# 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 2020

####################################################################### 
# 
# 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_exp_3823
_database_code_depnum_ccdc_archive 'CCDC 1974220'
loop_
_audit_author_name
_audit_author_address
'Florencia Di Salvo'
;INQUIMAE CONICET, FCEN, University of Buenos Aires, Buenos Aires
Argentina
;
_audit_update_record             
;
2019-12-26 deposited with the CCDC.	2020-04-17 downloaded from the CCDC.
;
_audit_creation_date             2019-12-23
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2014/7
loop_
_audit_author_email
?
?
_chemical_name_common            ?
_chemical_name_systematic        AMC22
_chemical_formula_moiety         'C20 H30 Br2 N2 O2'
_chemical_formula_sum            'C20 H30 Br2 N2 O2'
_chemical_formula_weight         490.26
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C20 H30 N2 O2 Br2'
_chemical_oxdiff_usercomment     AMC22_acetona_3
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'
Br Br -0.2901 2.4595 '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'

_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           15
_space_group_name_H-M_alt        'C 1 2/c 1'
_space_group_name_Hall           '-C 2yc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z-1/2'

_cell_length_a                   14.5709(14)
_cell_length_b                   17.1752(12)
_cell_length_c                   8.9783(10)
_cell_angle_alpha                90
_cell_angle_beta                 103.868(11)
_cell_angle_gamma                90
_cell_volume                     2181.4(4)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    1684
_cell_measurement_temperature    170
_cell_measurement_theta_max      26.7920
_cell_measurement_theta_min      4.3000
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    3.732
_exptl_absorpt_correction_T_max  0.689
_exptl_absorpt_correction_T_min  0.645
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_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.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.493
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             1000
_exptl_crystal_preparation       
'Slow evaporation of the solvent from acetone solution'
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.1
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0641
_diffrn_reflns_av_unetI/netI     0.0834
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.853
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            7402
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.853
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.310
_diffrn_reflns_theta_min         3.732
_diffrn_ambient_temperature      170
_diffrn_detector_area_resol_mean 16.1158
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.853
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega  -11.00   78.00   1.0000   72.2600
omega____ theta____ kappa____ phi______ frames
    -       21.0583   77.0000 -120.0000 89

#__ type_ start__ end____ width___ exp.time_
  2 omega   51.00   90.00   1.0000   72.2600
omega____ theta____ kappa____ phi______ frames
    -       21.0583   77.0000  120.0000 39

#__ type_ start__ end____ width___ exp.time_
  3 omega   54.00   81.00   1.0000   72.2600
omega____ theta____ kappa____ phi______ frames
    -       21.0583   77.0000  -90.0000 27

#__ type_ start__ end____ width___ exp.time_
  4 omega  -10.00   73.00   1.0000   72.2600
omega____ theta____ kappa____ phi______ frames
    -       21.0583   77.0000    0.0000 83

#__ type_ start__ end____ width___ exp.time_
  5 omega   35.00   83.00   1.0000   72.2600
omega____ theta____ kappa____ phi______ frames
    -       21.0583  178.0000   90.0000 48

#__ type_ start__ end____ width___ exp.time_
  6 omega  -25.00   66.00   1.0000   72.2600
omega____ theta____ kappa____ phi______ frames
    -       21.0583  -99.0000 -150.0000 91
;
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      0.0351402000
_diffrn_orient_matrix_UB_12      0.0154225000
_diffrn_orient_matrix_UB_13      -0.0343824000
_diffrn_orient_matrix_UB_21      -0.0356329000
_diffrn_orient_matrix_UB_22      0.0123743000
_diffrn_orient_matrix_UB_23      -0.0640856000
_diffrn_orient_matrix_UB_31      -0.0027944000
_diffrn_orient_matrix_UB_32      0.0362535000
_diffrn_orient_matrix_UB_33      0.0365263000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'Enhance (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1664
_reflns_number_total             2898
_reflns_odcompleteness_completeness 99.65
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_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       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_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    'olex2.solve (Bourhis et al., 2015)'
_refine_diff_density_max         0.505
_refine_diff_density_min         -0.378
_refine_diff_density_rms         0.094
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.998
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     119
_refine_ls_number_reflns         2551
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0879
_refine_ls_R_factor_gt           0.0445
_refine_ls_restrained_S_all      0.998
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0187P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0706
_refine_ls_wR_factor_ref         0.0845
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C6(H6A,H6B), C4(H4A,H4B), C5(H5A,H5B), C3(H3A,H3B), C2(H2A,H2B)
2.b Aromatic/amide H refined with riding coordinates:
 N1(H1), C9(H9)
2.c Idealised Me refined as rotating group:
 C1(H1A,H1B,H1C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_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
Br1 Br 0.42219(3) 1.30955(2) 0.36244(5) 0.03936(15) Uani 1 1 d . . . . .
N1 N 0.42466(18) 1.00737(15) 0.3384(3) 0.0230(7) Uani 1 1 d . . . . .
H1 H 0.4249 1.0040 0.4363 0.028 Uiso 1 1 calc R . . . .
C6 C 0.3477(2) 0.88229(19) 0.3283(4) 0.0272(8) Uani 1 1 d . . . . .
H6A H 0.3779 0.8847 0.4394 0.033 Uiso 1 1 calc R . . . .
H6B H 0.2789 0.8901 0.3154 0.033 Uiso 1 1 calc R . . . .
C9 C 0.4337(2) 1.1461(2) 0.3356(3) 0.0231(8) Uani 1 1 d . . . . .
H9 H 0.3882 1.1462 0.3958 0.028 Uiso 1 1 calc R . . . .
C4 C 0.3310(2) 0.73631(19) 0.3534(4) 0.0292(9) Uani 1 1 d . . . . .
H4A H 0.3615 0.7408 0.4642 0.035 Uiso 1 1 calc R . . . .
H4B H 0.2619 0.7408 0.3412 0.035 Uiso 1 1 calc R . . . .
C5 C 0.3642(3) 0.8031(2) 0.2689(5) 0.0388(10) Uani 1 1 d . . . . .
H5A H 0.4327 0.7967 0.2763 0.047 Uiso 1 1 calc R . . . .
H5B H 0.3311 0.8000 0.1591 0.047 Uiso 1 1 calc R . . . .
C10 C 0.4668(2) 1.21594(19) 0.2947(4) 0.0251(8) Uani 1 1 d . . . . .
C8 C 0.4649(2) 1.07553(19) 0.2911(3) 0.0208(8) Uani 1 1 d . . . . .
C3 C 0.3529(3) 0.6569(2) 0.2977(5) 0.0413(10) Uani 1 1 d . . . . .
H3A H 0.4211 0.6543 0.3003 0.050 Uiso 1 1 calc R . . . .
H3B H 0.3174 0.6505 0.1897 0.050 Uiso 1 1 calc R . . . .
C1 C 0.3604(3) 0.5116(2) 0.3477(6) 0.0668(14) Uani 1 1 d . . . . .
H1A H 0.4296 0.5098 0.3731 0.100 Uiso 1 1 calc GR . . . .
H1B H 0.3360 0.5034 0.2372 0.100 Uiso 1 1 calc GR . . . .
H1C H 0.3363 0.4708 0.4043 0.100 Uiso 1 1 calc GR . . . .
O1 O 0.38142(18) 0.94567(14) 0.1098(2) 0.0354(7) Uani 1 1 d . . . . .
C7 C 0.3860(2) 0.94728(19) 0.2482(4) 0.0233(8) Uani 1 1 d . . . . .
C2 C 0.3283(3) 0.5903(2) 0.3915(5) 0.0411(10) Uani 1 1 d . . . . .
H2A H 0.3577 0.6000 0.5013 0.049 Uiso 1 1 calc R . . . .
H2B H 0.2589 0.5891 0.3788 0.049 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
Br1 C10 1.889(3) . ?
N1 H1 0.8800 . ?
N1 C8 1.420(4) . ?
N1 C7 1.349(4) . ?
C6 H6A 0.9900 . ?
C6 H6B 0.9900 . ?
C6 C5 1.501(4) . ?
C6 C7 1.506(4) . ?
C9 H9 0.9500 . ?
C9 C10 1.376(4) . ?
C9 C8 1.386(4) . ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?
C4 C5 1.517(4) . ?
C4 C3 1.513(5) . ?
C5 H5A 0.9900 . ?
C5 H5B 0.9900 . ?
C10 C10 1.396(7) 2_655 ?
C8 C8 1.396(6) 2_655 ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C3 C2 1.514(5) . ?
C1 H1A 0.9800 . ?
C1 H1B 0.9800 . ?
C1 H1C 0.9800 . ?
C1 C2 1.512(5) . ?
O1 C7 1.228(4) . ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?

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
C8 N1 H1 116.8 . . ?
C7 N1 H1 116.8 . . ?
C7 N1 C8 126.4(3) . . ?
H6A C6 H6B 107.8 . . ?
C5 C6 H6A 108.9 . . ?
C5 C6 H6B 108.9 . . ?
C5 C6 C7 113.2(3) . . ?
C7 C6 H6A 108.9 . . ?
C7 C6 H6B 108.9 . . ?
C10 C9 H9 119.2 . . ?
C10 C9 C8 121.7(3) . . ?
C8 C9 H9 119.2 . . ?
H4A C4 H4B 107.7 . . ?
C5 C4 H4A 108.9 . . ?
C5 C4 H4B 108.9 . . ?
C3 C4 H4A 108.9 . . ?
C3 C4 H4B 108.9 . . ?
C3 C4 C5 113.5(3) . . ?
C6 C5 C4 114.2(3) . . ?
C6 C5 H5A 108.7 . . ?
C6 C5 H5B 108.7 . . ?
C4 C5 H5A 108.7 . . ?
C4 C5 H5B 108.7 . . ?
H5A C5 H5B 107.6 . . ?
C9 C10 Br1 119.1(2) . . ?
C9 C10 C10 119.28(19) . 2_655 ?
C10 C10 Br1 121.63(10) 2_655 . ?
C9 C8 N1 116.5(3) . . ?
C9 C8 C8 118.99(19) . 2_655 ?
C8 C8 N1 124.45(16) 2_655 . ?
C4 C3 H3A 108.8 . . ?
C4 C3 H3B 108.8 . . ?
C4 C3 C2 113.6(3) . . ?
H3A C3 H3B 107.7 . . ?
C2 C3 H3A 108.8 . . ?
C2 C3 H3B 108.8 . . ?
H1A C1 H1B 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
C2 C1 H1A 109.5 . . ?
C2 C1 H1B 109.5 . . ?
C2 C1 H1C 109.5 . . ?
N1 C7 C6 115.4(3) . . ?
O1 C7 N1 122.6(3) . . ?
O1 C7 C6 122.0(3) . . ?
C3 C2 H2A 108.8 . . ?
C3 C2 H2B 108.8 . . ?
C1 C2 C3 113.7(3) . . ?
C1 C2 H2A 108.8 . . ?
C1 C2 H2B 108.8 . . ?
H2A C2 H2B 107.7 . . ?

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
N1 H1 O1 0.88 2.01 2.778(3) 144.9 6_576

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
C4 C3 C2 C1 -173.3(3) . . . . ?
C5 C6 C7 N1 -142.4(3) . . . . ?
C5 C6 C7 O1 38.2(5) . . . . ?
C5 C4 C3 C2 174.5(3) . . . . ?
C10 C9 C8 N1 -179.2(3) . . . . ?
C10 C9 C8 C8 3.0(5) . . . 2_655 ?
C8 N1 C7 C6 -179.6(3) . . . . ?
C8 N1 C7 O1 -0.2(5) . . . . ?
C8 C9 C10 Br1 -179.0(2) . . . . ?
C8 C9 C10 C10 0.4(6) . . . 2_655 ?
C3 C4 C5 C6 -176.9(3) . . . . ?
C7 N1 C8 C9 129.5(3) . . . . ?
C7 N1 C8 C8 -52.9(6) . . . 2_655 ?
C7 C6 C5 C4 176.9(3) . . . . ?

_olex2_submission_original_sample_id AMC22
_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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_exp_5006
_database_code_depnum_ccdc_archive 'CCDC 1974435'
loop_
_audit_author_name
_audit_author_address
'Florencia Di Salvo'
;INQUIMAE CONICET, FCEN, University of Buenos Aires, Buenos Aires
Argentina
;
_audit_update_record             
;
2019-12-27 deposited with the CCDC.	2020-04-17 downloaded from the CCDC.
;
_audit_creation_date             2019-12-26
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C18 H27 Cl2 N O'
_chemical_formula_sum            'C18 H27 Cl2 N O'
_chemical_formula_weight         344.30
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C34 H58 Br2 N2 O2'
_chemical_oxdiff_usercomment     'aguja sin cortar'
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'

_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                   16.382(2)
_cell_length_b                   12.2314(14)
_cell_length_c                   9.8293(7)
_cell_angle_alpha                90
_cell_angle_beta                 102.916(9)
_cell_angle_gamma                90
_cell_volume                     1919.8(4)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    1720
_cell_measurement_temperature    298
_cell_measurement_theta_max      24.8520
_cell_measurement_theta_min      4.0330
_shelx_estimated_absorpt_T_max   0.929
_shelx_estimated_absorpt_T_min   0.905
_exptl_absorpt_coefficient_mu    0.340
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.83102
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.46 (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.191
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             736
_exptl_crystal_preparation       ?
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: acetone'
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.22
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0482
_diffrn_reflns_av_unetI/netI     0.0594
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.877
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            12878
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.877
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.939
_diffrn_reflns_theta_min         3.828
_diffrn_ambient_temperature      298
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.1158
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.877
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -54.00  96.00   1.00  175.76    --   20.98   0.00 -60.00  150
  2  ω    -51.00  54.00   1.00  175.76    --   20.98 -77.00 -60.00  105
  3  ω    -25.00  24.00   1.00  175.76    --  -21.29 -99.00  30.00   49
  4  ω   -103.00 -53.00   1.00  175.76    --  -21.29 178.00-120.00   50
  5  ω    -53.00 -28.00   1.00  175.76    --   20.98 -37.00 120.00   25
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0160717000
_diffrn_orient_matrix_UB_12      -0.0539878000
_diffrn_orient_matrix_UB_13      0.0080517000
_diffrn_orient_matrix_UB_21      0.0365360000
_diffrn_orient_matrix_UB_22      0.0178559000
_diffrn_orient_matrix_UB_23      -0.0209617000
_diffrn_orient_matrix_UB_31      0.0195017000
_diffrn_orient_matrix_UB_32      0.0113680000
_diffrn_orient_matrix_UB_33      0.0705646000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2310
_reflns_number_total             4456
_reflns_odcompleteness_completeness 99.59
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_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       'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_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    'ShelXD (Sheldrick, 2008)'
_refine_diff_density_max         0.293
_refine_diff_density_min         -0.247
_refine_diff_density_rms         0.036
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.009
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     200
_refine_ls_number_reflns         4456
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1241
_refine_ls_R_factor_gt           0.0572
_refine_ls_restrained_S_all      1.009
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0502P)²+0.1189P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1136
_refine_ls_wR_factor_ref         0.1445
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C14(H14A,H14B), C12(H12A,H12B), C15(H15A,H15B), C10(H10A,H10B), C13(H13A,
 H13B), C11(H11A,H11B), C9(H9A,H9B), C8(H8A,H8B), C16(H16A,H16B), C17(H17A,H17B)
2.b Aromatic/amide H refined with riding coordinates:
 N1(H1), C2(H2), C6(H6), C5(H5)
2.c Idealised Me refined as rotating group:
 C18(H18A,H18B,H18C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_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
Cl2 Cl 0.46155(5) -0.24690(6) 1.11440(8) 0.0865(3) Uani 1 1 d . . . . .
Cl1 Cl 0.47089(6) -0.05212(7) 1.32934(6) 0.1013(3) Uani 1 1 d . . . . .
N1 N 0.32731(12) 0.18840(16) 0.91856(16) 0.0550(5) Uani 1 1 d . . . . .
H1 H 0.3204 0.1974 0.8299 0.066 Uiso 1 1 calc R . . . .
C1 C 0.35971(14) 0.0865(2) 0.9701(2) 0.0484(6) Uani 1 1 d . . . . .
C7 C 0.30564(15) 0.2740(2) 0.9892(2) 0.0527(6) Uani 1 1 d . . . . .
C3 C 0.42600(15) -0.0337(2) 1.1533(2) 0.0582(7) Uani 1 1 d . . . . .
O1 O 0.31226(12) 0.27289(14) 1.11577(14) 0.0684(5) Uani 1 1 d . . . . .
C2 C 0.39530(15) 0.0685(2) 1.1100(2) 0.0552(6) Uani 1 1 d . . . . .
H2 H 0.3984 0.1250 1.1743 0.066 Uiso 1 1 calc R . . . .
C14 C 0.12663(18) 0.9636(2) 0.9079(2) 0.0692(7) Uani 1 1 d . . . . .
H14A H 0.0707 0.9440 0.8571 0.083 Uiso 1 1 calc R . . . .
H14B H 0.1581 0.9868 0.8403 0.083 Uiso 1 1 calc R . . . .
C6 C 0.35808(16) 0.0013(2) 0.8774(2) 0.0619(7) Uani 1 1 d . . . . .
H6 H 0.3352 0.0127 0.7831 0.074 Uiso 1 1 calc R . . . .
C12 C 0.17483(19) 0.7660(2) 0.8928(3) 0.0683(7) Uani 1 1 d . . . . .
H12A H 0.1191 0.7450 0.8425 0.082 Uiso 1 1 calc R . . . .
H12B H 0.2067 0.7862 0.8246 0.082 Uiso 1 1 calc R . . . .
C15 C 0.12069(18) 1.0581(2) 1.0047(2) 0.0682(7) Uani 1 1 d . . . . .
H15A H 0.0908 1.0333 1.0737 0.082 Uiso 1 1 calc R . . . .
H15B H 0.1769 1.0776 1.0540 0.082 Uiso 1 1 calc R . . . .
C10 C 0.22422(18) 0.5683(2) 0.8916(2) 0.0683(7) Uani 1 1 d . . . . .
H10A H 0.2581 0.5854 0.8252 0.082 Uiso 1 1 calc R . . . .
H10B H 0.1690 0.5472 0.8392 0.082 Uiso 1 1 calc R . . . .
C13 C 0.16814(17) 0.8642(2) 0.9838(2) 0.0671(7) Uani 1 1 d . . . . .
H13A H 0.1371 0.8427 1.0527 0.081 Uiso 1 1 calc R . . . .
H13B H 0.2241 0.8844 1.0337 0.081 Uiso 1 1 calc R . . . .
C11 C 0.21635(18) 0.6690(2) 0.9758(2) 0.0670(7) Uani 1 1 d . . . . .
H11A H 0.2719 0.6908 1.0257 0.080 Uiso 1 1 calc R . . . .
H11B H 0.1846 0.6503 1.0448 0.080 Uiso 1 1 calc R . . . .
C4 C 0.42332(15) -0.1185(2) 1.0608(2) 0.0584(6) Uani 1 1 d . . . . .
C9 C 0.26323(17) 0.4728(2) 0.9807(2) 0.0626(7) Uani 1 1 d . . . . .
H9A H 0.3188 0.4938 1.0315 0.075 Uiso 1 1 calc R . . . .
H9B H 0.2301 0.4573 1.0487 0.075 Uiso 1 1 calc R . . . .
C5 C 0.38928(17) -0.0994(2) 0.9212(2) 0.0675(7) Uani 1 1 d . . . . .
H5 H 0.3876 -0.1554 0.8566 0.081 Uiso 1 1 calc R . . . .
C8 C 0.27008(18) 0.3703(2) 0.9000(2) 0.0680(8) Uani 1 1 d . . . . .
H8A H 0.3052 0.3849 0.8347 0.082 Uiso 1 1 calc R . . . .
H8B H 0.2148 0.3510 0.8461 0.082 Uiso 1 1 calc R . . . .
C16 C 0.07823(18) 1.1591(2) 0.9364(3) 0.0716(8) Uani 1 1 d . . . . .
H16A H 0.0220 1.1402 0.8863 0.086 Uiso 1 1 calc R . . . .
H16B H 0.1085 1.1853 0.8686 0.086 Uiso 1 1 calc R . . . .
C17 C 0.0729(2) 1.2504(2) 1.0381(3) 0.0829(9) Uani 1 1 d . . . . .
H17A H 0.0428 1.2237 1.1059 0.100 Uiso 1 1 calc R . . . .
H17B H 0.1292 1.2689 1.0881 0.100 Uiso 1 1 calc R . . . .
C18 C 0.0307(2) 1.3525(3) 0.9725(4) 0.1156(12) Uani 1 1 d . . . . .
H18A H 0.0603 1.3803 0.9059 0.173 Uiso 1 1 calc GR . . . .
H18B H 0.0308 1.4064 1.0435 0.173 Uiso 1 1 calc GR . . . .
H18C H -0.0260 1.3360 0.9262 0.173 Uiso 1 1 calc GR . . . .


_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
Cl2 C4 1.728(3) . ?
Cl1 C3 1.737(2) . ?
N1 H1 0.8600 . ?
N1 C1 1.404(3) . ?
N1 C7 1.348(3) . ?
C1 C2 1.386(3) . ?
C1 C6 1.380(3) . ?
C7 O1 1.224(2) . ?
C7 C8 1.505(3) . ?
C3 C2 1.379(3) . ?
C3 C4 1.374(3) . ?
C2 H2 0.9300 . ?
C14 H14A 0.9700 . ?
C14 H14B 0.9700 . ?
C14 C15 1.514(3) . ?
C14 C13 1.507(3) . ?
C6 H6 0.9300 . ?
C6 C5 1.365(3) . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
C12 C13 1.517(3) . ?
C12 C11 1.512(3) . ?
C15 H15A 0.9700 . ?
C15 H15B 0.9700 . ?
C15 C16 1.501(3) . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C10 C11 1.506(3) . ?
C10 C9 1.513(3) . ?
C13 H13A 0.9700 . ?
C13 H13B 0.9700 . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C4 C5 1.381(3) . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C9 C8 1.502(3) . ?
C5 H5 0.9300 . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C16 H16A 0.9700 . ?
C16 H16B 0.9700 . ?
C16 C17 1.514(4) . ?
C17 H17A 0.9700 . ?
C17 H17B 0.9700 . ?
C17 C18 1.501(4) . ?
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
C1 N1 H1 115.6 . . ?
C7 N1 H1 115.6 . . ?
C7 N1 C1 128.75(17) . . ?
C2 C1 N1 122.7(2) . . ?
C6 C1 N1 118.82(19) . . ?
C6 C1 C2 118.5(2) . . ?
N1 C7 C8 114.81(17) . . ?
O1 C7 N1 122.8(2) . . ?
O1 C7 C8 122.4(2) . . ?
C2 C3 Cl1 117.95(19) . . ?
C4 C3 Cl1 120.3(2) . . ?
C4 C3 C2 121.7(2) . . ?
C1 C2 H2 120.2 . . ?
C3 C2 C1 119.5(2) . . ?
C3 C2 H2 120.2 . . ?
H14A C14 H14B 107.8 . . ?
C15 C14 H14A 109.0 . . ?
C15 C14 H14B 109.0 . . ?
C13 C14 H14A 109.0 . . ?
C13 C14 H14B 109.0 . . ?
C13 C14 C15 112.9(2) . . ?
C1 C6 H6 119.3 . . ?
C5 C6 C1 121.5(2) . . ?
C5 C6 H6 119.3 . . ?
H12A C12 H12B 107.8 . . ?
C13 C12 H12A 109.0 . . ?
C13 C12 H12B 109.0 . . ?
C11 C12 H12A 109.0 . . ?
C11 C12 H12B 109.0 . . ?
C11 C12 C13 112.7(2) . . ?
C14 C15 H15A 108.3 . . ?
C14 C15 H15B 108.3 . . ?
H15A C15 H15B 107.4 . . ?
C16 C15 C14 115.8(2) . . ?
C16 C15 H15A 108.3 . . ?
C16 C15 H15B 108.3 . . ?
H10A C10 H10B 107.8 . . ?
C11 C10 H10A 109.0 . . ?
C11 C10 H10B 109.0 . . ?
C11 C10 C9 112.99(19) . . ?
C9 C10 H10A 109.0 . . ?
C9 C10 H10B 109.0 . . ?
C14 C13 C12 115.5(2) . . ?
C14 C13 H13A 108.4 . . ?
C14 C13 H13B 108.4 . . ?
C12 C13 H13A 108.4 . . ?
C12 C13 H13B 108.4 . . ?
H13A C13 H13B 107.5 . . ?
C12 C11 H11A 108.4 . . ?
C12 C11 H11B 108.4 . . ?
C10 C11 C12 115.4(2) . . ?
C10 C11 H11A 108.4 . . ?
C10 C11 H11B 108.4 . . ?
H11A C11 H11B 107.5 . . ?
C3 C4 Cl2 121.95(18) . . ?
C3 C4 C5 118.4(2) . . ?
C5 C4 Cl2 119.7(2) . . ?
C10 C9 H9A 108.7 . . ?
C10 C9 H9B 108.7 . . ?
H9A C9 H9B 107.6 . . ?
C8 C9 C10 114.25(18) . . ?
C8 C9 H9A 108.7 . . ?
C8 C9 H9B 108.7 . . ?
C6 C5 C4 120.4(2) . . ?
C6 C5 H5 119.8 . . ?
C4 C5 H5 119.8 . . ?
C7 C8 H8A 108.7 . . ?
C7 C8 H8B 108.7 . . ?
C9 C8 C7 114.21(18) . . ?
C9 C8 H8A 108.7 . . ?
C9 C8 H8B 108.7 . . ?
H8A C8 H8B 107.6 . . ?
C15 C16 H16A 108.8 . . ?
C15 C16 H16B 108.8 . . ?
C15 C16 C17 113.6(2) . . ?
H16A C16 H16B 107.7 . . ?
C17 C16 H16A 108.8 . . ?
C17 C16 H16B 108.8 . . ?
C16 C17 H17A 108.6 . . ?
C16 C17 H17B 108.6 . . ?
H17A C17 H17B 107.6 . . ?
C18 C17 C16 114.8(3) . . ?
C18 C17 H17A 108.6 . . ?
C18 C17 H17B 108.6 . . ?
C17 C18 H18A 109.5 . . ?
C17 C18 H18B 109.5 . . ?
C17 C18 H18C 109.5 . . ?
H18A C18 H18B 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?

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
N1 H1 O1 0.86 2.11 2.969(2) 175.4 4_565

_olex2_exptl_crystal_mounting_method loop
_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 1.203
_oxdiff_exptl_absorpt_empirical_full_min 0.749
