# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 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_KAH11_T1_1_glassrod_0m_a
_database_code_depnum_ccdc_archive 'CCDC 1904044'
loop_
_audit_author_name
_audit_author_address
'Muhammad Usman Anwar'
;University of Nizwa
Oman
;
_audit_update_record             
;
2019-03-19 deposited with the CCDC.	2019-09-18 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2016/6
_shelx_SHELXL_version_number     2016/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C23 H26 N2 O2'
_chemical_formula_sum            'C23 H26 N2 O2'
_chemical_formula_weight         362.46

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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/n'
_space_group_name_Hall           '-P 2yn'

_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.
;

loop_
_space_group_symop_operation_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                   11.5219(11)
_cell_length_b                   11.4926(9)
_cell_length_c                   15.5242(14)
_cell_angle_alpha                90
_cell_angle_beta                 92.720(3)
_cell_angle_gamma                90
_cell_volume                     2053.3(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    9900
_cell_measurement_theta_min      3.17
_cell_measurement_theta_max      26.40

_exptl_crystal_description       plate
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.172
_exptl_crystal_F_000             776
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.5
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.15
_exptl_absorpt_coefficient_mu    0.075
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6766
_exptl_absorpt_correction_T_max  0.7454
_exptl_absorpt_process_details   sadabs
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'Bruker APEX-II CCD'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            29035
_diffrn_reflns_av_unetI/netI     0.0245
_diffrn_reflns_av_R_equivalents  0.0409
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         3.169
_diffrn_reflns_theta_max         26.436
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measured_fraction_theta_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.992
_diffrn_reflns_point_group_measured_fraction_full 0.994
_reflns_number_total             4207
_reflns_number_gt                3062
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_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.
;

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0741P)²+1.3337P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     'SHELXL-2016/6 (Sheldrick 2016)'
_refine_ls_extinction_coef       0.053(6)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         4207
_refine_ls_number_parameters     252
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0875
_refine_ls_R_factor_gt           0.0588
_refine_ls_wR_factor_ref         0.1773
_refine_ls_wR_factor_gt          0.1456
_refine_ls_goodness_of_fit_ref   1.067
_refine_ls_restrained_S_all      1.067
_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_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
O1 O 0.67271(13) 0.78686(12) 0.26583(11) 0.0487(4) Uani 1 1 d . . . . .
O2 O 0.4273(2) 0.51993(15) 0.18529(12) 0.0719(6) Uani 1 1 d . . . . .
N1 N 0.64067(14) 0.60298(14) 0.31134(11) 0.0373(4) Uani 1 1 d . . . . .
N2 N 0.47247(17) 0.71034(16) 0.17325(12) 0.0453(5) Uani 1 1 d D . . . .
H2A H 0.5119(19) 0.7614(17) 0.2003(15) 0.054 Uiso 1 1 d D U . . .
C1 C 0.51155(16) 0.61420(16) 0.31197(13) 0.0347(4) Uani 1 1 d . . . . .
C2 C 0.47987(19) 0.50250(18) 0.35805(14) 0.0437(5) Uani 1 1 d . . . . .
C3 C 0.5733(2) 0.44361(19) 0.38314(15) 0.0512(6) Uani 1 1 d . . . . .
H3 H 0.570751 0.375380 0.415204 0.061 Uiso 1 1 calc R U . . .
C4 C 0.6829(2) 0.49590(19) 0.35563(17) 0.0507(6) Uani 1 1 d . . . . .
H4A H 0.722244 0.444927 0.316625 0.061 Uiso 1 1 calc R U . . .
H4B H 0.735048 0.513938 0.404734 0.061 Uiso 1 1 calc R U . . .
C5 C 0.3559(2) 0.4726(2) 0.3733(2) 0.0650(7) Uani 1 1 d . . . . .
H5A H 0.313569 0.463712 0.318969 0.097 Uiso 1 1 calc R U . . .
H5B H 0.321636 0.533782 0.405688 0.097 Uiso 1 1 calc R U . . .
H5C H 0.353100 0.401082 0.405149 0.097 Uiso 1 1 calc R U . . .
C6 C 0.5339(2) 0.75354(19) 0.43691(14) 0.0444(5) Uani 1 1 d . . . . .
H6 H 0.607382 0.722402 0.449001 0.053 Uiso 1 1 calc R U . . .
C7 C 0.4899(2) 0.8360(2) 0.49189(15) 0.0533(6) Uani 1 1 d . . . . .
H7 H 0.533907 0.859458 0.540581 0.064 Uiso 1 1 calc R U . . .
C8 C 0.3816(2) 0.8832(2) 0.47477(17) 0.0562(6) Uani 1 1 d . . . . .
H8 H 0.352017 0.937810 0.512080 0.067 Uiso 1 1 calc R U . . .
C9 C 0.3174(2) 0.8493(2) 0.40244(17) 0.0559(6) Uani 1 1 d . . . . .
H9 H 0.244699 0.882086 0.390057 0.067 Uiso 1 1 calc R U . . .
C10 C 0.36084(18) 0.7660(2) 0.34762(15) 0.0468(5) Uani 1 1 d . . . . .
H10 H 0.316285 0.742694 0.299130 0.056 Uiso 1 1 calc R U . . .
C11 C 0.46955(17) 0.71702(17) 0.36414(13) 0.0359(4) Uani 1 1 d . . . . .
C12 C 0.46476(18) 0.61058(18) 0.21634(13) 0.0401(5) Uani 1 1 d . . . . .
C13 C 0.4580(2) 0.7252(2) 0.07879(15) 0.0536(6) Uani 1 1 d . . . . .
C14 C 0.3387(3) 0.6845(3) 0.04650(19) 0.0753(9) Uani 1 1 d . . . . .
H14A H 0.327559 0.702299 -0.013739 0.113 Uiso 1 1 calc R U . . .
H14B H 0.280385 0.723347 0.078043 0.113 Uiso 1 1 calc R U . . .
H14C H 0.332445 0.601954 0.054741 0.113 Uiso 1 1 calc R U . . .
C15 C 0.4686(4) 0.8549(3) 0.0627(2) 0.0974(12) Uani 1 1 d . . . . .
H15A H 0.455022 0.870471 0.002330 0.146 Uiso 1 1 calc R U . . .
H15B H 0.545306 0.880445 0.080763 0.146 Uiso 1 1 calc R U . . .
H15C H 0.412350 0.895750 0.094883 0.146 Uiso 1 1 calc R U . . .
C16 C 0.5532(3) 0.6574(4) 0.0369(2) 0.0977(13) Uani 1 1 d . . . . .
H16A H 0.542831 0.663156 -0.024703 0.147 Uiso 1 1 calc R U . . .
H16B H 0.549462 0.577169 0.053768 0.147 Uiso 1 1 calc R U . . .
H16C H 0.627530 0.688932 0.055029 0.147 Uiso 1 1 calc R U . . .
C17 C 0.71019(17) 0.68935(16) 0.28392(13) 0.0369(5) Uani 1 1 d . . . . .
C18 C 0.83567(17) 0.66210(17) 0.27220(13) 0.0370(5) Uani 1 1 d . . . . .
C19 C 0.91877(19) 0.7447(2) 0.29587(15) 0.0472(5) Uani 1 1 d . . . . .
H19 H 0.896643 0.813448 0.322119 0.057 Uiso 1 1 calc R U . . .
C20 C 1.0345(2) 0.7254(3) 0.28064(18) 0.0613(7) Uani 1 1 d . . . . .
H20 H 1.089962 0.780739 0.297358 0.074 Uiso 1 1 calc R U . . .
C21 C 1.0679(2) 0.6243(2) 0.24069(18) 0.0592(7) Uani 1 1 d . . . . .
H21 H 1.145870 0.610945 0.231331 0.071 Uiso 1 1 calc R U . . .
C22 C 0.9859(2) 0.5435(2) 0.21483(16) 0.0556(6) Uani 1 1 d . . . . .
H22 H 1.008278 0.475940 0.187119 0.067 Uiso 1 1 calc R U . . .
C23 C 0.8697(2) 0.56212(18) 0.22984(15) 0.0458(5) Uani 1 1 d . . . . .
H23 H 0.814377 0.507502 0.211493 0.055 Uiso 1 1 calc R U . . .


_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
O1 C17 1.229(2) . ?
O2 C12 1.218(3) . ?
N1 C17 1.357(2) . ?
N1 C4 1.481(3) . ?
N1 C1 1.494(2) . ?
N2 C12 1.333(3) . ?
N2 C13 1.478(3) . ?
N2 H2A 0.842(10) . ?
C1 C2 1.522(3) . ?
C1 C11 1.524(3) . ?
C1 C12 1.556(3) . ?
C2 C3 1.315(3) . ?
C2 C5 1.499(3) . ?
C3 C4 1.480(3) . ?
C3 H3 0.9300 . ?
C4 H4A 0.9700 . ?
C4 H4B 0.9700 . ?
C5 H5A 0.9600 . ?
C5 H5B 0.9600 . ?
C5 H5C 0.9600 . ?
C6 C11 1.387(3) . ?
C6 C7 1.387(3) . ?
C6 H6 0.9300 . ?
C7 C8 1.375(4) . ?
C7 H7 0.9300 . ?
C8 C9 1.372(4) . ?
C8 H8 0.9300 . ?
C9 C10 1.390(3) . ?
C9 H9 0.9300 . ?
C10 C11 1.386(3) . ?
C10 H10 0.9300 . ?
C13 C14 1.515(4) . ?
C13 C16 1.517(4) . ?
C13 C15 1.517(4) . ?
C14 H14A 0.9600 . ?
C14 H14B 0.9600 . ?
C14 H14C 0.9600 . ?
C15 H15A 0.9600 . ?
C15 H15B 0.9600 . ?
C15 H15C 0.9600 . ?
C16 H16A 0.9600 . ?
C16 H16B 0.9600 . ?
C16 H16C 0.9600 . ?
C17 C18 1.499(3) . ?
C18 C19 1.386(3) . ?
C18 C23 1.390(3) . ?
C19 C20 1.383(3) . ?
C19 H19 0.9300 . ?
C20 C21 1.381(4) . ?
C20 H20 0.9300 . ?
C21 C22 1.371(4) . ?
C21 H21 0.9300 . ?
C22 C23 1.386(3) . ?
C22 H22 0.9300 . ?
C23 H23 0.9300 . ?

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
C17 N1 C4 124.58(17) . . ?
C17 N1 C1 122.82(16) . . ?
C4 N1 C1 111.99(15) . . ?
C12 N2 C13 126.18(19) . . ?
C12 N2 H2A 113.3(18) . . ?
C13 N2 H2A 116.6(18) . . ?
N1 C1 C2 101.04(15) . . ?
N1 C1 C11 114.32(15) . . ?
C2 C1 C11 108.35(16) . . ?
N1 C1 C12 106.95(15) . . ?
C2 C1 C12 110.23(16) . . ?
C11 C1 C12 115.04(16) . . ?
C3 C2 C5 127.4(2) . . ?
C3 C2 C1 111.22(19) . . ?
C5 C2 C1 121.3(2) . . ?
C2 C3 C4 113.80(19) . . ?
C2 C3 H3 123.1 . . ?
C4 C3 H3 123.1 . . ?
C3 C4 N1 101.83(18) . . ?
C3 C4 H4A 111.4 . . ?
N1 C4 H4A 111.4 . . ?
C3 C4 H4B 111.4 . . ?
N1 C4 H4B 111.4 . . ?
H4A C4 H4B 109.3 . . ?
C2 C5 H5A 109.5 . . ?
C2 C5 H5B 109.5 . . ?
H5A C5 H5B 109.5 . . ?
C2 C5 H5C 109.5 . . ?
H5A C5 H5C 109.5 . . ?
H5B C5 H5C 109.5 . . ?
C11 C6 C7 120.7(2) . . ?
C11 C6 H6 119.6 . . ?
C7 C6 H6 119.6 . . ?
C8 C7 C6 120.4(2) . . ?
C8 C7 H7 119.8 . . ?
C6 C7 H7 119.8 . . ?
C9 C8 C7 119.7(2) . . ?
C9 C8 H8 120.1 . . ?
C7 C8 H8 120.1 . . ?
C8 C9 C10 120.0(2) . . ?
C8 C9 H9 120.0 . . ?
C10 C9 H9 120.0 . . ?
C11 C10 C9 121.0(2) . . ?
C11 C10 H10 119.5 . . ?
C9 C10 H10 119.5 . . ?
C10 C11 C6 118.14(19) . . ?
C10 C11 C1 121.55(18) . . ?
C6 C11 C1 119.77(18) . . ?
O2 C12 N2 124.6(2) . . ?
O2 C12 C1 120.05(18) . . ?
N2 C12 C1 115.32(17) . . ?
N2 C13 C14 110.5(2) . . ?
N2 C13 C16 108.5(2) . . ?
C14 C13 C16 111.3(3) . . ?
N2 C13 C15 105.7(2) . . ?
C14 C13 C15 109.2(3) . . ?
C16 C13 C15 111.6(3) . . ?
C13 C14 H14A 109.5 . . ?
C13 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
C13 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C13 C15 H15A 109.5 . . ?
C13 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
C13 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
C13 C16 H16A 109.5 . . ?
C13 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
C13 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
O1 C17 N1 122.18(18) . . ?
O1 C17 C18 119.57(17) . . ?
N1 C17 C18 118.20(16) . . ?
C19 C18 C23 119.00(19) . . ?
C19 C18 C17 118.89(18) . . ?
C23 C18 C17 121.73(18) . . ?
C20 C19 C18 120.3(2) . . ?
C20 C19 H19 119.9 . . ?
C18 C19 H19 119.9 . . ?
C21 C20 C19 120.2(2) . . ?
C21 C20 H20 119.9 . . ?
C19 C20 H20 119.9 . . ?
C22 C21 C20 119.9(2) . . ?
C22 C21 H21 120.0 . . ?
C20 C21 H21 120.0 . . ?
C21 C22 C23 120.2(2) . . ?
C21 C22 H22 119.9 . . ?
C23 C22 H22 119.9 . . ?
C22 C23 C18 120.3(2) . . ?
C22 C23 H23 119.9 . . ?
C18 C23 H23 119.9 . . ?

_refine_diff_density_max         0.674
_refine_diff_density_min         -0.187
_refine_diff_density_rms         0.044

####################################################################### 
# 
# 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_KAJ13T2_0ma_a
_database_code_depnum_ccdc_archive 'CCDC 1904045'
loop_
_audit_author_name
_audit_author_address
'Muhammad Usman Anwar'
;University of Nizwa
Oman
;
_audit_update_record             
;
2019-03-19 deposited with the CCDC.	2019-09-18 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2016/6
_shelx_SHELXL_version_number     2016/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C25 H26 Cl2 N2 O2'
_chemical_formula_sum            'C25 H26 Cl2 N2 O2'
_chemical_formula_weight         457.38

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 21/n'
_space_group_name_Hall           '-P 2yn'

_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.
;

loop_
_space_group_symop_operation_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                   16.0878(15)
_cell_length_b                   7.3312(8)
_cell_length_c                   19.996(2)
_cell_angle_alpha                90
_cell_angle_beta                 101.831(5)
_cell_angle_gamma                90
_cell_volume                     2308.3(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    9938
_cell_measurement_theta_min      2.97
_cell_measurement_theta_max      24.56

_exptl_crystal_description       plate
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.316
_exptl_crystal_F_000             960
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.290
_exptl_crystal_size_mid          0.270
_exptl_crystal_size_min          0.060
_exptl_absorpt_coefficient_mu    0.306
_shelx_estimated_absorpt_T_min   0.917
_shelx_estimated_absorpt_T_max   0.982
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.7086
_exptl_absorpt_correction_T_max  0.7452
_exptl_absorpt_process_details   sadabs
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            62396
_diffrn_reflns_av_unetI/netI     0.0244
_diffrn_reflns_av_R_equivalents  0.0714
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_theta_min         3.065
_diffrn_reflns_theta_max         25.132
_diffrn_reflns_theta_full        25.132
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_point_group_measured_fraction_full 0.997
_reflns_number_total             4114
_reflns_number_gt                3107
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_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.
;

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0552P)²+1.4989P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         4114
_refine_ls_number_parameters     281
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0687
_refine_ls_R_factor_gt           0.0457
_refine_ls_wR_factor_ref         0.1252
_refine_ls_wR_factor_gt          0.1082
_refine_ls_goodness_of_fit_ref   1.045
_refine_ls_restrained_S_all      1.045
_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_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 0.11770(6) 1.06540(15) 0.05535(6) 0.1067(4) Uani 1 1 d . . . . .
O1 O 0.42792(9) 0.8714(2) 0.19565(8) 0.0393(4) Uani 1 1 d . . . . .
N1 N 0.41932(10) 0.5658(2) 0.18012(9) 0.0313(4) Uani 1 1 d . . . . .
C1 C 0.16508(15) 0.9038(4) 0.11407(14) 0.0523(7) Uani 1 1 d . . . . .
O2 O 0.57856(11) 0.4119(2) 0.30254(8) 0.0506(4) Uani 1 1 d . . . . .
Cl2 Cl 0.43176(4) 0.67136(11) 0.03803(3) 0.0586(2) Uani 1 1 d . . . . .
N2 N 0.54844(12) 0.7120(3) 0.29718(9) 0.0400(5) Uani 1 1 d . . . . .
H2 H 0.521937 0.796750 0.271654 0.048 Uiso 1 1 calc R U . . .
C2 C 0.11621(15) 0.8055(4) 0.15016(15) 0.0556(7) Uani 1 1 d . . . . .
H2A H 0.057966 0.825164 0.143295 0.067 Uiso 1 1 calc R U . . .
C3 C 0.15475(16) 0.6781(4) 0.19637(14) 0.0534(7) Uani 1 1 d . . . . .
H3 H 0.122438 0.611488 0.221355 0.064 Uiso 1 1 calc R U . . .
C4 C 0.24083(15) 0.6476(4) 0.20619(12) 0.0452(6) Uani 1 1 d . . . . .
H4 H 0.266240 0.560021 0.237419 0.054 Uiso 1 1 calc R U . . .
C5 C 0.28974(13) 0.7472(3) 0.16968(11) 0.0334(5) Uani 1 1 d . . . . .
C6 C 0.25167(14) 0.8774(3) 0.12390(12) 0.0415(5) Uani 1 1 d . . . . .
H6 H 0.283997 0.946827 0.099794 0.050 Uiso 1 1 calc R U . . .
C7 C 0.38498(13) 0.7318(3) 0.18282(11) 0.0320(5) Uani 1 1 d . . . . .
C8 C 0.37065(15) 0.4036(3) 0.15030(13) 0.0424(6) Uani 1 1 d . . . . .
H8A H 0.334880 0.357510 0.180089 0.051 Uiso 1 1 calc R U . . .
H8B H 0.335722 0.430732 0.105829 0.051 Uiso 1 1 calc R U . . .
C9 C 0.43887(16) 0.2734(3) 0.14481(13) 0.0444(6) Uani 1 1 d . . . . .
H9 H 0.428336 0.156634 0.126936 0.053 Uiso 1 1 calc R U . . .
C10 C 0.51575(15) 0.3372(3) 0.16738(12) 0.0389(5) Uani 1 1 d . . . . .
C11 C 0.59728(18) 0.2402(4) 0.16842(15) 0.0570(7) Uani 1 1 d . . . . .
H11A H 0.585821 0.116168 0.154116 0.085 Uiso 1 1 calc R U . . .
H11B H 0.631137 0.242168 0.213927 0.085 Uiso 1 1 calc R U . . .
H11C H 0.627486 0.299873 0.137889 0.085 Uiso 1 1 calc R U . . .
C12 C 0.51278(12) 0.5336(3) 0.19157(11) 0.0310(5) Uani 1 1 d . . . . .
C13 C 0.55025(13) 0.5469(3) 0.27008(11) 0.0337(5) Uani 1 1 d . . . . .
C14 C 0.56244(13) 0.6560(3) 0.15068(11) 0.0321(5) Uani 1 1 d . . . . .
C15 C 0.53385(14) 0.7156(3) 0.08413(11) 0.0376(5) Uani 1 1 d . . . . .
C16 C 0.58541(17) 0.8125(3) 0.04917(13) 0.0485(6) Uani 1 1 d . . . . .
H16 H 0.563934 0.853346 0.004971 0.058 Uiso 1 1 calc R U . . .
C17 C 0.66806(17) 0.8482(4) 0.07977(15) 0.0537(7) Uani 1 1 d . . . . .
H17 H 0.702807 0.912920 0.056307 0.064 Uiso 1 1 calc R U . . .
C18 C 0.69935(16) 0.7886(4) 0.14476(14) 0.0501(6) Uani 1 1 d . . . . .
H18 H 0.755530 0.811964 0.165539 0.060 Uiso 1 1 calc R U . . .
C19 C 0.64728(14) 0.6935(3) 0.17960(12) 0.0411(5) Uani 1 1 d . . . . .
H19 H 0.669509 0.653234 0.223740 0.049 Uiso 1 1 calc R U . . .
C20 C 0.58817(14) 0.7589(4) 0.36694(12) 0.0419(6) Uani 1 1 d . . . . .
H20 H 0.582482 0.655305 0.396657 0.050 Uiso 1 1 calc R U . . .
C21 C 0.54513(15) 0.9230(4) 0.39058(14) 0.0543(7) Uani 1 1 d . . . . .
H21A H 0.486033 0.894303 0.389590 0.065 Uiso 1 1 calc R U . . .
H21B H 0.546839 1.023808 0.359478 0.065 Uiso 1 1 calc R U . . .
C22 C 0.58780(18) 0.9796(5) 0.46226(15) 0.0690(9) Uani 1 1 d . . . . .
H22A H 0.560224 1.087994 0.475101 0.083 Uiso 1 1 calc R U . . .
H22B H 0.581492 0.883109 0.494029 0.083 Uiso 1 1 calc R U . . .
C23 C 0.6804(2) 1.0180(6) 0.46697(18) 0.0924(13) Uani 1 1 d . . . . .
H23A H 0.686646 1.123387 0.439052 0.111 Uiso 1 1 calc R U . . .
H23B H 0.706719 1.046597 0.513905 0.111 Uiso 1 1 calc R U . . .
C24 C 0.72455(18) 0.8583(7) 0.44352(17) 0.0976(14) Uani 1 1 d . . . . .
H24A H 0.724458 0.757560 0.474943 0.117 Uiso 1 1 calc R U . . .
H24B H 0.783183 0.890429 0.444084 0.117 Uiso 1 1 calc R U . . .
C25 C 0.68217(15) 0.7986(5) 0.37217(14) 0.0655(9) Uani 1 1 d . . . . .
H25A H 0.710122 0.689858 0.360072 0.079 Uiso 1 1 calc R U . . .
H25B H 0.688511 0.893808 0.339893 0.079 Uiso 1 1 calc R U . . .


_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 C1 1.731(3) . ?
O1 C7 1.232(3) . ?
N1 C7 1.343(3) . ?
N1 C8 1.480(3) . ?
N1 C12 1.492(3) . ?
C1 C2 1.375(4) . ?
C1 C6 1.380(3) . ?
O2 C13 1.219(3) . ?
Cl2 C15 1.741(2) . ?
N2 C13 1.329(3) . ?
N2 C20 1.452(3) . ?
N2 H2 0.8600 . ?
C2 C3 1.370(4) . ?
C2 H2A 0.9300 . ?
C3 C4 1.377(3) . ?
C3 H3 0.9300 . ?
C4 C5 1.386(3) . ?
C4 H4 0.9300 . ?
C5 C6 1.376(3) . ?
C5 C7 1.505(3) . ?
C6 H6 0.9300 . ?
C8 C9 1.476(3) . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C9 C10 1.313(3) . ?
C9 H9 0.9300 . ?
C10 C11 1.488(3) . ?
C10 C12 1.523(3) . ?
C11 H11A 0.9600 . ?
C11 H11B 0.9600 . ?
C11 H11C 0.9600 . ?
C12 C14 1.543(3) . ?
C12 C13 1.565(3) . ?
C14 C15 1.386(3) . ?
C14 C19 1.396(3) . ?
C15 C16 1.385(3) . ?
C16 C17 1.370(4) . ?
C16 H16 0.9300 . ?
C17 C18 1.366(4) . ?
C17 H17 0.9300 . ?
C18 C19 1.383(3) . ?
C18 H18 0.9300 . ?
C19 H19 0.9300 . ?
C20 C21 1.511(3) . ?
C20 C25 1.523(3) . ?
C20 H20 0.9800 . ?
C21 C22 1.515(4) . ?
C21 H21A 0.9700 . ?
C21 H21B 0.9700 . ?
C22 C23 1.500(4) . ?
C22 H22A 0.9700 . ?
C22 H22B 0.9700 . ?
C23 C24 1.494(5) . ?
C23 H23A 0.9700 . ?
C23 H23B 0.9700 . ?
C24 C25 1.514(4) . ?
C24 H24A 0.9700 . ?
C24 H24B 0.9700 . ?
C25 H25A 0.9700 . ?
C25 H25B 0.9700 . ?

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
C7 N1 C8 123.81(17) . . ?
C7 N1 C12 123.15(17) . . ?
C8 N1 C12 111.61(16) . . ?
C2 C1 C6 121.4(2) . . ?
C2 C1 Cl1 119.7(2) . . ?
C6 C1 Cl1 119.0(2) . . ?
C13 N2 C20 124.4(2) . . ?
C13 N2 H2 117.8 . . ?
C20 N2 H2 117.8 . . ?
C3 C2 C1 118.9(2) . . ?
C3 C2 H2A 120.6 . . ?
C1 C2 H2A 120.6 . . ?
C2 C3 C4 120.7(2) . . ?
C2 C3 H3 119.7 . . ?
C4 C3 H3 119.7 . . ?
C3 C4 C5 120.2(2) . . ?
C3 C4 H4 119.9 . . ?
C5 C4 H4 119.9 . . ?
C6 C5 C4 119.5(2) . . ?
C6 C5 C7 117.81(19) . . ?
C4 C5 C7 122.4(2) . . ?
C5 C6 C1 119.4(2) . . ?
C5 C6 H6 120.3 . . ?
C1 C6 H6 120.3 . . ?
O1 C7 N1 122.96(19) . . ?
O1 C7 C5 118.78(19) . . ?
N1 C7 C5 118.26(18) . . ?
C9 C8 N1 102.08(18) . . ?
C9 C8 H8A 111.4 . . ?
N1 C8 H8A 111.4 . . ?
C9 C8 H8B 111.4 . . ?
N1 C8 H8B 111.4 . . ?
H8A C8 H8B 109.2 . . ?
C10 C9 C8 114.0(2) . . ?
C10 C9 H9 123.0 . . ?
C8 C9 H9 123.0 . . ?
C9 C10 C11 126.9(2) . . ?
C9 C10 C12 110.9(2) . . ?
C11 C10 C12 122.1(2) . . ?
C10 C11 H11A 109.5 . . ?
C10 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
C10 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
N1 C12 C10 101.35(17) . . ?
N1 C12 C14 116.21(17) . . ?
C10 C12 C14 109.17(17) . . ?
N1 C12 C13 108.23(16) . . ?
C10 C12 C13 110.27(17) . . ?
C14 C12 C13 111.14(17) . . ?
O2 C13 N2 124.0(2) . . ?
O2 C13 C12 120.6(2) . . ?
N2 C13 C12 115.44(19) . . ?
C15 C14 C19 116.1(2) . . ?
C15 C14 C12 125.87(19) . . ?
C19 C14 C12 117.62(19) . . ?
C16 C15 C14 122.1(2) . . ?
C16 C15 Cl2 115.20(19) . . ?
C14 C15 Cl2 122.73(17) . . ?
C17 C16 C15 120.0(2) . . ?
C17 C16 H16 120.0 . . ?
C15 C16 H16 120.0 . . ?
C18 C17 C16 119.9(2) . . ?
C18 C17 H17 120.1 . . ?
C16 C17 H17 120.1 . . ?
C17 C18 C19 119.8(2) . . ?
C17 C18 H18 120.1 . . ?
C19 C18 H18 120.1 . . ?
C18 C19 C14 122.2(2) . . ?
C18 C19 H19 118.9 . . ?
C14 C19 H19 118.9 . . ?
N2 C20 C21 110.46(19) . . ?
N2 C20 C25 110.28(19) . . ?
C21 C20 C25 109.8(2) . . ?
N2 C20 H20 108.8 . . ?
C21 C20 H20 108.8 . . ?
C25 C20 H20 108.8 . . ?
C20 C21 C22 111.5(2) . . ?
C20 C21 H21A 109.3 . . ?
C22 C21 H21A 109.3 . . ?
C20 C21 H21B 109.3 . . ?
C22 C21 H21B 109.3 . . ?
H21A C21 H21B 108.0 . . ?
C23 C22 C21 111.3(2) . . ?
C23 C22 H22A 109.4 . . ?
C21 C22 H22A 109.4 . . ?
C23 C22 H22B 109.4 . . ?
C21 C22 H22B 109.4 . . ?
H22A C22 H22B 108.0 . . ?
C24 C23 C22 111.3(3) . . ?
C24 C23 H23A 109.4 . . ?
C22 C23 H23A 109.4 . . ?
C24 C23 H23B 109.4 . . ?
C22 C23 H23B 109.4 . . ?
H23A C23 H23B 108.0 . . ?
C23 C24 C25 111.8(3) . . ?
C23 C24 H24A 109.3 . . ?
C25 C24 H24A 109.3 . . ?
C23 C24 H24B 109.3 . . ?
C25 C24 H24B 109.3 . . ?
H24A C24 H24B 107.9 . . ?
C24 C25 C20 111.6(2) . . ?
C24 C25 H25A 109.3 . . ?
C20 C25 H25A 109.3 . . ?
C24 C25 H25B 109.3 . . ?
C20 C25 H25B 109.3 . . ?
H25A C25 H25B 108.0 . . ?

_refine_diff_density_max         0.298
_refine_diff_density_min         -0.465
_refine_diff_density_rms         0.050

