# 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 2019

####################################################################### 
# 
# 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_chalc_0ma
_database_code_depnum_ccdc_archive 'CCDC 1936534'
loop_
_audit_author_name
_audit_author_address
'Hamilton Napolitano'
;State University of Goias
Brazil
;
_audit_update_record             
;
2019-09-24 deposited with the CCDC.	2019-10-16 downloaded from the CCDC.
;
_audit_creation_date             2019-06-21
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C20 H23 Cl O'
_chemical_formula_sum            'C20 H23 Cl O'
_chemical_formula_weight         314.83
_chemical_melting_point          ?
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'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   11.4168(13)
_cell_length_b                   14.2639(18)
_cell_length_c                   11.1744(14)
_cell_angle_alpha                90
_cell_angle_beta                 106.469(3)
_cell_angle_gamma                90
_cell_volume                     1745.1(4)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    4445
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      22.22
_cell_measurement_theta_min      2.35
_shelx_estimated_absorpt_T_max   0.948
_shelx_estimated_absorpt_T_min   0.930
_exptl_absorpt_coefficient_mu    0.219
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            white
_exptl_crystal_density_diffrn    1.198
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       prismatic
_exptl_crystal_F_000             672
_exptl_crystal_size_max          0.337
_exptl_crystal_size_mid          0.246
_exptl_crystal_size_min          0.245
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0738
_diffrn_reflns_av_unetI/netI     0.0590
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_number            19668
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.489
_diffrn_reflns_theta_min         1.860
_diffrn_ambient_temperature      296.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2104
_reflns_number_total             3603
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(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  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXS-1997 (Sheldrick, 2008)'
_refine_diff_density_max         0.678
_refine_diff_density_min         -0.692
_refine_diff_density_rms         0.064
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.030
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     213
_refine_ls_number_reflns         3603
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1374
_refine_ls_R_factor_gt           0.0823
_refine_ls_restrained_S_all      1.030
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0877P)²+2.3944P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1985
_refine_ls_wR_factor_ref         0.2431
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Uiso/Uaniso restraints and constraints
Uanis(C2) = Uanis(C1)
3.a Secondary CH2 refined with riding coordinates:
 C14(H14A,H14B), C15(H15A,H15B), C16(H16A,H16B)
3.b Aromatic/amide H refined with riding coordinates:
 C4(H4), C2(H2), C8(H8), C10(H10), C5(H5)
3.c Idealised Me refined as rotating group:
 C20(H20A,H20B,H20C), C18(H18A,H18B,H18C)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   ?
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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Cl1 Cl 0.98208(13) 0.31973(10) 0.58321(11) 0.0876(5) Uani 1 1 d . . . . .
O1 O 0.7241(3) 0.7991(2) 0.4557(3) 0.0794(10) Uani 1 1 d . . . . .
C4 C 0.9358(4) 0.3566(3) 0.7989(4) 0.0629(11) Uani 1 1 d . . . . .
H4 H 0.967225 0.297350 0.823788 0.075 Uiso 1 1 calc R . . . .
C3 C 0.9276(3) 0.3896(3) 0.6820(4) 0.0538(9) Uani 1 1 d . . . . .
C2 C 0.8792(3) 0.4781(3) 0.6442(4) 0.0554(7) Uani 1 1 d . . . . .
H2 H 0.872231 0.498977 0.563649 0.067 Uiso 1 1 calc R . . . .
C1 C 0.8413(3) 0.5352(3) 0.7277(4) 0.0554(7) Uani 1 1 d . . . . .
C7 C 0.7944(3) 0.6331(3) 0.6970(4) 0.0572(10) Uani 1 1 d . . . . .
H7 H 0.775(4) 0.672(3) 0.768(4) 0.069 Uiso 1 1 d R . . . .
C8 C 0.7778(4) 0.6740(3) 0.5910(4) 0.0615(10) Uani 1 1 d . . . . .
H8 H 0.794208 0.639120 0.527314 0.074 Uiso 1 1 calc R . . . .
C9 C 0.7346(3) 0.7720(3) 0.5607(4) 0.0541(9) Uani 1 1 d . . . . .
C10 C 0.7063(3) 0.8332(2) 0.6567(3) 0.0509(9) Uani 1 1 d . . . . .
H10 H 0.713915 0.809718 0.736259 0.061 Uiso 1 1 calc R . . . .
C11 C 0.6699(3) 0.9213(3) 0.6295(3) 0.0477(9) Uani 1 1 d . . . . .
H11 H 0.666(3) 0.942(3) 0.544(4) 0.057 Uiso 1 1 d R . . . .
C12 C 0.6393(3) 0.9936(2) 0.7101(3) 0.0442(8) Uani 1 1 d . . . . .
C13 C 0.6966(3) 1.0896(2) 0.7009(4) 0.0526(9) Uani 1 1 d . . . . .
C14 C 0.6769(4) 1.1555(3) 0.8059(5) 0.0766(13) Uani 1 1 d . . . . .
H14A H 0.737845 1.140352 0.883526 0.092 Uiso 1 1 calc R . . . .
H14B H 0.690939 1.219741 0.784949 0.092 Uiso 1 1 calc R . . . .
C15 C 0.5576(5) 1.1499(3) 0.8260(5) 0.0830(14) Uani 1 1 d . . . . .
H15A H 0.495781 1.167629 0.750120 0.100 Uiso 1 1 calc R . . . .
H15B H 0.553114 1.193326 0.891288 0.100 Uiso 1 1 calc R . . . .
C6 C 0.8504(4) 0.5022(3) 0.8438(5) 0.0736(12) Uani 1 1 d . . . . .
H6 H 0.813(4) 0.546(3) 0.898(4) 0.088 Uiso 1 1 d R . . . .
C5 C 0.8962(5) 0.4136(3) 0.8788(4) 0.0797(14) Uani 1 1 d . . . . .
H5 H 0.900343 0.391927 0.958344 0.096 Uiso 1 1 calc R . . . .
C16 C 0.5331(4) 1.0533(3) 0.8621(4) 0.0681(11) Uani 1 1 d . . . . .
H16A H 0.447028 1.047977 0.856792 0.082 Uiso 1 1 calc R . . . .
H16B H 0.579136 1.042912 0.948423 0.082 Uiso 1 1 calc R . . . .
C17 C 0.5656(3) 0.9778(2) 0.7825(3) 0.0520(9) Uani 1 1 d . . . . .
C20 C 0.5040(4) 0.8860(3) 0.7912(4) 0.0686(12) Uani 1 1 d . . . . .
H20A H 0.510399 0.845518 0.724696 0.103 Uiso 1 1 calc GR . . . .
H20B H 0.419364 0.896885 0.784507 0.103 Uiso 1 1 calc GR . . . .
H20C H 0.542705 0.856895 0.869954 0.103 Uiso 1 1 calc GR . . . .
C18 C 0.6399(5) 1.1326(3) 0.5723(5) 0.0908(16) Uani 1 1 d . . . . .
H18A H 0.656477 1.093033 0.509497 0.136 Uiso 1 1 calc GR . . . .
H18B H 0.674282 1.193532 0.568696 0.136 Uiso 1 1 calc GR . . . .
H18C H 0.553145 1.138089 0.557825 0.136 Uiso 1 1 calc GR . . . .
C19 C 0.8333(4) 1.0790(4) 0.7224(5) 0.0679(12) Uani 1 1 d . . . . .
H19A H 0.873(5) 1.050(4) 0.803(5) 0.102 Uiso 1 1 d R . . . .
H19B H 0.874(5) 1.140(4) 0.719(5) 0.102 Uiso 1 1 d R . . . .
H19C H 0.852(5) 1.034(4) 0.664(5) 0.102 Uiso 1 1 d 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 C3 1.729(4) . ?
O1 C9 1.209(5) . ?
C4 H4 0.9300 . ?
C4 C3 1.366(5) . ?
C4 C5 1.374(6) . ?
C3 C2 1.394(5) . ?
C2 H2 0.9300 . ?
C2 C1 1.397(6) . ?
C1 C7 1.500(6) . ?
C1 C6 1.356(6) . ?
C7 H7 1.05(4) . ?
C7 C8 1.285(5) . ?
C8 H8 0.9300 . ?
C8 C9 1.489(5) . ?
C9 C10 1.489(5) . ?
C10 H10 0.9300 . ?
C10 C11 1.332(5) . ?
C11 H11 0.98(4) . ?
C11 C12 1.474(5) . ?
C12 C13 1.534(5) . ?
C12 C17 1.341(5) . ?
C13 C14 1.568(6) . ?
C13 C18 1.527(6) . ?
C13 C19 1.518(5) . ?
C14 H14A 0.9700 . ?
C14 H14B 0.9700 . ?
C14 C15 1.445(7) . ?
C15 H15A 0.9700 . ?
C15 H15B 0.9700 . ?
C15 C16 1.484(6) . ?
C6 H6 1.04(5) . ?
C6 C5 1.381(6) . ?
C5 H5 0.9300 . ?
C16 H16A 0.9700 . ?
C16 H16B 0.9700 . ?
C16 C17 1.510(5) . ?
C17 C20 1.503(5) . ?
C20 H20A 0.9600 . ?
C20 H20B 0.9600 . ?
C20 H20C 0.9600 . ?
C18 H18A 0.9600 . ?
C18 H18B 0.9600 . ?
C18 H18C 0.9600 . ?
C19 H19A 0.98(5) . ?
C19 H19B 0.99(6) . ?
C19 H19C 0.98(5) . ?

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
C3 C4 H4 120.9 . . ?
C3 C4 C5 118.1(4) . . ?
C5 C4 H4 120.9 . . ?
C4 C3 Cl1 118.2(3) . . ?
C4 C3 C2 121.0(4) . . ?
C2 C3 Cl1 120.8(3) . . ?
C3 C2 H2 120.1 . . ?
C3 C2 C1 119.8(4) . . ?
C1 C2 H2 120.1 . . ?
C2 C1 C7 123.2(4) . . ?
C6 C1 C2 118.9(4) . . ?
C6 C1 C7 117.9(4) . . ?
C1 C7 H7 118(2) . . ?
C8 C7 C1 125.7(4) . . ?
C8 C7 H7 117(2) . . ?
C7 C8 H8 117.0 . . ?
C7 C8 C9 126.1(4) . . ?
C9 C8 H8 117.0 . . ?
O1 C9 C8 117.2(4) . . ?
O1 C9 C10 122.0(3) . . ?
C10 C9 C8 120.8(4) . . ?
C9 C10 H10 119.8 . . ?
C11 C10 C9 120.4(3) . . ?
C11 C10 H10 119.8 . . ?
C10 C11 H11 116(2) . . ?
C10 C11 C12 129.2(3) . . ?
C12 C11 H11 115(2) . . ?
C11 C12 C13 113.8(3) . . ?
C17 C12 C11 123.3(3) . . ?
C17 C12 C13 122.8(3) . . ?
C12 C13 C14 109.3(3) . . ?
C18 C13 C12 110.2(3) . . ?
C18 C13 C14 110.6(4) . . ?
C19 C13 C12 109.8(3) . . ?
C19 C13 C14 107.5(3) . . ?
C19 C13 C18 109.3(4) . . ?
C13 C14 H14A 108.5 . . ?
C13 C14 H14B 108.5 . . ?
H14A C14 H14B 107.5 . . ?
C15 C14 C13 115.1(4) . . ?
C15 C14 H14A 108.5 . . ?
C15 C14 H14B 108.5 . . ?
C14 C15 H15A 109.5 . . ?
C14 C15 H15B 109.5 . . ?
C14 C15 C16 110.7(4) . . ?
H15A C15 H15B 108.1 . . ?
C16 C15 H15A 109.5 . . ?
C16 C15 H15B 109.5 . . ?
C1 C6 H6 114(3) . . ?
C1 C6 C5 120.6(5) . . ?
C5 C6 H6 125(3) . . ?
C4 C5 C6 121.7(4) . . ?
C4 C5 H5 119.2 . . ?
C6 C5 H5 119.2 . . ?
C15 C16 H16A 108.8 . . ?
C15 C16 H16B 108.8 . . ?
C15 C16 C17 113.9(4) . . ?
H16A C16 H16B 107.7 . . ?
C17 C16 H16A 108.8 . . ?
C17 C16 H16B 108.8 . . ?
C12 C17 C16 122.5(3) . . ?
C12 C17 C20 124.8(3) . . ?
C20 C17 C16 112.7(3) . . ?
C17 C20 H20A 109.5 . . ?
C17 C20 H20B 109.5 . . ?
C17 C20 H20C 109.5 . . ?
H20A C20 H20B 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
C13 C18 H18A 109.5 . . ?
C13 C18 H18B 109.5 . . ?
C13 C18 H18C 109.5 . . ?
H18A C18 H18B 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
C13 C19 H19A 112(3) . . ?
C13 C19 H19B 112(3) . . ?
C13 C19 H19C 112(3) . . ?
H19A C19 H19B 107(4) . . ?
H19A C19 H19C 102(4) . . ?
H19B C19 H19C 111(4) . . ?

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
Cl1 C3 C2 C1 -176.8(3) . . . . ?
O1 C9 C10 C11 -1.2(6) . . . . ?
C4 C3 C2 C1 1.7(5) . . . . ?
C3 C4 C5 C6 -0.7(7) . . . . ?
C3 C2 C1 C7 176.7(3) . . . . ?
C3 C2 C1 C6 -1.2(6) . . . . ?
C2 C1 C7 C8 3.7(6) . . . . ?
C2 C1 C6 C5 -0.1(7) . . . . ?
C1 C7 C8 C9 -178.2(4) . . . . ?
C1 C6 C5 C4 1.1(8) . . . . ?
C7 C1 C6 C5 -178.2(4) . . . . ?
C7 C8 C9 O1 180.0(4) . . . . ?
C7 C8 C9 C10 0.1(6) . . . . ?
C8 C9 C10 C11 178.7(3) . . . . ?
C9 C10 C11 C12 -179.0(3) . . . . ?
C10 C11 C12 C13 134.0(4) . . . . ?
C10 C11 C12 C17 -47.7(6) . . . . ?
C11 C12 C13 C14 -170.4(3) . . . . ?
C11 C12 C13 C18 67.9(4) . . . . ?
C11 C12 C13 C19 -52.7(4) . . . . ?
C11 C12 C17 C16 -178.6(3) . . . . ?
C11 C12 C17 C20 -0.5(6) . . . . ?
C12 C13 C14 C15 -41.6(5) . . . . ?
C13 C12 C17 C16 -0.3(5) . . . . ?
C13 C12 C17 C20 177.8(3) . . . . ?
C13 C14 C15 C16 60.0(6) . . . . ?
C14 C15 C16 C17 -45.9(6) . . . . ?
C15 C16 C17 C12 17.3(6) . . . . ?
C15 C16 C17 C20 -161.1(4) . . . . ?
C6 C1 C7 C8 -178.4(4) . . . . ?
C5 C4 C3 Cl1 177.8(3) . . . . ?
C5 C4 C3 C2 -0.7(6) . . . . ?
C17 C12 C13 C14 11.2(5) . . . . ?
C17 C12 C13 C18 -110.5(4) . . . . ?
C17 C12 C13 C19 128.9(4) . . . . ?
C18 C13 C14 C15 80.0(5) . . . . ?
C19 C13 C14 C15 -160.8(4) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
