1306 0.9238 0.2905 0.106 Uiso 1 1 calc R . .


_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 C22 1.746(4) . ?
C8 C10 1.525(4) . ?
C8 C16 1.529(5) . ?
C8 C17 1.536(4) . ?
C17 C18 1.387(5) . ?
C17 C22 1.397(4) . ?
C16 C15 1.392(5) . ?
C16 C11 1.406(5) . ?
C22 C21 1.410(5) . ?
C5 C4 1.395(5) . ?
C5 C6 1.412(5) . ?
C5 C10 1.451(5) . ?
C18 C19 1.411(5) . ?
C11 C12 1.388(5) . ?
C11 C9 1.449(5) . ?
C9 C10 1.350(5) . ?
C9 O1 1.364(4) . ?
O1 C7 1.416(5) . ?
C6 C1 1.393(6) . ?
C6 C7 1.495(6) . ?
C19 C20 1.379(6) . ?
C4 C3 1.402(5) . ?
C1 C2 1.381(6) . ?
C21 C20 1.378(6) . ?
C15 C14 1.395(5) . ?
C14 C13 1.387(6) . ?
C12 C13 1.389(6) . ?
C3 C2 1.380(6) . ?

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
C10 C8 C16 101.8(3) . . ?
C10 C8 C17 114.5(3) . . ?
C16 C8 C17 114.0(2) . . ?
C18 C17 C22 117.6(3) . . ?
C18 C17 C8 120.6(3) . . ?
C22 C17 C8 121.8(3) . . ?
C15 C16 C11 119.6(3) . . ?
C15 C16 C8 130.5(3) . . ?
C11 C16 C8 110.0(3) . . ?
C17 C22 C21 121.7(3) . . ?
C17 C22 Cl1 121.1(3) . . ?
C21 C22 Cl1 117.1(3) . . ?
C4 C5 C6 118.9(3) . . ?
C4 C5 C10 124.8(3) . . ?
C6 C5 C10 116.3(3) . . ?
C17 C18 C19 121.4(3) . . ?
C12 C11 C16 121.5(3) . . ?
C12 C11 C9 131.8(3) . . ?
C16 C11 C9 106.7(3) . . ?
C10 C9 O1 125.4(3) . . ?
C10 C9 C11 112.4(3) . . ?
O1 C9 C11 122.2(3) . . ?
C9 O1 C7 116.5(3) . . ?
C1 C6 C5 120.2(4) . . ?
C1 C6 C7 120.1(4) . . ?
C5 C6 C7 119.7(3) . . ?
C9 C10 C5 120.8(3) . . ?
C9 C10 C8 109.2(3) . . ?
C5 C10 C8 130.0(3) . . ?
C20 C19 C18 119.3(4) . . ?
C5 C4 C3 120.2(4) . . ?
C2 C1 C6 120.0(4) . . ?
C20 C21 C22 118.9(4) . . ?
C16 C15 C14 118.7(4) . . ?
C13 C14 C15 121.1(4) . . ?
C11 C12 C13 118.2(4) . . ?
O1 C7 C6 118.4(3) . . ?
C21 C20 C19 121.0(3) . . ?
C14 C13 C12 120.8(4) . . ?
C2 C3 C4 120.0(4) . . ?
C3 C2 C1 120.7(4) . . ?

_diffrn_measured_fraction_theta_max 0.998
_diffrn_reflns_theta_full        25.25
_diffrn_measured_fraction_theta_full 0.998
_refine_diff_density_max         0.241
_refine_diff_density_min         -0.327
_refine_diff_density_rms         0.056
