# Electronic Supplementary Material (ESI) for Dalton Transactions.
# 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. 
# 
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data_Compound_1a_0m
_database_code_depnum_ccdc_archive 'CCDC 1581992'
_audit_update_record             
;
2017-10-25 deposited with the CCDC.
2018-03-08 downloaded from the CCDC.
;
_audit_creation_date             2017-10-24
_audit_creation_method           
;
Olex2 1.2
(compiled 2017.08.10 svn.r3458 for OlexSys, GUI svn.r5381)
;
_shelx_SHELXL_version_number     2017/1
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C20 H31 Br2 Hg N'
_chemical_formula_sum            'C20 H31 Br2 Hg N'
_chemical_formula_weight         645.87
_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'
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Hg Hg -2.3894 9.2266 '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'

_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                   9.4766(4)
_cell_length_b                   14.5595(7)
_cell_length_c                   16.1070(7)
_cell_angle_alpha                90
_cell_angle_beta                 91.540(3)
_cell_angle_gamma                90
_cell_volume                     2221.55(17)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    2077
_cell_measurement_temperature    273(2)
_cell_measurement_theta_max      18.44
_cell_measurement_theta_min      2.46
_shelx_estimated_absorpt_T_max   0.419
_shelx_estimated_absorpt_T_min   0.419
_exptl_absorpt_coefficient_mu    10.528
_exptl_absorpt_correction_T_max  0.7454
_exptl_absorpt_correction_T_min  0.5689
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details   
'SADABS-2014/5 (Bruker,2014/5) was used for absorption correction. wR2(int) was 0.0914 before and 0.0580 after correction. The Ratio of minimum to maximum transmission is 0.7632. The λ/2 correction factor is 0.00150.'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.931
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1232
_exptl_crystal_size_max          0.1
_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  0.0811
_diffrn_reflns_av_unetI/netI     0.0799
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            16937
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.000
_diffrn_reflns_theta_max         25.026
_diffrn_reflns_theta_min         2.465
_diffrn_ambient_temperature      273.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_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                2665
_reflns_number_total             3922
_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         1.068
_refine_diff_density_min         -0.757
_refine_diff_density_rms         0.157
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.960
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     225
_refine_ls_number_reflns         3922
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0796
_refine_ls_R_factor_gt           0.0451
_refine_ls_restrained_S_all      0.960
_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)+(0.0430P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0886
_refine_ls_wR_factor_ref         0.0996
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C11(H11), C18(H18)
2.b Secondary CH2 refined with riding coordinates:
 C5(H5a,H5b)
2.c Aromatic/amide H refined with riding coordinates:
 C14(H14), C15(H15), C16(H16)
2.d Idealised Me refined as rotating group:
 C3(H3a,H3b,H3c), C4(H4a,H4b,H4c), C7(H7a,H7b,H7c), C8(H8a,H8b,H8c), C12(H12a,
 H12b,H12c), C13(H13a,H13b,H13c), C19(H19a,H19b,H19c), C20(H20a,H20b,H20c)
;
_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
Hg1 Hg 0.51069(4) 0.60998(3) 0.42727(2) 0.04132(14) Uani 1 1 d . . . . .
Br1 Br 0.27394(11) 0.68424(9) 0.44124(8) 0.0754(4) Uani 1 1 d . . . . .
Br2 Br 0.57789(11) 0.57339(8) 0.59512(6) 0.0550(3) Uani 1 1 d . . . . .
N1 N 0.7119(6) 0.7052(5) 0.3113(4) 0.0292(17) Uani 1 1 d . . . . .
C1 C 0.7029(8) 0.6372(5) 0.3621(5) 0.025(2) Uani 1 1 d . . . . .
C2 C 0.8383(9) 0.5828(6) 0.3708(6) 0.035(2) Uani 1 1 d . . . . .
C3 C 0.9041(10) 0.6041(7) 0.4561(6) 0.053(3) Uani 1 1 d . . . . .
H3A H 0.908240 0.669387 0.463850 0.080 Uiso 1 1 calc GR . . . .
H3B H 0.997777 0.579043 0.459728 0.080 Uiso 1 1 calc GR . . . .
H3C H 0.847689 0.577161 0.498316 0.080 Uiso 1 1 calc GR . . . .
C4 C 0.8106(10) 0.4786(6) 0.3627(6) 0.056(3) Uani 1 1 d . . . . .
H4A H 0.746561 0.459526 0.404529 0.084 Uiso 1 1 calc GR . . . .
H4B H 0.897996 0.445845 0.369676 0.084 Uiso 1 1 calc GR . . . .
H4C H 0.769880 0.465636 0.308699 0.084 Uiso 1 1 calc GR . . . .
C5 C 0.9224(9) 0.6209(6) 0.2974(6) 0.041(2) Uani 1 1 d . . . . .
H5A H 1.020821 0.628778 0.314002 0.049 Uiso 1 1 calc R . . . .
H5B H 0.917160 0.578495 0.251025 0.049 Uiso 1 1 calc R . . . .
C6 C 0.8580(9) 0.7134(6) 0.2721(6) 0.037(2) Uani 1 1 d . . . . .
C7 C 0.8471(10) 0.7245(7) 0.1791(5) 0.048(3) Uani 1 1 d . . . . .
H7A H 0.799102 0.672360 0.155185 0.072 Uiso 1 1 calc GR . . . .
H7B H 0.940074 0.728755 0.157148 0.072 Uiso 1 1 calc GR . . . .
H7C H 0.795175 0.779368 0.165682 0.072 Uiso 1 1 calc GR . . . .
C8 C 0.9406(9) 0.7956(6) 0.3081(6) 0.048(3) Uani 1 1 d . . . . .
H8A H 0.887138 0.850840 0.298899 0.072 Uiso 1 1 calc GR . . . .
H8B H 1.029523 0.800543 0.281323 0.072 Uiso 1 1 calc GR . . . .
H8C H 0.956671 0.786755 0.366668 0.072 Uiso 1 1 calc GR . . . .
C9 C 0.5947(8) 0.7687(6) 0.2931(5) 0.029(2) Uani 1 1 d . . . . .
C10 C 0.5796(9) 0.8446(6) 0.3455(6) 0.036(2) Uani 1 1 d . . . . .
C11 C 0.6710(10) 0.8654(6) 0.4220(6) 0.043(2) Uani 1 1 d . . . . .
H11 H 0.747554 0.820161 0.424692 0.051 Uiso 1 1 calc R . . . .
C12 C 0.5836(12) 0.8548(7) 0.5015(6) 0.064(3) Uani 1 1 d . . . . .
H12A H 0.499939 0.891815 0.496519 0.096 Uiso 1 1 calc GR . . . .
H12B H 0.639180 0.874440 0.548918 0.096 Uiso 1 1 calc GR . . . .
H12C H 0.557493 0.791571 0.508212 0.096 Uiso 1 1 calc GR . . . .
C13 C 0.7375(11) 0.9610(7) 0.4200(6) 0.062(3) Uani 1 1 d . . . . .
H13A H 0.794476 0.970261 0.469524 0.093 Uiso 1 1 calc GR . . . .
H13B H 0.664428 1.006637 0.417054 0.093 Uiso 1 1 calc GR . . . .
H13C H 0.795508 0.966215 0.372283 0.093 Uiso 1 1 calc GR . . . .
C14 C 0.4650(10) 0.9033(7) 0.3247(7) 0.053(3) Uani 1 1 d . . . . .
H14 H 0.450963 0.955264 0.356939 0.064 Uiso 1 1 calc R . . . .
C15 C 0.3767(10) 0.8871(7) 0.2609(7) 0.056(3) Uani 1 1 d . . . . .
H15 H 0.304427 0.928378 0.248000 0.067 Uiso 1 1 calc R . . . .
C16 C 0.3926(10) 0.8093(7) 0.2141(6) 0.051(3) Uani 1 1 d . . . . .
H16 H 0.328212 0.798724 0.170504 0.061 Uiso 1 1 calc R . . . .
C17 C 0.5003(9) 0.7447(6) 0.2281(5) 0.038(2) Uani 1 1 d . . . . .
C18 C 0.5038(10) 0.6568(7) 0.1800(6) 0.046(3) Uani 1 1 d . . . . .
H18 H 0.591062 0.624467 0.195936 0.056 Uiso 1 1 calc R . . . .
C19 C 0.3805(12) 0.5942(7) 0.1998(7) 0.071(4) Uani 1 1 d . . . . .
H19A H 0.391110 0.572412 0.255854 0.107 Uiso 1 1 calc GR . . . .
H19B H 0.378910 0.542884 0.162339 0.107 Uiso 1 1 calc GR . . . .
H19C H 0.293701 0.627828 0.193638 0.107 Uiso 1 1 calc GR . . . .
C20 C 0.5058(10) 0.6742(7) 0.0854(6) 0.057(3) Uani 1 1 d . . . . .
H20A H 0.416486 0.699010 0.066879 0.086 Uiso 1 1 calc GR . . . .
H20B H 0.522731 0.617445 0.057053 0.086 Uiso 1 1 calc GR . . . .
H20C H 0.579472 0.717136 0.073405 0.086 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
Hg1 Br1 2.5061(11) . ?
Hg1 Br2 2.8188(11) 3_666 ?
Hg1 Br2 2.8117(11) . ?
Hg1 C1 2.163(7) . ?
N1 C1 1.288(10) . ?
N1 C6 1.543(9) . ?
N1 C9 1.469(10) . ?
C1 C2 1.512(11) . ?
C2 C3 1.524(13) . ?
C2 C4 1.544(12) . ?
C2 C5 1.547(11) . ?
C3 H3A 0.9600 . ?
C3 H3B 0.9600 . ?
C3 H3C 0.9600 . ?
C4 H4A 0.9600 . ?
C4 H4B 0.9600 . ?
C4 H4C 0.9600 . ?
C5 H5A 0.9700 . ?
C5 H5B 0.9700 . ?
C5 C6 1.530(11) . ?
C6 C7 1.507(12) . ?
C6 C8 1.534(12) . ?
C7 H7A 0.9600 . ?
C7 H7B 0.9600 . ?
C7 H7C 0.9600 . ?
C8 H8A 0.9600 . ?
C8 H8B 0.9600 . ?
C8 H8C 0.9600 . ?
C9 C10 1.401(12) . ?
C9 C17 1.402(11) . ?
C10 C11 1.517(12) . ?
C10 C14 1.415(12) . ?
C11 H11 0.9800 . ?
C11 C12 1.551(12) . ?
C11 C13 1.529(12) . ?
C12 H12A 0.9600 . ?
C12 H12B 0.9600 . ?
C12 H12C 0.9600 . ?
C13 H13A 0.9600 . ?
C13 H13B 0.9600 . ?
C13 H13C 0.9600 . ?
C14 H14 0.9300 . ?
C14 C15 1.329(14) . ?
C15 H15 0.9300 . ?
C15 C16 1.372(13) . ?
C16 H16 0.9300 . ?
C16 C17 1.401(12) . ?
C17 C18 1.498(12) . ?
C18 H18 0.9800 . ?
C18 C19 1.522(12) . ?
C18 C20 1.546(12) . ?
C19 H19A 0.9600 . ?
C19 H19B 0.9600 . ?
C19 H19C 0.9600 . ?
C20 H20A 0.9600 . ?
C20 H20B 0.9600 . ?
C20 H20C 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
Br1 Hg1 Br2 100.11(4) . . ?
Br1 Hg1 Br2 98.97(4) . 3_666 ?
Br2 Hg1 Br2 90.14(3) . 3_666 ?
C1 Hg1 Br1 137.1(2) . . ?
C1 Hg1 Br2 111.3(2) . 3_666 ?
C1 Hg1 Br2 109.2(2) . . ?
Hg1 Br2 Hg1 89.86(3) . 3_666 ?
C1 N1 C6 113.3(6) . . ?
C1 N1 C9 123.2(6) . . ?
C9 N1 C6 123.5(6) . . ?
N1 C1 Hg1 121.3(6) . . ?
N1 C1 C2 113.0(7) . . ?
C2 C1 Hg1 125.6(6) . . ?
C1 C2 C3 107.6(7) . . ?
C1 C2 C4 111.4(7) . . ?
C1 C2 C5 101.2(7) . . ?
C3 C2 C4 109.9(7) . . ?
C3 C2 C5 114.1(7) . . ?
C4 C2 C5 112.2(7) . . ?
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 . . ?
C2 C4 H4A 109.5 . . ?
C2 C4 H4B 109.5 . . ?
C2 C4 H4C 109.5 . . ?
H4A C4 H4B 109.5 . . ?
H4A C4 H4C 109.5 . . ?
H4B C4 H4C 109.5 . . ?
C2 C5 H5A 110.1 . . ?
C2 C5 H5B 110.1 . . ?
H5A C5 H5B 108.4 . . ?
C6 C5 C2 108.1(7) . . ?
C6 C5 H5A 110.1 . . ?
C6 C5 H5B 110.1 . . ?
C5 C6 N1 100.2(6) . . ?
C5 C6 C8 112.9(8) . . ?
C7 C6 N1 112.1(7) . . ?
C7 C6 C5 112.1(7) . . ?
C7 C6 C8 108.3(7) . . ?
C8 C6 N1 111.1(7) . . ?
C6 C7 H7A 109.5 . . ?
C6 C7 H7B 109.5 . . ?
C6 C7 H7C 109.5 . . ?
H7A C7 H7B 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
C6 C8 H8A 109.5 . . ?
C6 C8 H8B 109.5 . . ?
C6 C8 H8C 109.5 . . ?
H8A C8 H8B 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
C10 C9 N1 117.7(7) . . ?
C10 C9 C17 125.0(8) . . ?
C17 C9 N1 117.2(8) . . ?
C9 C10 C11 125.6(8) . . ?
C9 C10 C14 115.0(9) . . ?
C14 C10 C11 119.3(9) . . ?
C10 C11 H11 107.9 . . ?
C10 C11 C12 110.1(8) . . ?
C10 C11 C13 113.1(8) . . ?
C12 C11 H11 107.9 . . ?
C13 C11 H11 107.9 . . ?
C13 C11 C12 109.7(8) . . ?
C11 C12 H12A 109.5 . . ?
C11 C12 H12B 109.5 . . ?
C11 C12 H12C 109.5 . . ?
H12A C12 H12B 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C11 C13 H13A 109.5 . . ?
C11 C13 H13B 109.5 . . ?
C11 C13 H13C 109.5 . . ?
H13A C13 H13B 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
C10 C14 H14 118.6 . . ?
C15 C14 C10 122.7(10) . . ?
C15 C14 H14 118.6 . . ?
C14 C15 H15 120.2 . . ?
C14 C15 C16 119.7(9) . . ?
C16 C15 H15 120.2 . . ?
C15 C16 H16 118.1 . . ?
C15 C16 C17 123.8(9) . . ?
C17 C16 H16 118.1 . . ?
C9 C17 C18 125.2(8) . . ?
C16 C17 C9 113.7(9) . . ?
C16 C17 C18 121.0(9) . . ?
C17 C18 H18 107.7 . . ?
C17 C18 C19 112.0(9) . . ?
C17 C18 C20 111.8(8) . . ?
C19 C18 H18 107.7 . . ?
C19 C18 C20 109.6(8) . . ?
C20 C18 H18 107.7 . . ?
C18 C19 H19A 109.5 . . ?
C18 C19 H19B 109.5 . . ?
C18 C19 H19C 109.5 . . ?
H19A C19 H19B 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
C18 C20 H20A 109.5 . . ?
C18 C20 H20B 109.5 . . ?
C18 C20 H20C 109.5 . . ?
H20A C20 H20B 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?

_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_Compound_3b
_database_code_depnum_ccdc_archive 'CCDC 1581995'
_audit_update_record             
;
2017-10-25 deposited with the CCDC.
2018-03-08 downloaded from the CCDC.
;
_audit_creation_date             2017-10-07
_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 H36 Hg0.5 N O0.5, N O3'
_chemical_formula_sum            'C23 H36 Hg0.50 N2 O3.50'
_chemical_formula_weight         496.83
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Hg Hg -2.3894 9.2266 '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                   21.355(3)
_cell_length_b                   10.4818(8)
_cell_length_c                   20.973(2)
_cell_angle_alpha                90
_cell_angle_beta                 106.496(4)
_cell_angle_gamma                90
_cell_volume                     4501.4(8)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    5798
_cell_measurement_temperature    180.0(2)
_cell_measurement_theta_max      27.5
_cell_measurement_theta_min      3.2
_shelx_estimated_absorpt_T_max   0.543
_shelx_estimated_absorpt_T_min   0.543
_exptl_absorpt_coefficient_mu    3.473
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.604
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'Blessing 1995'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.466
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             2048
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.2
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.046
_diffrn_reflns_av_unetI/netI     0.071
_diffrn_reflns_Laue_measured_fraction_full 0.990
_diffrn_reflns_Laue_measured_fraction_max 0.984
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_h_min       -27
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_number            15566
_diffrn_reflns_point_group_measured_fraction_full 0.990
_diffrn_reflns_point_group_measured_fraction_max 0.984
_diffrn_reflns_theta_full        25.000
_diffrn_reflns_theta_max         27.525
_diffrn_reflns_theta_min         3.165
_diffrn_ambient_temperature      180.0(2)
_diffrn_detector_area_resol_mean 13.6612
_diffrn_measured_fraction_theta_full 0.990
_diffrn_measured_fraction_theta_max 0.984
_diffrn_measurement_details      
;
scan:
	Number of images: 629
	           Slice: -69.0000 - 119.7000
	     Image width: 0.3000
	        Exp time: 5.0000
	   Rotation axis: Omega
	           Omega: 0.0000
	             Chi: 54.0000
	             Phi: 120.0000
	             XTD: 49.8600
	          2theta: 29.8900
scan:
	Number of images: 629
	           Slice: -69.0000 - 119.7000
	     Image width: 0.3000
	        Exp time: 5.0000
	   Rotation axis: Omega
	           Omega: 0.0000
	             Chi: 54.0000
	             Phi: 240.0000
	             XTD: 49.8600
	          2theta: 29.8900
scan:
	Number of images: 629
	           Slice: -69.0000 - 119.7000
	     Image width: 0.3000
	        Exp time: 5.0000
	   Rotation axis: Omega
	           Omega: 0.0000
	             Chi: 54.0000
	             Phi: 0.0000
	             XTD: 49.8600
	          2theta: 29.8900
;
_diffrn_measurement_device_type  'XtaLAB Mini (ROW)'
_diffrn_measurement_method       'profile data from ω-scans'
_diffrn_orient_matrix_type       d*Trek
_diffrn_orient_matrix_UB_11      0.003300
_diffrn_orient_matrix_UB_12      0.048185
_diffrn_orient_matrix_UB_13      -0.007242
_diffrn_orient_matrix_UB_21      0.042468
_diffrn_orient_matrix_UB_22      0.009846
_diffrn_orient_matrix_UB_23      0.084861
_diffrn_orient_matrix_UB_31      0.043528
_diffrn_orient_matrix_UB_32      0.007917
_diffrn_orient_matrix_UB_33      -0.022702
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71075
_diffrn_source                   ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                4587
_reflns_number_total             5118
_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       
;
CrystalClear-SM Expert 2.0 r15 (Rigaku, 2011)
;
_computing_data_collection       
;
CrystalClear-SM Expert 2.0 r15 (Rigaku, 2011)
;
_computing_data_reduction        
;
CrystalClear-SM Expert 2.0 r15 (Rigaku, 2011)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         1.294
_refine_diff_density_min         -1.731
_refine_diff_density_rms         0.133
_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     270
_refine_ls_number_reflns         5118
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0429
_refine_ls_R_factor_gt           0.0360
_refine_ls_restrained_S_all      1.081
_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)+(0.0240P)²+5.5677P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0792
_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
 At 1.5 times of:
  All C(H,H,H) groups, All O(H,H) groups
2. Others
 Fixed Sof: H1A(0.5) H1B(0.5)
3.a Rotating group:
 O1(H1A,H1B)
3.b Ternary CH refined with riding coordinates:
 C14(H14), C21(H21)
3.c Secondary CH2 refined with riding coordinates:
 C3(H3A,H3B), C4(H4A,H4B), C5(H5A,H5B), C6(H6A,H6B), C7(H7A,H7B), C8(H8A,H8B)
3.d Aromatic/amide H refined with riding coordinates:
 C17(H17), C18(H18), C19(H19)
3.e Idealised Me refined as rotating group:
 C10(H10A,H10B,H10C), C11(H11A,H11B,H11C), C15(H15A,H15B,H15C), C16(H16A,H16B,
 H16C), C22(H22A,H22B,H22C), C23(H23A,H23B,H23C)
;
_atom_sites_solution_hydrogens   mixed
_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
Hg1 Hg 0.5000 0.25979(2) 0.7500 0.01932(8) Uani 1 2 d S T P . .
O1 O 0.5000 0.4964(3) 0.7500 0.0378(10) Uani 1 2 d S T P . .
H1A H 0.5278 0.5301 0.7280 0.057 Uiso 0.5 1 d GR . . . .
H1B H 0.5127 0.5301 0.7921 0.057 Uiso 0.5 1 d GR . . . .
O2 O 0.4115(2) 0.6879(4) 0.8294(2) 0.0841(14) Uani 1 1 d . . . . .
O3 O 0.47634(17) 0.8296(3) 0.88466(17) 0.0457(8) Uani 1 1 d . . . . .
O4 O 0.51379(19) 0.6494(3) 0.8653(3) 0.0826(16) Uani 1 1 d . . . . .
N1 N 0.42824(15) 0.2349(2) 0.60479(15) 0.0156(6) Uani 1 1 d . . . . .
N2 N 0.4686(2) 0.7223(4) 0.8598(2) 0.0375(9) Uani 1 1 d . . . . .
C1 C 0.48384(19) 0.2453(3) 0.64808(18) 0.0156(7) Uani 1 1 d . . . . .
C2 C 0.53975(18) 0.2415(3) 0.61792(18) 0.0170(7) Uani 1 1 d . . . . .
C3 C 0.58935(19) 0.1406(3) 0.6547(2) 0.0276(8) Uani 1 1 d . . . . .
H3A H 0.6026 0.1595 0.7029 0.033 Uiso 1 1 calc R . . . .
H3B H 0.5683 0.0555 0.6482 0.033 Uiso 1 1 calc R . . . .
C4 C 0.6501(2) 0.1377(4) 0.6296(2) 0.0345(10) Uani 1 1 d . . . . .
H4A H 0.6810 0.0728 0.6547 0.041 Uiso 1 1 calc R . . . .
H4B H 0.6373 0.1132 0.5820 0.041 Uiso 1 1 calc R . . . .
C5 C 0.6832(2) 0.2671(4) 0.6379(3) 0.0349(10) Uani 1 1 d . . . . .
H5A H 0.7211 0.2643 0.6197 0.042 Uiso 1 1 calc R . . . .
H5B H 0.6993 0.2882 0.6858 0.042 Uiso 1 1 calc R . . . .
C6 C 0.63553(19) 0.3700(4) 0.6020(2) 0.0320(9) Uani 1 1 d . . . . .
H6A H 0.6226 0.3531 0.5536 0.038 Uiso 1 1 calc R . . . .
H6B H 0.6573 0.4542 0.6098 0.038 Uiso 1 1 calc R . . . .
C7 C 0.57460(18) 0.3729(3) 0.6265(2) 0.0251(8) Uani 1 1 d . . . . .
H7A H 0.5440 0.4382 0.6012 0.030 Uiso 1 1 calc R . . . .
H7B H 0.5872 0.3973 0.6740 0.030 Uiso 1 1 calc R . . . .
C8 C 0.50605(18) 0.2024(4) 0.54547(18) 0.0251(8) Uani 1 1 d . . . . .
H8A H 0.5127 0.1104 0.5390 0.030 Uiso 1 1 calc R . . . .
H8B H 0.5241 0.2516 0.5145 0.030 Uiso 1 1 calc R . . . .
C9 C 0.43286(19) 0.2319(3) 0.53294(18) 0.0206(8) Uani 1 1 d . . . . .
C10 C 0.4137(2) 0.3620(4) 0.5008(2) 0.0374(10) Uani 1 1 d . . . . .
H10A H 0.3669 0.3759 0.4938 0.056 Uiso 1 1 calc GR . . . .
H10B H 0.4236 0.3649 0.4579 0.056 Uiso 1 1 calc GR . . . .
H10C H 0.4384 0.4287 0.5300 0.056 Uiso 1 1 calc GR . . . .
C11 C 0.3905(2) 0.1294(4) 0.4929(2) 0.0366(10) Uani 1 1 d . . . . .
H11A H 0.4019 0.0471 0.5154 0.055 Uiso 1 1 calc GR . . . .
H11B H 0.3972 0.1254 0.4487 0.055 Uiso 1 1 calc GR . . . .
H11C H 0.3445 0.1487 0.4886 0.055 Uiso 1 1 calc GR . . . .
C12 C 0.36664(18) 0.2190(3) 0.62235(17) 0.0184(7) Uani 1 1 d . . . . .
C13 C 0.32767(18) 0.3240(3) 0.62662(18) 0.0231(8) Uani 1 1 d . . . . .
C14 C 0.34425(19) 0.4625(3) 0.61685(19) 0.0249(8) Uani 1 1 d . . . . .
H14 H 0.3884 0.4653 0.6093 0.030 Uiso 1 1 calc R . . . .
C15 C 0.3463(2) 0.5421(4) 0.6786(2) 0.0332(9) Uani 1 1 d . . . . .
H15A H 0.3024 0.5476 0.6841 0.050 Uiso 1 1 calc GR . . . .
H15B H 0.3622 0.6281 0.6733 0.050 Uiso 1 1 calc GR . . . .
H15C H 0.3758 0.5016 0.7179 0.050 Uiso 1 1 calc GR . . . .
C16 C 0.2948(2) 0.5210(4) 0.5563(2) 0.0344(10) Uani 1 1 d . . . . .
H16A H 0.2536 0.5367 0.5668 0.052 Uiso 1 1 calc GR . . . .
H16B H 0.2872 0.4620 0.5187 0.052 Uiso 1 1 calc GR . . . .
H16C H 0.3119 0.6018 0.5448 0.052 Uiso 1 1 calc GR . . . .
C17 C 0.26998(19) 0.3005(4) 0.6428(2) 0.0286(9) Uani 1 1 d . . . . .
H17 H 0.2425 0.3703 0.6458 0.034 Uiso 1 1 calc R . . . .
C18 C 0.2514(2) 0.1789(4) 0.6548(2) 0.0337(9) Uani 1 1 d . . . . .
H18 H 0.2113 0.1653 0.6648 0.040 Uiso 1 1 calc R . . . .
C19 C 0.29155(19) 0.0774(4) 0.6520(2) 0.0311(9) Uani 1 1 d . . . . .
H19 H 0.2792 -0.0058 0.6617 0.037 Uiso 1 1 calc R . . . .
C20 C 0.34980(18) 0.0933(3) 0.63534(18) 0.0225(8) Uani 1 1 d . . . . .
C21 C 0.39166(19) -0.0239(3) 0.63571(19) 0.0254(8) Uani 1 1 d . . . . .
H21 H 0.4309 0.0026 0.6220 0.030 Uiso 1 1 calc R . . . .
C22 C 0.4148(2) -0.0816(4) 0.7048(2) 0.0344(10) Uani 1 1 d . . . . .
H22A H 0.4387 -0.0171 0.7363 0.052 Uiso 1 1 calc GR . . . .
H22B H 0.4436 -0.1541 0.7043 0.052 Uiso 1 1 calc GR . . . .
H22C H 0.3770 -0.1108 0.7186 0.052 Uiso 1 1 calc GR . . . .
C23 C 0.3546(2) -0.1262(3) 0.5866(2) 0.0304(9) Uani 1 1 d . . . . .
H23A H 0.3176 -0.1577 0.6011 0.046 Uiso 1 1 calc GR . . . .
H23B H 0.3841 -0.1972 0.5854 0.046 Uiso 1 1 calc GR . . . .
H23C H 0.3384 -0.0889 0.5421 0.046 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
Hg1 O1 2.480(4) . ?
Hg1 C1 2.072(4) . ?
Hg1 C1 2.072(4) 2_656 ?
O1 H1A 0.9184 . ?
O1 H1B 0.9186 . ?
O2 N2 1.257(6) . ?
O3 N2 1.231(5) . ?
O4 N2 1.211(5) . ?
N1 C1 1.278(5) . ?
N1 C9 1.538(5) . ?
N1 C12 1.473(5) . ?
C1 C2 1.502(5) . ?
C2 C3 1.540(5) . ?
C2 C7 1.551(4) . ?
C2 C8 1.541(5) . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C3 C4 1.531(5) . ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?
C4 C5 1.516(5) . ?
C5 H5A 0.9900 . ?
C5 H5B 0.9900 . ?
C5 C6 1.526(6) . ?
C6 H6A 0.9900 . ?
C6 H6B 0.9900 . ?
C6 C7 1.528(5) . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C8 C9 1.541(5) . ?
C9 C10 1.524(5) . ?
C9 C11 1.499(5) . ?
C10 H10A 0.9800 . ?
C10 H10B 0.9800 . ?
C10 H10C 0.9800 . ?
C11 H11A 0.9800 . ?
C11 H11B 0.9800 . ?
C11 H11C 0.9800 . ?
C12 C13 1.398(5) . ?
C12 C20 1.413(5) . ?
C13 C14 1.522(5) . ?
C13 C17 1.390(5) . ?
C14 H14 1.0000 . ?
C14 C15 1.530(5) . ?
C14 C16 1.530(5) . ?
C15 H15A 0.9800 . ?
C15 H15B 0.9800 . ?
C15 H15C 0.9800 . ?
C16 H16A 0.9800 . ?
C16 H16B 0.9800 . ?
C16 H16C 0.9800 . ?
C17 H17 0.9500 . ?
C17 C18 1.378(6) . ?
C18 H18 0.9500 . ?
C18 C19 1.378(5) . ?
C19 H19 0.9500 . ?
C19 C20 1.394(5) . ?
C20 C21 1.518(5) . ?
C21 H21 1.0000 . ?
C21 C22 1.518(5) . ?
C21 C23 1.541(5) . ?
C22 H22A 0.9800 . ?
C22 H22B 0.9800 . ?
C22 H22C 0.9800 . ?
C23 H23A 0.9800 . ?
C23 H23B 0.9800 . ?
C23 H23C 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
C1 Hg1 O1 94.21(8) . . ?
C1 Hg1 O1 94.21(8) 2_656 . ?
C1 Hg1 C1 171.58(16) . 2_656 ?
Hg1 O1 H1A 112.6 . . ?
Hg1 O1 H1B 112.6 . . ?
H1A O1 H1B 106.2 . . ?
C1 N1 C9 113.1(3) . . ?
C1 N1 C12 123.2(3) . . ?
C12 N1 C9 123.6(3) . . ?
O3 N2 O2 118.1(5) . . ?
O4 N2 O2 120.0(4) . . ?
O4 N2 O3 121.9(4) . . ?
N1 C1 Hg1 126.0(3) . . ?
N1 C1 C2 112.8(3) . . ?
C2 C1 Hg1 121.1(3) . . ?
C1 C2 C3 108.9(3) . . ?
C1 C2 C7 109.9(3) . . ?
C1 C2 C8 102.6(3) . . ?
C3 C2 C7 108.2(3) . . ?
C3 C2 C8 111.9(3) . . ?
C8 C2 C7 115.1(3) . . ?
C2 C3 H3A 109.3 . . ?
C2 C3 H3B 109.3 . . ?
H3A C3 H3B 107.9 . . ?
C4 C3 C2 111.8(3) . . ?
C4 C3 H3A 109.3 . . ?
C4 C3 H3B 109.3 . . ?
C3 C4 H4A 109.5 . . ?
C3 C4 H4B 109.5 . . ?
H4A C4 H4B 108.1 . . ?
C5 C4 C3 110.8(3) . . ?
C5 C4 H4A 109.5 . . ?
C5 C4 H4B 109.5 . . ?
C4 C5 H5A 109.5 . . ?
C4 C5 H5B 109.5 . . ?
C4 C5 C6 110.6(4) . . ?
H5A C5 H5B 108.1 . . ?
C6 C5 H5A 109.5 . . ?
C6 C5 H5B 109.5 . . ?
C5 C6 H6A 109.4 . . ?
C5 C6 H6B 109.4 . . ?
C5 C6 C7 111.1(3) . . ?
H6A C6 H6B 108.0 . . ?
C7 C6 H6A 109.4 . . ?
C7 C6 H6B 109.4 . . ?
C2 C7 H7A 109.3 . . ?
C2 C7 H7B 109.3 . . ?
C6 C7 C2 111.7(3) . . ?
C6 C7 H7A 109.3 . . ?
C6 C7 H7B 109.3 . . ?
H7A C7 H7B 107.9 . . ?
C2 C8 H8A 110.5 . . ?
C2 C8 H8B 110.5 . . ?
C2 C8 C9 106.4(3) . . ?
H8A C8 H8B 108.6 . . ?
C9 C8 H8A 110.5 . . ?
C9 C8 H8B 110.5 . . ?
N1 C9 C8 100.4(3) . . ?
C10 C9 N1 109.3(3) . . ?
C10 C9 C8 112.7(3) . . ?
C11 C9 N1 111.5(3) . . ?
C11 C9 C8 112.0(3) . . ?
C11 C9 C10 110.5(4) . . ?
C9 C10 H10A 109.5 . . ?
C9 C10 H10B 109.5 . . ?
C9 C10 H10C 109.5 . . ?
H10A C10 H10B 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
C9 C11 H11A 109.5 . . ?
C9 C11 H11B 109.5 . . ?
C9 C11 H11C 109.5 . . ?
H11A C11 H11B 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
C13 C12 N1 121.1(3) . . ?
C13 C12 C20 122.2(3) . . ?
C20 C12 N1 116.6(3) . . ?
C12 C13 C14 125.2(3) . . ?
C17 C13 C12 117.5(3) . . ?
C17 C13 C14 117.3(3) . . ?
C13 C14 H14 108.4 . . ?
C13 C14 C15 111.0(3) . . ?
C13 C14 C16 111.2(3) . . ?
C15 C14 H14 108.4 . . ?
C16 C14 H14 108.4 . . ?
C16 C14 C15 109.3(3) . . ?
C14 C15 H15A 109.5 . . ?
C14 C15 H15B 109.5 . . ?
C14 C15 H15C 109.5 . . ?
H15A C15 H15B 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
C14 C16 H16A 109.5 . . ?
C14 C16 H16B 109.5 . . ?
C14 C16 H16C 109.5 . . ?
H16A C16 H16B 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
C13 C17 H17 119.0 . . ?
C18 C17 C13 121.9(4) . . ?
C18 C17 H17 119.0 . . ?
C17 C18 H18 120.3 . . ?
C19 C18 C17 119.5(4) . . ?
C19 C18 H18 120.3 . . ?
C18 C19 H19 119.1 . . ?
C18 C19 C20 121.9(4) . . ?
C20 C19 H19 119.1 . . ?
C12 C20 C21 125.0(3) . . ?
C19 C20 C12 117.0(3) . . ?
C19 C20 C21 117.9(3) . . ?
C20 C21 H21 108.3 . . ?
C20 C21 C22 111.0(3) . . ?
C20 C21 C23 111.7(3) . . ?
C22 C21 H21 108.3 . . ?
C22 C21 C23 109.1(3) . . ?
C23 C21 H21 108.3 . . ?
C21 C22 H22A 109.5 . . ?
C21 C22 H22B 109.5 . . ?
C21 C22 H22C 109.5 . . ?
H22A C22 H22B 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
C21 C23 H23A 109.5 . . ?
C21 C23 H23B 109.5 . . ?
C21 C23 H23C 109.5 . . ?
H23A C23 H23B 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 109.5 . . ?

_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_Compound_2b
_database_code_depnum_ccdc_archive 'CCDC 1581993'
_audit_update_record             
;
2017-10-25 deposited with the CCDC.
2018-03-08 downloaded from the CCDC.
;
_audit_creation_date             2017-10-11
_audit_creation_method           
;
Olex2 1.2
(compiled 2017.08.10 svn.r3458 for OlexSys, GUI svn.r5381)
;
_shelxl_version_number           2013-2
_chemical_name_common            ?
_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         'Cl3 Hg, C23 H36 N'
_chemical_formula_sum            'C23 H36 Cl3 Hg N'
_chemical_formula_weight         633.47
_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'
Hg Hg -2.3894 9.2266 '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'

_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                   14.5606(12)
_cell_length_b                   11.7853(8)
_cell_length_c                   15.6669(13)
_cell_angle_alpha                90
_cell_angle_beta                 104.559(3)
_cell_angle_gamma                90
_cell_volume                     2602.1(4)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    5770
_cell_measurement_temperature    298.0(2)
_cell_measurement_theta_max      27.5
_cell_measurement_theta_min      3.2
_shelx_estimated_absorpt_T_max   0.575
_shelx_estimated_absorpt_T_min   0.575
_exptl_absorpt_coefficient_mu    6.232
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.783
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'Blesiing 1995'
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.617
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1248
_exptl_crystal_size_max          0.1
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.1
_exptl_special_details           
;
 ?
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.1042
_diffrn_reflns_av_unetI/netI     0.0580
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            27612
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        25.000
_diffrn_reflns_theta_max         27.475
_diffrn_reflns_theta_min         3.195
_diffrn_ambient_temperature      298.0(2)
_diffrn_detector_area_resol_mean 13.6612
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'XtaLAB Mini (ROW)'
_diffrn_measurement_method       'profile data from ω-scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71075
_diffrn_source                   'Sealed Tube'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                4414
_reflns_number_total             5945
_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       
;
CrystalClear-SM Expert 2.0 r15 (Rigaku, 2011)
;
_computing_data_collection       
;
CrystalClear-SM Expert 2.0 r15 (Rigaku, 2011)
;
_computing_data_reduction        
;
CrystalClear-SM Expert 2.0 r15 (Rigaku, 2011)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         1.541
_refine_diff_density_min         -1.169
_refine_diff_density_rms         0.131
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.059
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     259
_refine_ls_number_reflns         5945
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0640
_refine_ls_R_factor_gt           0.0476
_refine_ls_restrained_S_all      1.059
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
;
 w=1/[σ²(Fo²)+(0.0731P)²+0.1902P]
 where P=(Fo²+2Fc²)/3
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1236
_refine_ls_wR_factor_ref         0.1377
_refine_special_details          
;
 ?
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C14(H14), C21(H21)
2.b Secondary CH2 refined with riding coordinates:
 C3(H3a,H3b), C4(H4a,H4b), C5(H5b,H5a), C6(H6a,H6b), C7(H7a,H7b), C8(H8a,H8b)
2.c Aromatic/amide H refined with riding coordinates:
 C1(H1), C17(H17), C18(H18), C19(H19)
2.d Idealised Me refined as rotating group:
 C10(H10a,H10b,H10c), C11(H11a,H11b,H11c), C15(H15a,H15b,H15c), C16(H16a,H16b,
 H16c), C22(H22a,H22b,H22c), C23(H23a,H23b,H23c)
;
_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
Hg1 Hg 0.46361(2) 0.85045(2) 0.46839(2) 0.06851(13) Uani 1 1 d . . . . .
Cl1 Cl 0.53478(12) 0.75693(17) 0.36598(13) 0.0921(5) Uani 1 1 d . . . . .
Cl2 Cl 0.36389(10) 0.77869(14) 0.55673(11) 0.0805(5) Uani 1 1 d . . . . .
Cl3 Cl 0.39665(10) 1.04941(12) 0.41181(10) 0.0814(5) Uani 1 1 d . . . . .
N1 N 0.5170(2) 0.5927(3) 0.7987(2) 0.0392(7) Uani 1 1 d . . . . .
C1 C 0.5319(3) 0.6310(3) 0.7271(3) 0.0428(9) Uani 1 1 d . . . . .
H1 H 0.4920 0.6836 0.6919 0.051 Uiso 1 1 calc R . . . .
C2 C 0.6167(3) 0.5856(4) 0.7046(3) 0.0439(9) Uani 1 1 d . . . . .
C3 C 0.6930(4) 0.6808(5) 0.7188(4) 0.0681(15) Uani 1 1 d . . . . .
H3A H 0.6656 0.7480 0.6865 0.082 Uiso 1 1 calc R . . . .
H3B H 0.7124 0.7002 0.7809 0.082 Uiso 1 1 calc R . . . .
C4 C 0.7788(5) 0.6445(5) 0.6881(6) 0.086(2) Uani 1 1 d . . . . .
H4A H 0.8099 0.5817 0.7241 0.103 Uiso 1 1 calc R . . . .
H4B H 0.8235 0.7069 0.6952 0.103 Uiso 1 1 calc R . . . .
C5 C 0.7504(6) 0.6083(8) 0.5920(5) 0.105(3) Uani 1 1 d . . . . .
H5B H 0.8063 0.5853 0.5734 0.127 Uiso 1 1 calc R . . . .
H5A H 0.7217 0.6720 0.5556 0.127 Uiso 1 1 calc R . . . .
C6 C 0.6794(5) 0.5091(6) 0.5792(4) 0.089(2) Uani 1 1 d . . . . .
H6A H 0.7086 0.4445 0.6140 0.107 Uiso 1 1 calc R . . . .
H6B H 0.6620 0.4864 0.5177 0.107 Uiso 1 1 calc R . . . .
C7 C 0.5897(4) 0.5455(5) 0.6080(3) 0.0679(14) Uani 1 1 d . . . . .
H7A H 0.5581 0.6066 0.5703 0.082 Uiso 1 1 calc R . . . .
H7B H 0.5461 0.4821 0.6016 0.082 Uiso 1 1 calc R . . . .
C8 C 0.6440(3) 0.4877(4) 0.7711(3) 0.0500(10) Uani 1 1 d . . . . .
H8A H 0.6248 0.4157 0.7421 0.060 Uiso 1 1 calc R . . . .
H8B H 0.7122 0.4864 0.7955 0.060 Uiso 1 1 calc R . . . .
C9 C 0.5935(3) 0.5068(4) 0.8443(3) 0.0447(9) Uani 1 1 d . . . . .
C10 C 0.5490(4) 0.3986(5) 0.8686(4) 0.0636(14) Uani 1 1 d . . . . .
H10A H 0.5093 0.4167 0.9072 0.095 Uiso 1 1 calc GR . . . .
H10B H 0.5982 0.3474 0.8978 0.095 Uiso 1 1 calc GR . . . .
H10C H 0.5115 0.3635 0.8160 0.095 Uiso 1 1 calc GR . . . .
C11 C 0.6545(4) 0.5612(5) 0.9272(3) 0.0636(14) Uani 1 1 d . . . . .
H11A H 0.6807 0.6310 0.9121 0.095 Uiso 1 1 calc GR . . . .
H11B H 0.7051 0.5105 0.9542 0.095 Uiso 1 1 calc GR . . . .
H11C H 0.6164 0.5765 0.9677 0.095 Uiso 1 1 calc GR . . . .
C12 C 0.4407(3) 0.6315(3) 0.8362(3) 0.0411(9) Uani 1 1 d . . . . .
C13 C 0.3567(3) 0.5682(4) 0.8203(3) 0.0469(10) Uani 1 1 d . . . . .
C14 C 0.3353(4) 0.4725(5) 0.7536(3) 0.0572(12) Uani 1 1 d . . . . .
H14 H 0.3948 0.4494 0.7402 0.069 Uiso 1 1 calc R . . . .
C15 C 0.2683(4) 0.5164(6) 0.6690(4) 0.0767(17) Uani 1 1 d . . . . .
H15A H 0.2090 0.5377 0.6806 0.115 Uiso 1 1 calc GR . . . .
H15B H 0.2577 0.4580 0.6249 0.115 Uiso 1 1 calc GR . . . .
H15C H 0.2962 0.5814 0.6482 0.115 Uiso 1 1 calc GR . . . .
C16 C 0.2926(5) 0.3691(5) 0.7876(4) 0.0798(18) Uani 1 1 d . . . . .
H16A H 0.3345 0.3437 0.8417 0.120 Uiso 1 1 calc GR . . . .
H16B H 0.2839 0.3095 0.7445 0.120 Uiso 1 1 calc GR . . . .
H16C H 0.2323 0.3891 0.7979 0.120 Uiso 1 1 calc GR . . . .
C17 C 0.2889(3) 0.6038(5) 0.8622(3) 0.0586(12) Uani 1 1 d . . . . .
H17 H 0.2328 0.5628 0.8545 0.070 Uiso 1 1 calc R . . . .
C18 C 0.3023(4) 0.6980(5) 0.9147(3) 0.0628(13) Uani 1 1 d . . . . .
H18 H 0.2563 0.7187 0.9435 0.075 Uiso 1 1 calc R . . . .
C19 C 0.3826(4) 0.7619(5) 0.9252(3) 0.0591(13) Uani 1 1 d . . . . .
H19 H 0.3890 0.8273 0.9595 0.071 Uiso 1 1 calc R . . . .
C20 C 0.4557(3) 0.7318(4) 0.8858(3) 0.0474(10) Uani 1 1 d . . . . .
C21 C 0.5381(4) 0.8105(5) 0.8917(3) 0.0587(12) Uani 1 1 d . . . . .
H21 H 0.5854 0.7689 0.8692 0.070 Uiso 1 1 calc R . . . .
C22 C 0.5871(6) 0.8491(5) 0.9850(4) 0.084(2) Uani 1 1 d . . . . .
H22A H 0.5431 0.8915 1.0091 0.126 Uiso 1 1 calc GR . . . .
H22B H 0.6404 0.8963 0.9834 0.126 Uiso 1 1 calc GR . . . .
H22C H 0.6086 0.7840 1.0214 0.126 Uiso 1 1 calc GR . . . .
C23 C 0.5064(5) 0.9125(6) 0.8301(4) 0.0823(17) Uani 1 1 d . . . . .
H23A H 0.4742 0.8859 0.7724 0.123 Uiso 1 1 calc GR . . . .
H23B H 0.5610 0.9560 0.8263 0.123 Uiso 1 1 calc GR . . . .
H23C H 0.4643 0.9594 0.8531 0.123 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
Hg1 Cl1 2.3873(15) . ?
Hg1 Cl2 2.3978(14) . ?
Hg1 Cl3 2.6077(14) . ?
Hg1 Cl3 2.6713(14) 3_676 ?
Cl3 Hg1 2.6713(14) 3_676 ?
N1 C1 1.277(5) . ?
N1 C9 1.541(5) . ?
N1 C12 1.455(5) . ?
C1 H1 0.9300 . ?
C1 C2 1.467(6) . ?
C2 C3 1.555(7) . ?
C2 C7 1.540(6) . ?
C2 C8 1.537(6) . ?
C3 H3A 0.9700 . ?
C3 H3B 0.9700 . ?
C3 C4 1.509(8) . ?
C4 H4A 0.9700 . ?
C4 H4B 0.9700 . ?
C4 C5 1.520(11) . ?
C5 H5B 0.9700 . ?
C5 H5A 0.9700 . ?
C5 C6 1.540(11) . ?
C6 H6A 0.9700 . ?
C6 H6B 0.9700 . ?
C6 C7 1.546(8) . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C8 C9 1.526(6) . ?
C9 C10 1.521(7) . ?
C9 C11 1.519(6) . ?
C10 H10A 0.9600 . ?
C10 H10B 0.9600 . ?
C10 H10C 0.9600 . ?
C11 H11A 0.9600 . ?
C11 H11B 0.9600 . ?
C11 H11C 0.9600 . ?
C12 C13 1.401(6) . ?
C12 C20 1.400(6) . ?
C13 C14 1.516(7) . ?
C13 C17 1.382(7) . ?
C14 H14 0.9800 . ?
C14 C15 1.525(7) . ?
C14 C16 1.523(7) . ?
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 H17 0.9300 . ?
C17 C18 1.365(9) . ?
C18 H18 0.9300 . ?
C18 C19 1.365(8) . ?
C19 H19 0.9300 . ?
C19 C20 1.404(7) . ?
C20 C21 1.501(7) . ?
C21 H21 0.9800 . ?
C21 C22 1.527(7) . ?
C21 C23 1.539(8) . ?
C22 H22A 0.9600 . ?
C22 H22B 0.9600 . ?
C22 H22C 0.9600 . ?
C23 H23A 0.9600 . ?
C23 H23B 0.9600 . ?
C23 H23C 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
Cl1 Hg1 Cl2 130.79(7) . . ?
Cl1 Hg1 Cl3 112.03(7) . . ?
Cl1 Hg1 Cl3 107.07(6) . 3_676 ?
Cl2 Hg1 Cl3 106.53(5) . . ?
Cl2 Hg1 Cl3 102.42(6) . 3_676 ?
Cl3 Hg1 Cl3 89.73(4) . 3_676 ?
Hg1 Cl3 Hg1 90.27(4) . 3_676 ?
C1 N1 C9 112.1(3) . . ?
C1 N1 C12 124.0(4) . . ?
C12 N1 C9 123.8(3) . . ?
N1 C1 H1 122.6 . . ?
N1 C1 C2 114.9(4) . . ?
C2 C1 H1 122.6 . . ?
C1 C2 C3 108.5(4) . . ?
C1 C2 C7 109.0(4) . . ?
C1 C2 C8 101.6(3) . . ?
C7 C2 C3 110.9(4) . . ?
C8 C2 C3 113.0(4) . . ?
C8 C2 C7 113.3(4) . . ?
C2 C3 H3A 109.3 . . ?
C2 C3 H3B 109.3 . . ?
H3A C3 H3B 108.0 . . ?
C4 C3 C2 111.7(5) . . ?
C4 C3 H3A 109.3 . . ?
C4 C3 H3B 109.3 . . ?
C3 C4 H4A 109.5 . . ?
C3 C4 H4B 109.5 . . ?
C3 C4 C5 110.7(6) . . ?
H4A C4 H4B 108.1 . . ?
C5 C4 H4A 109.5 . . ?
C5 C4 H4B 109.5 . . ?
C4 C5 H5B 109.6 . . ?
C4 C5 H5A 109.6 . . ?
C4 C5 C6 110.4(5) . . ?
H5B C5 H5A 108.1 . . ?
C6 C5 H5B 109.6 . . ?
C6 C5 H5A 109.6 . . ?
C5 C6 H6A 109.7 . . ?
C5 C6 H6B 109.7 . . ?
C5 C6 C7 109.8(5) . . ?
H6A C6 H6B 108.2 . . ?
C7 C6 H6A 109.7 . . ?
C7 C6 H6B 109.7 . . ?
C2 C7 C6 110.3(5) . . ?
C2 C7 H7A 109.6 . . ?
C2 C7 H7B 109.6 . . ?
C6 C7 H7A 109.6 . . ?
C6 C7 H7B 109.6 . . ?
H7A C7 H7B 108.1 . . ?
C2 C8 H8A 110.1 . . ?
C2 C8 H8B 110.1 . . ?
H8A C8 H8B 108.5 . . ?
C9 C8 C2 107.8(3) . . ?
C9 C8 H8A 110.1 . . ?
C9 C8 H8B 110.1 . . ?
C8 C9 N1 100.2(3) . . ?
C10 C9 N1 111.2(4) . . ?
C10 C9 C8 112.3(4) . . ?
C11 C9 N1 108.6(3) . . ?
C11 C9 C8 114.6(4) . . ?
C11 C9 C10 109.5(4) . . ?
C9 C10 H10A 109.5 . . ?
C9 C10 H10B 109.5 . . ?
C9 C10 H10C 109.5 . . ?
H10A C10 H10B 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
C9 C11 H11A 109.5 . . ?
C9 C11 H11B 109.5 . . ?
C9 C11 H11C 109.5 . . ?
H11A C11 H11B 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
C13 C12 N1 118.8(4) . . ?
C20 C12 N1 117.5(4) . . ?
C20 C12 C13 123.7(4) . . ?
C12 C13 C14 122.6(4) . . ?
C17 C13 C12 116.7(4) . . ?
C17 C13 C14 120.4(4) . . ?
C13 C14 H14 108.3 . . ?
C13 C14 C15 108.8(5) . . ?
C13 C14 C16 112.7(4) . . ?
C15 C14 H14 108.3 . . ?
C16 C14 H14 108.3 . . ?
C16 C14 C15 110.3(4) . . ?
C14 C15 H15A 109.5 . . ?
C14 C15 H15B 109.5 . . ?
C14 C15 H15C 109.5 . . ?
H15A C15 H15B 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
C14 C16 H16A 109.5 . . ?
C14 C16 H16B 109.5 . . ?
C14 C16 H16C 109.5 . . ?
H16A C16 H16B 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
C13 C17 H17 119.3 . . ?
C18 C17 C13 121.4(5) . . ?
C18 C17 H17 119.3 . . ?
C17 C18 H18 119.7 . . ?
C17 C18 C19 120.7(4) . . ?
C19 C18 H18 119.7 . . ?
C18 C19 H19 119.1 . . ?
C18 C19 C20 121.8(5) . . ?
C20 C19 H19 119.1 . . ?
C12 C20 C19 115.4(4) . . ?
C12 C20 C21 124.5(4) . . ?
C19 C20 C21 119.9(4) . . ?
C20 C21 H21 107.0 . . ?
C20 C21 C22 114.7(5) . . ?
C20 C21 C23 109.6(4) . . ?
C22 C21 H21 107.0 . . ?
C22 C21 C23 111.2(5) . . ?
C23 C21 H21 107.0 . . ?
C21 C22 H22A 109.5 . . ?
C21 C22 H22B 109.5 . . ?
C21 C22 H22C 109.5 . . ?
H22A C22 H22B 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
C21 C23 H23A 109.5 . . ?
C21 C23 H23B 109.5 . . ?
C21 C23 H23C 109.5 . . ?
H23A C23 H23B 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 109.5 . . ?

_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_Compound_2a
_database_code_depnum_ccdc_archive 'CCDC 1581996'
_audit_update_record             
;
2017-10-25 deposited with the CCDC.
2018-03-08 downloaded from the CCDC.
;
_audit_creation_date             2017-10-11
_audit_creation_method           
;
Olex2 1.2
(compiled 2017.08.10 svn.r3458 for OlexSys, GUI svn.r5381)
;
_shelxl_version_number           2013-2
_chemical_name_common            ?
_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         'Cl3 Hg, C20 H32 N'
_chemical_formula_sum            'C20 H32 Cl3 Hg N'
_chemical_formula_weight         593.40
_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'
Hg Hg -2.3894 9.2266 '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'

_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                   9.6074(7)
_cell_length_b                   16.5076(13)
_cell_length_c                   15.0341(14)
_cell_angle_alpha                90
_cell_angle_beta                 95.868(4)
_cell_angle_gamma                90
_cell_volume                     2371.8(3)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    5365
_cell_measurement_temperature    298.0(2)
_cell_measurement_theta_max      27.5
_cell_measurement_theta_min      3.3
_shelx_estimated_absorpt_T_max   0.548
_shelx_estimated_absorpt_T_min   0.548
_exptl_absorpt_coefficient_mu    6.831
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.879
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'Blessing 1995'
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.662
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1160
_exptl_crystal_size_max          0.1
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.1
_exptl_special_details           
;
 ?
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0856
_diffrn_reflns_av_unetI/netI     0.0467
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            25293
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.485
_diffrn_reflns_theta_min         3.261
_diffrn_ambient_temperature      298.0(2)
_diffrn_detector_area_resol_mean 13.6612
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'XtaLAB Mini (ROW)'
_diffrn_measurement_method       'profile data from ω-scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71075
_diffrn_source                   'Sealed Tube'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                4256
_reflns_number_total             5408
_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       
;
CrystalClear-SM Expert 2.0 r15 (Rigaku, 2011)
;
_computing_data_collection       
;
CrystalClear-SM Expert 2.0 r15 (Rigaku, 2011)
;
_computing_data_reduction        
;
CrystalClear-SM Expert 2.0 r15 (Rigaku, 2011)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         1.028
_refine_diff_density_min         -1.196
_refine_diff_density_rms         0.096
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.065
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     234
_refine_ls_number_reflns         5408
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0500
_refine_ls_R_factor_gt           0.0369
_refine_ls_restrained_S_all      1.065
_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)+(0.0420P)²+0.3740P]
 where P=(Fo²+2Fc²)/3
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0877
_refine_ls_wR_factor_ref         0.0961
_refine_special_details          
;
 ?
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C11(H11), C18(H18)
2.b Secondary CH2 refined with riding coordinates:
 C5(H5A,H5B)
2.c Aromatic/amide H refined with riding coordinates:
 C1(H1), C14(H14), C15(H15), C16(H16)
2.d Idealised Me refined as rotating group:
 C3(H3A,H3B,H3C), C4(H4A,H4B,H4C), C7(H7A,H7B,H7C), C8(H8A,H8B,H8C), C12(H12A,
 H12B,H12C), C13(H13A,H13B,H13C), C19(H19A,H19B,H19C), C20(H20A,H20B,H20C)
;
_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
Hg1 Hg 0.07424(2) 0.59709(2) 0.46317(2) 0.06801(10) Uani 1 1 d . . . . .
Cl1 Cl -0.17510(11) 0.53218(7) 0.44528(9) 0.0731(3) Uani 1 1 d . . . . .
Cl2 Cl 0.16610(19) 0.59472(9) 0.32265(11) 0.0971(5) Uani 1 1 d . . . . .
Cl3 Cl 0.07064(12) 0.69896(7) 0.57319(9) 0.0759(3) Uani 1 1 d . . . . .
N1 N 0.4409(3) 0.41703(16) 0.2468(2) 0.0398(6) Uani 1 1 d . . . . .
C1 C 0.3893(4) 0.4149(2) 0.3211(3) 0.0450(8) Uani 1 1 d . . . . .
H1 H 0.3237 0.4525 0.3365 0.054 Uiso 1 1 calc R . . . .
C2 C 0.4414(4) 0.3480(2) 0.3815(3) 0.0505(9) Uani 1 1 d . . . . .
C3 C 0.3186(5) 0.2972(3) 0.4078(4) 0.0786(14) Uani 1 1 d . . . . .
H3A H 0.2608 0.3298 0.4419 0.118 Uiso 1 1 calc GR . . . .
H3B H 0.3538 0.2517 0.4431 0.118 Uiso 1 1 calc GR . . . .
H3C H 0.2644 0.2780 0.3547 0.118 Uiso 1 1 calc GR . . . .
C4 C 0.5205(6) 0.3847(3) 0.4653(3) 0.0732(12) Uani 1 1 d . . . . .
H4A H 0.5947 0.4186 0.4484 0.110 Uiso 1 1 calc GR . . . .
H4B H 0.5592 0.3421 0.5037 0.110 Uiso 1 1 calc GR . . . .
H4C H 0.4573 0.4166 0.4964 0.110 Uiso 1 1 calc GR . . . .
C5 C 0.5330(5) 0.2998(3) 0.3224(3) 0.0684(12) Uani 1 1 d . . . . .
H5A H 0.4904 0.2477 0.3070 0.082 Uiso 1 1 calc R . . . .
H5B H 0.6248 0.2905 0.3540 0.082 Uiso 1 1 calc R . . . .
C6 C 0.5463(4) 0.3496(2) 0.2371(3) 0.0487(8) Uani 1 1 d . . . . .
C7 C 0.6907(4) 0.3849(3) 0.2329(4) 0.0676(12) Uani 1 1 d . . . . .
H7A H 0.6903 0.4193 0.1814 0.101 Uiso 1 1 calc GR . . . .
H7B H 0.7568 0.3417 0.2286 0.101 Uiso 1 1 calc GR . . . .
H7C H 0.7169 0.4160 0.2859 0.101 Uiso 1 1 calc GR . . . .
C8 C 0.5055(5) 0.3019(3) 0.1522(3) 0.0768(14) Uani 1 1 d . . . . .
H8A H 0.4199 0.2732 0.1577 0.115 Uiso 1 1 calc GR . . . .
H8B H 0.5782 0.2639 0.1428 0.115 Uiso 1 1 calc GR . . . .
H8C H 0.4925 0.3384 0.1023 0.115 Uiso 1 1 calc GR . . . .
C9 C 0.3937(3) 0.4748(2) 0.1761(2) 0.0428(7) Uani 1 1 d . . . . .
C10 C 0.4667(4) 0.5468(2) 0.1684(2) 0.0480(8) Uani 1 1 d . . . . .
C11 C 0.5870(5) 0.5754(3) 0.2344(3) 0.0577(10) Uani 1 1 d . . . . .
H11 H 0.6098 0.5322 0.2782 0.069 Uiso 1 1 calc R . . . .
C12 C 0.5412(6) 0.6506(3) 0.2843(3) 0.0804(15) Uani 1 1 d . . . . .
H12A H 0.5249 0.6948 0.2430 0.121 Uiso 1 1 calc GR . . . .
H12B H 0.6134 0.6653 0.3304 0.121 Uiso 1 1 calc GR . . . .
H12C H 0.4566 0.6387 0.3107 0.121 Uiso 1 1 calc GR . . . .
C13 C 0.7188(6) 0.5957(3) 0.1901(4) 0.0817(16) Uani 1 1 d . . . . .
H13A H 0.7435 0.5505 0.1549 0.122 Uiso 1 1 calc GR . . . .
H13B H 0.7942 0.6072 0.2354 0.122 Uiso 1 1 calc GR . . . .
H13C H 0.7016 0.6423 0.1523 0.122 Uiso 1 1 calc GR . . . .
C14 C 0.4203(6) 0.5976(2) 0.0973(3) 0.0649(12) Uani 1 1 d . . . . .
H14 H 0.4683 0.6453 0.0882 0.078 Uiso 1 1 calc R . . . .
C15 C 0.3029(6) 0.5772(3) 0.0401(3) 0.0700(13) Uani 1 1 d . . . . .
H15 H 0.2737 0.6112 -0.0075 0.084 Uiso 1 1 calc R . . . .
C16 C 0.2300(5) 0.5081(3) 0.0529(3) 0.0660(11) Uani 1 1 d . . . . .
H16 H 0.1499 0.4968 0.0148 0.079 Uiso 1 1 calc R . . . .
C17 C 0.2717(4) 0.4546(2) 0.1208(3) 0.0494(8) Uani 1 1 d . . . . .
C18 C 0.1803(4) 0.3820(3) 0.1372(3) 0.0643(11) Uani 1 1 d . . . . .
H18 H 0.2341 0.3464 0.1801 0.077 Uiso 1 1 calc R . . . .
C19 C 0.1409(6) 0.3333(3) 0.0522(4) 0.0959(18) Uani 1 1 d . . . . .
H19B H 0.0877 0.2866 0.0661 0.144 Uiso 1 1 calc GR . . . .
H19A H 0.2244 0.3162 0.0275 0.144 Uiso 1 1 calc GR . . . .
H19C H 0.0858 0.3664 0.0095 0.144 Uiso 1 1 calc GR . . . .
C20 C 0.0500(6) 0.4091(4) 0.1790(5) 0.0953(19) Uani 1 1 d . . . . .
H20A H 0.0772 0.4385 0.2331 0.143 Uiso 1 1 calc GR . . . .
H20B H -0.0038 0.3625 0.1924 0.143 Uiso 1 1 calc GR . . . .
H20C H -0.0055 0.4434 0.1378 0.143 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
Hg1 Cl1 2.6129(11) . ?
Hg1 Cl1 2.6672(11) 3_566 ?
Hg1 Cl2 2.3717(15) . ?
Hg1 Cl3 2.3615(11) . ?
Cl1 Hg1 2.6672(11) 3_566 ?
N1 C1 1.268(5) . ?
N1 C6 1.521(4) . ?
N1 C9 1.465(4) . ?
C1 H1 0.9300 . ?
C1 C2 1.485(5) . ?
C2 C3 1.532(5) . ?
C2 C4 1.528(6) . ?
C2 C5 1.535(6) . ?
C3 H3A 0.9600 . ?
C3 H3B 0.9600 . ?
C3 H3C 0.9600 . ?
C4 H4A 0.9600 . ?
C4 H4B 0.9600 . ?
C4 H4C 0.9600 . ?
C5 H5A 0.9700 . ?
C5 H5B 0.9700 . ?
C5 C6 1.538(6) . ?
C6 C7 1.512(5) . ?
C6 C8 1.518(6) . ?
C7 H7A 0.9600 . ?
C7 H7B 0.9600 . ?
C7 H7C 0.9600 . ?
C8 H8A 0.9600 . ?
C8 H8B 0.9600 . ?
C8 H8C 0.9600 . ?
C9 C10 1.390(5) . ?
C9 C17 1.406(5) . ?
C10 C11 1.520(5) . ?
C10 C14 1.395(6) . ?
C11 H11 0.9800 . ?
C11 C12 1.538(7) . ?
C11 C13 1.527(7) . ?
C12 H12A 0.9600 . ?
C12 H12B 0.9600 . ?
C12 H12C 0.9600 . ?
C13 H13A 0.9600 . ?
C13 H13B 0.9600 . ?
C13 H13C 0.9600 . ?
C14 H14 0.9300 . ?
C14 C15 1.387(7) . ?
C15 H15 0.9300 . ?
C15 C16 1.363(7) . ?
C16 H16 0.9300 . ?
C16 C17 1.378(6) . ?
C17 C18 1.522(6) . ?
C18 H18 0.9800 . ?
C18 C19 1.524(7) . ?
C18 C20 1.524(7) . ?
C19 H19B 0.9600 . ?
C19 H19A 0.9600 . ?
C19 H19C 0.9600 . ?
C20 H20A 0.9600 . ?
C20 H20B 0.9600 . ?
C20 H20C 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
Cl1 Hg1 Cl1 90.34(3) . 3_566 ?
Cl2 Hg1 Cl1 107.32(4) . 3_566 ?
Cl2 Hg1 Cl1 108.80(6) . . ?
Cl3 Hg1 Cl1 106.57(4) . . ?
Cl3 Hg1 Cl1 103.82(4) . 3_566 ?
Cl3 Hg1 Cl2 132.00(5) . . ?
Hg1 Cl1 Hg1 89.66(3) . 3_566 ?
C1 N1 C6 112.8(3) . . ?
C1 N1 C9 122.5(3) . . ?
C9 N1 C6 124.5(3) . . ?
N1 C1 H1 122.5 . . ?
N1 C1 C2 114.9(3) . . ?
C2 C1 H1 122.5 . . ?
C1 C2 C3 110.2(3) . . ?
C1 C2 C4 108.5(3) . . ?
C1 C2 C5 102.0(3) . . ?
C3 C2 C5 111.6(4) . . ?
C4 C2 C3 109.6(4) . . ?
C4 C2 C5 114.7(4) . . ?
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 . . ?
C2 C4 H4A 109.5 . . ?
C2 C4 H4B 109.5 . . ?
C2 C4 H4C 109.5 . . ?
H4A C4 H4B 109.5 . . ?
H4A C4 H4C 109.5 . . ?
H4B C4 H4C 109.5 . . ?
C2 C5 H5A 110.1 . . ?
C2 C5 H5B 110.1 . . ?
C2 C5 C6 107.9(3) . . ?
H5A C5 H5B 108.4 . . ?
C6 C5 H5A 110.1 . . ?
C6 C5 H5B 110.1 . . ?
N1 C6 C5 101.5(3) . . ?
C7 C6 N1 110.2(3) . . ?
C7 C6 C5 113.3(4) . . ?
C7 C6 C8 108.9(4) . . ?
C8 C6 N1 110.0(3) . . ?
C8 C6 C5 112.8(4) . . ?
C6 C7 H7A 109.5 . . ?
C6 C7 H7B 109.5 . . ?
C6 C7 H7C 109.5 . . ?
H7A C7 H7B 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
C6 C8 H8A 109.5 . . ?
C6 C8 H8B 109.5 . . ?
C6 C8 H8C 109.5 . . ?
H8A C8 H8B 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
C10 C9 N1 119.7(3) . . ?
C10 C9 C17 123.4(3) . . ?
C17 C9 N1 116.9(3) . . ?
C9 C10 C11 124.6(3) . . ?
C9 C10 C14 117.0(4) . . ?
C14 C10 C11 118.4(4) . . ?
C10 C11 H11 108.3 . . ?
C10 C11 C12 109.5(4) . . ?
C10 C11 C13 113.1(4) . . ?
C12 C11 H11 108.3 . . ?
C13 C11 H11 108.3 . . ?
C13 C11 C12 109.1(4) . . ?
C11 C12 H12A 109.5 . . ?
C11 C12 H12B 109.5 . . ?
C11 C12 H12C 109.5 . . ?
H12A C12 H12B 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C11 C13 H13A 109.5 . . ?
C11 C13 H13B 109.5 . . ?
C11 C13 H13C 109.5 . . ?
H13A C13 H13B 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
C10 C14 H14 119.8 . . ?
C15 C14 C10 120.3(4) . . ?
C15 C14 H14 119.8 . . ?
C14 C15 H15 119.6 . . ?
C16 C15 C14 120.8(4) . . ?
C16 C15 H15 119.6 . . ?
C15 C16 H16 119.1 . . ?
C15 C16 C17 121.7(4) . . ?
C17 C16 H16 119.1 . . ?
C9 C17 C18 123.4(3) . . ?
C16 C17 C9 116.6(4) . . ?
C16 C17 C18 119.8(4) . . ?
C17 C18 H18 107.8 . . ?
C17 C18 C19 112.2(4) . . ?
C17 C18 C20 110.4(4) . . ?
C19 C18 H18 107.8 . . ?
C20 C18 H18 107.8 . . ?
C20 C18 C19 110.9(4) . . ?
C18 C19 H19B 109.5 . . ?
C18 C19 H19A 109.5 . . ?
C18 C19 H19C 109.5 . . ?
H19B C19 H19A 109.5 . . ?
H19B C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
C18 C20 H20A 109.5 . . ?
C18 C20 H20B 109.5 . . ?
C18 C20 H20C 109.5 . . ?
H20A C20 H20B 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?

_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_Compound_1b
_database_code_depnum_ccdc_archive 'CCDC 1581994'
_audit_update_record             
;
2017-10-25 deposited with the CCDC.
2018-03-08 downloaded from the CCDC.
;
_audit_creation_date             2017-10-20
_audit_creation_method           
;
Olex2 1.2
(compiled 2017.08.10 svn.r3458 for OlexSys, GUI svn.r5381)
;
_shelxl_version_number           2013-2
_chemical_name_common            ?
_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         'C23 H35 Br2 Hg N'
_chemical_formula_sum            'C23 H35 Br2 Hg N'
_chemical_formula_weight         685.93
_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'
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Hg Hg -2.3894 9.2266 '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'

_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                   14.0140(8)
_cell_length_b                   9.5780(6)
_cell_length_c                   18.4054(12)
_cell_angle_alpha                90
_cell_angle_beta                 97.958(3)
_cell_angle_gamma                90
_cell_volume                     2446.7(3)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    6511
_cell_measurement_temperature    298.0(2)
_cell_measurement_theta_max      27.5
_cell_measurement_theta_min      3.1
_shelx_estimated_absorpt_T_max   0.448
_shelx_estimated_absorpt_T_min   0.448
_exptl_absorpt_coefficient_mu    9.565
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.814
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'Blessing 1995'
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.862
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             1320
_exptl_crystal_size_max          0.1
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.1
_exptl_special_details           
;
 ?
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0662
_diffrn_reflns_av_unetI/netI     0.0402
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            25747
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        25.000
_diffrn_reflns_theta_max         27.488
_diffrn_reflns_theta_min         3.085
_diffrn_ambient_temperature      298.0(2)
_diffrn_detector_area_resol_mean 13.6612
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'XtaLAB Mini (ROW)'
_diffrn_measurement_method       'profile data from ω-scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71075
_diffrn_source                   'Sealed Tube'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                4772
_reflns_number_total             5599
_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       
;
CrystalClear-SM Expert 2.0 r15 (Rigaku, 2011)
;
_computing_data_collection       
;
CrystalClear-SM Expert 2.0 r15 (Rigaku, 2011)
;
_computing_data_reduction        
;
CrystalClear-SM Expert 2.0 r15 (Rigaku, 2011)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         1.500
_refine_diff_density_min         -1.257
_refine_diff_density_rms         0.114
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.027
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     259
_refine_ls_number_reflns         5599
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0371
_refine_ls_R_factor_gt           0.0299
_refine_ls_restrained_S_all      1.027
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
;
 w=1/[σ²(Fo²)+(0.0424P)²]
 where P=(Fo²+2Fc²)/3
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0724
_refine_ls_wR_factor_ref         0.0769
_refine_special_details          
;
 ?
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Others
 Fixed Sof: C8A(0.5) H8AA(0.5) H8AB(0.5) C8B(0.5) H8BA(0.5) H8BB(0.5)
3.a Ternary CH refined with riding coordinates:
 C14(H14), C21(H21)
3.b Secondary CH2 refined with riding coordinates:
 C3(H3A,H3B), C4(H4A,H4B), C5(H5A,H5B), C6(H6A,H6B), C7(H7A,H7B), C8A(H8AA,
 H8AB), C8B(H8BA,H8BB)
3.c Aromatic/amide H refined with riding coordinates:
 C17(H17), C18(H18), C19(H19)
3.d Idealised Me refined as rotating group:
 C10(H10A,H10B,H10C), C11(H11A,H11B,H11C), C15(H15A,H15B,H15C), C16(H16A,H16B,
 H16C), C22(H22A,H22B,H22C), C23(H23A,H23B,H23C)
;
_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
Hg1 Hg 0.63434(2) 0.58142(2) 0.52906(2) 0.04417(7) Uani 1 1 d . . . . .
Br1 Br 0.73808(3) 0.46405(6) 0.44534(3) 0.06690(15) Uani 1 1 d . . . . .
Br2 Br 0.47683(3) 0.65149(4) 0.42969(2) 0.05253(11) Uani 1 1 d . . . . .
N1 N 0.74018(19) 0.7296(3) 0.66316(15) 0.0335(6) Uani 1 1 d . . . . .
C1 C 0.6574(2) 0.7119(4) 0.62457(18) 0.0352(7) Uani 1 1 d . . . . .
C2 C 0.5799(2) 0.7910(4) 0.6557(2) 0.0436(9) Uani 1 1 d . . . . .
C3 C 0.5393(3) 0.9031(4) 0.6005(3) 0.0588(12) Uani 1 1 d . . . . .
H3A H 0.5900 0.9688 0.5937 0.071 Uiso 1 1 calc R . . . .
H3B H 0.5178 0.8594 0.5536 0.071 Uiso 1 1 calc R . . . .
C4 C 0.4556(4) 0.9816(5) 0.6257(3) 0.0696(14) Uani 1 1 d . . . . .
H4A H 0.4295 1.0469 0.5878 0.084 Uiso 1 1 calc R . . . .
H4B H 0.4786 1.0347 0.6695 0.084 Uiso 1 1 calc R . . . .
C5 C 0.3766(3) 0.8826(5) 0.6419(3) 0.0610(12) Uani 1 1 d . . . . .
H5A H 0.3269 0.9351 0.6617 0.073 Uiso 1 1 calc R . . . .
H5B H 0.3475 0.8389 0.5966 0.073 Uiso 1 1 calc R . . . .
C6 C 0.4155(3) 0.7715(5) 0.6958(3) 0.0548(10) Uani 1 1 d . . . . .
H6A H 0.3644 0.7064 0.7025 0.066 Uiso 1 1 calc R . . . .
H6B H 0.4377 0.8143 0.7429 0.066 Uiso 1 1 calc R . . . .
C7 C 0.4982(3) 0.6928(4) 0.6692(2) 0.0465(9) Uani 1 1 d . . . . .
H7A H 0.4747 0.6441 0.6241 0.056 Uiso 1 1 calc R . . . .
H7B H 0.5228 0.6237 0.7055 0.056 Uiso 1 1 calc R . . . .
C8A C 0.6337(7) 0.8874(11) 0.7146(6) 0.047(2) Uani 0.5 1 d . . P A 1
H8AA H 0.6012 0.8911 0.7578 0.056 Uiso 0.5 1 calc R . P A 1
H8AB H 0.6389 0.9813 0.6958 0.056 Uiso 0.5 1 calc R . P A 1
C8B C 0.6326(6) 0.8203(11) 0.7366(5) 0.0390(18) Uani 0.5 1 d . . P A 2
H8BA H 0.6139 0.9110 0.7535 0.047 Uiso 0.5 1 calc R . P A 2
H8BB H 0.6153 0.7496 0.7702 0.047 Uiso 0.5 1 calc R . P A 2
C9 C 0.7378(3) 0.8167(4) 0.73327(18) 0.0410(8) Uani 1 1 d . . . . .
C10 C 0.7735(7) 0.7323(6) 0.7996(3) 0.124(3) Uani 1 1 d . . . . .
H10A H 0.7262 0.6635 0.8074 0.186 Uiso 1 1 calc GR . . . .
H10B H 0.7850 0.7925 0.8416 0.186 Uiso 1 1 calc GR . . . .
H10C H 0.8325 0.6866 0.7924 0.186 Uiso 1 1 calc GR . . . .
C11 C 0.8004(4) 0.9431(6) 0.7330(3) 0.0786(17) Uani 1 1 d . . . . .
H11A H 0.8651 0.9148 0.7289 0.118 Uiso 1 1 calc GR . . . .
H11B H 0.7997 0.9941 0.7778 0.118 Uiso 1 1 calc GR . . . .
H11C H 0.7765 1.0015 0.6921 0.118 Uiso 1 1 calc GR . . . .
C12 C 0.8289(2) 0.6760(4) 0.64124(18) 0.0377(8) Uani 1 1 d . . . . .
C13 C 0.8777(3) 0.7612(4) 0.5961(2) 0.0451(9) Uani 1 1 d . . . . .
C14 C 0.8396(3) 0.8972(5) 0.5622(2) 0.0512(10) Uani 1 1 d . . . . .
H14 H 0.7821 0.9220 0.5842 0.061 Uiso 1 1 calc R . . . .
C15 C 0.9113(4) 1.0168(6) 0.5770(3) 0.0701(13) Uani 1 1 d . . . . .
H15A H 0.9253 1.0324 0.6289 0.105 Uiso 1 1 calc GR . . . .
H15B H 0.8842 1.1000 0.5535 0.105 Uiso 1 1 calc GR . . . .
H15C H 0.9697 0.9933 0.5580 0.105 Uiso 1 1 calc GR . . . .
C16 C 0.8087(4) 0.8791(7) 0.4795(3) 0.0797(16) Uani 1 1 d . . . . .
H16A H 0.8639 0.8555 0.4563 0.120 Uiso 1 1 calc GR . . . .
H16B H 0.7812 0.9647 0.4592 0.120 Uiso 1 1 calc GR . . . .
H16C H 0.7618 0.8058 0.4712 0.120 Uiso 1 1 calc GR . . . .
C17 C 0.9634(3) 0.7088(6) 0.5766(3) 0.0603(12) Uani 1 1 d . . . . .
H17 H 0.9972 0.7619 0.5463 0.072 Uiso 1 1 calc R . . . .
C18 C 0.9992(3) 0.5828(6) 0.6005(3) 0.0701(15) Uani 1 1 d . . . . .
H18 H 1.0573 0.5515 0.5875 0.084 Uiso 1 1 calc R . . . .
C19 C 0.9495(3) 0.5018(6) 0.6437(3) 0.0656(13) Uani 1 1 d . . . . .
H19 H 0.9746 0.4153 0.6593 0.079 Uiso 1 1 calc R . . . .
C20 C 0.8627(3) 0.5446(5) 0.6651(2) 0.0476(9) Uani 1 1 d . . . . .
C21 C 0.8076(3) 0.4425(5) 0.7069(3) 0.0553(11) Uani 1 1 d . . . . .
H21 H 0.7496 0.4899 0.7184 0.066 Uiso 1 1 calc R . . . .
C22 C 0.8657(4) 0.3952(7) 0.7791(3) 0.0861(18) Uani 1 1 d . . . . .
H22A H 0.8297 0.3265 0.8019 0.129 Uiso 1 1 calc GR . . . .
H22B H 0.8784 0.4740 0.8112 0.129 Uiso 1 1 calc GR . . . .
H22C H 0.9256 0.3554 0.7696 0.129 Uiso 1 1 calc GR . . . .
C23 C 0.7760(4) 0.3164(5) 0.6604(3) 0.0759(15) Uani 1 1 d . . . . .
H23A H 0.7368 0.3459 0.6161 0.114 Uiso 1 1 calc GR . . . .
H23B H 0.7394 0.2550 0.6872 0.114 Uiso 1 1 calc GR . . . .
H23C H 0.8317 0.2680 0.6483 0.114 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
Hg1 Br1 2.5243(4) . ?
Hg1 Br2 2.7477(5) . ?
Hg1 Br2 2.8823(5) 3_666 ?
Hg1 C1 2.144(3) . ?
Br2 Hg1 2.8823(4) 3_666 ?
N1 C1 1.285(4) . ?
N1 C9 1.541(4) . ?
N1 C12 1.453(4) . ?
C1 C2 1.502(5) . ?
C2 C3 1.533(6) . ?
C2 C7 1.528(5) . ?
C2 C8A 1.540(10) . ?
C2 C8B 1.593(9) . ?
C3 H3A 0.9700 . ?
C3 H3B 0.9700 . ?
C3 C4 1.518(6) . ?
C4 H4A 0.9700 . ?
C4 H4B 0.9700 . ?
C4 C5 1.518(7) . ?
C5 H5A 0.9700 . ?
C5 H5B 0.9700 . ?
C5 C6 1.506(7) . ?
C6 H6A 0.9700 . ?
C6 H6B 0.9700 . ?
C6 C7 1.519(5) . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C8A H8AA 0.9700 . ?
C8A H8AB 0.9700 . ?
C8A C9 1.601(11) . ?
C8B H8BA 0.9700 . ?
C8B H8BB 0.9700 . ?
C8B C9 1.484(9) . ?
C9 C10 1.491(6) . ?
C9 C11 1.496(6) . ?
C10 H10A 0.9600 . ?
C10 H10B 0.9600 . ?
C10 H10C 0.9600 . ?
C11 H11A 0.9600 . ?
C11 H11B 0.9600 . ?
C11 H11C 0.9600 . ?
C12 C13 1.408(5) . ?
C12 C20 1.394(6) . ?
C13 C14 1.509(6) . ?
C13 C17 1.393(6) . ?
C14 H14 0.9800 . ?
C14 C15 1.523(6) . ?
C14 C16 1.534(6) . ?
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 H17 0.9300 . ?
C17 C18 1.356(7) . ?
C18 H18 0.9300 . ?
C18 C19 1.368(7) . ?
C19 H19 0.9300 . ?
C19 C20 1.391(6) . ?
C20 C21 1.520(6) . ?
C21 H21 0.9800 . ?
C21 C22 1.529(7) . ?
C21 C23 1.511(7) . ?
C22 H22A 0.9600 . ?
C22 H22B 0.9600 . ?
C22 H22C 0.9600 . ?
C23 H23A 0.9600 . ?
C23 H23B 0.9600 . ?
C23 H23C 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
Br1 Hg1 Br2 101.195(17) . 3_666 ?
Br1 Hg1 Br2 100.364(17) . . ?
Br2 Hg1 Br2 87.174(13) . 3_666 ?
C1 Hg1 Br1 136.53(9) . . ?
C1 Hg1 Br2 114.79(10) . . ?
C1 Hg1 Br2 105.11(9) . 3_666 ?
Hg1 Br2 Hg1 92.826(13) . 3_666 ?
C1 N1 C9 114.3(3) . . ?
C1 N1 C12 122.8(3) . . ?
C12 N1 C9 122.9(3) . . ?
N1 C1 Hg1 123.5(2) . . ?
N1 C1 C2 111.6(3) . . ?
C2 C1 Hg1 124.9(2) . . ?
C1 C2 C3 108.8(3) . . ?
C1 C2 C7 110.5(3) . . ?
C1 C2 C8A 105.1(4) . . ?
C1 C2 C8B 100.3(4) . . ?
C3 C2 C8A 98.5(5) . . ?
C3 C2 C8B 125.2(5) . . ?
C7 C2 C3 108.7(3) . . ?
C7 C2 C8A 124.0(5) . . ?
C7 C2 C8B 102.6(4) . . ?
C2 C3 H3A 109.2 . . ?
C2 C3 H3B 109.2 . . ?
H3A C3 H3B 107.9 . . ?
C4 C3 C2 112.2(4) . . ?
C4 C3 H3A 109.2 . . ?
C4 C3 H3B 109.2 . . ?
C3 C4 H4A 109.3 . . ?
C3 C4 H4B 109.3 . . ?
C3 C4 C5 111.5(4) . . ?
H4A C4 H4B 108.0 . . ?
C5 C4 H4A 109.3 . . ?
C5 C4 H4B 109.3 . . ?
C4 C5 H5A 109.4 . . ?
C4 C5 H5B 109.4 . . ?
H5A C5 H5B 108.0 . . ?
C6 C5 C4 111.3(4) . . ?
C6 C5 H5A 109.4 . . ?
C6 C5 H5B 109.4 . . ?
C5 C6 H6A 109.4 . . ?
C5 C6 H6B 109.4 . . ?
C5 C6 C7 111.1(3) . . ?
H6A C6 H6B 108.0 . . ?
C7 C6 H6A 109.4 . . ?
C7 C6 H6B 109.4 . . ?
C2 C7 H7A 109.3 . . ?
C2 C7 H7B 109.3 . . ?
C6 C7 C2 111.7(3) . . ?
C6 C7 H7A 109.3 . . ?
C6 C7 H7B 109.3 . . ?
H7A C7 H7B 107.9 . . ?
C2 C8A H8AA 111.0 . . ?
C2 C8A H8AB 111.0 . . ?
C2 C8A C9 103.9(6) . . ?
H8AA C8A H8AB 109.0 . . ?
C9 C8A H8AA 111.0 . . ?
C9 C8A H8AB 111.0 . . ?
C2 C8B H8BA 110.3 . . ?
C2 C8B H8BB 110.3 . . ?
H8BA C8B H8BB 108.6 . . ?
C9 C8B C2 107.0(5) . . ?
C9 C8B H8BA 110.3 . . ?
C9 C8B H8BB 110.3 . . ?
N1 C9 C8A 100.0(4) . . ?
C8B C9 N1 100.6(4) . . ?
C8B C9 C10 101.7(6) . . ?
C8B C9 C11 124.6(5) . . ?
C10 C9 N1 110.4(4) . . ?
C10 C9 C8A 126.7(6) . . ?
C10 C9 C11 108.1(5) . . ?
C11 C9 N1 110.7(3) . . ?
C11 C9 C8A 100.0(5) . . ?
C9 C10 H10A 109.5 . . ?
C9 C10 H10B 109.5 . . ?
C9 C10 H10C 109.5 . . ?
H10A C10 H10B 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
C9 C11 H11A 109.5 . . ?
C9 C11 H11B 109.5 . . ?
C9 C11 H11C 109.5 . . ?
H11A C11 H11B 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
C13 C12 N1 117.6(3) . . ?
C20 C12 N1 119.9(3) . . ?
C20 C12 C13 122.5(3) . . ?
C12 C13 C14 124.8(3) . . ?
C17 C13 C12 116.7(4) . . ?
C17 C13 C14 118.2(4) . . ?
C13 C14 H14 107.6 . . ?
C13 C14 C15 112.8(4) . . ?
C13 C14 C16 110.3(4) . . ?
C15 C14 H14 107.6 . . ?
C15 C14 C16 110.5(4) . . ?
C16 C14 H14 107.6 . . ?
C14 C15 H15A 109.5 . . ?
C14 C15 H15B 109.5 . . ?
C14 C15 H15C 109.5 . . ?
H15A C15 H15B 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
C14 C16 H16A 109.5 . . ?
C14 C16 H16B 109.5 . . ?
C14 C16 H16C 109.5 . . ?
H16A C16 H16B 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
C13 C17 H17 119.0 . . ?
C18 C17 C13 122.0(4) . . ?
C18 C17 H17 119.0 . . ?
C17 C18 H18 120.0 . . ?
C17 C18 C19 119.9(4) . . ?
C19 C18 H18 120.0 . . ?
C18 C19 H19 118.9 . . ?
C18 C19 C20 122.2(5) . . ?
C20 C19 H19 118.9 . . ?
C12 C20 C21 124.4(3) . . ?
C19 C20 C12 116.7(4) . . ?
C19 C20 C21 118.7(4) . . ?
C20 C21 H21 107.9 . . ?
C20 C21 C22 112.5(4) . . ?
C22 C21 H21 107.9 . . ?
C23 C21 C20 110.9(4) . . ?
C23 C21 H21 107.9 . . ?
C23 C21 C22 109.6(4) . . ?
C21 C22 H22A 109.5 . . ?
C21 C22 H22B 109.5 . . ?
C21 C22 H22C 109.5 . . ?
H22A C22 H22B 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
C21 C23 H23A 109.5 . . ?
C21 C23 H23B 109.5 . . ?
C21 C23 H23C 109.5 . . ?
H23A C23 H23B 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 109.5 . . ?

_olex2_submission_special_instructions 'No special instructions were received'
