# Electronic Supplementary Material (ESI) for ChemComm.
# This journal is © The Royal Society of Chemistry 2018

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_mo_2017968_0m
_database_code_depnum_ccdc_archive 'CCDC 1852787'
_audit_update_record             
;
2018-07-02 deposited with the CCDC.
2018-10-01 downloaded from the CCDC.
;
_audit_creation_date             2017-11-08
_audit_creation_method           
;
Olex2 1.2
(compiled 2017.08.10 svn.r3458 for OlexSys, GUI svn.r5381)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C17 H17 N O'
_chemical_formula_sum            'C17 H17 N O'
_chemical_formula_weight         251.31
_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'
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/n 1'
_space_group_name_Hall           '-P 2yn'
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                   13.587(6)
_cell_length_b                   6.230(3)
_cell_length_c                   15.598(7)
_cell_angle_alpha                90
_cell_angle_beta                 92.110(11)
_cell_angle_gamma                90
_cell_volume                     1319.4(10)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    419
_cell_measurement_temperature    173
_cell_measurement_theta_max      17.805
_cell_measurement_theta_min      2.61
_shelx_estimated_absorpt_T_max   0.991
_shelx_estimated_absorpt_T_min   0.985
_exptl_absorpt_coefficient_mu    0.078
_exptl_absorpt_correction_T_max  0.7455
_exptl_absorpt_correction_T_min  0.6465
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'SADABS-2014/5 (Bruker,2014/5) was used for absorption correction. wR2(int) was 0.0844 before and 0.0608 after correction. The Ratio of minimum to maximum transmission is 0.8672. The λ/2 correction factor is 0.00150.'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.265
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             536
_exptl_crystal_size_max          0.19
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.11
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0972
_diffrn_reflns_av_unetI/netI     0.1127
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.984
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            9583
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.984
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.343
_diffrn_reflns_theta_min         1.952
_diffrn_ambient_temperature      173
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.984
_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                1277
_reflns_number_total             2927
_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       'SAINT v8.34A (Bruker, 2013)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT v8.34A (Bruker, 2013)'
_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    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.161
_refine_diff_density_min         -0.205
_refine_diff_density_rms         0.046
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.942
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     181
_refine_ls_number_reflns         2927
_refine_ls_number_restraints     202
_refine_ls_R_factor_all          0.1533
_refine_ls_R_factor_gt           0.0556
_refine_ls_restrained_S_all      0.928
_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)+(0.0350P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0988
_refine_ls_wR_factor_ref         0.1279
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All C(H,H,H,H) groups
2. Restrained distances
 O0AA-C11 \\sim O1-C11 \\sim O1-C10 \\sim O0AA-C10
 with sigma of 0.02
3. Rigid bond restraints
 All non-hydrogen atoms
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
4. Uiso/Uaniso restraints and constraints
All non-hydrogen atoms have similar U: within 2A with sigma of 0.04 and sigma
for terminal atoms of 0.08
5. Others
 Fixed Sof: O1(0.85) H11A(0.85) H11B(0.85) H11C(0.15) H11D(0.15) H10A(0.85)
 H10B(0.85) H10C(0.15) H10D(0.15) O0AA(0.15)
6.a Secondary CH2 refined with riding coordinates:
 C9(H9A,H9B), C11(H11A,H11B), C11(H11C,H11D), C10(H10A,H10B), C10(H10C,H10D)
6.b Aromatic/amide H refined with riding coordinates:
 C8(H8), C1(H1), C13(H13), C5(H5), C17(H17), C16(H16), C2(H2), C3(H3),
 C15(H15), C4(H4), C14(H14)
;
_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
N1 N 0.63652(14) 0.6395(3) 0.82894(13) 0.0355(5) Uani 1 1 d . U . . .
O1 O 0.55628(15) 0.8574(3) 0.93059(14) 0.0442(6) Uani 0.85 1 d D U P A 1
C12 C 0.62853(16) 0.6351(4) 0.73912(16) 0.0328(6) Uani 1 1 d . U . . .
C6 C 0.31840(18) 0.5729(4) 0.87057(15) 0.0351(6) Uani 1 1 d . U . . .
C7 C 0.42732(18) 0.6052(4) 0.87809(15) 0.0323(6) Uani 1 1 d . U . . .
C8 C 0.48993(18) 0.4409(4) 0.87601(15) 0.0382(7) Uani 1 1 d . U . . .
H8 H 0.4625 0.3007 0.8731 0.046 Uiso 1 1 calc R . . . .
C9 C 0.60046(18) 0.4587(4) 0.87793(17) 0.0412(7) Uani 1 1 d . U . . .
H9A H 0.6247 0.4730 0.9383 0.049 Uiso 1 1 calc R . . . .
H9B H 0.6282 0.3245 0.8549 0.049 Uiso 1 1 calc R . . . .
C1 C 0.27418(19) 0.3837(4) 0.89762(16) 0.0429(7) Uani 1 1 d . U . . .
H1 H 0.3137 0.2727 0.9226 0.051 Uiso 1 1 calc R . . . .
C13 C 0.59396(17) 0.4532(4) 0.69468(17) 0.0416(7) Uani 1 1 d . U . . .
H13 H 0.5732 0.3316 0.7260 0.050 Uiso 1 1 calc R . . . .
C5 C 0.25776(19) 0.7312(4) 0.83361(17) 0.0450(7) Uani 1 1 d . U . . .
H5 H 0.2861 0.8606 0.8139 0.054 Uiso 1 1 calc R . . . .
C17 C 0.65901(18) 0.8086(4) 0.68951(18) 0.0440(7) Uani 1 1 d . U . . .
H17 H 0.6845 0.9336 0.7172 0.053 Uiso 1 1 calc R . . . .
C11 C 0.46244(19) 0.8337(4) 0.88864(19) 0.0486(7) Uani 1 1 d D U . . .
H11A H 0.4646 0.9005 0.8311 0.058 Uiso 0.85 1 calc R . P A 1
H11B H 0.4135 0.9140 0.9215 0.058 Uiso 0.85 1 calc R . P A 1
H11C H 0.4048 0.9228 0.8711 0.058 Uiso 0.15 1 calc R . P A 2
H11D H 0.4715 0.8539 0.9514 0.058 Uiso 0.15 1 calc R . P A 2
C16 C 0.65273(19) 0.8009(5) 0.60139(19) 0.0525(8) Uani 1 1 d . U . . .
H16 H 0.6730 0.9215 0.5693 0.063 Uiso 1 1 calc R . . . .
C10 C 0.63673(19) 0.8399(4) 0.87554(18) 0.0498(7) Uani 1 1 d D U . . .
H10A H 0.6991 0.8523 0.9101 0.060 Uiso 0.85 1 calc R . P A 1
H10B H 0.6341 0.9603 0.8341 0.060 Uiso 0.85 1 calc R . P A 1
H10C H 0.6895 0.9359 0.8561 0.060 Uiso 0.15 1 calc R . P A 2
H10D H 0.6464 0.8149 0.9380 0.060 Uiso 0.15 1 calc R . P A 2
C2 C 0.1734(2) 0.3561(5) 0.88850(17) 0.0536(8) Uani 1 1 d . U . . .
H2 H 0.1443 0.2266 0.9074 0.064 Uiso 1 1 calc R . . . .
C3 C 0.1144(2) 0.5151(5) 0.85216(18) 0.0565(8) Uani 1 1 d . U . . .
H3 H 0.0452 0.4951 0.8458 0.068 Uiso 1 1 calc R . . . .
C15 C 0.6175(2) 0.6212(6) 0.55885(19) 0.0587(8) Uani 1 1 d . U . . .
H15 H 0.6128 0.6180 0.4979 0.070 Uiso 1 1 calc R . . . .
C4 C 0.15691(19) 0.7021(5) 0.82533(18) 0.0532(8) Uani 1 1 d . U . . .
H4 H 0.1167 0.8125 0.8008 0.064 Uiso 1 1 calc R . . . .
C14 C 0.5894(2) 0.4472(5) 0.60580(19) 0.0561(8) Uani 1 1 d . U . . .
H14 H 0.5666 0.3212 0.5771 0.067 Uiso 1 1 calc R . . . .
O0AA O 0.5390(7) 0.9326(18) 0.8555(9) 0.054(3) Uani 0.15 1 d D U P A 2


_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
N1 C12 1.401(3) . ?
N1 C9 1.456(3) . ?
N1 C10 1.445(3) . ?
O1 C11 1.419(3) . ?
O1 C10 1.419(3) . ?
C12 C13 1.401(3) . ?
C12 C17 1.400(3) . ?
C6 C7 1.494(3) . ?
C6 C1 1.395(3) . ?
C6 C5 1.396(3) . ?
C7 C8 1.332(3) . ?
C7 C11 1.509(3) . ?
C8 H8 0.9500 . ?
C8 C9 1.505(3) . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C1 H1 0.9500 . ?
C1 C2 1.383(4) . ?
C13 H13 0.9500 . ?
C13 C14 1.386(4) . ?
C5 H5 0.9500 . ?
C5 C4 1.383(3) . ?
C17 H17 0.9500 . ?
C17 C16 1.375(4) . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
C11 H11C 0.9900 . ?
C11 H11D 0.9900 . ?
C11 O0AA 1.330(10) . ?
C16 H16 0.9500 . ?
C16 C15 1.378(4) . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C10 H10C 0.9900 . ?
C10 H10D 0.9900 . ?
C10 O0AA 1.471(10) . ?
C2 H2 0.9500 . ?
C2 C3 1.382(4) . ?
C3 H3 0.9500 . ?
C3 C4 1.372(4) . ?
C15 H15 0.9500 . ?
C15 C14 1.370(4) . ?
C4 H4 0.9500 . ?
C14 H14 0.9500 . ?

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
C12 N1 C9 119.6(2) . . ?
C12 N1 C10 121.2(2) . . ?
C10 N1 C9 113.5(2) . . ?
C10 O1 C11 114.3(2) . . ?
C13 C12 N1 121.5(2) . . ?
C17 C12 N1 121.6(2) . . ?
C17 C12 C13 116.8(2) . . ?
C1 C6 C7 121.8(2) . . ?
C1 C6 C5 117.9(2) . . ?
C5 C6 C7 120.3(2) . . ?
C6 C7 C11 116.4(2) . . ?
C8 C7 C6 121.7(2) . . ?
C8 C7 C11 121.9(2) . . ?
C7 C8 H8 117.3 . . ?
C7 C8 C9 125.5(2) . . ?
C9 C8 H8 117.3 . . ?
N1 C9 C8 113.7(2) . . ?
N1 C9 H9A 108.8 . . ?
N1 C9 H9B 108.8 . . ?
C8 C9 H9A 108.8 . . ?
C8 C9 H9B 108.8 . . ?
H9A C9 H9B 107.7 . . ?
C6 C1 H1 119.7 . . ?
C2 C1 C6 120.7(3) . . ?
C2 C1 H1 119.7 . . ?
C12 C13 H13 119.4 . . ?
C14 C13 C12 121.2(3) . . ?
C14 C13 H13 119.4 . . ?
C6 C5 H5 119.6 . . ?
C4 C5 C6 120.9(3) . . ?
C4 C5 H5 119.6 . . ?
C12 C17 H17 119.4 . . ?
C16 C17 C12 121.1(3) . . ?
C16 C17 H17 119.4 . . ?
O1 C11 C7 115.1(2) . . ?
O1 C11 H11A 108.5 . . ?
O1 C11 H11B 108.5 . . ?
C7 C11 H11A 108.5 . . ?
C7 C11 H11B 108.5 . . ?
C7 C11 H11C 104.8 . . ?
C7 C11 H11D 104.8 . . ?
H11A C11 H11B 107.5 . . ?
H11C C11 H11D 105.8 . . ?
O0AA C11 C7 130.0(6) . . ?
O0AA C11 H11C 104.8 . . ?
O0AA C11 H11D 104.8 . . ?
C17 C16 H16 119.4 . . ?
C17 C16 C15 121.2(3) . . ?
C15 C16 H16 119.4 . . ?
N1 C10 H10A 109.1 . . ?
N1 C10 H10B 109.1 . . ?
N1 C10 H10C 110.9 . . ?
N1 C10 H10D 110.9 . . ?
N1 C10 O0AA 104.3(5) . . ?
O1 C10 N1 112.6(2) . . ?
O1 C10 H10A 109.1 . . ?
O1 C10 H10B 109.1 . . ?
H10A C10 H10B 107.8 . . ?
H10C C10 H10D 108.9 . . ?
O0AA C10 H10C 110.9 . . ?
O0AA C10 H10D 110.9 . . ?
C1 C2 H2 119.7 . . ?
C3 C2 C1 120.7(3) . . ?
C3 C2 H2 119.7 . . ?
C2 C3 H3 120.4 . . ?
C4 C3 C2 119.3(3) . . ?
C4 C3 H3 120.4 . . ?
C16 C15 H15 120.5 . . ?
C14 C15 C16 118.9(3) . . ?
C14 C15 H15 120.5 . . ?
C5 C4 H4 119.7 . . ?
C3 C4 C5 120.6(3) . . ?
C3 C4 H4 119.7 . . ?
C13 C14 H14 119.7 . . ?
C15 C14 C13 120.7(3) . . ?
C15 C14 H14 119.7 . . ?
C11 O0AA C10 116.7(8) . . ?

_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_2017770-yyw-85_0m_sqd
_database_code_depnum_ccdc_archive 'CCDC 1852788'
_audit_update_record             
;
2018-07-02 deposited with the CCDC.
2018-10-01 downloaded from the CCDC.
;
_audit_creation_date             2017-09-11
_audit_creation_method           
;
Olex2 1.2
(compiled 2017.08.10 svn.r3458 for OlexSys, GUI svn.r5381)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C23 H20 Cl2 N2'
_chemical_formula_sum            'C23 H20 Cl2 N2'
_chemical_formula_weight         395.31
_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 0.0181 0.0091 '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 0.3639 0.7018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 '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      orthorhombic
_space_group_IT_number           61
_space_group_name_H-M_alt        'P b c a'
_space_group_name_Hall           '-P 2ac 2ab'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'x, -y-1/2, z-1/2'
'-x-1/2, y-1/2, z'

_cell_length_a                   5.8417(2)
_cell_length_b                   26.8280(9)
_cell_length_c                   28.4867(11)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     4464.5(3)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    5889
_cell_measurement_temperature    173
_cell_measurement_theta_max      68.499
_cell_measurement_theta_min      3.103
_shelx_estimated_absorpt_T_max   0.924
_shelx_estimated_absorpt_T_min   0.740
_exptl_absorpt_coefficient_mu    2.671
_exptl_absorpt_correction_T_max  0.7532
_exptl_absorpt_correction_T_min  0.5390
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.1346 before and 0.0783 after correction. The Ratio of minimum to maximum transmission is 0.7156. The λ/2 correction factor is Not present.'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.176
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             1648
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.03
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.1037
_diffrn_reflns_av_unetI/netI     0.0538
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       4
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       29
_diffrn_reflns_limit_k_min       -30
_diffrn_reflns_limit_l_max       33
_diffrn_reflns_limit_l_min       -32
_diffrn_reflns_number            27104
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        63.995
_diffrn_reflns_theta_max         63.995
_diffrn_reflns_theta_min         3.103
_diffrn_ambient_temperature      173.0
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_source                   ?
_diffrn_special_details          ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2833
_reflns_number_total             3698
_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       'SAINT V8.38A (?, 2016)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.38A (?, 2016)'
_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    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.235
_refine_diff_density_min         -0.294
_refine_diff_density_rms         0.057
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.081
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     244
_refine_ls_number_reflns         3698
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0917
_refine_ls_R_factor_gt           0.0668
_refine_ls_restrained_S_all      1.081
_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)+(0.0470P)²+8.0463P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1439
_refine_ls_wR_factor_ref         0.1557
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2.a Ternary CH refined with riding coordinates:
 C8(H8)
2.b Secondary CH2 refined with riding coordinates:
 C9(H9A,H9B), C7(H7A,H7B)
2.c Aromatic/amide H refined with riding coordinates:
 C15(H15), C11(H11), C5(H5), C12(H12), C14(H14), C6(H6), C3(H3), C2(H2),
 C19(H19), C23(H23), C20(H20), C22(H22), C21(H21)
2.d X=CH2 refined with riding coordinates:
 C17(H17A,H17B)
;
_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
Cl1 Cl -0.21363(19) 0.86404(4) 0.28801(4) 0.0489(3) Uani 1 1 d . . . . .
Cl2 Cl 1.2755(2) 0.65970(4) 0.57064(4) 0.0521(3) Uani 1 1 d . . . . .
N2 N 0.6356(5) 0.66492(11) 0.40880(10) 0.0322(7) Uani 1 1 d . . . . .
N1 N 0.3781(6) 0.70240(11) 0.36091(10) 0.0340(8) Uani 1 1 d . . . . .
C10 C 0.2393(6) 0.74009(13) 0.34319(12) 0.0302(8) Uani 1 1 d . . . . .
C16 C 0.3491(6) 0.62027(13) 0.32061(12) 0.0274(8) Uani 1 1 d . . . . .
C18 C 0.2514(7) 0.56901(14) 0.31987(13) 0.0331(9) Uani 1 1 d . . . . .
C15 C 0.2926(7) 0.78964(14) 0.35170(13) 0.0362(9) Uani 1 1 d . . . . .
H15 H 0.4256 0.7978 0.3693 0.043 Uiso 1 1 calc R . . . .
C9 C 0.5571(7) 0.71389(13) 0.39357(12) 0.0313(9) Uani 1 1 d . . . . .
H9A H 0.4979 0.7335 0.4204 0.038 Uiso 1 1 calc R . . . .
H9B H 0.6820 0.7327 0.3782 0.038 Uiso 1 1 calc R . . . .
C11 C 0.0464(7) 0.72942(14) 0.31560(13) 0.0349(9) Uani 1 1 d . . . . .
H11 H 0.0094 0.6957 0.3087 0.042 Uiso 1 1 calc R . . . .
C7 C 0.4406(7) 0.63138(13) 0.40699(13) 0.0327(9) Uani 1 1 d . . . . .
H7A H 0.3487 0.6335 0.4361 0.039 Uiso 1 1 calc R . . . .
H7B H 0.4903 0.5965 0.4022 0.039 Uiso 1 1 calc R . . . .
C8 C 0.3046(7) 0.65055(12) 0.36453(12) 0.0302(8) Uani 1 1 d . . . . .
H8 H 0.1374 0.6495 0.3720 0.036 Uiso 1 1 calc R . . . .
C5 C 0.9455(7) 0.70118(14) 0.45407(13) 0.0350(9) Uani 1 1 d . . . . .
H5 H 0.9528 0.7281 0.4324 0.042 Uiso 1 1 calc R . . . .
C12 C -0.0903(7) 0.76723(15) 0.29837(13) 0.0366(9) Uani 1 1 d . . . . .
H12 H -0.2197 0.7595 0.2795 0.044 Uiso 1 1 calc R . . . .
C4 C 0.7833(7) 0.66357(14) 0.44766(12) 0.0319(8) Uani 1 1 d . . . . .
C13 C -0.0386(7) 0.81618(14) 0.30859(13) 0.0363(9) Uani 1 1 d . . . . .
C14 C 0.1522(7) 0.82768(14) 0.33460(14) 0.0388(10) Uani 1 1 d . . . . .
H14 H 0.1888 0.8615 0.3410 0.047 Uiso 1 1 calc R . . . .
C6 C 1.0955(7) 0.69980(15) 0.49148(13) 0.0374(9) Uani 1 1 d . . . . .
H6 H 1.2061 0.7255 0.4952 0.045 Uiso 1 1 calc R . . . .
C3 C 0.7748(7) 0.62493(15) 0.48024(14) 0.0414(10) Uani 1 1 d . . . . .
H3 H 0.6651 0.5991 0.4766 0.050 Uiso 1 1 calc R . . . .
C2 C 0.9244(8) 0.62393(16) 0.51777(15) 0.0455(11) Uani 1 1 d . . . . .
H2 H 0.9168 0.5974 0.5398 0.055 Uiso 1 1 calc R . . . .
C17 C 0.4729(7) 0.63851(15) 0.28569(14) 0.0414(10) Uani 1 1 d . . . . .
H17A H 0.5026 0.6187 0.2587 0.050 Uiso 1 1 calc R . . . .
H17B H 0.5321 0.6714 0.2876 0.050 Uiso 1 1 calc R . . . .
C19 C 0.3698(8) 0.53022(15) 0.29838(14) 0.0445(11) Uani 1 1 d . . . . .
H19 H 0.5134 0.5369 0.2841 0.053 Uiso 1 1 calc R . . . .
C23 C 0.0406(7) 0.55820(16) 0.33982(16) 0.0447(10) Uani 1 1 d . . . . .
H23 H -0.0451 0.5840 0.3544 0.054 Uiso 1 1 calc R . . . .
C1 C 1.0850(7) 0.66120(15) 0.52352(14) 0.0396(10) Uani 1 1 d . . . . .
C20 C 0.2841(10) 0.48259(16) 0.29737(18) 0.0618(14) Uani 1 1 d . . . . .
H20 H 0.3680 0.4568 0.2823 0.074 Uiso 1 1 calc R . . . .
C22 C -0.0470(9) 0.50965(18) 0.3387(2) 0.0654(15) Uani 1 1 d . . . . .
H22 H -0.1924 0.5026 0.3521 0.079 Uiso 1 1 calc R . . . .
C21 C 0.0788(11) 0.47207(17) 0.3180(2) 0.0687(16) Uani 1 1 d . . . . .
H21 H 0.0224 0.4389 0.3181 0.082 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
Cl1 C13 1.743(4) . ?
Cl2 C1 1.744(4) . ?
N2 C9 1.458(4) . ?
N2 C7 1.453(5) . ?
N2 C4 1.404(5) . ?
N1 C10 1.391(5) . ?
N1 C9 1.433(5) . ?
N1 C8 1.460(4) . ?
C10 C15 1.387(5) . ?
C10 C11 1.403(5) . ?
C16 C18 1.489(5) . ?
C16 C8 1.514(5) . ?
C16 C17 1.324(5) . ?
C18 C19 1.391(5) . ?
C18 C23 1.387(6) . ?
C15 H15 0.9500 . ?
C15 C14 1.397(5) . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C11 H11 0.9500 . ?
C11 C12 1.381(5) . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C7 C8 1.536(5) . ?
C8 H8 1.0000 . ?
C5 H5 0.9500 . ?
C5 C4 1.396(5) . ?
C5 C6 1.380(5) . ?
C12 H12 0.9500 . ?
C12 C13 1.379(5) . ?
C4 C3 1.392(5) . ?
C13 C14 1.374(6) . ?
C14 H14 0.9500 . ?
C6 H6 0.9500 . ?
C6 C1 1.382(6) . ?
C3 H3 0.9500 . ?
C3 C2 1.381(6) . ?
C2 H2 0.9500 . ?
C2 C1 1.381(6) . ?
C17 H17A 0.9500 . ?
C17 H17B 0.9500 . ?
C19 H19 0.9500 . ?
C19 C20 1.373(6) . ?
C23 H23 0.9500 . ?
C23 C22 1.400(6) . ?
C20 H20 0.9500 . ?
C20 C21 1.365(8) . ?
C22 H22 0.9500 . ?
C22 C21 1.380(7) . ?
C21 H21 0.9500 . ?

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 N2 C9 107.5(3) . . ?
C4 N2 C9 116.8(3) . . ?
C4 N2 C7 119.6(3) . . ?
C10 N1 C9 120.3(3) . . ?
C10 N1 C8 123.1(3) . . ?
C9 N1 C8 112.0(3) . . ?
N1 C10 C11 121.5(3) . . ?
C15 C10 N1 120.2(3) . . ?
C15 C10 C11 118.3(3) . . ?
C18 C16 C8 116.2(3) . . ?
C17 C16 C18 122.7(3) . . ?
C17 C16 C8 121.1(3) . . ?
C19 C18 C16 120.4(4) . . ?
C23 C18 C16 121.9(4) . . ?
C23 C18 C19 117.7(4) . . ?
C10 C15 H15 119.7 . . ?
C10 C15 C14 120.5(4) . . ?
C14 C15 H15 119.7 . . ?
N2 C9 H9A 111.1 . . ?
N2 C9 H9B 111.1 . . ?
N1 C9 N2 103.2(3) . . ?
N1 C9 H9A 111.1 . . ?
N1 C9 H9B 111.1 . . ?
H9A C9 H9B 109.1 . . ?
C10 C11 H11 119.6 . . ?
C12 C11 C10 120.9(4) . . ?
C12 C11 H11 119.6 . . ?
N2 C7 H7A 111.1 . . ?
N2 C7 H7B 111.2 . . ?
N2 C7 C8 103.1(3) . . ?
H7A C7 H7B 109.1 . . ?
C8 C7 H7A 111.2 . . ?
C8 C7 H7B 111.2 . . ?
N1 C8 C16 113.7(3) . . ?
N1 C8 C7 102.9(3) . . ?
N1 C8 H8 109.2 . . ?
C16 C8 C7 112.5(3) . . ?
C16 C8 H8 109.2 . . ?
C7 C8 H8 109.2 . . ?
C4 C5 H5 119.6 . . ?
C6 C5 H5 119.6 . . ?
C6 C5 C4 120.8(4) . . ?
C11 C12 H12 120.1 . . ?
C13 C12 C11 119.9(4) . . ?
C13 C12 H12 120.1 . . ?
C5 C4 N2 120.1(3) . . ?
C3 C4 N2 121.5(3) . . ?
C3 C4 C5 118.4(4) . . ?
C12 C13 Cl1 120.1(3) . . ?
C14 C13 Cl1 119.5(3) . . ?
C14 C13 C12 120.4(4) . . ?
C15 C14 H14 120.0 . . ?
C13 C14 C15 120.0(4) . . ?
C13 C14 H14 120.0 . . ?
C5 C6 H6 119.9 . . ?
C5 C6 C1 120.1(4) . . ?
C1 C6 H6 119.9 . . ?
C4 C3 H3 119.7 . . ?
C2 C3 C4 120.5(4) . . ?
C2 C3 H3 119.7 . . ?
C3 C2 H2 119.7 . . ?
C1 C2 C3 120.5(4) . . ?
C1 C2 H2 119.7 . . ?
C16 C17 H17A 120.0 . . ?
C16 C17 H17B 120.0 . . ?
H17A C17 H17B 120.0 . . ?
C18 C19 H19 119.2 . . ?
C20 C19 C18 121.6(5) . . ?
C20 C19 H19 119.2 . . ?
C18 C23 H23 119.7 . . ?
C18 C23 C22 120.7(4) . . ?
C22 C23 H23 119.7 . . ?
C6 C1 Cl2 119.8(3) . . ?
C2 C1 Cl2 120.5(3) . . ?
C2 C1 C6 119.6(4) . . ?
C19 C20 H20 119.9 . . ?
C21 C20 C19 120.3(5) . . ?
C21 C20 H20 119.9 . . ?
C23 C22 H22 120.2 . . ?
C21 C22 C23 119.6(5) . . ?
C21 C22 H22 120.2 . . ?
C20 C21 C22 120.1(4) . . ?
C20 C21 H21 120.0 . . ?
C22 C21 H21 120.0 . . ?

_olex2_submission_special_instructions 'No special instructions were received'
