# Electronic Supplementary Material (ESI) for New Journal of Chemistry.
# This journal is © The Royal Society of Chemistry and the Centre National de la Recherche Scientifique 2018

####################################################################### 
# 
# 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_r2-3-red
_database_code_depnum_ccdc_archive 'CCDC 1560310'
_audit_update_record             
;
2017-07-05 deposited with the CCDC.
2018-05-07 downloaded from the CCDC.
;
_audit_creation_date             2017-07-04
_audit_creation_method           
;
Olex2 1.2
(compiled 2017.03.28 svn.r3405 for OlexSys, GUI svn.r5337)
;
_chemical_name_common            ?
_chemical_name_systematic        
1-chloroethylene-5-chloro-1,9-pyrazoloanthrone
_chemical_formula_moiety         'C16 H10 Cl2 N2 O'
_chemical_formula_sum            'C16 H10 Cl2 N2 O'
_chemical_formula_weight         317.16
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C H N O Cl'
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'

_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_id
_space_group_symop_operation_xyz
1 'x, y, z'
2 '-x+1/2, y+1/2, -z+1/2'
3 '-x, -y, -z'
4 'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   6.7039(5)
_cell_length_b                   14.5890(10)
_cell_length_c                   13.9378(9)
_cell_angle_alpha                90.00
_cell_angle_beta                 96.283(6)
_cell_angle_gamma                90.00
_cell_volume                     1354.97(16)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    2668
_cell_measurement_temperature    100.08(2)
_cell_measurement_theta_max      25.5690
_cell_measurement_theta_min      3.1580
_exptl_absorpt_coefficient_mu    0.478
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_type   ?
_exptl_absorpt_process_details   ?
_exptl_crystal_colour            'clear yellowish colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   yellowish
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.555
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             648
_exptl_crystal_preparation       ?
_exptl_crystal_size_max          0.24
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.13
_exptl_special_details           
;
 ?
;
_diffrn_reflns_av_R_equivalents  0.1024
_diffrn_reflns_av_unetI/netI     0.0790
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            18436
_diffrn_reflns_theta_full        27.48
_diffrn_reflns_theta_max         27.48
_diffrn_reflns_theta_min         3.36
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.08(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean ?
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -89.00  12.00   1.00   16.00    --  -18.48 -77.00 120.00  101
  2  ω     -8.00  93.00   1.00   16.00    --   22.54  77.00  60.00  101
  3  ω      1.00  91.00   1.00   16.00    --   22.54  57.00   0.00   90
  4  ω    -48.00  53.00   1.00   16.00    --   22.54 -77.00 -60.00  101
  5  ω    -48.00  53.00   1.00   16.00    --   22.54 -77.00-150.00  101
  6  ω    -44.00  54.00   1.00   16.00    --  -18.48  37.00  90.00   98
  7  ω      1.00  79.00   1.00   16.00    --   22.54  57.00 -90.00   78
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  ?
_diffrn_measurement_method       ?
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0500017000
_diffrn_orient_matrix_UB_12      0.0221867000
_diffrn_orient_matrix_UB_13      0.0358356000
_diffrn_orient_matrix_UB_21      -0.0404397000
_diffrn_orient_matrix_UB_22      0.0324919000
_diffrn_orient_matrix_UB_23      -0.0346696000
_diffrn_orient_matrix_UB_31      -0.0848187000
_diffrn_orient_matrix_UB_32      -0.0285612000
_diffrn_orient_matrix_UB_33      -0.0116323000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'Mova (Mo) X-ray Source'
_diffrn_standards_decay_%        ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_number         ?
_reflns_number_gt                2314
_reflns_number_total             3099
_reflns_odcompleteness_completeness 99.72
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     27.42
_reflns_threshold_expression     >2sigma(I)
_computing_cell_refinement       ?
_computing_data_collection       ?
_computing_data_reduction        ?
_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    'XS (Sheldrick, 2008)'
_refine_diff_density_max         0.677
_refine_diff_density_min         -0.506
_refine_diff_density_rms         0.115
_refine_ls_extinction_coef       ?
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.111
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     190
_refine_ls_number_reflns         3099
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1271
_refine_ls_R_factor_gt           0.0964
_refine_ls_restrained_S_all      1.111
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0603P)²+8.7860P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2226
_refine_ls_wR_factor_ref         0.2391
_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.
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C16(H16a,H16b), C15(H15a,H15b)
2.b Aromatic/amide H refined with riding coordinates:
 C9(H9), C11(H11), C10(H10), C4(H4), C2(H2), C3(H3)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
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_calc_flag
_atom_site_disorder_assembly
_atom_site_disorder_group
_atom_site_refinement_flags_posn
Cl1 Cl 0.2390(2) 0.55952(9) 0.49500(9) 0.0224(3) Uani 1 d . . .
Cl2 Cl 0.1863(3) 0.64781(12) -0.29509(11) 0.0414(5) Uani 1 d . . .
O1 O 0.2058(7) 0.4782(3) -0.1974(3) 0.0344(10) Uani 1 d . . .
C6 C 0.2372(8) 0.6134(4) -0.0982(4) 0.0244(12) Uani 1 d . . .
C9 C 0.2264(9) 0.3554(4) -0.0284(5) 0.0308(14) Uani 1 d . . .
H9 H 0.2096 0.3226 -0.0859 0.037 Uiso 1 calc . . R
C11 C 0.2738(9) 0.3517(5) 0.1502(5) 0.0342(14) Uani 1 d . . .
H11 H 0.2859 0.3187 0.2076 0.041 Uiso 1 calc . . R
C16 C 0.1744(10) 0.5524(5) 0.3646(4) 0.0338(14) Uani 1 d . . .
H16A H 0.0559 0.5146 0.3501 0.041 Uiso 1 calc . . R
H16B H 0.1452 0.6131 0.3384 0.041 Uiso 1 calc . . R
N1 N 0.3129(8) 0.6023(4) 0.1722(4) 0.0299(11) Uani 1 d . . .
C13 C 0.2668(8) 0.4926(4) 0.0591(4) 0.0250(12) Uani 1 d . . .
C1 C 0.2217(9) 0.6782(4) -0.1733(4) 0.0277(13) Uani 1 d . . .
C10 C 0.2419(9) 0.3095(4) 0.0605(5) 0.0329(14) Uani 1 d . . .
H10 H 0.2299 0.2460 0.0593 0.039 Uiso 1 calc . . R
N2 N 0.3132(8) 0.5172(3) 0.2143(4) 0.0284(11) Uani 1 d . . .
C7 C 0.2250(8) 0.5107(4) -0.1165(4) 0.0268(13) Uani 1 d . . .
C8 C 0.2365(8) 0.4501(4) -0.0294(4) 0.0259(12) Uani 1 d . . .
C5 C 0.2669(9) 0.6505(4) -0.0026(4) 0.0263(12) Uani 1 d . . .
C4 C 0.2785(9) 0.7450(4) 0.0127(5) 0.0316(14) Uani 1 d . . .
H4 H 0.2980 0.7676 0.0754 0.038 Uiso 1 calc . . R
C14 C 0.2853(8) 0.5869(4) 0.0769(4) 0.0265(12) Uani 1 d . . .
C2 C 0.2318(9) 0.7720(4) -0.1574(5) 0.0318(14) Uani 1 d . . .
H2 H 0.2187 0.8125 -0.2093 0.038 Uiso 1 calc . . R
C15 C 0.3494(9) 0.5110(5) 0.3192(4) 0.0347(15) Uani 1 d . . .
H15A H 0.4719 0.5434 0.3417 0.042 Uiso 1 calc . . R
H15B H 0.3658 0.4472 0.3383 0.042 Uiso 1 calc . . R
C3 C 0.2615(9) 0.8050(4) -0.0639(5) 0.0327(14) Uani 1 d . . .
H3 H 0.2700 0.8678 -0.0527 0.039 Uiso 1 calc . . R
C12 C 0.2866(8) 0.4483(4) 0.1477(4) 0.0281(13) Uani 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
Cl1 C16 1.824(6) . ?
Cl2 C1 1.746(6) . ?
O1 C7 1.217(7) . ?
C6 C1 1.406(8) . ?
C6 C7 1.520(8) . ?
C6 C5 1.432(8) . ?
C9 C10 1.403(9) . ?
C9 C8 1.382(8) . ?
C11 C10 1.388(9) . ?
C11 C12 1.414(9) . ?
C16 C15 1.518(9) . ?
N1 N2 1.373(7) . ?
N1 C14 1.340(7) . ?
C13 C8 1.377(8) . ?
C13 C14 1.400(8) . ?
C13 C12 1.387(8) . ?
C1 C2 1.387(8) . ?
N2 C15 1.458(7) . ?
N2 C12 1.366(8) . ?
C7 C8 1.496(8) . ?
C5 C4 1.395(8) . ?
C5 C14 1.441(8) . ?
C4 C3 1.376(9) . ?
C2 C3 1.384(9) . ?

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 C6 C7 122.7(5) . . ?
C1 C6 C5 115.4(5) . . ?
C5 C6 C7 121.9(5) . . ?
C8 C9 C10 119.2(6) . . ?
C10 C11 C12 115.1(6) . . ?
C15 C16 Cl1 109.2(4) . . ?
C14 N1 N2 105.4(5) . . ?
C8 C13 C14 127.1(6) . . ?
C8 C13 C12 125.3(6) . . ?
C12 C13 C14 107.6(5) . . ?
C6 C1 Cl2 123.0(5) . . ?
C2 C1 Cl2 113.9(5) . . ?
C2 C1 C6 123.2(5) . . ?
C11 C10 C9 124.9(6) . . ?
N1 N2 C15 118.5(5) . . ?
C12 N2 N1 112.4(5) . . ?
C12 N2 C15 129.1(5) . . ?
O1 C7 C6 122.5(6) . . ?
O1 C7 C8 120.8(6) . . ?
C8 C7 C6 116.7(5) . . ?
C9 C8 C7 126.9(6) . . ?
C13 C8 C9 116.3(6) . . ?
C13 C8 C7 116.7(5) . . ?
C6 C5 C14 117.6(5) . . ?
C4 C5 C6 121.1(5) . . ?
C4 C5 C14 121.3(5) . . ?
C3 C4 C5 120.8(6) . . ?
N1 C14 C13 109.9(5) . . ?
N1 C14 C5 130.2(5) . . ?
C13 C14 C5 119.9(5) . . ?
C3 C2 C1 119.5(6) . . ?
N2 C15 C16 110.0(5) . . ?
C4 C3 C2 120.0(6) . . ?
C13 C12 C11 119.1(6) . . ?
N2 C12 C11 136.1(6) . . ?
N2 C12 C13 104.8(5) . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.218
_oxdiff_exptl_absorpt_empirical_full_min 0.873
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: MeoH-THF'
