# 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 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_monika-cd-re
_database_code_depnum_ccdc_archive 'CCDC 1038945'
_audit_update_record             
;
2014-12-12 deposited with the CCDC.
2015-02-03 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
 2-amino-4-(4-chlorophenyl)-6,6,8,8-tetrahydro-7,
7-dimethyl-5-oxo-4H-chromene-3-carbonitrile
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C18 H17 Cl N2 O2'
_chemical_formula_sum            'C18 H17 Cl N2 O2'
_chemical_formula_weight         328.79

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'
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'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   P21/n

loop_
_symmetry_equiv_pos_as_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                   9.3992(8)
_cell_length_b                   16.8270(11)
_cell_length_c                   10.9101(9)
_cell_angle_alpha                90.00
_cell_angle_beta                 112.042(10)
_cell_angle_gamma                90.00
_cell_volume                     1599.4(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    1912
_cell_measurement_theta_min      4.1380
_cell_measurement_theta_max      27.6080

_exptl_crystal_description       ?
_exptl_crystal_colour            ?
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.365
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             688
_exptl_absorpt_coefficient_mu    0.250
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.95269
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   'Crys Alis RED'

_exptl_special_details           
;
 CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;

_diffrn_ambient_temperature      293(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  'Xcalibur, Sapphire3'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean 16.1049
_diffrn_standards_number         0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_decay_%        0
_diffrn_reflns_number            6916
_diffrn_reflns_av_R_equivalents  0.0315
_diffrn_reflns_av_sigmaI/netI    0.0505
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         3.81
_diffrn_reflns_theta_max         26.00
_reflns_number_total             3128
_reflns_number_gt                2093
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'CrysAlisPro (Oxford Diffraction,2010)'
_computing_cell_refinement       'CrysAlisPro (Oxford Diffraction,2010)'
_computing_data_reduction        'CrysAlisPro (Oxford Diffraction,2010)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'ORTEP3 (Farrugia, 2012)'
_computing_publication_material  'PLATON (Spek,2009)'

_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)+(0.0508P)²+0.1663P] 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         3128
_refine_ls_number_parameters     216
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0794
_refine_ls_R_factor_gt           0.0472
_refine_ls_wR_factor_ref         0.1209
_refine_ls_wR_factor_gt          0.1039
_refine_ls_goodness_of_fit_ref   1.028
_refine_ls_restrained_S_all      1.028
_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 0.30284(8) 0.03020(4) 0.73001(7) 0.0694(3) Uani 1 1 d . . .
O1 O 0.87402(15) 0.12734(9) 1.42790(13) 0.0371(4) Uani 1 1 d . . .
C3 C 0.6919(2) 0.22470(13) 1.3081(2) 0.0334(5) Uani 1 1 d . . .
O9 O 0.97124(18) 0.25746(10) 1.08733(17) 0.0513(5) Uani 1 1 d . . .
C2 C 0.7539(2) 0.17767(13) 1.4149(2) 0.0327(5) Uani 1 1 d . . .
N20 N 0.7126(2) 0.16914(14) 1.5190(2) 0.0442(5) Uani 1 1 d . . .
C4 C 0.7393(2) 0.21979(13) 1.1906(2) 0.0323(5) Uani 1 1 d . . .
H4 H 0.7440 0.2740 1.1595 0.039 Uiso 1 1 calc R . .
C5 C 0.8997(2) 0.18547(12) 1.2387(2) 0.0314(5) Uani 1 1 d . . .
C5A C 0.9535(2) 0.13956(12) 1.3459(2) 0.0319(5) Uani 1 1 d . . .
C10 C 0.6279(2) 0.17168(12) 1.0738(2) 0.0330(5) Uani 1 1 d . . .
C6 C 1.1018(2) 0.09650(14) 1.3951(2) 0.0417(6) Uani 1 1 d . . .
H6A H 1.0863 0.0441 1.4252 0.050 Uiso 1 1 calc R . .
H6B H 1.1736 0.1249 1.4703 0.050 Uiso 1 1 calc R . .
C13 C 0.4276(3) 0.08486(14) 0.8621(2) 0.0451(6) Uani 1 1 d . . .
C7 C 1.1708(2) 0.08779(13) 1.2894(2) 0.0395(5) Uani 1 1 d . . .
C9 C 1.0066(2) 0.20718(14) 1.1751(2) 0.0378(5) Uani 1 1 d . . .
C16 C 0.5747(3) 0.27841(14) 1.3043(2) 0.0405(5) Uani 1 1 d . . .
C12 C 0.3934(3) 0.09672(15) 0.9717(2) 0.0506(6) Uani 1 1 d . . .
H12 H 0.3037 0.0759 0.9760 0.061 Uiso 1 1 calc R . .
C15 C 0.6588(3) 0.15860(15) 0.9607(2) 0.0463(6) Uani 1 1 d . . .
H15 H 0.7480 0.1794 0.9554 0.056 Uiso 1 1 calc R . .
C14 C 0.5600(3) 0.11530(15) 0.8557(2) 0.0511(6) Uani 1 1 d . . .
H14 H 0.5831 0.1068 0.7810 0.061 Uiso 1 1 calc R . .
C11 C 0.4941(2) 0.14024(15) 1.0770(2) 0.0452(6) Uani 1 1 d . . .
H11 H 0.4704 0.1483 1.1516 0.054 Uiso 1 1 calc R . .
N19 N 0.4776(2) 0.32141(13) 1.2988(2) 0.0609(6) Uani 1 1 d . . .
C8 C 1.1634(2) 0.16966(14) 1.2261(3) 0.0468(6) Uani 1 1 d . . .
H8A H 1.2339 0.2050 1.2909 0.056 Uiso 1 1 calc R . .
H8B H 1.1984 0.1646 1.1533 0.056 Uiso 1 1 calc R . .
C17 C 1.0807(3) 0.02805(15) 1.1840(3) 0.0610(7) Uani 1 1 d . . .
H17A H 0.9764 0.0457 1.1423 0.091 Uiso 1 1 calc R . .
H17B H 1.0827 -0.0229 1.2243 0.091 Uiso 1 1 calc R . .
H17C H 1.1263 0.0237 1.1189 0.091 Uiso 1 1 calc R . .
C18 C 1.3371(3) 0.06038(17) 1.3555(3) 0.0604(8) Uani 1 1 d . . .
H18A H 1.3814 0.0544 1.2897 0.091 Uiso 1 1 calc R . .
H18B H 1.3401 0.0103 1.3986 0.091 Uiso 1 1 calc R . .
H18C H 1.3943 0.0991 1.4196 0.091 Uiso 1 1 calc R . .
H30 H 0.638(3) 0.1966(14) 1.526(2) 0.051(7) Uiso 1 1 d . . .
H40 H 0.777(3) 0.1522(14) 1.589(3) 0.050(8) Uiso 1 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 C13 1.741(2) . ?
O1 C2 1.375(2) . ?
O1 C5A 1.379(2) . ?
C3 C2 1.347(3) . ?
C3 C16 1.414(3) . ?
C3 C4 1.510(3) . ?
O9 C9 1.226(3) . ?
C2 N20 1.339(3) . ?
N20 H30 0.87(2) . ?
N20 H40 0.83(3) . ?
C4 C5 1.512(3) . ?
C4 C10 1.541(3) . ?
C4 H4 0.9800 . ?
C5 C5A 1.332(3) . ?
C5 C9 1.467(3) . ?
C5A C6 1.481(3) . ?
C10 C11 1.377(3) . ?
C10 C15 1.388(3) . ?
C6 C7 1.528(3) . ?
C6 H6A 0.9700 . ?
C6 H6B 0.9700 . ?
C13 C12 1.365(3) . ?
C13 C14 1.372(3) . ?
C7 C17 1.523(3) . ?
C7 C18 1.526(3) . ?
C7 C8 1.531(3) . ?
C9 C8 1.505(3) . ?
C16 N19 1.148(3) . ?
C12 C11 1.391(3) . ?
C12 H12 0.9300 . ?
C15 C14 1.381(3) . ?
C15 H15 0.9300 . ?
C14 H14 0.9300 . ?
C11 H11 0.9300 . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C17 H17A 0.9600 . ?
C17 H17B 0.9600 . ?
C17 H17C 0.9600 . ?
C18 H18A 0.9600 . ?
C18 H18B 0.9600 . ?
C18 H18C 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
_geom_angle_publ_flag
C2 O1 C5A 117.69(16) . . ?
C2 C3 C16 118.71(19) . . ?
C2 C3 C4 122.18(18) . . ?
C16 C3 C4 119.07(19) . . ?
N20 C2 C3 128.9(2) . . ?
N20 C2 O1 109.55(19) . . ?
C3 C2 O1 121.55(17) . . ?
C2 N20 H30 121.6(16) . . ?
C2 N20 H40 118.3(17) . . ?
H30 N20 H40 116(2) . . ?
C3 C4 C5 107.42(16) . . ?
C3 C4 C10 113.90(16) . . ?
C5 C4 C10 111.49(16) . . ?
C3 C4 H4 107.9 . . ?
C5 C4 H4 107.9 . . ?
C10 C4 H4 107.9 . . ?
C5A C5 C9 117.25(18) . . ?
C5A C5 C4 121.82(17) . . ?
C9 C5 C4 120.74(18) . . ?
C5 C5A O1 122.39(18) . . ?
C5 C5A C6 126.71(18) . . ?
O1 C5A C6 110.90(17) . . ?
C11 C10 C15 117.4(2) . . ?
C11 C10 C4 121.63(19) . . ?
C15 C10 C4 120.96(18) . . ?
C5A C6 C7 112.42(18) . . ?
C5A C6 H6A 109.1 . . ?
C7 C6 H6A 109.1 . . ?
C5A C6 H6B 109.1 . . ?
C7 C6 H6B 109.1 . . ?
H6A C6 H6B 107.9 . . ?
C12 C13 C14 120.4(2) . . ?
C12 C13 Cl1 119.73(19) . . ?
C14 C13 Cl1 119.82(19) . . ?
C17 C7 C18 109.7(2) . . ?
C17 C7 C6 111.11(19) . . ?
C18 C7 C6 108.81(19) . . ?
C17 C7 C8 109.6(2) . . ?
C18 C7 C8 110.48(19) . . ?
C6 C7 C8 107.10(18) . . ?
O9 C9 C5 120.6(2) . . ?
O9 C9 C8 121.28(19) . . ?
C5 C9 C8 118.1(2) . . ?
N19 C16 C3 178.6(3) . . ?
C13 C12 C11 119.3(2) . . ?
C13 C12 H12 120.3 . . ?
C11 C12 H12 120.3 . . ?
C14 C15 C10 121.4(2) . . ?
C14 C15 H15 119.3 . . ?
C10 C15 H15 119.3 . . ?
C13 C14 C15 119.7(2) . . ?
C13 C14 H14 120.1 . . ?
C15 C14 H14 120.1 . . ?
C10 C11 C12 121.7(2) . . ?
C10 C11 H11 119.1 . . ?
C12 C11 H11 119.1 . . ?
C9 C8 C7 114.62(18) . . ?
C9 C8 H8A 108.6 . . ?
C7 C8 H8A 108.6 . . ?
C9 C8 H8B 108.6 . . ?
C7 C8 H8B 108.6 . . ?
H8A C8 H8B 107.6 . . ?
C7 C17 H17A 109.5 . . ?
C7 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
C7 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
C7 C18 H18A 109.5 . . ?
C7 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
C7 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 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
C16 C3 C2 N20 5.7(4) . . . . ?
C4 C3 C2 N20 -172.1(2) . . . . ?
C16 C3 C2 O1 -176.36(18) . . . . ?
C4 C3 C2 O1 5.9(3) . . . . ?
C5A O1 C2 N20 -166.37(18) . . . . ?
C5A O1 C2 C3 15.3(3) . . . . ?
C2 C3 C4 C5 -24.3(3) . . . . ?
C16 C3 C4 C5 157.97(18) . . . . ?
C2 C3 C4 C10 99.7(2) . . . . ?
C16 C3 C4 C10 -78.0(3) . . . . ?
C3 C4 C5 C5A 24.9(3) . . . . ?
C10 C4 C5 C5A -100.5(2) . . . . ?
C3 C4 C5 C9 -149.86(19) . . . . ?
C10 C4 C5 C9 84.7(2) . . . . ?
C9 C5 C5A O1 167.71(18) . . . . ?
C4 C5 C5A O1 -7.3(3) . . . . ?
C9 C5 C5A C6 -11.3(3) . . . . ?
C4 C5 C5A C6 173.7(2) . . . . ?
C2 O1 C5A C5 -14.7(3) . . . . ?
C2 O1 C5A C6 164.48(17) . . . . ?
C3 C4 C10 C11 3.1(3) . . . . ?
C5 C4 C10 C11 124.9(2) . . . . ?
C3 C4 C10 C15 -177.1(2) . . . . ?
C5 C4 C10 C15 -55.3(3) . . . . ?
C5 C5A C6 C7 -17.8(3) . . . . ?
O1 C5A C6 C7 163.06(18) . . . . ?
C5A C6 C7 C17 -71.8(3) . . . . ?
C5A C6 C7 C18 167.26(19) . . . . ?
C5A C6 C7 C8 47.8(2) . . . . ?
C5A C5 C9 O9 -170.3(2) . . . . ?
C4 C5 C9 O9 4.8(3) . . . . ?
C5A C5 C9 C8 6.2(3) . . . . ?
C4 C5 C9 C8 -178.82(19) . . . . ?
C14 C13 C12 C11 0.2(4) . . . . ?
Cl1 C13 C12 C11 179.75(18) . . . . ?
C11 C10 C15 C14 -0.4(3) . . . . ?
C4 C10 C15 C14 179.7(2) . . . . ?
C12 C13 C14 C15 -0.4(4) . . . . ?
Cl1 C13 C14 C15 -179.95(18) . . . . ?
C10 C15 C14 C13 0.5(4) . . . . ?
C15 C10 C11 C12 0.2(3) . . . . ?
C4 C10 C11 C12 -179.9(2) . . . . ?
C13 C12 C11 C10 -0.1(4) . . . . ?
O9 C9 C8 C7 -156.0(2) . . . . ?
C5 C9 C8 C7 27.6(3) . . . . ?
C17 C7 C8 C9 67.2(2) . . . . ?
C18 C7 C8 C9 -171.8(2) . . . . ?
C6 C7 C8 C9 -53.4(3) . . . . ?

_diffrn_measured_fraction_theta_max 0.997
_diffrn_reflns_theta_full        26.00
_diffrn_measured_fraction_theta_full 0.997
_refine_diff_density_max         0.238
_refine_diff_density_min         -0.271
_refine_diff_density_rms         0.042
