# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 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_151209a
_database_code_depnum_ccdc_archive 'CCDC 1993682'
loop_
_audit_author_name
_audit_author_address
'Xinwei He'
;Anhui Normal University
China
;
_audit_update_record             
;
2020-03-30 deposited with the CCDC.	2020-05-18 downloaded from the CCDC.
;
_audit_creation_date             2020-03-30
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        
;
 ? 
;
_chemical_formula_moiety         'C14 H23 Cl N2 O2'
_chemical_formula_sum            'C14 H23 Cl N2 O2'
_chemical_formula_weight         286.79
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
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                   13.9531(13)
_cell_length_b                   18.3735(17)
_cell_length_c                   12.4880(12)
_cell_angle_alpha                90
_cell_angle_beta                 90.003(3)
_cell_angle_gamma                90
_cell_volume                     3201.5(5)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    7023
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      25.614
_cell_measurement_theta_min      2.454
_shelx_estimated_absorpt_T_max   0.951
_shelx_estimated_absorpt_T_min   0.947
_exptl_absorpt_coefficient_mu    0.239
_exptl_absorpt_correction_T_max  0.9515
_exptl_absorpt_correction_T_min  0.9470
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.190
_exptl_crystal_density_meas      .
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1232
_exptl_crystal_size_max          0.23
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.21
_exptl_special_details           
;
 ? 
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.1008
_diffrn_reflns_av_unetI/netI     0.0660
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.981
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            27226
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.981
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.474
_diffrn_reflns_theta_min         1.459
_diffrn_ambient_temperature      293.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.981
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                4315
_reflns_number_total             7192
_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 v7.34A (Bruker, 200?)'
_computing_data_collection       'SAINT v7.34A (Bruker, 200?)'
_computing_data_reduction        'SAINT v7.34A (Bruker, 200?)'
_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         0.314
_refine_diff_density_min         -0.289
_refine_diff_density_rms         0.043
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.018
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     392
_refine_ls_number_reflns         7192
_refine_ls_number_restraints     55
_refine_ls_R_factor_all          0.1040
_refine_ls_R_factor_gt           0.0580
_refine_ls_restrained_S_all      1.021
_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)+(0.0693P)²+0.6597P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1420
_refine_ls_wR_factor_ref         0.1678
_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, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All C(H,H,H,H,H,H) groups
2. Restrained distances
 C2-C1 \\sim C2-C1A
 with sigma of 0.02
 C3-C2 \\sim C3A-C2
 with sigma of 0.02
 C1-C3 \\sim C1A-C3A
 with sigma of 0.02
 C12A-C14 \\sim C14-C12
 with sigma of 0.02
 C13-C12 \\sim C12A-C13
 with sigma of 0.02
 C12-C11 \\sim C12A-C11A
 with sigma of 0.02
 C11-C10 \\sim C11A-C10
 with sigma of 0.02
3. Uiso/Uaniso restraints and constraints
Uanis(C1A) \\sim Ueq: with sigma of 0.01 and sigma for terminal atoms of 0.02
4. Rigid body (RIGU) restrains
 C3, C2, C1
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.002
 C1A, C2, C3A
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.002
 C10, C11A, C12A, C14, C13
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.002
5. Others
 Sof(H2B)=Sof(H13C)=Sof(H13D)=Sof(H14D)=Sof(H14E)=Sof(H14F)=Sof(C3A)=Sof(H3AA)=
 Sof(H3AB)=Sof(H3AC)=Sof(C1A)=Sof(H1AA)=Sof(H1AB)=Sof(H1AC)=Sof(C11A)=Sof(H11C)=
 Sof(H11D)=Sof(C12A)=Sof(H12A)=1-FVAR(1)
 Sof(C1)=Sof(H1A)=Sof(H1B)=Sof(H1C)=Sof(H2A)=Sof(C3)=Sof(H3A)=Sof(H3B)=
 Sof(H3C)=Sof(C11)=Sof(H11A)=Sof(H11B)=Sof(C12)=Sof(H12)=Sof(H13A)=Sof(H13B)=
 Sof(H14A)=Sof(H14B)=Sof(H14C)=FVAR(1)
6.a Ternary CH refined with riding coordinates:
 C2(H2A), C2(H2B), C5(H5), C12(H12), C16(H16), C19(H19), C24(H24), C12A(H12A)
6.b Secondary CH2 refined with riding coordinates:
 C11(H11A,H11B), C13(H13A,H13B), C13(H13C,H13D), C23(H23A,H23B), C25(H25A,
 H25B), C11A(H11C,H11D)
6.c Aromatic/amide H refined with riding coordinates:
 N1(H1), N3(H3)
6.d Idealised Me refined as rotating group:
 C1(H1A,H1B,H1C), C3(H3A,H3B,H3C), C6(H6A,H6B,H6C), C7(H7A,H7B,H7C), C14(H14A,
 H14B,H14C), C14(H14D,H14E,H14F), C15(H15A,H15B,H15C), C17(H17A,H17B,H17C),
 C20(H20A,H20B,H20C), C21(H21A,H21B,H21C), C28(H28A,H28B,H28C), C3A(H3AA,H3AB,
 H3AC), C1A(H1AA,H1AB,H1AC)
;
_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
C1 C 0.3953(3) 0.1124(3) 0.3075(5) 0.1136(19) Uani 0.877(6) 1 d D U P A 1
H1A H 0.436374 0.071522 0.293893 0.170 Uiso 0.877(6) 1 calc GR . P A 1
H1B H 0.388643 0.140669 0.243248 0.170 Uiso 0.877(6) 1 calc GR . P A 1
H1C H 0.333496 0.095441 0.330044 0.170 Uiso 0.877(6) 1 calc GR . P A 1
C2 C 0.43786(16) 0.15825(14) 0.3929(2) 0.0598(6) Uani 1 1 d D U . . .
H2A H 0.393245 0.198212 0.407613 0.072 Uiso 0.877(6) 1 calc R . P A 1
H2B H 0.385243 0.186240 0.361174 0.072 Uiso 0.123(6) 1 calc R . P A 2
C3 C 0.4539(4) 0.1179(4) 0.4954(4) 0.124(2) Uani 0.877(6) 1 d D U P A 1
H3A H 0.394116 0.098222 0.520207 0.186 Uiso 0.877(6) 1 calc GR . P A 1
H3B H 0.479291 0.150506 0.548222 0.186 Uiso 0.877(6) 1 calc GR . P A 1
H3C H 0.498472 0.078915 0.483378 0.186 Uiso 0.877(6) 1 calc GR . P A 1
C4 C 0.53070(15) 0.25637(12) 0.31037(19) 0.0517(5) Uani 1 1 d . . . . .
C5 C 0.62601(17) 0.35595(12) 0.2346(2) 0.0584(6) Uani 1 1 d . . . . .
H5 H 0.563274 0.368791 0.204797 0.070 Uiso 1 1 calc R . . . .
C6 C 0.6455(2) 0.40948(13) 0.3241(2) 0.0706(7) Uani 1 1 d . . . . .
H6A H 0.599523 0.402472 0.380344 0.106 Uiso 1 1 calc GR . . . .
H6B H 0.640379 0.458237 0.297020 0.106 Uiso 1 1 calc GR . . . .
H6C H 0.708891 0.401708 0.351628 0.106 Uiso 1 1 calc GR . . . .
C7 C 0.6972(2) 0.36223(15) 0.1439(3) 0.0790(8) Uani 1 1 d . . . . .
H7A H 0.759879 0.349174 0.169176 0.118 Uiso 1 1 calc GR . . . .
H7B H 0.698168 0.411424 0.118022 0.118 Uiso 1 1 calc GR . . . .
H7C H 0.678840 0.330081 0.086886 0.118 Uiso 1 1 calc GR . . . .
C8 C 0.70312(15) 0.23738(11) 0.28200(19) 0.0483(5) Uani 1 1 d . . . . .
C9 C 0.72190(16) 0.18313(12) 0.2136(2) 0.0531(6) Uani 1 1 d . . . . .
C10 C 0.81076(17) 0.13966(13) 0.2192(2) 0.0665(7) Uani 1 1 d D U . . .
C11 C 0.8821(2) 0.16381(19) 0.2980(3) 0.0664(10) Uani 0.877(6) 1 d D . P A 1
H11A H 0.921314 0.201805 0.266550 0.080 Uiso 0.877(6) 1 calc R . P A 1
H11B H 0.923739 0.123323 0.315897 0.080 Uiso 0.877(6) 1 calc R . P A 1
C12 C 0.8358(2) 0.1924(2) 0.3992(2) 0.0626(9) Uani 0.877(6) 1 d D . P A 1
H12 H 0.797035 0.153601 0.431193 0.075 Uiso 0.877(6) 1 calc R . P A 1
C13 C 0.77105(16) 0.25559(13) 0.3705(2) 0.0586(6) Uani 1 1 d D U . . .
H13A H 0.734732 0.269812 0.433371 0.070 Uiso 0.877(6) 1 calc R . P A 1
H13B H 0.810144 0.296751 0.349145 0.070 Uiso 0.877(6) 1 calc R . P A 1
H13C H 0.739239 0.243490 0.437266 0.070 Uiso 0.123(6) 1 calc R . P A 2
H13D H 0.779489 0.307989 0.369999 0.070 Uiso 0.123(6) 1 calc R . P A 2
C14 C 0.9111(2) 0.2182(2) 0.4821(3) 0.1027(11) Uani 1 1 d D U . . .
H14A H 0.952073 0.178188 0.500915 0.154 Uiso 0.877(6) 1 calc GR . P A 1
H14B H 0.879031 0.235676 0.545008 0.154 Uiso 0.877(6) 1 calc GR . P A 1
H14C H 0.948903 0.256634 0.451666 0.154 Uiso 0.877(6) 1 calc GR . P A 1
H14D H 0.939417 0.264213 0.499985 0.154 Uiso 0.123(6) 1 calc GR . P A 2
H14E H 0.959320 0.180920 0.484298 0.154 Uiso 0.123(6) 1 calc GR . P A 2
H14F H 0.861449 0.206928 0.532629 0.154 Uiso 0.123(6) 1 calc GR . P A 2
C15 C 1.1049(2) 0.49533(18) 0.8078(3) 0.0909(10) Uani 1 1 d . . . . .
H15A H 1.063734 0.456209 0.829798 0.136 Uiso 1 1 calc GR . . . .
H15B H 1.100174 0.534553 0.858344 0.136 Uiso 1 1 calc GR . . . .
H15C H 1.169923 0.478372 0.804935 0.136 Uiso 1 1 calc GR . . . .
C16 C 1.07477(17) 0.52183(16) 0.6984(3) 0.0740(8) Uani 1 1 d . . . . .
H16 H 1.119945 0.559548 0.675364 0.089 Uiso 1 1 calc R . . . .
C17 C 1.0773(3) 0.4606(2) 0.6175(3) 0.1183(14) Uani 1 1 d . . . . .
H17A H 1.071961 0.480333 0.546546 0.177 Uiso 1 1 calc GR . . . .
H17B H 1.024929 0.427925 0.630519 0.177 Uiso 1 1 calc GR . . . .
H17C H 1.136780 0.434637 0.623968 0.177 Uiso 1 1 calc GR . . . .
C18 C 0.96743(16) 0.62217(14) 0.7418(2) 0.0571(6) Uani 1 1 d . . . . .
C19 C 0.8595(2) 0.72099(15) 0.7954(3) 0.0779(8) Uani 1 1 d . . . . .
H19 H 0.916997 0.736166 0.834584 0.094 Uiso 1 1 calc R . . . .
C20 C 0.8485(2) 0.77231(16) 0.7014(3) 0.1001(11) Uani 1 1 d . . . . .
H20A H 0.787730 0.763988 0.667429 0.150 Uiso 1 1 calc GR . . . .
H20B H 0.899102 0.763780 0.650887 0.150 Uiso 1 1 calc GR . . . .
H20C H 0.851588 0.821693 0.726252 0.150 Uiso 1 1 calc GR . . . .
C21 C 0.7762(3) 0.72601(19) 0.8728(3) 0.1144(13) Uani 1 1 d . . . . .
H21A H 0.788446 0.695546 0.933733 0.172 Uiso 1 1 calc GR . . . .
H21B H 0.718601 0.710152 0.837776 0.172 Uiso 1 1 calc GR . . . .
H21C H 0.768679 0.775510 0.895926 0.172 Uiso 1 1 calc GR . . . .
C22 C 0.79391(14) 0.60059(11) 0.73705(18) 0.0443(5) Uani 1 1 d . . . . .
C23 C 0.74344(15) 0.61539(11) 0.63376(18) 0.0486(5) Uani 1 1 d . . . . .
H23A H 0.790878 0.624871 0.578726 0.058 Uiso 1 1 calc R . . . .
H23B H 0.704848 0.658967 0.641781 0.058 Uiso 1 1 calc R . . . .
C24 C 0.67942(17) 0.55356(13) 0.5971(2) 0.0564(6) Uani 1 1 d . . . . .
H24 H 0.720321 0.512920 0.574860 0.068 Uiso 1 1 calc R . . . .
C25 C 0.61844(16) 0.52849(13) 0.6906(2) 0.0606(6) Uani 1 1 d . . . . .
H25A H 0.576562 0.567961 0.712320 0.073 Uiso 1 1 calc R . . . .
H25B H 0.578408 0.488266 0.667564 0.073 Uiso 1 1 calc R . . . .
C26 C 0.67620(16) 0.50513(12) 0.7836(2) 0.0543(6) Uani 1 1 d . . . . .
C27 C 0.76365(16) 0.54899(12) 0.80398(18) 0.0503(5) Uani 1 1 d . . . . .
C28 C 0.6194(2) 0.57715(16) 0.5011(2) 0.0776(8) Uani 1 1 d . . . . .
H28A H 0.660960 0.590358 0.443033 0.116 Uiso 1 1 calc GR . . . .
H28B H 0.580624 0.618245 0.520607 0.116 Uiso 1 1 calc GR . . . .
H28C H 0.578717 0.537698 0.479250 0.116 Uiso 1 1 calc GR . . . .
Cl1 Cl 0.64369(5) 0.16111(4) 0.11179(6) 0.0744(2) Uani 1 1 d . . . . .
Cl2 Cl 0.82284(6) 0.52955(5) 0.92184(6) 0.0822(3) Uani 1 1 d . . . . .
N1 N 0.52783(12) 0.19002(11) 0.35582(17) 0.0579(5) Uani 1 1 d . . . . .
H1 H 0.580151 0.165793 0.363196 0.070 Uiso 1 1 calc R . . . .
N2 N 0.61824(12) 0.28009(10) 0.27281(16) 0.0528(5) Uani 1 1 d . . . . .
N3 N 0.97854(13) 0.55392(12) 0.70254(17) 0.0594(5) Uani 1 1 d . . . . .
H3 H 0.929710 0.529679 0.680318 0.071 Uiso 1 1 calc R . . . .
N4 N 0.87500(13) 0.64479(10) 0.76141(16) 0.0547(5) Uani 1 1 d . . . . .
O1 O 0.46032(11) 0.29577(9) 0.30443(16) 0.0712(5) Uani 1 1 d . . . . .
O2 O 0.82610(14) 0.08920(10) 0.1590(2) 0.0930(7) Uani 1 1 d . . . . .
O3 O 0.65395(14) 0.45533(10) 0.84261(17) 0.0772(5) Uani 1 1 d . . . . .
O4 O 1.03506(12) 0.66265(11) 0.75771(18) 0.0831(6) Uani 1 1 d . . . . .
C3A C 0.438(4) 0.172(2) 0.5064(15) 0.128(17) Uani 0.123(6) 1 d D U P A 2
H3AA H 0.429654 0.222821 0.519351 0.193 Uiso 0.123(6) 1 calc GR . P A 2
H3AB H 0.497170 0.155656 0.536755 0.193 Uiso 0.123(6) 1 calc GR . P A 2
H3AC H 0.385640 0.145461 0.538981 0.193 Uiso 0.123(6) 1 calc GR . P A 2
C1A C 0.424(2) 0.0790(10) 0.362(3) 0.086(8) Uani 0.123(6) 1 d D U P A 2
H1AA H 0.358724 0.065253 0.372633 0.129 Uiso 0.123(6) 1 calc GR . P A 2
H1AB H 0.465145 0.048917 0.404930 0.129 Uiso 0.123(6) 1 calc GR . P A 2
H1AC H 0.440711 0.072725 0.287512 0.129 Uiso 0.123(6) 1 calc GR . P A 2
C11A C 0.853(2) 0.1452(13) 0.3339(17) 0.079(5) Uani 0.123(6) 1 d D U P A 2
H11C H 0.810092 0.120683 0.383041 0.095 Uiso 0.123(6) 1 calc R . P A 2
H11D H 0.913702 0.119085 0.335300 0.095 Uiso 0.123(6) 1 calc R . P A 2
C12A C 0.8704(13) 0.2219(12) 0.3748(15) 0.068(4) Uani 0.123(6) 1 d D U P A 2
H12A H 0.913963 0.247959 0.326671 0.081 Uiso 0.123(6) 1 calc R . 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
C1 H1A 0.9600 . ?
C1 H1B 0.9600 . ?
C1 H1C 0.9600 . ?
C1 C2 1.483(4) . ?
C2 H2A 0.9800 . ?
C2 H2B 0.9800 . ?
C2 C3 1.496(5) . ?
C2 N1 1.460(3) . ?
C2 C3A 1.439(17) . ?
C2 C1A 1.520(15) . ?
C3 H3A 0.9600 . ?
C3 H3B 0.9600 . ?
C3 H3C 0.9600 . ?
C4 N1 1.345(3) . ?
C4 N2 1.379(3) . ?
C4 O1 1.222(3) . ?
C5 H5 0.9800 . ?
C5 C6 1.513(4) . ?
C5 C7 1.511(4) . ?
C5 N2 1.477(3) . ?
C6 H6A 0.9600 . ?
C6 H6B 0.9600 . ?
C6 H6C 0.9600 . ?
C7 H7A 0.9600 . ?
C7 H7B 0.9600 . ?
C7 H7C 0.9600 . ?
C8 C9 1.339(3) . ?
C8 C13 1.494(3) . ?
C8 N2 1.425(3) . ?
C9 C10 1.477(3) . ?
C9 Cl1 1.724(3) . ?
C10 C11 1.468(4) . ?
C10 O2 1.213(3) . ?
C10 C11A 1.554(17) . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C11 C12 1.513(4) . ?
C12 H12 0.9800 . ?
C12 C13 1.514(4) . ?
C12 C14 1.549(4) . ?
C13 H13A 0.9700 . ?
C13 H13B 0.9700 . ?
C13 H13C 0.9700 . ?
C13 H13D 0.9700 . ?
C13 C12A 1.519(15) . ?
C14 H14A 0.9600 . ?
C14 H14B 0.9600 . ?
C14 H14C 0.9600 . ?
C14 H14D 0.9600 . ?
C14 H14E 0.9600 . ?
C14 H14F 0.9600 . ?
C14 C12A 1.456(16) . ?
C15 H15A 0.9600 . ?
C15 H15B 0.9600 . ?
C15 H15C 0.9600 . ?
C15 C16 1.510(4) . ?
C16 H16 0.9800 . ?
C16 C17 1.513(5) . ?
C16 N3 1.468(3) . ?
C17 H17A 0.9600 . ?
C17 H17B 0.9600 . ?
C17 H17C 0.9600 . ?
C18 N3 1.355(3) . ?
C18 N4 1.377(3) . ?
C18 O4 1.218(3) . ?
C19 H19 0.9800 . ?
C19 C20 1.514(5) . ?
C19 C21 1.514(5) . ?
C19 N4 1.479(3) . ?
C20 H20A 0.9600 . ?
C20 H20B 0.9600 . ?
C20 H20C 0.9600 . ?
C21 H21A 0.9600 . ?
C21 H21B 0.9600 . ?
C21 H21C 0.9600 . ?
C22 C23 1.494(3) . ?
C22 C27 1.333(3) . ?
C22 N4 1.426(3) . ?
C23 H23A 0.9700 . ?
C23 H23B 0.9700 . ?
C23 C24 1.516(3) . ?
C24 H24 0.9800 . ?
C24 C25 1.517(3) . ?
C24 C28 1.526(3) . ?
C25 H25A 0.9700 . ?
C25 H25B 0.9700 . ?
C25 C26 1.477(4) . ?
C26 C27 1.484(3) . ?
C26 O3 1.215(3) . ?
C27 Cl2 1.725(2) . ?
C28 H28A 0.9600 . ?
C28 H28B 0.9600 . ?
C28 H28C 0.9600 . ?
N1 H1 0.8600 . ?
N3 H3 0.8600 . ?
C3A H3AA 0.9600 . ?
C3A H3AB 0.9600 . ?
C3A H3AC 0.9600 . ?
C1A H1AA 0.9600 . ?
C1A H1AB 0.9600 . ?
C1A H1AC 0.9600 . ?
C11A H11C 0.9700 . ?
C11A H11D 0.9700 . ?
C11A C12A 1.518(18) . ?
C12A H12A 0.9800 . ?

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
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 . . ?
C1 C2 H2A 107.8 . . ?
C1 C2 C3 113.2(4) . . ?
C3 C2 H2A 107.8 . . ?
N1 C2 C1 110.1(3) . . ?
N1 C2 H2A 107.8 . . ?
N1 C2 H2B 107.8 . . ?
N1 C2 C3 110.0(3) . . ?
N1 C2 C1A 114.1(11) . . ?
C3A C2 H2B 107.8 . . ?
C3A C2 N1 104.3(15) . . ?
C3A C2 C1A 114.6(15) . . ?
C1A C2 H2B 107.8 . . ?
C2 C3 H3A 109.5 . . ?
C2 C3 H3B 109.5 . . ?
C2 C3 H3C 109.5 . . ?
H3A C3 H3B 109.5 . . ?
H3A C3 H3C 109.5 . . ?
H3B C3 H3C 109.5 . . ?
N1 C4 N2 117.15(19) . . ?
O1 C4 N1 122.6(2) . . ?
O1 C4 N2 120.3(2) . . ?
C6 C5 H5 106.5 . . ?
C7 C5 H5 106.5 . . ?
C7 C5 C6 112.7(2) . . ?
N2 C5 H5 106.5 . . ?
N2 C5 C6 112.8(2) . . ?
N2 C5 C7 111.3(2) . . ?
C5 C6 H6A 109.5 . . ?
C5 C6 H6B 109.5 . . ?
C5 C6 H6C 109.5 . . ?
H6A C6 H6B 109.5 . . ?
H6A C6 H6C 109.5 . . ?
H6B C6 H6C 109.5 . . ?
C5 C7 H7A 109.5 . . ?
C5 C7 H7B 109.5 . . ?
C5 C7 H7C 109.5 . . ?
H7A C7 H7B 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
C9 C8 C13 121.0(2) . . ?
C9 C8 N2 121.4(2) . . ?
N2 C8 C13 117.60(19) . . ?
C8 C9 C10 122.5(2) . . ?
C8 C9 Cl1 121.43(18) . . ?
C10 C9 Cl1 116.08(18) . . ?
C9 C10 C11A 109.2(11) . . ?
C11 C10 C9 116.0(2) . . ?
O2 C10 C9 122.2(3) . . ?
O2 C10 C11 121.8(3) . . ?
O2 C10 C11A 123.6(10) . . ?
C10 C11 H11A 109.2 . . ?
C10 C11 H11B 109.2 . . ?
C10 C11 C12 112.0(3) . . ?
H11A C11 H11B 107.9 . . ?
C12 C11 H11A 109.2 . . ?
C12 C11 H11B 109.2 . . ?
C11 C12 H12 108.9 . . ?
C11 C12 C13 108.9(3) . . ?
C11 C12 C14 112.0(3) . . ?
C13 C12 H12 108.9 . . ?
C13 C12 C14 109.1(3) . . ?
C14 C12 H12 108.9 . . ?
C8 C13 C12 112.4(2) . . ?
C8 C13 H13A 109.1 . . ?
C8 C13 H13B 109.1 . . ?
C8 C13 H13C 107.1 . . ?
C8 C13 H13D 107.1 . . ?
C8 C13 C12A 120.9(7) . . ?
C12 C13 H13A 109.1 . . ?
C12 C13 H13B 109.1 . . ?
H13A C13 H13B 107.8 . . ?
H13C C13 H13D 106.8 . . ?
C12A C13 H13C 107.1 . . ?
C12A C13 H13D 107.1 . . ?
C12 C14 H14A 109.5 . . ?
C12 C14 H14B 109.5 . . ?
C12 C14 H14C 109.5 . . ?
H14A C14 H14B 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
H14D C14 H14E 109.5 . . ?
H14D C14 H14F 109.5 . . ?
H14E C14 H14F 109.5 . . ?
C12A C14 H14D 109.5 . . ?
C12A C14 H14E 109.5 . . ?
C12A C14 H14F 109.5 . . ?
H15A C15 H15B 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
C16 C15 H15A 109.5 . . ?
C16 C15 H15B 109.5 . . ?
C16 C15 H15C 109.5 . . ?
C15 C16 H16 108.3 . . ?
C15 C16 C17 111.0(3) . . ?
C17 C16 H16 108.3 . . ?
N3 C16 C15 110.6(2) . . ?
N3 C16 H16 108.3 . . ?
N3 C16 C17 110.1(2) . . ?
C16 C17 H17A 109.5 . . ?
C16 C17 H17B 109.5 . . ?
C16 C17 H17C 109.5 . . ?
H17A C17 H17B 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
N3 C18 N4 116.8(2) . . ?
O4 C18 N3 122.4(2) . . ?
O4 C18 N4 120.8(2) . . ?
C20 C19 H19 107.0 . . ?
C20 C19 C21 112.3(3) . . ?
C21 C19 H19 107.0 . . ?
N4 C19 H19 107.0 . . ?
N4 C19 C20 112.4(3) . . ?
N4 C19 C21 110.7(2) . . ?
C19 C20 H20A 109.5 . . ?
C19 C20 H20B 109.5 . . ?
C19 C20 H20C 109.5 . . ?
H20A C20 H20B 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
C19 C21 H21A 109.5 . . ?
C19 C21 H21B 109.5 . . ?
C19 C21 H21C 109.5 . . ?
H21A C21 H21B 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
C27 C22 C23 121.44(19) . . ?
C27 C22 N4 121.5(2) . . ?
N4 C22 C23 117.03(18) . . ?
C22 C23 H23A 108.8 . . ?
C22 C23 H23B 108.8 . . ?
C22 C23 C24 113.69(18) . . ?
H23A C23 H23B 107.7 . . ?
C24 C23 H23A 108.8 . . ?
C24 C23 H23B 108.8 . . ?
C23 C24 H24 108.3 . . ?
C23 C24 C25 109.0(2) . . ?
C23 C24 C28 110.4(2) . . ?
C25 C24 H24 108.3 . . ?
C25 C24 C28 112.5(2) . . ?
C28 C24 H24 108.3 . . ?
C24 C25 H25A 109.0 . . ?
C24 C25 H25B 109.0 . . ?
H25A C25 H25B 107.8 . . ?
C26 C25 C24 112.79(19) . . ?
C26 C25 H25A 109.0 . . ?
C26 C25 H25B 109.0 . . ?
C25 C26 C27 115.2(2) . . ?
O3 C26 C25 123.8(2) . . ?
O3 C26 C27 121.0(2) . . ?
C22 C27 C26 122.6(2) . . ?
C22 C27 Cl2 122.06(18) . . ?
C26 C27 Cl2 115.30(17) . . ?
C24 C28 H28A 109.5 . . ?
C24 C28 H28B 109.5 . . ?
C24 C28 H28C 109.5 . . ?
H28A C28 H28B 109.5 . . ?
H28A C28 H28C 109.5 . . ?
H28B C28 H28C 109.5 . . ?
C2 N1 H1 119.3 . . ?
C4 N1 C2 121.45(19) . . ?
C4 N1 H1 119.3 . . ?
C4 N2 C5 118.24(18) . . ?
C4 N2 C8 122.31(18) . . ?
C8 N2 C5 118.98(17) . . ?
C16 N3 H3 120.4 . . ?
C18 N3 C16 119.3(2) . . ?
C18 N3 H3 120.4 . . ?
C18 N4 C19 118.3(2) . . ?
C18 N4 C22 122.23(19) . . ?
C22 N4 C19 118.98(18) . . ?
C2 C3A H3AA 109.5 . . ?
C2 C3A H3AB 109.5 . . ?
C2 C3A H3AC 109.5 . . ?
H3AA C3A H3AB 109.5 . . ?
H3AA C3A H3AC 109.5 . . ?
H3AB C3A H3AC 109.5 . . ?
C2 C1A H1AA 109.5 . . ?
C2 C1A H1AB 109.5 . . ?
C2 C1A H1AC 109.5 . . ?
H1AA C1A H1AB 109.5 . . ?
H1AA C1A H1AC 109.5 . . ?
H1AB C1A H1AC 109.5 . . ?
C10 C11A H11C 108.4 . . ?
C10 C11A H11D 108.4 . . ?
H11C C11A H11D 107.5 . . ?
C12A C11A C10 115.5(16) . . ?
C12A C11A H11C 108.4 . . ?
C12A C11A H11D 108.4 . . ?
C13 C12A H12A 110.2 . . ?
C14 C12A C13 114.0(12) . . ?
C14 C12A C11A 109.1(15) . . ?
C14 C12A H12A 110.2 . . ?
C11A C12A C13 102.9(18) . . ?
C11A C12A H12A 110.2 . . ?

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
C1 C2 N1 C4 93.1(4) . . . . ?
C3 C2 N1 C4 -141.5(4) . . . . ?
C6 C5 N2 C4 85.0(3) . . . . ?
C6 C5 N2 C8 -87.3(3) . . . . ?
C7 C5 N2 C4 -147.2(2) . . . . ?
C7 C5 N2 C8 40.5(3) . . . . ?
C8 C9 C10 C11 -5.7(4) . . . . ?
C8 C9 C10 O2 177.8(2) . . . . ?
C8 C9 C10 C11A 22.0(11) . . . . ?
C8 C13 C12A C14 -154.6(10) . . . . ?
C8 C13 C12A C11A -37(2) . . . . ?
C9 C8 C13 C12 -22.2(3) . . . . ?
C9 C8 C13 C12A 10.2(12) . . . . ?
C9 C8 N2 C4 80.1(3) . . . . ?
C9 C8 N2 C5 -107.9(2) . . . . ?
C9 C10 C11 C12 36.4(4) . . . . ?
C9 C10 C11A C12A -54(2) . . . . ?
C10 C11 C12 C13 -59.0(4) . . . . ?
C10 C11 C12 C14 -179.7(3) . . . . ?
C10 C11A C12A C13 59(3) . . . . ?
C10 C11A C12A C14 -179.3(15) . . . . ?
C11 C12 C13 C8 51.2(3) . . . . ?
C13 C8 C9 C10 -1.7(3) . . . . ?
C13 C8 C9 Cl1 179.48(17) . . . . ?
C13 C8 N2 C4 -100.3(3) . . . . ?
C13 C8 N2 C5 71.7(3) . . . . ?
C14 C12 C13 C8 173.7(2) . . . . ?
C15 C16 N3 C18 78.0(3) . . . . ?
C17 C16 N3 C18 -158.9(3) . . . . ?
C20 C19 N4 C18 87.5(3) . . . . ?
C20 C19 N4 C22 -84.6(3) . . . . ?
C21 C19 N4 C18 -146.1(3) . . . . ?
C21 C19 N4 C22 41.9(4) . . . . ?
C22 C23 C24 C25 47.4(2) . . . . ?
C22 C23 C24 C28 171.4(2) . . . . ?
C23 C22 C27 C26 -2.8(3) . . . . ?
C23 C22 C27 Cl2 178.26(16) . . . . ?
C23 C22 N4 C18 -97.6(2) . . . . ?
C23 C22 N4 C19 74.1(3) . . . . ?
C23 C24 C25 C26 -57.6(3) . . . . ?
C24 C25 C26 C27 37.8(3) . . . . ?
C24 C25 C26 O3 -144.5(2) . . . . ?
C25 C26 C27 C22 -7.0(3) . . . . ?
C25 C26 C27 Cl2 172.00(16) . . . . ?
C27 C22 C23 C24 -18.7(3) . . . . ?
C27 C22 N4 C18 83.2(3) . . . . ?
C27 C22 N4 C19 -105.0(3) . . . . ?
C28 C24 C25 C26 179.6(2) . . . . ?
Cl1 C9 C10 C11 173.3(2) . . . . ?
Cl1 C9 C10 O2 -3.3(3) . . . . ?
Cl1 C9 C10 C11A -159.1(10) . . . . ?
N1 C4 N2 C5 -172.7(2) . . . . ?
N1 C4 N2 C8 -0.7(3) . . . . ?
N2 C4 N1 C2 -176.7(2) . . . . ?
N2 C8 C9 C10 177.9(2) . . . . ?
N2 C8 C9 Cl1 -0.9(3) . . . . ?
N2 C8 C13 C12 158.1(2) . . . . ?
N2 C8 C13 C12A -169.4(12) . . . . ?
N3 C18 N4 C19 -174.9(2) . . . . ?
N3 C18 N4 C22 -3.1(3) . . . . ?
N4 C18 N3 C16 -168.9(2) . . . . ?
N4 C22 C23 C24 162.14(18) . . . . ?
N4 C22 C27 C26 176.35(19) . . . . ?
N4 C22 C27 Cl2 -2.6(3) . . . . ?
O1 C4 N1 C2 5.4(4) . . . . ?
O1 C4 N2 C5 5.3(3) . . . . ?
O1 C4 N2 C8 177.3(2) . . . . ?
O2 C10 C11 C12 -147.0(3) . . . . ?
O2 C10 C11A C12A 150.2(17) . . . . ?
O3 C26 C27 C22 175.2(2) . . . . ?
O3 C26 C27 Cl2 -5.8(3) . . . . ?
O4 C18 N3 C16 12.2(4) . . . . ?
O4 C18 N4 C19 4.0(4) . . . . ?
O4 C18 N4 C22 175.8(2) . . . . ?
C3A C2 N1 C4 -99(2) . . . . ?
C1A C2 N1 C4 135.0(17) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
