# Electronic Supplementary Material (ESI) for ChemComm.
# 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_lycorine-N-amine-trans
_audit_block_doi                 10.5517/ccdc.csd.cc2444jz
_database_code_depnum_ccdc_archive 'CCDC 1970190'
loop_
_audit_author_name
_audit_author_address
lycorine-N-amine-transe
;sustech
China
;
_audit_update_record             
;
2019-12-05 deposited with the CCDC.	2020-07-01 downloaded from the CCDC.
;
_audit_creation_date             2019-08-14
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C16 H19 N2 O4, H2 O, Cl'
_chemical_formula_sum            'C16 H20 Cl N2 O5'
_chemical_formula_weight         356.79
_chemical_absolute_configuration rm
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.3639 0.7018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 '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      trigonal
_space_group_IT_number           145
_space_group_name_H-M_alt        'P 32'
_space_group_name_Hall           'P 32'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-y, x-y, z+2/3'
'-x+y, -x, z+1/3'

_cell_length_a                   11.3090(4)
_cell_length_b                   11.3090(4)
_cell_length_c                   11.3065(4)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                120
_cell_volume                     1252.30(10)
_cell_formula_units_Z            3
_cell_measurement_reflns_used    9923
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      79.51
_cell_measurement_theta_min      4.51
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    2.290
_exptl_absorpt_correction_T_max  0.7543
_exptl_absorpt_correction_T_min  0.6518
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0719 before and 0.0453 after correction.
The Ratio of minimum to maximum transmission is 0.8641.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            ?
_exptl_crystal_density_diffrn    1.415
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             561
_exptl_crystal_size_max          0.1468
_exptl_crystal_size_mid          0.1253
_exptl_crystal_size_min          0.1106
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0317
_diffrn_reflns_av_unetI/netI     0.0257
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.979
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            13796
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.949
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         79.517
_diffrn_reflns_theta_min         4.514
_diffrn_ambient_temperature      100.01
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.979
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_source                   ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.940
_reflns_Friedel_fraction_full    0.997
_reflns_Friedel_fraction_max     0.920
_reflns_number_gt                3426
_reflns_number_total             3457
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT V8.38A (?, 2016)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.38A (?, 2016)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.202
_refine_diff_density_min         -0.282
_refine_diff_density_rms         0.057
_refine_ls_abs_structure_details 
;
 Flack x determined using 1624 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.019(13)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.064
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     253
_refine_ls_number_reflns         3457
_refine_ls_number_restraints     115
_refine_ls_R_factor_all          0.0350
_refine_ls_R_factor_gt           0.0347
_refine_ls_restrained_S_all      1.056
_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)+(0.0569P)²+0.4216P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0894
_refine_ls_wR_factor_ref         0.0898
_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 Cl(H) groups
 At 1.5 times of:
  All O(H) groups
2. Uiso/Uaniso restraints and constraints
C00D \\sim O2 \\sim C00O \\sim O3 \\sim C00J: within 3.8A with sigma of 0.01
and sigma for terminal atoms of 0.01
C00D \\sim O4 \\sim C00O \\sim O1 \\sim C00J: within 4A with sigma of 0.01 and
sigma for terminal atoms of 0.01
Uanis(O4) \\sim Ueq, Uanis(O1) \\sim Ueq: with sigma of 0.1 and sigma for
terminal atoms of 0.2
3. Rigid body (RIGU) restrains
 O4, O1
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
4. Others
 Sof(O1)=Sof(H00Q)=Sof(H00R)=Sof(O4)=1-FVAR(1)
 Sof(H00O)=Sof(H00P)=Sof(O2)=Sof(O3)=FVAR(1)
5.a Ternary CH refined with riding coordinates:
 C00F(H00F), C00G(H00G), C00K(H00K), C00L(H00L)
5.b Secondary CH2 refined with riding coordinates:
 C00I(H00D,H00E), C00M(H00I,H00J), C00N(H00M,H00N), C00O(H00Q,H00R), C00O(H00O,
 H00P)
5.c Aromatic/amide H refined with riding coordinates:
 C009(H009), C00B(H00C), C00H(H00H)
5.d Idealised tetrahedral OH refined as rotating group:
 O002(H002), O003(H003)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     ?
_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
O002 O 0.7173(2) 0.7311(2) 0.31937(16) 0.0207(4) Uani 1 1 d . . . . .
H002 H 0.6708 0.7545 0.2780 0.031 Uiso 1 1 calc GR . . . .
O003 O 0.6366(2) 0.8426(2) 0.59835(17) 0.0216(4) Uani 1 1 d . . . . .
H003 H 0.5533 0.8129 0.5853 0.032 Uiso 1 1 calc GR . . . .
N006 N 1.0040(2) 0.7484(2) 0.55577(19) 0.0153(4) Uani 1 1 d . . . . .
N007 N 0.9682(2) 0.7356(2) 0.68018(19) 0.0175(4) Uani 1 1 d . . . . .
O1 O 0.6589(12) 0.1352(12) 0.452(2) 0.0284(18) Uani 0.79(9) 1 d . U P A 2
C009 C 0.6047(3) 0.4180(3) 0.4829(2) 0.0185(5) Uani 1 1 d . . . . .
H009 H 0.5275 0.4301 0.4839 0.022 Uiso 1 1 calc R . . . .
C00A C 0.8504(3) 0.5087(3) 0.4930(2) 0.0167(5) Uani 1 1 d . . . . .
C00B C 0.8549(3) 0.9595(3) 0.5148(2) 0.0185(5) Uani 1 1 d . . . . .
H00C H 0.8832 1.0526 0.5296 0.022 Uiso 1 1 calc R . . . .
C00C C 0.9472(3) 0.9191(3) 0.5182(2) 0.0177(5) Uani 1 1 d . . . . .
C00D C 0.5905(3) 0.2907(3) 0.4728(2) 0.0203(5) Uani 1 1 d . U . . .
C00E C 0.7387(3) 0.5303(3) 0.4918(2) 0.0165(5) Uani 1 1 d . . . . .
C00F C 0.9071(3) 0.7763(3) 0.4869(2) 0.0153(5) Uani 1 1 d . . . . .
H00F H 0.9250 0.7730 0.4007 0.018 Uiso 1 1 calc R . . . .
C00G C 0.7603(3) 0.6723(3) 0.5115(2) 0.0154(5) Uani 1 1 d . . . . .
H00G H 0.7430 0.6799 0.5971 0.018 Uiso 1 1 calc R . . . .
C00H C 0.8324(3) 0.3765(3) 0.4824(3) 0.0215(6) Uani 1 1 d . . . . .
H00H H 0.9080 0.3617 0.4829 0.026 Uiso 1 1 calc R . . . .
C00I C 1.1375(3) 0.8820(3) 0.5421(2) 0.0191(5) Uani 1 1 d . . . . .
H00D H 1.1792 0.8873 0.4638 0.023 Uiso 1 1 calc R . . . .
H00E H 1.2032 0.8920 0.6047 0.023 Uiso 1 1 calc R . . . .
C00J C 0.7019(3) 0.2708(3) 0.4714(3) 0.0225(6) Uani 1 1 d . U . . .
C00K C 0.7067(3) 0.8610(3) 0.4882(2) 0.0178(5) Uani 1 1 d . . . . .
H00K H 0.6730 0.9040 0.4300 0.021 Uiso 1 1 calc R . . . .
C00L C 0.6769(3) 0.7208(3) 0.4398(2) 0.0164(5) Uani 1 1 d . . . . .
H00L H 0.5773 0.6532 0.4475 0.020 Uiso 1 1 calc R . . . .
C00M C 1.0962(3) 0.9918(3) 0.5542(2) 0.0204(5) Uani 1 1 d . . . . .
H00I H 1.1076 1.0252 0.6367 0.024 Uiso 1 1 calc R . . . .
H00J H 1.1515 1.0701 0.5012 0.024 Uiso 1 1 calc R . . . .
C00N C 0.9980(3) 0.6234(3) 0.5045(2) 0.0186(5) Uani 1 1 d . . . . .
H00M H 1.0488 0.5934 0.5561 0.022 Uiso 1 1 calc R . . . .
H00N H 1.0419 0.6451 0.4256 0.022 Uiso 1 1 calc R . . . .
C00O C 0.5138(3) 0.0663(3) 0.4659(4) 0.0351(7) Uani 1 1 d . U . . .
H00Q H 0.4692 -0.0001 0.4009 0.042 Uiso 0.79(9) 1 calc R . P A 2
H00R H 0.4873 0.0160 0.5419 0.042 Uiso 0.79(9) 1 calc R . P A 2
H00O H 0.4677 0.0106 0.5367 0.042 Uiso 0.21(9) 1 calc R . P A 1
H00P H 0.4864 0.0045 0.3967 0.042 Uiso 0.21(9) 1 calc R . P A 1
O0AA O 0.3656(2) 0.7663(2) 0.5865(2) 0.0293(5) Uani 1 1 d . . . . .
Cl1 Cl 1.20950(8) 0.73549(8) 0.82825(7) 0.0321(2) Uani 1 1 d . . . . .
H00A H 1.039(5) 0.733(5) 0.724(4) 0.039 Uiso 1 1 d R . . . .
H0AA H 0.330(5) 0.681(5) 0.558(4) 0.043(12) Uiso 1 1 d . . . . .
H0AB H 0.332(6) 0.759(5) 0.660(5) 0.053(14) Uiso 1 1 d . . . . .
H00B H 0.887(4) 0.651(5) 0.689(4) 0.032(10) Uiso 1 1 d . . . . .
O2 O 0.471(8) 0.169(8) 0.448(6) 0.023(4) Uani 0.21(9) 1 d . U P A 1
O3 O 0.653(4) 0.129(4) 0.481(5) 0.024(4) Uani 0.21(9) 1 d . U P A 1
O4 O 0.472(2) 0.166(2) 0.4639(16) 0.025(2) Uani 0.79(9) 1 d . U P A 2


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O002 C00L 1.423(3) . ?
O003 C00K 1.434(3) . ?
N006 N007 1.451(3) . ?
N006 C00F 1.500(3) . ?
N006 C00I 1.518(3) . ?
N006 C00N 1.498(3) . ?
O1 C00J 1.374(12) . ?
O1 C00O 1.430(14) . ?
C009 C00D 1.370(4) . ?
C009 C00E 1.412(4) . ?
C00A C00E 1.402(3) . ?
C00A C00H 1.410(4) . ?
C00A C00N 1.523(4) . ?
C00B C00C 1.333(4) . ?
C00B C00K 1.508(4) . ?
C00C C00F 1.486(4) . ?
C00C C00M 1.515(4) . ?
C00D C00J 1.387(4) . ?
C00D O2 1.39(7) . ?
C00D O4 1.378(17) . ?
C00E C00G 1.516(3) . ?
C00F C00G 1.505(4) . ?
C00G C00L 1.537(3) . ?
C00H C00J 1.363(4) . ?
C00I C00M 1.536(4) . ?
C00J O3 1.41(5) . ?
C00K C00L 1.546(3) . ?
C00O O2 1.48(8) . ?
C00O O3 1.37(4) . ?
C00O O4 1.43(2) . ?

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
N007 N006 C00F 109.11(19) . . ?
N007 N006 C00I 106.69(19) . . ?
N007 N006 C00N 113.74(19) . . ?
C00F N006 C00I 101.90(19) . . ?
C00N N006 C00F 107.69(19) . . ?
C00N N006 C00I 116.9(2) . . ?
C00J O1 C00O 105.1(10) . . ?
C00D C009 C00E 117.4(2) . . ?
C00E C00A C00H 121.3(2) . . ?
C00E C00A C00N 123.5(2) . . ?
C00H C00A C00N 115.2(2) . . ?
C00C C00B C00K 121.6(2) . . ?
C00B C00C C00F 120.0(2) . . ?
C00B C00C C00M 132.1(3) . . ?
C00F C00C C00M 107.8(2) . . ?
C009 C00D C00J 122.2(3) . . ?
C009 C00D O2 127(4) . . ?
C009 C00D O4 128.4(10) . . ?
C00J C00D O2 111(4) . . ?
O4 C00D C00J 109.4(10) . . ?
C009 C00E C00G 119.7(2) . . ?
C00A C00E C009 120.0(2) . . ?
C00A C00E C00G 120.1(2) . . ?
N006 C00F C00G 112.1(2) . . ?
C00C C00F N006 104.3(2) . . ?
C00C C00F C00G 115.0(2) . . ?
C00E C00G C00L 119.9(2) . . ?
C00F C00G C00E 109.3(2) . . ?
C00F C00G C00L 104.9(2) . . ?
C00J C00H C00A 117.2(2) . . ?
N006 C00I C00M 104.0(2) . . ?
O1 C00J C00D 109.9(6) . . ?
C00D C00J O3 108(2) . . ?
C00H C00J O1 128.1(6) . . ?
C00H C00J C00D 122.0(3) . . ?
C00H C00J O3 129(2) . . ?
O003 C00K C00B 105.2(2) . . ?
O003 C00K C00L 109.7(2) . . ?
C00B C00K C00L 114.8(2) . . ?
O002 C00L C00G 107.7(2) . . ?
O002 C00L C00K 111.0(2) . . ?
C00G C00L C00K 108.8(2) . . ?
C00C C00M C00I 104.1(2) . . ?
N006 C00N C00A 110.5(2) . . ?
O3 C00O O2 110(4) . . ?
O4 C00O O1 108.1(9) . . ?
C00D O2 C00O 102(5) . . ?
C00O O3 C00J 106(4) . . ?
C00D O4 C00O 105.6(14) . . ?

_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_zsl-sinomenine-n-amine
_audit_block_doi                 10.5517/ccdc.csd.cc2444k0
_database_code_depnum_ccdc_archive 'CCDC 1970191'
loop_
_audit_author_name
_audit_author_address
sinomenine-N-amine
;sustech
China
;
_audit_update_record             
;
2019-12-05 deposited with the CCDC.	2020-07-01 downloaded from the CCDC.
;
_audit_creation_date             2019-09-17
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2016/6
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C19 H25 N2 O4, Cl, 2(H2 O)'
_chemical_formula_sum            'C19 H29 Cl N2 O6'
_chemical_formula_weight         416.89
_chemical_absolute_configuration ad
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.3639 0.7018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'x+1/2, -y+1/2, -z'
'-x, y+1/2, -z+1/2'

_cell_length_a                   7.2666(5)
_cell_length_b                   14.4440(9)
_cell_length_c                   19.5127(13)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2048.0(2)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9942
_cell_measurement_temperature    100
_cell_measurement_theta_max      68.56
_cell_measurement_theta_min      3.81
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    1.980
_exptl_absorpt_correction_T_max  0.7531
_exptl_absorpt_correction_T_min  0.6195
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.1111 before and 0.0550 after correction. The Ratio of minimum to maximum transmission is 0.8226. The λ/2 correction factor is Not present.'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.352
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             888
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.32
_exptl_crystal_size_min          0.31
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0383
_diffrn_reflns_av_unetI/netI     0.0198
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            32519
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         68.553
_diffrn_reflns_theta_min         3.807
_diffrn_ambient_temperature      100.15
_diffrn_detector                 'Bruker PHOTON 100 area detector'
_diffrn_detector_area_resol_mean 7.9
_diffrn_detector_type            'CMOS area detector'
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device       'three-circle diffractometer'
_diffrn_measurement_device_type  'Bruker CMOS area detector'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_radiation_monochromator  'mirror optics'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_source                   'microfocus sealed X-ray tube'
_diffrn_source_type              'Incoatec I\ms'
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.735
_reflns_Friedel_fraction_full    0.999
_reflns_Friedel_fraction_max     0.998
_reflns_number_gt                3753
_reflns_number_total             3771
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT V8.38A (?, 2016)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.38A (?, 2016)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.223
_refine_diff_density_min         -0.144
_refine_diff_density_rms         0.036
_refine_ls_abs_structure_details 
;
 Flack x determined using 1567 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.001(3)
_refine_ls_extinction_coef       0.0069(5)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2016/6 (Sheldrick 2016)'
_refine_ls_goodness_of_fit_ref   1.046
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     257
_refine_ls_number_reflns         3771
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0215
_refine_ls_R_factor_gt           0.0214
_refine_ls_restrained_S_all      1.046
_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)+(0.0287P)²+0.5696P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0566
_refine_ls_wR_factor_ref         0.0567
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups, All O(H,H) groups
2.a Riding coordinates:
 O3(H3), N2(H2A,H2B), O5(H5A,H5B), O6(H6A,H6B)
2.b Ternary CH refined with riding coordinates:
 C6(H6), C5(H5)
2.c Secondary CH2 refined with riding coordinates:
 C7(H7A,H7B), C18(H18A,H18B), C10(H10A,H10B), C8(H8A,H8B)
2.d Aromatic/amide H refined with riding coordinates:
 C16(H16), C4(H4), C15(H15)
2.e Idealised Me refined as rotating group:
 C19(H19A,H19B,H19C), C14(H14A,H14B,H14C), C3(H3A,H3B,H3C)
;
_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
O3 O 0.59937(17) 0.36430(9) 0.14272(6) 0.0176(3) Uani 1 1 d . . . . .
H3 H 0.582033 0.394174 0.106354 0.026 Uiso 1 1 d R . . . .
O2 O 0.95166(17) 0.58064(8) 0.34033(6) 0.0166(3) Uani 1 1 d . . . . .
O1 O 0.64422(18) 0.57191(9) 0.26855(8) 0.0246(3) Uani 1 1 d . . . . .
O4 O 0.81743(19) 0.37225(10) 0.03356(6) 0.0214(3) Uani 1 1 d . . . . .
N2 N 0.7444(2) 0.14199(9) 0.40524(7) 0.0126(3) Uani 1 1 d . . . . .
H2A H 0.815056 0.150211 0.442412 0.015 Uiso 1 1 d R . . . .
H2B H 0.657916 0.186781 0.405802 0.015 Uiso 1 1 d R . . . .
N1 N 0.85928(18) 0.15414(9) 0.34438(7) 0.0103(3) Uani 1 1 d . . . . .
C7 C 0.7344(2) 0.15065(11) 0.28241(8) 0.0116(3) Uani 1 1 d . . . . .
H7A H 0.657496 0.094151 0.284809 0.014 Uiso 1 1 calc R . . . .
H7B H 0.810460 0.146714 0.240427 0.014 Uiso 1 1 calc R . . . .
C6 C 0.9700(2) 0.24528(11) 0.34726(8) 0.0106(3) Uani 1 1 d . . . . .
H6 H 1.037993 0.246898 0.391810 0.013 Uiso 1 1 calc R . . . .
C12 C 0.7827(2) 0.34889(11) 0.15117(9) 0.0124(3) Uani 1 1 d . . . . .
C5 C 0.8343(2) 0.32580(11) 0.34660(8) 0.0103(3) Uani 1 1 d . . . . .
H5 H 0.746125 0.316398 0.385321 0.012 Uiso 1 1 calc R . . . .
C2 C 0.8736(2) 0.49525(11) 0.33280(8) 0.0133(3) Uani 1 1 d . . . . .
C1 C 0.7001(2) 0.49905(11) 0.29224(9) 0.0145(4) Uani 1 1 d . . . . .
C18 C 1.1096(2) 0.25894(11) 0.28962(8) 0.0118(3) Uani 1 1 d . . . . .
H18A H 1.207092 0.301289 0.306185 0.014 Uiso 1 1 calc R . . . .
H18B H 1.168368 0.198518 0.279837 0.014 Uiso 1 1 calc R . . . .
C11 C 0.8497(2) 0.32690(11) 0.21664(8) 0.0104(3) Uani 1 1 d . . . . .
C17 C 1.0334(2) 0.29737(11) 0.22302(8) 0.0111(3) Uani 1 1 d . . . . .
C9 C 0.7225(2) 0.32531(11) 0.27936(8) 0.0103(3) Uani 1 1 d . . . . .
C10 C 0.5948(2) 0.41018(11) 0.28488(8) 0.0126(3) Uani 1 1 d . . . . .
H10A H 0.516637 0.413608 0.243390 0.015 Uiso 1 1 calc R . . . .
H10B H 0.512749 0.402443 0.324982 0.015 Uiso 1 1 calc R . . . .
C16 C 1.1492(2) 0.29999(12) 0.16619(9) 0.0138(3) Uani 1 1 d . . . . .
H16 H 1.274509 0.282588 0.171306 0.017 Uiso 1 1 calc R . . . .
C19 C 0.9844(2) 0.07157(11) 0.34298(9) 0.0150(4) Uani 1 1 d . . . . .
H19A H 1.067766 0.073882 0.382413 0.022 Uiso 1 1 calc GR . . . .
H19B H 1.056388 0.072060 0.300519 0.022 Uiso 1 1 calc GR . . . .
H19C H 0.910691 0.014812 0.345092 0.022 Uiso 1 1 calc GR . . . .
C14 C 0.9290(3) 0.37266(18) -0.02652(10) 0.0333(5) Uani 1 1 d . . . . .
H14A H 0.851932 0.385135 -0.066682 0.050 Uiso 1 1 calc GR . . . .
H14B H 0.988632 0.312210 -0.031742 0.050 Uiso 1 1 calc GR . . . .
H14C H 1.023195 0.420908 -0.022438 0.050 Uiso 1 1 calc GR . . . .
C4 C 0.9346(2) 0.41565(12) 0.35910(8) 0.0122(3) Uani 1 1 d . . . . .
H4 H 1.043224 0.415590 0.386190 0.015 Uiso 1 1 calc R . . . .
C3 C 1.1121(3) 0.58501(13) 0.38306(9) 0.0206(4) Uani 1 1 d . . . . .
H3A H 1.208349 0.545104 0.363983 0.031 Uiso 1 1 calc GR . . . .
H3B H 1.080729 0.563936 0.429355 0.031 Uiso 1 1 calc GR . . . .
H3C H 1.156697 0.648982 0.385051 0.031 Uiso 1 1 calc GR . . . .
C8 C 0.6102(2) 0.23485(11) 0.27771(8) 0.0113(3) Uani 1 1 d . . . . .
H8A H 0.522350 0.234364 0.316486 0.014 Uiso 1 1 calc R . . . .
H8B H 0.538438 0.232031 0.234634 0.014 Uiso 1 1 calc R . . . .
C13 C 0.9013(3) 0.34990(11) 0.09433(8) 0.0142(3) Uani 1 1 d . . . . .
C15 C 1.0857(2) 0.32745(12) 0.10221(8) 0.0156(3) Uani 1 1 d . . . . .
H15 H 1.167536 0.330810 0.064315 0.019 Uiso 1 1 calc R . . . .
Cl1 Cl 0.39990(6) 0.31139(3) 0.44343(2) 0.02010(12) Uani 1 1 d . . . . .
O5 O 0.47664(18) 0.48143(8) 0.04756(6) 0.0186(3) Uani 1 1 d . . . . .
H5A H 0.569545 0.514198 0.033217 0.028 Uiso 1 1 d R . . . .
H5B H 0.401415 0.521788 0.065177 0.028 Uiso 1 1 d R . . . .
O6 O 0.2527(2) 0.11233(10) 0.48003(7) 0.0261(3) Uani 1 1 d . . . . .
H6A H 0.301833 0.165419 0.469609 0.039 Uiso 1 1 d R . . . .
H6B H 0.159923 0.121129 0.507469 0.039 Uiso 1 1 d R . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O3 H3 0.8400 . ?
O3 C12 1.361(2) . ?
O2 C2 1.366(2) . ?
O2 C3 1.435(2) . ?
O1 C1 1.219(2) . ?
O4 C14 1.425(2) . ?
O4 C13 1.372(2) . ?
N2 H2A 0.8963 . ?
N2 H2B 0.9022 . ?
N2 N1 1.4620(19) . ?
N1 C7 1.513(2) . ?
N1 C6 1.544(2) . ?
N1 C19 1.500(2) . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C7 C8 1.517(2) . ?
C6 H6 1.0000 . ?
C6 C5 1.525(2) . ?
C6 C18 1.527(2) . ?
C12 C11 1.403(2) . ?
C12 C13 1.405(2) . ?
C5 H5 1.0000 . ?
C5 C9 1.543(2) . ?
C5 C4 1.508(2) . ?
C2 C1 1.489(3) . ?
C2 C4 1.335(2) . ?
C1 C10 1.502(2) . ?
C18 H18A 0.9900 . ?
C18 H18B 0.9900 . ?
C18 C17 1.518(2) . ?
C11 C17 1.407(2) . ?
C11 C9 1.534(2) . ?
C17 C16 1.392(2) . ?
C9 C10 1.541(2) . ?
C9 C8 1.541(2) . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C16 H16 0.9500 . ?
C16 C15 1.389(2) . ?
C19 H19A 0.9800 . ?
C19 H19B 0.9800 . ?
C19 H19C 0.9800 . ?
C14 H14A 0.9800 . ?
C14 H14B 0.9800 . ?
C14 H14C 0.9800 . ?
C4 H4 0.9500 . ?
C3 H3A 0.9800 . ?
C3 H3B 0.9800 . ?
C3 H3C 0.9800 . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C13 C15 1.387(3) . ?
C15 H15 0.9500 . ?
O5 H5A 0.8707 . ?
O5 H5B 0.8700 . ?
O6 H6A 0.8701 . ?
O6 H6B 0.8700 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C12 O3 H3 109.5 . . ?
C2 O2 C3 116.10(13) . . ?
C13 O4 C14 117.33(15) . . ?
H2A N2 H2B 107.1 . . ?
N1 N2 H2A 108.3 . . ?
N1 N2 H2B 108.8 . . ?
N2 N1 C7 107.63(11) . . ?
N2 N1 C6 111.73(11) . . ?
N2 N1 C19 105.39(12) . . ?
C7 N1 C6 111.73(12) . . ?
C19 N1 C7 108.82(12) . . ?
C19 N1 C6 111.27(12) . . ?
N1 C7 H7A 109.2 . . ?
N1 C7 H7B 109.2 . . ?
N1 C7 C8 112.24(12) . . ?
H7A C7 H7B 107.9 . . ?
C8 C7 H7A 109.2 . . ?
C8 C7 H7B 109.2 . . ?
N1 C6 H6 108.0 . . ?
C5 C6 N1 108.23(12) . . ?
C5 C6 H6 108.0 . . ?
C5 C6 C18 108.95(13) . . ?
C18 C6 N1 115.43(13) . . ?
C18 C6 H6 108.0 . . ?
O3 C12 C11 119.13(15) . . ?
O3 C12 C13 120.22(15) . . ?
C11 C12 C13 120.56(15) . . ?
C6 C5 H5 107.7 . . ?
C6 C5 C9 110.14(13) . . ?
C9 C5 H5 107.7 . . ?
C4 C5 C6 110.02(13) . . ?
C4 C5 H5 107.7 . . ?
C4 C5 C9 113.32(13) . . ?
O2 C2 C1 112.06(14) . . ?
C4 C2 O2 126.76(16) . . ?
C4 C2 C1 121.15(15) . . ?
O1 C1 C2 121.02(15) . . ?
O1 C1 C10 122.13(16) . . ?
C2 C1 C10 116.80(14) . . ?
C6 C18 H18A 108.3 . . ?
C6 C18 H18B 108.3 . . ?
H18A C18 H18B 107.4 . . ?
C17 C18 C6 115.81(14) . . ?
C17 C18 H18A 108.3 . . ?
C17 C18 H18B 108.3 . . ?
C12 C11 C17 118.56(14) . . ?
C12 C11 C9 121.39(14) . . ?
C17 C11 C9 119.78(14) . . ?
C11 C17 C18 122.19(14) . . ?
C16 C17 C18 118.13(14) . . ?
C16 C17 C11 119.64(15) . . ?
C11 C9 C5 111.16(12) . . ?
C11 C9 C10 113.99(13) . . ?
C11 C9 C8 108.37(13) . . ?
C10 C9 C5 104.71(12) . . ?
C8 C9 C5 107.49(12) . . ?
C8 C9 C10 110.92(13) . . ?
C1 C10 C9 112.31(14) . . ?
C1 C10 H10A 109.1 . . ?
C1 C10 H10B 109.1 . . ?
C9 C10 H10A 109.1 . . ?
C9 C10 H10B 109.1 . . ?
H10A C10 H10B 107.9 . . ?
C17 C16 H16 119.2 . . ?
C15 C16 C17 121.54(15) . . ?
C15 C16 H16 119.2 . . ?
N1 C19 H19A 109.5 . . ?
N1 C19 H19B 109.5 . . ?
N1 C19 H19C 109.5 . . ?
H19A C19 H19B 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
O4 C14 H14A 109.5 . . ?
O4 C14 H14B 109.5 . . ?
O4 C14 H14C 109.5 . . ?
H14A C14 H14B 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C5 C4 H4 119.4 . . ?
C2 C4 C5 121.22(15) . . ?
C2 C4 H4 119.4 . . ?
O2 C3 H3A 109.5 . . ?
O2 C3 H3B 109.5 . . ?
O2 C3 H3C 109.5 . . ?
H3A C3 H3B 109.5 . . ?
H3A C3 H3C 109.5 . . ?
H3B C3 H3C 109.5 . . ?
C7 C8 C9 111.33(13) . . ?
C7 C8 H8A 109.4 . . ?
C7 C8 H8B 109.4 . . ?
C9 C8 H8A 109.4 . . ?
C9 C8 H8B 109.4 . . ?
H8A C8 H8B 108.0 . . ?
O4 C13 C12 114.35(16) . . ?
O4 C13 C15 125.45(15) . . ?
C15 C13 C12 120.19(15) . . ?
C16 C15 H15 120.4 . . ?
C13 C15 C16 119.15(15) . . ?
C13 C15 H15 120.4 . . ?
H5A O5 H5B 104.5 . . ?
H6A O6 H6B 109.5 . . ?

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
O3 C12 C11 C17 170.43(14) . . . . ?
O3 C12 C11 C9 -3.5(2) . . . . ?
O3 C12 C13 O4 3.4(2) . . . . ?
O3 C12 C13 C15 -175.22(16) . . . . ?
O2 C2 C1 O1 1.6(2) . . . . ?
O2 C2 C1 C10 -175.75(14) . . . . ?
O2 C2 C4 C5 -179.95(15) . . . . ?
O1 C1 C10 C9 147.25(17) . . . . ?
O4 C13 C15 C16 -175.57(16) . . . . ?
N2 N1 C7 C8 69.52(16) . . . . ?
N2 N1 C6 C5 -64.02(15) . . . . ?
N2 N1 C6 C18 173.62(13) . . . . ?
N1 C7 C8 C9 54.54(17) . . . . ?
N1 C6 C5 C9 -62.12(15) . . . . ?
N1 C6 C5 C4 172.27(12) . . . . ?
N1 C6 C18 C17 83.18(17) . . . . ?
C7 N1 C6 C5 56.63(15) . . . . ?
C7 N1 C6 C18 -65.73(17) . . . . ?
C6 N1 C7 C8 -53.50(17) . . . . ?
C6 C5 C9 C11 -55.52(16) . . . . ?
C6 C5 C9 C10 -179.05(13) . . . . ?
C6 C5 C9 C8 62.92(16) . . . . ?
C6 C5 C4 C2 150.25(15) . . . . ?
C6 C18 C17 C11 5.8(2) . . . . ?
C6 C18 C17 C16 -171.87(14) . . . . ?
C12 C11 C17 C18 -170.91(14) . . . . ?
C12 C11 C17 C16 6.8(2) . . . . ?
C12 C11 C9 C5 -164.56(14) . . . . ?
C12 C11 C9 C10 -46.5(2) . . . . ?
C12 C11 C9 C8 77.54(18) . . . . ?
C12 C13 C15 C16 2.9(2) . . . . ?
C5 C6 C18 C17 -38.80(18) . . . . ?
C5 C9 C10 C1 59.80(16) . . . . ?
C5 C9 C8 C7 -58.05(16) . . . . ?
C2 C1 C10 C9 -35.4(2) . . . . ?
C1 C2 C4 C5 2.3(2) . . . . ?
C18 C6 C5 C9 64.13(16) . . . . ?
C18 C6 C5 C4 -61.49(16) . . . . ?
C18 C17 C16 C15 174.98(15) . . . . ?
C11 C12 C13 O4 179.82(15) . . . . ?
C11 C12 C13 C15 1.2(2) . . . . ?
C11 C17 C16 C15 -2.8(2) . . . . ?
C11 C9 C10 C1 -61.90(18) . . . . ?
C11 C9 C8 C7 62.17(16) . . . . ?
C17 C11 C9 C5 21.59(19) . . . . ?
C17 C11 C9 C10 139.64(15) . . . . ?
C17 C11 C9 C8 -96.32(16) . . . . ?
C17 C16 C15 C13 -2.1(3) . . . . ?
C9 C5 C4 C2 26.5(2) . . . . ?
C9 C11 C17 C18 3.1(2) . . . . ?
C9 C11 C17 C16 -179.20(14) . . . . ?
C10 C9 C8 C7 -171.98(13) . . . . ?
C19 N1 C7 C8 -176.76(13) . . . . ?
C19 N1 C6 C5 178.49(13) . . . . ?
C19 N1 C6 C18 56.12(17) . . . . ?
C14 O4 C13 C12 -178.70(17) . . . . ?
C14 O4 C13 C15 -0.1(3) . . . . ?
C4 C5 C9 C11 68.20(16) . . . . ?
C4 C5 C9 C10 -55.33(16) . . . . ?
C4 C5 C9 C8 -173.35(13) . . . . ?
C4 C2 C1 O1 179.64(17) . . . . ?
C4 C2 C1 C10 2.3(2) . . . . ?
C3 O2 C2 C1 175.47(15) . . . . ?
C3 O2 C2 C4 -2.4(2) . . . . ?
C8 C9 C10 C1 175.45(14) . . . . ?
C13 C12 C11 C17 -6.0(2) . . . . ?
C13 C12 C11 C9 -179.94(15) . . . . ?

_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_zsl-NMnTDCPP
_audit_block_doi                 10.5517/ccdc.csd.cc2444l1
_database_code_depnum_ccdc_archive 'CCDC 1970192'
loop_
_audit_author_name
_audit_author_address
'Nitrido-manganese porphyrin-NMnTDCPP'
;sustech
China
;
_audit_update_record             
;
2019-12-05 deposited with the CCDC.	2020-07-01 downloaded from the CCDC.
;
_audit_creation_date             2019-11-01
_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         '0.5(C116 H72 Cl16 Mn2 N10)'
_chemical_formula_sum            'C58 H36 Cl8 Mn N5'
_chemical_formula_weight         1141.46
_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'
Mn Mn 0.3368 0.7283 '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      orthorhombic
_space_group_IT_number           61
_space_group_name_H-M_alt        'P b c a'
_space_group_name_Hall           '-P 2ac 2ab'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'x+1/2, -y+1/2, -z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'-x-1/2, y-1/2, z'
'x, -y-1/2, z-1/2'

_cell_length_a                   12.6724(19)
_cell_length_b                   19.811(3)
_cell_length_c                   20.784(3)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     5217.9(13)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9717
_cell_measurement_temperature    100
_cell_measurement_theta_max      28.48
_cell_measurement_theta_min      2.28
_shelx_estimated_absorpt_T_max   0.972
_shelx_estimated_absorpt_T_min   0.728
_exptl_absorpt_coefficient_mu    0.708
_exptl_absorpt_correction_T_max  0.7272
_exptl_absorpt_correction_T_min  0.6461
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.1423 before and 0.0994 after correction. The Ratio of minimum to maximum transmission is 0.8885. The λ/2 correction factor is Not present.'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'dark red'
_exptl_crystal_colour_modifier   dark
_exptl_crystal_colour_primary    red
_exptl_crystal_density_diffrn    1.453
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             2320
_exptl_crystal_size_max          0.48
_exptl_crystal_size_mid          0.35
_exptl_crystal_size_min          0.04
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0684
_diffrn_reflns_av_unetI/netI     0.0321
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       26
_diffrn_reflns_limit_k_min       -26
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_number            70468
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.527
_diffrn_reflns_theta_min         2.145
_diffrn_ambient_temperature      100
_diffrn_detector                 'Bruker PHOTON 100 area detector'
_diffrn_detector_area_resol_mean 7.9
_diffrn_detector_type            'CMOS area detector'
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device       'three-circle diffractometer'
_diffrn_measurement_device_type  'BrukerD8 venture microsource'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_radiation_monochromator  'mirror optics'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'microfocus sealed X-ray tube'
_diffrn_source_type              'Incoatec I\ms'
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                6238
_reflns_number_total             6616
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT V8.38A (?, 2016)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.38A (?, 2016)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.826
_refine_diff_density_min         -0.710
_refine_diff_density_rms         0.136
_refine_ls_extinction_coef       0.0031(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.362
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     341
_refine_ls_number_reflns         6616
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1039
_refine_ls_R_factor_gt           0.1003
_refine_ls_restrained_S_all      1.362
_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)+47.7934P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2313
_refine_ls_wR_factor_ref         0.2327
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Uiso/Uaniso restraints and constraints
Uanis(C29) = Uanis(C29A)
3. Others
 Sof(H28)=Sof(C29A)=Sof(H29D)=Sof(H29E)=Sof(H29F)=1-FVAR(1)
 Sof(H24)=Sof(C29)=Sof(H29A)=Sof(H29B)=Sof(H29C)=FVAR(1)
 Fixed Sof: Mn1(0.5) N3(0.5)
4.a Aromatic/amide H refined with riding coordinates:
 C15(H15), C14(H14), C22(H22), C7(H7), C10(H10), C18(H18), C12(H12), C20(H20),
 C19(H19), C11(H11), C23(H23), C24(H24), C25(H25), C27(H27), C28(H28), C26(H26)
4.b Idealised Me refined as rotating group:
 C29(H29A,H29B,H29C), C29A(H29D,H29E,H29F)
;
_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
Mn1 Mn -0.02390(11) 0.49009(7) 0.00109(7) 0.0102(3) Uani 0.5 1 d . . P A 1
Cl1 Cl 0.14356(12) 0.61842(8) -0.22846(7) 0.0294(3) Uani 1 1 d . . . . .
Cl4 Cl -0.38984(11) 0.60618(8) 0.01859(8) 0.0302(3) Uani 1 1 d . . . . .
Cl3 Cl -0.06216(12) 0.77024(7) 0.07624(8) 0.0315(4) Uani 1 1 d . . . . .
Cl2 Cl -0.20418(14) 0.46345(9) -0.22383(8) 0.0388(4) Uani 1 1 d . . . . .
N2 N -0.0720(3) 0.5694(2) -0.0530(2) 0.0140(8) Uani 1 1 d . . . . .
N1 N -0.0537(3) 0.5436(2) 0.0786(2) 0.0156(8) Uani 1 1 d . . . . .
N3 N -0.1214(7) 0.4465(4) -0.0007(4) 0.0151(16) Uani 0.5 1 d . . P . .
C8 C -0.0322(4) 0.5416(2) -0.2323(2) 0.0162(9) Uani 1 1 d . . . . .
C3 C -0.1335(4) 0.6226(2) -0.0317(2) 0.0154(9) Uani 1 1 d . . . . .
C16 C -0.2310(4) 0.6930(3) 0.0469(2) 0.0193(10) Uani 1 1 d . . . . .
C2 C -0.1561(4) 0.6360(2) 0.0317(2) 0.0159(9) Uani 1 1 d . . . . .
C15 C -0.1714(4) 0.6618(3) -0.0855(3) 0.0187(10) Uani 1 1 d . . . . .
H15 H -0.213946 0.701207 -0.083402 0.022 Uiso 1 1 calc R . . . .
C4 C -0.0726(4) 0.5747(2) -0.1191(2) 0.0152(9) Uani 1 1 d . . . . .
C1 C -0.1181(4) 0.5996(2) 0.0832(2) 0.0170(10) Uani 1 1 d . . . . .
C5 C -0.0224(4) 0.5310(2) -0.1612(2) 0.0149(9) Uani 1 1 d . . . . .
C17 C -0.1970(4) 0.7561(3) 0.0678(3) 0.0207(10) Uani 1 1 d . . . . .
C14 C -0.1347(4) 0.6316(3) -0.1392(3) 0.0180(10) Uani 1 1 d . . . . .
H14 H -0.147654 0.645366 -0.182282 0.022 Uiso 1 1 calc R . . . .
C9 C 0.0402(5) 0.5789(3) -0.2684(3) 0.0215(11) Uani 1 1 d . . . . .
C6 C 0.0358(4) 0.4754(2) -0.1418(2) 0.0167(10) Uani 1 1 d . . . . .
C22 C -0.1398(5) 0.6155(3) 0.1490(3) 0.0227(11) Uani 1 1 d . . . . .
H22 H -0.182826 0.651312 0.164369 0.027 Uiso 1 1 calc R . . . .
C7 C 0.0870(5) 0.4302(3) -0.1850(3) 0.0233(11) Uani 1 1 d . . . . .
H7 H 0.084602 0.431855 -0.230671 0.028 Uiso 1 1 calc R . . . .
C13 C -0.1141(5) 0.5114(3) -0.2667(3) 0.0241(11) Uani 1 1 d . . . . .
C10 C 0.0338(5) 0.5844(3) -0.3347(3) 0.0254(12) Uani 1 1 d . . . . .
H10 H 0.085107 0.609468 -0.357870 0.031 Uiso 1 1 calc R . . . .
C18 C -0.2657(5) 0.8080(3) 0.0833(3) 0.0253(12) Uani 1 1 d . . . . .
H18 H -0.239288 0.850571 0.096841 0.030 Uiso 1 1 calc R . . . .
C12 C -0.1230(5) 0.5162(3) -0.3330(3) 0.0295(13) Uani 1 1 d . . . . .
H12 H -0.179375 0.494808 -0.355133 0.035 Uiso 1 1 calc R . . . .
C21 C -0.3403(5) 0.6843(3) 0.0431(3) 0.0229(11) Uani 1 1 d . . . . .
C20 C -0.4105(5) 0.7348(3) 0.0590(3) 0.0292(13) Uani 1 1 d . . . . .
H20 H -0.484299 0.726921 0.056456 0.035 Uiso 1 1 calc R . . . .
C19 C -0.3725(5) 0.7971(3) 0.0788(3) 0.0299(13) Uani 1 1 d . . . . .
H19 H -0.420485 0.832319 0.089324 0.036 Uiso 1 1 calc R . . . .
C11 C -0.0473(5) 0.5532(3) -0.3664(3) 0.0300(13) Uani 1 1 d . . . . .
H11 H -0.052086 0.556881 -0.411847 0.036 Uiso 1 1 calc R . . . .
C23 C 0.1343(7) 0.1456(4) 0.1349(4) 0.0446(18) Uani 1 1 d . . . . .
H23 H 0.069751 0.123350 0.125255 0.054 Uiso 1 1 calc R . . . .
C24 C 0.2228(7) 0.1337(4) 0.0968(4) 0.0456(18) Uani 1 1 d . . . . .
H24 H 0.218927 0.104040 0.060945 0.055 Uiso 0.535(13) 1 calc R . P B 1
C25 C 0.3168(6) 0.1662(4) 0.1120(4) 0.0454(18) Uani 1 1 d . . . . .
H25 H 0.377706 0.159436 0.086190 0.054 Uiso 1 1 calc R . . . .
C27 C 0.2347(6) 0.2200(3) 0.2015(3) 0.0386(16) Uani 1 1 d . . . . .
H27 H 0.239634 0.249453 0.237433 0.046 Uiso 1 1 calc R . . . .
C28 C 0.1393(7) 0.1892(4) 0.1865(3) 0.0400(16) Uani 1 1 d . . . . .
H28 H 0.078101 0.198104 0.211521 0.048 Uiso 0.465(13) 1 calc R . P B 2
C26 C 0.3211(6) 0.2076(4) 0.1643(4) 0.0431(18) Uani 1 1 d . . . . .
H26 H 0.386264 0.228528 0.175111 0.052 Uiso 1 1 calc R . . . .
C29 C 0.0348(13) 0.2111(8) 0.2245(8) 0.049(3) Uani 0.535(13) 1 d . . P B 1
H29A H 0.001680 0.249391 0.202410 0.074 Uiso 0.535(13) 1 calc GR . P B 1
H29B H 0.053415 0.224336 0.268466 0.074 Uiso 0.535(13) 1 calc GR . P B 1
H29C H -0.014653 0.173128 0.225760 0.074 Uiso 0.535(13) 1 calc GR . P B 1
C29A C 0.2224(15) 0.0723(9) 0.0449(8) 0.049(3) Uani 0.465(13) 1 d . . P B 2
H29D H 0.191135 0.032081 0.064642 0.074 Uiso 0.465(13) 1 calc GR . P B 2
H29E H 0.294997 0.062401 0.031728 0.074 Uiso 0.465(13) 1 calc GR . P B 2
H29F H 0.180853 0.085463 0.007192 0.074 Uiso 0.465(13) 1 calc GR . P B 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
Mn1 Mn1 0.723(3) 5_565 ?
Mn1 N2 2.026(4) . ?
Mn1 N2 2.007(4) 5_565 ?
Mn1 N1 2.039(4) 5_565 ?
Mn1 N1 1.965(4) . ?
Mn1 N3 2.229(8) 5_565 ?
Mn1 N3 1.508(8) . ?
Cl1 C9 1.737(6) . ?
Cl4 C21 1.746(6) . ?
Cl3 C17 1.740(6) . ?
Cl2 C13 1.732(6) . ?
N2 C3 1.383(6) . ?
N2 C4 1.379(6) . ?
N1 C1 1.381(6) . ?
N1 C6 1.386(6) 5_565 ?
C8 C5 1.497(7) . ?
C8 C9 1.397(7) . ?
C8 C13 1.395(7) . ?
C3 C2 1.374(7) . ?
C3 C15 1.443(7) . ?
C16 C2 1.508(7) . ?
C16 C17 1.392(7) . ?
C16 C21 1.398(8) . ?
C2 C1 1.377(7) . ?
C15 H15 0.9500 . ?
C15 C14 1.350(7) . ?
C4 C5 1.385(7) . ?
C4 C14 1.437(7) . ?
C1 C22 1.430(7) . ?
C5 C6 1.386(7) . ?
C17 C18 1.386(7) . ?
C14 H14 0.9500 . ?
C9 C10 1.384(7) . ?
C6 C7 1.424(7) . ?
C22 H22 0.9500 . ?
C22 C7 1.352(8) 5_565 ?
C7 H7 0.9500 . ?
C13 C12 1.386(8) . ?
C10 H10 0.9500 . ?
C10 C11 1.368(9) . ?
C18 H18 0.9500 . ?
C18 C19 1.374(9) . ?
C12 H12 0.9500 . ?
C12 C11 1.392(9) . ?
C21 C20 1.378(8) . ?
C20 H20 0.9500 . ?
C20 C19 1.388(9) . ?
C19 H19 0.9500 . ?
C11 H11 0.9500 . ?
C23 H23 0.9500 . ?
C23 C24 1.393(11) . ?
C23 C28 1.378(11) . ?
C24 H24 0.9500 . ?
C24 C25 1.390(11) . ?
C24 C29A 1.625(19) . ?
C25 H25 0.9500 . ?
C25 C26 1.363(12) . ?
C27 H27 0.9500 . ?
C27 C28 1.390(11) . ?
C27 C26 1.363(11) . ?
C28 H28 0.9500 . ?
C28 C29 1.601(17) . ?
C26 H26 0.9500 . ?
C29 H29A 0.9800 . ?
C29 H29B 0.9800 . ?
C29 H29C 0.9800 . ?
C29A H29D 0.9800 . ?
C29A H29E 0.9800 . ?
C29A H29F 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
Mn1 Mn1 N2 78.2(3) 5_565 . ?
Mn1 Mn1 N2 81.1(3) 5_565 5_565 ?
Mn1 Mn1 N1 73.9(3) 5_565 5_565 ?
Mn1 Mn1 N1 85.4(3) 5_565 . ?
Mn1 Mn1 N3 174.6(4) 5_565 . ?
Mn1 Mn1 N3 3.7(3) 5_565 5_565 ?
N2 Mn1 N2 159.35(8) 5_565 . ?
N2 Mn1 N1 87.04(17) . 5_565 ?
N2 Mn1 N1 87.26(18) 5_565 5_565 ?
N2 Mn1 N3 79.0(3) . 5_565 ?
N2 Mn1 N3 80.3(3) 5_565 5_565 ?
N1 Mn1 N2 89.58(18) . 5_565 ?
N1 Mn1 N2 88.77(18) . . ?
N1 Mn1 N1 159.29(9) . 5_565 ?
N1 Mn1 N3 77.5(3) 5_565 5_565 ?
N1 Mn1 N3 81.8(3) . 5_565 ?
N3 Mn1 N2 100.6(4) . . ?
N3 Mn1 N2 100.0(4) . 5_565 ?
N3 Mn1 N1 100.8(3) . 5_565 ?
N3 Mn1 N1 99.9(3) . . ?
N3 Mn1 N3 178.24(14) . 5_565 ?
Mn1 N2 Mn1 20.65(8) 5_565 . ?
C3 N2 Mn1 125.7(3) . . ?
C3 N2 Mn1 128.1(3) . 5_565 ?
C4 N2 Mn1 125.7(3) . 5_565 ?
C4 N2 Mn1 127.9(3) . . ?
C4 N2 C3 104.9(4) . . ?
Mn1 N1 Mn1 20.71(9) . 5_565 ?
C1 N1 Mn1 127.2(3) . 5_565 ?
C1 N1 Mn1 127.1(3) . . ?
C1 N1 C6 104.5(4) . 5_565 ?
C6 N1 Mn1 126.8(3) 5_565 . ?
C6 N1 Mn1 127.1(3) 5_565 5_565 ?
Mn1 N3 Mn1 1.76(14) . 5_565 ?
C9 C8 C5 123.4(5) . . ?
C13 C8 C5 120.5(5) . . ?
C13 C8 C9 116.1(5) . . ?
N2 C3 C15 110.5(4) . . ?
C2 C3 N2 124.9(5) . . ?
C2 C3 C15 124.6(5) . . ?
C17 C16 C2 122.8(5) . . ?
C17 C16 C21 115.8(5) . . ?
C21 C16 C2 121.3(5) . . ?
C3 C2 C16 118.5(4) . . ?
C3 C2 C1 124.8(5) . . ?
C1 C2 C16 116.7(4) . . ?
C3 C15 H15 126.6 . . ?
C14 C15 C3 106.7(4) . . ?
C14 C15 H15 126.6 . . ?
N2 C4 C5 125.4(4) . . ?
N2 C4 C14 110.6(4) . . ?
C5 C4 C14 124.0(5) . . ?
N1 C1 C22 110.9(4) . . ?
C2 C1 N1 125.0(5) . . ?
C2 C1 C22 124.1(5) . . ?
C4 C5 C8 119.8(4) . . ?
C4 C5 C6 124.0(5) . . ?
C6 C5 C8 116.3(4) . . ?
C16 C17 Cl3 118.7(4) . . ?
C18 C17 Cl3 118.3(5) . . ?
C18 C17 C16 123.0(5) . . ?
C15 C14 C4 107.2(4) . . ?
C15 C14 H14 126.4 . . ?
C4 C14 H14 126.4 . . ?
C8 C9 Cl1 118.5(4) . . ?
C10 C9 Cl1 119.0(5) . . ?
C10 C9 C8 122.5(5) . . ?
N1 C6 C5 125.3(5) 5_565 . ?
N1 C6 C7 110.6(4) 5_565 . ?
C5 C6 C7 124.0(5) . . ?
C1 C22 H22 126.6 . . ?
C7 C22 C1 106.7(5) 5_565 . ?
C7 C22 H22 126.6 5_565 . ?
C6 C7 H7 126.4 . . ?
C22 C7 C6 107.3(5) 5_565 . ?
C22 C7 H7 126.4 5_565 . ?
C8 C13 Cl2 117.5(4) . . ?
C12 C13 Cl2 119.7(5) . . ?
C12 C13 C8 122.7(5) . . ?
C9 C10 H10 120.4 . . ?
C11 C10 C9 119.2(6) . . ?
C11 C10 H10 120.4 . . ?
C17 C18 H18 120.4 . . ?
C19 C18 C17 119.2(6) . . ?
C19 C18 H18 120.4 . . ?
C13 C12 H12 120.8 . . ?
C13 C12 C11 118.4(6) . . ?
C11 C12 H12 120.8 . . ?
C16 C21 Cl4 118.8(4) . . ?
C20 C21 Cl4 118.8(5) . . ?
C20 C21 C16 122.4(6) . . ?
C21 C20 H20 120.2 . . ?
C21 C20 C19 119.6(6) . . ?
C19 C20 H20 120.2 . . ?
C18 C19 C20 120.0(5) . . ?
C18 C19 H19 120.0 . . ?
C20 C19 H19 120.0 . . ?
C10 C11 C12 121.0(5) . . ?
C10 C11 H11 119.5 . . ?
C12 C11 H11 119.5 . . ?
C24 C23 H23 119.6 . . ?
C28 C23 H23 119.6 . . ?
C28 C23 C24 120.7(7) . . ?
C23 C24 H24 120.6 . . ?
C23 C24 C29A 120.1(10) . . ?
C25 C24 C23 118.8(8) . . ?
C25 C24 H24 120.6 . . ?
C25 C24 C29A 120.0(10) . . ?
C24 C25 H25 120.2 . . ?
C26 C25 C24 119.7(8) . . ?
C26 C25 H25 120.2 . . ?
C28 C27 H27 120.2 . . ?
C26 C27 H27 120.2 . . ?
C26 C27 C28 119.6(7) . . ?
C23 C28 C27 119.3(8) . . ?
C23 C28 H28 120.3 . . ?
C23 C28 C29 121.0(9) . . ?
C27 C28 H28 120.3 . . ?
C27 C28 C29 119.3(9) . . ?
C25 C26 H26 119.1 . . ?
C27 C26 C25 121.8(7) . . ?
C27 C26 H26 119.1 . . ?
C28 C29 H29A 109.5 . . ?
C28 C29 H29B 109.5 . . ?
C28 C29 H29C 109.5 . . ?
H29A C29 H29B 109.5 . . ?
H29A C29 H29C 109.5 . . ?
H29B C29 H29C 109.5 . . ?
C24 C29A H29D 109.5 . . ?
C24 C29A H29E 109.5 . . ?
C24 C29A H29F 109.5 . . ?
H29D C29A H29E 109.5 . . ?
H29D C29A H29F 109.5 . . ?
H29E C29A H29F 109.5 . . ?

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
Mn1 N2 C3 C2 -13.8(7) 5_565 . . . ?
Mn1 N2 C3 C2 12.0(7) . . . . ?
Mn1 N2 C3 C15 -167.6(3) . . . . ?
Mn1 N2 C3 C15 166.7(3) 5_565 . . . ?
Mn1 N2 C4 C5 -12.3(7) . . . . ?
Mn1 N2 C4 C5 13.4(7) 5_565 . . . ?
Mn1 N2 C4 C14 -167.8(3) 5_565 . . . ?
Mn1 N2 C4 C14 166.4(3) . . . . ?
Mn1 N1 C1 C2 12.1(8) 5_565 . . . ?
Mn1 N1 C1 C2 -13.9(8) . . . . ?
Mn1 N1 C1 C22 -167.3(4) 5_565 . . . ?
Mn1 N1 C1 C22 166.6(4) . . . . ?
Cl1 C9 C10 C11 179.9(5) . . . . ?
Cl4 C21 C20 C19 179.8(5) . . . . ?
Cl3 C17 C18 C19 -178.1(5) . . . . ?
Cl2 C13 C12 C11 -177.8(5) . . . . ?
N2 Mn1 N3 Mn1 -101(5) 5_565 . . 5_565 ?
N2 Mn1 N3 Mn1 77(5) . . . 5_565 ?
N2 C3 C2 C16 -175.5(5) . . . . ?
N2 C3 C2 C1 2.1(8) . . . . ?
N2 C3 C15 C14 1.2(6) . . . . ?
N2 C4 C5 C8 178.2(5) . . . . ?
N2 C4 C5 C6 -0.1(8) . . . . ?
N2 C4 C14 C15 0.8(6) . . . . ?
N1 Mn1 N3 Mn1 -12(5) 5_565 . . 5_565 ?
N1 Mn1 N3 Mn1 167(5) . . . 5_565 ?
N1 C1 C22 C7 1.0(7) . . . 5_565 ?
N1 C6 C7 C22 -2.1(7) 5_565 . . 5_565 ?
C8 C5 C6 N1 -179.5(5) . . . 5_565 ?
C8 C5 C6 C7 1.4(8) . . . . ?
C8 C9 C10 C11 1.1(9) . . . . ?
C8 C13 C12 C11 -0.5(9) . . . . ?
C3 N2 C4 C5 -178.7(5) . . . . ?
C3 N2 C4 C14 0.0(6) . . . . ?
C3 C2 C1 N1 -1.5(9) . . . . ?
C3 C2 C1 C22 177.9(5) . . . . ?
C3 C15 C14 C4 -1.2(6) . . . . ?
C16 C2 C1 N1 176.2(5) . . . . ?
C16 C2 C1 C22 -4.3(8) . . . . ?
C16 C17 C18 C19 0.9(9) . . . . ?
C16 C21 C20 C19 0.8(9) . . . . ?
C2 C3 C15 C14 -178.3(5) . . . . ?
C2 C16 C17 Cl3 0.6(7) . . . . ?
C2 C16 C17 C18 -178.4(5) . . . . ?
C2 C16 C21 Cl4 -1.5(7) . . . . ?
C2 C16 C21 C20 177.6(5) . . . . ?
C2 C1 C22 C7 -178.5(5) . . . 5_565 ?
C15 C3 C2 C16 3.9(8) . . . . ?
C15 C3 C2 C1 -178.4(5) . . . . ?
C4 N2 C3 C2 178.8(5) . . . . ?
C4 N2 C3 C15 -0.7(6) . . . . ?
C4 C5 C6 N1 -1.2(8) . . . 5_565 ?
C4 C5 C6 C7 179.7(5) . . . . ?
C5 C8 C9 Cl1 -3.3(7) . . . . ?
C5 C8 C9 C10 175.5(5) . . . . ?
C5 C8 C13 Cl2 1.4(7) . . . . ?
C5 C8 C13 C12 -175.9(5) . . . . ?
C5 C4 C14 C15 179.5(5) . . . . ?
C5 C6 C7 C22 177.1(5) . . . 5_565 ?
C17 C16 C2 C3 -101.7(6) . . . . ?
C17 C16 C2 C1 80.4(7) . . . . ?
C17 C16 C21 Cl4 -178.9(4) . . . . ?
C17 C16 C21 C20 0.1(8) . . . . ?
C17 C18 C19 C20 0.0(9) . . . . ?
C14 C4 C5 C8 -0.4(8) . . . . ?
C14 C4 C5 C6 -178.7(5) . . . . ?
C9 C8 C5 C4 92.9(6) . . . . ?
C9 C8 C5 C6 -88.6(6) . . . . ?
C9 C8 C13 Cl2 178.7(4) . . . . ?
C9 C8 C13 C12 1.5(8) . . . . ?
C9 C10 C11 C12 0.0(9) . . . . ?
C6 N1 C1 C2 179.8(5) 5_565 . . . ?
C6 N1 C1 C22 0.3(6) 5_565 . . . ?
C13 C8 C5 C4 -89.9(6) . . . . ?
C13 C8 C5 C6 88.5(6) . . . . ?
C13 C8 C9 Cl1 179.5(4) . . . . ?
C13 C8 C9 C10 -1.7(8) . . . . ?
C13 C12 C11 C10 -0.2(10) . . . . ?
C21 C16 C2 C3 81.0(7) . . . . ?
C21 C16 C2 C1 -96.9(6) . . . . ?
C21 C16 C17 Cl3 178.0(4) . . . . ?
C21 C16 C17 C18 -1.0(8) . . . . ?
C21 C20 C19 C18 -0.8(10) . . . . ?
C23 C24 C25 C26 1.2(11) . . . . ?
C24 C23 C28 C27 -1.9(11) . . . . ?
C24 C23 C28 C29 171.3(9) . . . . ?
C24 C25 C26 C27 -1.8(11) . . . . ?
C28 C23 C24 C25 0.7(12) . . . . ?
C28 C23 C24 C29A 168.5(9) . . . . ?
C28 C27 C26 C25 0.6(11) . . . . ?
C26 C27 C28 C23 1.3(10) . . . . ?
C26 C27 C28 C29 -172.1(8) . . . . ?
C29A C24 C25 C26 -166.7(9) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
