# Electronic Supplementary Material (ESI) for CrystEngComm.
# This journal is © The Royal Society of Chemistry 2021

####################################################################### 
# 
# 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_lmf-fa
_database_code_depnum_ccdc_archive 'CCDC 2025163'
loop_
_audit_author_name
_audit_author_address
'Anilkumar Gunnam'
;University of Hyderabad
India
;
_audit_update_record             
;
2021-10-04 deposited with the CCDC.	2021-10-12 downloaded from the CCDC.
;
_audit_creation_date             2021-09-04
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6272)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            'Lumifantrine-Fumaric Acid 2:1 salt'
_chemical_name_systematic        
'2-(dibutylamino)-1-[(9Z)-2,7-dichloro-9-[(4-chlorophenyl)methylidene]-9H-fluoren-4-yl]ethan-1-ol - (2E)-but-2-enedioic acid'
_chemical_formula_moiety         'C30 H33 Cl3 N O, C2 H O2'
_chemical_formula_sum            'C32 H34 Cl3 N O3'
_chemical_formula_weight         586.95
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   11.4556(3)
_cell_length_b                   26.8887(7)
_cell_length_c                   9.5696(3)
_cell_angle_alpha                90
_cell_angle_beta                 91.164(2)
_cell_angle_gamma                90
_cell_volume                     2947.08(14)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    15902
_cell_measurement_temperature    103(5)
_cell_measurement_theta_max      26.9140
_cell_measurement_theta_min      2.2490
_shelx_estimated_absorpt_T_max   0.966
_shelx_estimated_absorpt_T_min   0.934
_exptl_absorpt_coefficient_mu    0.345
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.40902
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.35a (Rigaku Oxford Diffraction, 2018)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.323
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       hexagonal
_exptl_crystal_F_000             1232
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.1
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0349
_diffrn_reflns_av_unetI/netI     0.0300
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       33
_diffrn_reflns_limit_k_min       -31
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            27047
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.371
_diffrn_reflns_theta_min         2.259
_diffrn_ambient_temperature      103
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix3000
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     -9.00  17.00   0.50    9.00    --   16.22 -30.00  30.00   52
  2  ω     -7.00  85.00   0.50    9.00    --   16.22  61.00  30.00  184
  3  ω     -7.00  83.00   0.50    9.00    --   16.22  45.00 120.00  180
  4  ω     40.00  89.00   0.50    9.00    --   16.22  77.00 150.00   98
  5  ω     -9.00  32.00   0.50    9.00    --   16.22  77.00 150.00   82
  6  ω    -32.00  -6.00   0.50    9.00    --  -14.97 109.00 -16.00   52
  7  ω    -15.00  10.00   0.50    9.00    --  -14.97 -61.00 -60.00   50
  8  ω    -34.00  11.00   0.50    9.00    --  -14.97 -94.00 -60.00   90
  9  ω      9.00  41.00   0.50    9.00    --   16.22-109.00-112.00   64
 10  ω    -44.00  10.00   0.50    9.00    --  -14.97 -45.00-180.00  108
 11  ω     51.00  89.00   0.50    9.00    --   16.22  30.00-150.00   76
 12  ω     -8.00  43.00   0.50    9.00    --   16.22  30.00-150.00  102
 13  ω    -63.00 -11.00   0.50    9.00    --  -14.97 125.00-180.00  104
 14  ω    -60.00 -19.00   0.50    9.00    --  -14.97 125.00 -90.00   82
 15  ω    -78.00 -51.00   0.50    9.00    --  -14.97 -61.00 -60.00   54
 16  ω    -73.00 -48.00   0.50    9.00    --  -14.97 -45.00-180.00   50
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  
'XtaLAB Synergy, Single source at offset/far, HyPix3000'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                4785
_reflns_number_total             6001
_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       'CrysAlisPro 1.171.40.35a (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.40.35a (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.40.35a (Rigaku OD, 2018)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.470
_refine_diff_density_min         -0.566
_refine_diff_density_rms         0.050
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.023
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     427
_refine_ls_number_reflns         6001
_refine_ls_number_restraints     6
_refine_ls_R_factor_all          0.0692
_refine_ls_R_factor_gt           0.0554
_refine_ls_restrained_S_all      1.023
_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)+(0.0505P)²+2.9567P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1315
_refine_ls_wR_factor_ref         0.1389
_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) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2. Restrained distances
 O4-C34 \\sim O2-C31
 with sigma of 0.02
 O5-C34 \\sim O3-C31
 with sigma of 0.02
 C34-C33 \\sim C31-C32
 with sigma of 0.02
 O5-C33 \\sim O3-C32
 with sigma of 0.04
 O4-O5 \\sim O2-O3
 with sigma of 0.04
 O4-C33 \\sim O2-C32
 with sigma of 0.04
3. Uiso/Uaniso restraints and constraints
Uanis(C30B) = Uanis(C21)
Uanis(C21B) = Uanis(C21A)
4. Others
 Sof(C29B)=Sof(H29C)=Sof(H29D)=Sof(C30B)=Sof(H30A)=Sof(H30B)=Sof(H30C)=
 Sof(O1B)=Sof(H1B)=Sof(C21B)=1-FVAR(1)
 Sof(C21A)=Sof(C29A)=Sof(H29A)=Sof(H29B)=Sof(C21)=Sof(H21B)=Sof(H21C)=
 Sof(H21D)=Sof(O1A)=Sof(H1A)=FVAR(1)
 Sof(O2)=Sof(O3)=Sof(C31)=Sof(C32)=Sof(H32)=1-FVAR(2)
 Sof(O4)=Sof(O5)=Sof(C34)=Sof(C33)=Sof(H33)=FVAR(2)
5.a Ternary CH refined with riding coordinates:
 N1(H1), C21A(H21A)
5.b Secondary CH2 refined with riding coordinates:
 C23(H23A,H23B), C24(H24A,H24B), C25(H25A,H25B), C27(H27A,H27B), C28(H28A,
 H28B), C29A(H29A,H29B), C29B(H29C,H29D)
5.c Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C5(H5), C6(H6), C7(H7), C10(H10), C12(H12), C16(H16),
 C17(H17), C19(H19), C33(H33), C32(H32)
5.d Idealised Me refined as rotating group:
 C26(H26A,H26B,H26C), C21(H21B,H21C,H21D), C30B(H30A,H30B,H30C)
5.e Idealised tetrahedral OH refined as rotating group:
 O1A(H1A), O1B(H1B)
;
_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
Cl1 Cl 1.16897(6) 0.80831(3) 1.17677(8) 0.0648(2) Uani 1 1 d . . . . .
Cl2 Cl 0.81029(7) 0.59879(3) 0.96218(8) 0.0594(2) Uani 1 1 d . . . . .
Cl3 Cl 0.39047(6) 0.87826(2) 0.43002(7) 0.04877(19) Uani 1 1 d . . . . .
N1 N 0.3616(2) 0.56977(8) 0.4597(2) 0.0483(6) Uani 1 1 d . . . . .
H1 H 0.415956 0.553281 0.393637 0.058 Uiso 1 1 calc R U . . .
C1 C 1.0490(2) 0.80793(12) 1.0613(3) 0.0476(7) Uani 1 1 d . . . . .
C2 C 0.9653(2) 0.84429(11) 1.0734(3) 0.0458(6) Uani 1 1 d . . . . .
H2 H 0.972365 0.869046 1.143910 0.055 Uiso 1 1 calc R U . . .
C3 C 0.8709(2) 0.84423(10) 0.9815(3) 0.0431(6) Uani 1 1 d . . . . .
H3 H 0.814475 0.870027 0.986809 0.052 Uiso 1 1 calc R U . . .
C4 C 0.8566(2) 0.80697(10) 0.8808(3) 0.0417(6) Uani 1 1 d . . . . .
C5 C 0.9447(2) 0.77158(11) 0.8692(3) 0.0479(7) Uani 1 1 d . . . . .
H5 H 0.938703 0.746878 0.798466 0.058 Uiso 1 1 calc R U . . .
C6 C 1.0410(2) 0.77184(12) 0.9593(3) 0.0521(7) Uani 1 1 d . . . . .
H6 H 1.100567 0.747508 0.950880 0.063 Uiso 1 1 calc R U . . .
C7 C 0.7526(2) 0.80862(10) 0.7883(3) 0.0413(6) Uani 1 1 d . . . . .
H7 H 0.727826 0.841086 0.762168 0.050 Uiso 1 1 calc R U . . .
C8 C 0.6870(2) 0.77145(10) 0.7346(2) 0.0381(5) Uani 1 1 d . . . . .
C9 C 0.6919(2) 0.71665(10) 0.7512(2) 0.0371(5) Uani 1 1 d . . . . .
C10 C 0.7521(2) 0.68739(10) 0.8484(3) 0.0412(6) Uani 1 1 d . . . . .
H10 H 0.800774 0.702001 0.918670 0.049 Uiso 1 1 calc R U . . .
C11 C 0.7389(2) 0.63622(11) 0.8395(3) 0.0430(6) Uani 1 1 d . . . . .
C12 C 0.6728(2) 0.61380(10) 0.7353(3) 0.0423(6) Uani 1 1 d . . . . .
H12 H 0.669962 0.578548 0.729426 0.051 Uiso 1 1 calc R U . . .
C13 C 0.6102(2) 0.64259(10) 0.6384(3) 0.0397(6) Uani 1 1 d . . . . .
C14 C 0.6150(2) 0.69430(9) 0.6516(2) 0.0364(5) Uani 1 1 d . . . . .
C15 C 0.5502(2) 0.73443(9) 0.5787(2) 0.0362(5) Uani 1 1 d . . . . .
C16 C 0.4592(2) 0.73398(10) 0.4799(3) 0.0416(6) Uani 1 1 d . . . . .
H16 H 0.430265 0.703317 0.444039 0.050 Uiso 1 1 calc R U . . .
C17 C 0.4112(2) 0.77843(10) 0.4345(3) 0.0430(6) Uani 1 1 d . . . . .
H17 H 0.349373 0.778423 0.366783 0.052 Uiso 1 1 calc R U . . .
C18 C 0.4532(2) 0.82277(9) 0.4875(3) 0.0396(6) Uani 1 1 d . . . . .
C19 C 0.5431(2) 0.82486(9) 0.5859(2) 0.0383(6) Uani 1 1 d . . . . .
H19 H 0.571393 0.855745 0.620903 0.046 Uiso 1 1 calc R U . . .
C20 C 0.5904(2) 0.78010(9) 0.6314(2) 0.0357(5) Uani 1 1 d . . . . .
C21A C 0.5517(3) 0.61703(17) 0.5199(5) 0.0366(10) Uani 0.832(4) 1 d . . P A 1
H21A H 0.533131 0.641646 0.444307 0.044 Uiso 1 1 calc R U . A 1
C22 C 0.4370(3) 0.59355(11) 0.5724(3) 0.0473(7) Uani 1 1 d . . . . .
C23 C 0.2875(3) 0.52934(10) 0.5196(3) 0.0514(7) Uani 1 1 d . . . . .
H23A H 0.339457 0.505329 0.568631 0.062 Uiso 1 1 calc R U . . .
H23B H 0.248412 0.511415 0.441330 0.062 Uiso 1 1 calc R U . . .
C24 C 0.1958(3) 0.54599(12) 0.6194(4) 0.0657(9) Uani 1 1 d . . . . .
H24A H 0.139305 0.568015 0.570020 0.079 Uiso 1 1 calc R U . . .
H24B H 0.232940 0.565205 0.696497 0.079 Uiso 1 1 calc R U . . .
C25 C 0.1319(3) 0.50164(14) 0.6788(5) 0.0788(11) Uani 1 1 d . . . . .
H25A H 0.095383 0.482577 0.601009 0.095 Uiso 1 1 calc R U . . .
H25B H 0.189221 0.479590 0.726779 0.095 Uiso 1 1 calc R U . . .
C26 C 0.0399(5) 0.51588(19) 0.7796(7) 0.136(2) Uani 1 1 d . . . . .
H26A H -0.018417 0.536975 0.732191 0.204 Uiso 1 1 calc R U . . .
H26B H 0.075592 0.534200 0.857953 0.204 Uiso 1 1 calc R U . . .
H26C H 0.001943 0.485827 0.814651 0.204 Uiso 1 1 calc R U . . .
C27 C 0.2985(3) 0.60927(11) 0.3779(3) 0.0608(8) Uani 1 1 d . . . . .
H27A H 0.357067 0.631295 0.335100 0.073 Uiso 1 1 calc R U . . .
H27B H 0.253043 0.629691 0.443520 0.073 Uiso 1 1 calc R U . . .
C28 C 0.2171(3) 0.59077(14) 0.2645(4) 0.0740(10) Uani 1 1 d . . . . .
H28A H 0.153437 0.570722 0.304461 0.089 Uiso 1 1 calc R U . A 1
H28B H 0.259617 0.570055 0.196819 0.089 Uiso 1 1 calc R U . A 1
C29A C 0.1666(4) 0.63927(18) 0.1913(5) 0.0686(12) Uani 0.832(4) 1 d . . P A 1
H29A H 0.128648 0.660559 0.261483 0.082 Uiso 0.832(4) 1 calc R U P A 1
H29B H 0.231040 0.658436 0.149821 0.082 Uiso 0.832(4) 1 calc R U P A 1
C21 C 0.0808(5) 0.6254(2) 0.0810(7) 0.124(3) Uani 0.832(4) 1 d . . P A 1
H21B H 0.118096 0.603539 0.013138 0.186 Uiso 0.832(4) 1 calc R U P A 1
H21C H 0.052252 0.655439 0.033670 0.186 Uiso 0.832(4) 1 calc R U P A 1
H21D H 0.015191 0.607903 0.123095 0.186 Uiso 0.832(4) 1 calc R U P A 1
C29B C 0.0967(12) 0.6148(6) 0.2085(15) 0.039(4) Uani 0.168(4) 1 d . . P A 2
H29C H 0.042833 0.620826 0.286330 0.047 Uiso 0.168(4) 1 calc R U P A 2
H29D H 0.057691 0.592871 0.138694 0.047 Uiso 0.168(4) 1 calc R U P A 2
C30B C 0.137(3) 0.6666(12) 0.138(4) 0.124(3) Uani 0.168(4) 1 d . . P A 2
H30A H 0.068820 0.683988 0.099280 0.186 Uiso 0.168(4) 1 calc R U P A 2
H30B H 0.192032 0.659623 0.063114 0.186 Uiso 0.168(4) 1 calc R U P A 2
H30C H 0.175696 0.687515 0.209147 0.186 Uiso 0.168(4) 1 calc R U P A 2
O4 O 0.5397(6) 0.4849(2) -0.2571(6) 0.0397(13) Uani 0.717(16) 1 d D . P B 1
O5 O 0.3950(6) 0.4322(2) -0.2076(5) 0.0470(12) Uani 0.717(16) 1 d D . P B 1
C34 C 0.4671(7) 0.4659(3) -0.1760(6) 0.0345(16) Uani 0.717(16) 1 d D . P B 1
C33 C 0.4622(4) 0.48461(18) -0.0274(6) 0.0374(16) Uani 0.717(16) 1 d D . P B 1
H33 H 0.400471 0.473235 0.029159 0.045 Uiso 0.717(16) 1 calc R U P B 1
O2 O 0.5552(18) 0.5565(5) 0.2026(12) 0.049(3) Uani 0.283(16) 1 d D . P B 2
O3 O 0.4155(16) 0.5068(5) 0.2864(15) 0.059(3) Uani 0.283(16) 1 d D . P B 2
C31 C 0.480(2) 0.5224(5) 0.1917(17) 0.038(4) Uani 0.283(16) 1 d D . P B 2
C32 C 0.4701(12) 0.4952(4) 0.0546(14) 0.038(4) Uani 0.283(16) 1 d D . P B 2
H32 H 0.415198 0.468800 0.048064 0.045 Uiso 0.283(16) 1 calc R U P B 2
O1A O 0.62690(19) 0.58064(8) 0.4688(2) 0.0422(6) Uani 0.832(4) 1 d . . P A 1
H1A H 0.608590 0.574190 0.385314 0.063 Uiso 0.832(4) 1 calc R U P A 1
O1B O 0.5367(13) 0.6237(5) 0.3916(11) 0.062(4) Uani 0.168(4) 1 d . . P A 2
H1B H 0.552945 0.598734 0.343091 0.092 Uiso 0.168(4) 1 calc R U P A 2
C21B C 0.518(2) 0.6090(11) 0.529(3) 0.0366(10) Uani 0.168(4) 1 d . . P A 2
H22A H 0.386(2) 0.6173(11) 0.611(3) 0.045(8) Uiso 1 1 d . . . . .
H22B H 0.461(3) 0.5667(12) 0.645(3) 0.058(9) Uiso 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Cl1 C1 1.746(3) . ?
Cl2 C11 1.738(3) . ?
Cl3 C18 1.740(3) . ?
N1 H1 1.0000 . ?
N1 C22 1.510(3) . ?
N1 C23 1.500(4) . ?
N1 C27 1.497(4) . ?
C1 C2 1.376(4) . ?
C1 C6 1.378(4) . ?
C2 H2 0.9500 . ?
C2 C3 1.380(4) . ?
C3 H3 0.9500 . ?
C3 C4 1.397(4) . ?
C4 C5 1.393(4) . ?
C4 C7 1.471(4) . ?
C5 H5 0.9500 . ?
C5 C6 1.386(4) . ?
C6 H6 0.9500 . ?
C7 H7 0.9500 . ?
C7 C8 1.346(4) . ?
C8 C9 1.483(4) . ?
C8 C20 1.487(3) . ?
C9 C10 1.391(3) . ?
C9 C14 1.418(3) . ?
C10 H10 0.9500 . ?
C10 C11 1.387(4) . ?
C11 C12 1.378(4) . ?
C12 H12 0.9500 . ?
C12 C13 1.396(4) . ?
C13 C14 1.397(4) . ?
C13 C21A 1.475(5) . ?
C13 C21B 1.73(3) . ?
C14 C15 1.477(3) . ?
C15 C16 1.393(3) . ?
C15 C20 1.402(3) . ?
C16 H16 0.9500 . ?
C16 C17 1.382(4) . ?
C17 H17 0.9500 . ?
C17 C18 1.378(4) . ?
C18 C19 1.383(4) . ?
C19 H19 0.9500 . ?
C19 C20 1.386(3) . ?
C21A H21A 1.0000 . ?
C21A C22 1.551(4) . ?
C21A O1A 1.398(5) . ?
C22 C21B 1.10(2) . ?
C22 H22A 0.95(3) . ?
C22 H22B 1.03(3) . ?
C23 H23A 0.9900 . ?
C23 H23B 0.9900 . ?
C23 C24 1.502(4) . ?
C24 H24A 0.9900 . ?
C24 H24B 0.9900 . ?
C24 C25 1.516(5) . ?
C25 H25A 0.9900 . ?
C25 H25B 0.9900 . ?
C25 C26 1.493(6) . ?
C26 H26A 0.9800 . ?
C26 H26B 0.9800 . ?
C26 H26C 0.9800 . ?
C27 H27A 0.9900 . ?
C27 H27B 0.9900 . ?
C27 C28 1.500(5) . ?
C28 H28A 0.9900 . ?
C28 H28B 0.9900 . ?
C28 C29A 1.585(6) . ?
C28 C29B 1.605(14) . ?
C29A H29A 0.9900 . ?
C29A H29B 0.9900 . ?
C29A C21 1.475(6) . ?
C21 H21B 0.9800 . ?
C21 H21C 0.9800 . ?
C21 H21D 0.9800 . ?
C29B H29C 0.9900 . ?
C29B H29D 0.9900 . ?
C29B C30B 1.62(3) . ?
C30B H30A 0.9800 . ?
C30B H30B 0.9800 . ?
C30B H30C 0.9800 . ?
O4 C34 1.256(6) . ?
O5 C34 1.260(6) . ?
C34 C33 1.510(7) . ?
C33 C33 1.301(12) 3_665 ?
C33 H33 0.9500 . ?
O2 C31 1.260(13) . ?
O3 C31 1.254(13) . ?
C31 C32 1.505(14) . ?
C32 C32 1.29(3) 3_665 ?
C32 H32 0.9500 . ?
O1A H1A 0.8400 . ?
O1B H1B 0.8400 . ?
O1B C21B 1.39(3) . ?

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
C22 N1 H1 106.5 . . ?
C23 N1 H1 106.5 . . ?
C23 N1 C22 110.7(2) . . ?
C27 N1 H1 106.5 . . ?
C27 N1 C22 109.7(2) . . ?
C27 N1 C23 116.3(2) . . ?
C2 C1 Cl1 118.9(2) . . ?
C2 C1 C6 121.5(3) . . ?
C6 C1 Cl1 119.5(2) . . ?
C1 C2 H2 120.5 . . ?
C1 C2 C3 119.0(3) . . ?
C3 C2 H2 120.5 . . ?
C2 C3 H3 119.4 . . ?
C2 C3 C4 121.3(3) . . ?
C4 C3 H3 119.4 . . ?
C3 C4 C7 118.4(2) . . ?
C5 C4 C3 118.0(2) . . ?
C5 C4 C7 123.5(2) . . ?
C4 C5 H5 119.5 . . ?
C6 C5 C4 121.0(3) . . ?
C6 C5 H5 119.5 . . ?
C1 C6 C5 119.0(3) . . ?
C1 C6 H6 120.5 . . ?
C5 C6 H6 120.5 . . ?
C4 C7 H7 114.9 . . ?
C8 C7 C4 130.3(3) . . ?
C8 C7 H7 114.9 . . ?
C7 C8 C9 132.7(2) . . ?
C7 C8 C20 122.7(2) . . ?
C9 C8 C20 104.6(2) . . ?
C10 C9 C8 130.6(2) . . ?
C10 C9 C14 120.2(2) . . ?
C14 C9 C8 109.1(2) . . ?
C9 C10 H10 121.0 . . ?
C11 C10 C9 117.9(2) . . ?
C11 C10 H10 121.0 . . ?
C10 C11 Cl2 118.9(2) . . ?
C12 C11 Cl2 118.6(2) . . ?
C12 C11 C10 122.4(2) . . ?
C11 C12 H12 119.8 . . ?
C11 C12 C13 120.4(2) . . ?
C13 C12 H12 119.8 . . ?
C12 C13 C14 118.2(2) . . ?
C12 C13 C21A 118.2(3) . . ?
C12 C13 C21B 114.4(11) . . ?
C14 C13 C21A 123.4(3) . . ?
C14 C13 C21B 126.7(11) . . ?
C9 C14 C15 107.9(2) . . ?
C13 C14 C9 120.4(2) . . ?
C13 C14 C15 131.8(2) . . ?
C16 C15 C14 132.5(2) . . ?
C16 C15 C20 119.2(2) . . ?
C20 C15 C14 108.2(2) . . ?
C15 C16 H16 120.2 . . ?
C17 C16 C15 119.6(2) . . ?
C17 C16 H16 120.2 . . ?
C16 C17 H17 120.0 . . ?
C18 C17 C16 119.9(2) . . ?
C18 C17 H17 120.0 . . ?
C17 C18 Cl3 119.1(2) . . ?
C17 C18 C19 122.4(2) . . ?
C19 C18 Cl3 118.5(2) . . ?
C18 C19 H19 121.3 . . ?
C18 C19 C20 117.4(2) . . ?
C20 C19 H19 121.3 . . ?
C15 C20 C8 109.7(2) . . ?
C19 C20 C8 128.7(2) . . ?
C19 C20 C15 121.6(2) . . ?
C13 C21A H21A 109.5 . . ?
C13 C21A C22 108.3(3) . . ?
C22 C21A H21A 109.5 . . ?
O1A C21A C13 108.8(3) . . ?
O1A C21A H21A 109.5 . . ?
O1A C21A C22 111.1(3) . . ?
N1 C22 C21A 114.6(3) . . ?
N1 C22 H22A 102.3(17) . . ?
N1 C22 H22B 109.0(17) . . ?
C21A C22 H22A 112.8(17) . . ?
C21A C22 H22B 106.3(17) . . ?
C21B C22 N1 111.2(16) . . ?
C21B C22 H22A 115(2) . . ?
C21B C22 H22B 107(2) . . ?
H22A C22 H22B 112(2) . . ?
N1 C23 H23A 108.3 . . ?
N1 C23 H23B 108.3 . . ?
N1 C23 C24 115.8(2) . . ?
H23A C23 H23B 107.4 . . ?
C24 C23 H23A 108.3 . . ?
C24 C23 H23B 108.3 . . ?
C23 C24 H24A 109.5 . . ?
C23 C24 H24B 109.5 . . ?
C23 C24 C25 110.7(3) . . ?
H24A C24 H24B 108.1 . . ?
C25 C24 H24A 109.5 . . ?
C25 C24 H24B 109.5 . . ?
C24 C25 H25A 108.9 . . ?
C24 C25 H25B 108.9 . . ?
H25A C25 H25B 107.8 . . ?
C26 C25 C24 113.1(3) . . ?
C26 C25 H25A 108.9 . . ?
C26 C25 H25B 108.9 . . ?
C25 C26 H26A 109.5 . . ?
C25 C26 H26B 109.5 . . ?
C25 C26 H26C 109.5 . . ?
H26A C26 H26B 109.5 . . ?
H26A C26 H26C 109.5 . . ?
H26B C26 H26C 109.5 . . ?
N1 C27 H27A 108.4 . . ?
N1 C27 H27B 108.4 . . ?
N1 C27 C28 115.4(3) . . ?
H27A C27 H27B 107.5 . . ?
C28 C27 H27A 108.4 . . ?
C28 C27 H27B 108.4 . . ?
C27 C28 H28A 110.7 . . ?
C27 C28 H28B 110.7 . . ?
C27 C28 C29A 105.2(3) . . ?
C27 C28 C29B 128.7(7) . . ?
H28A C28 H28B 108.8 . . ?
C29A C28 H28A 110.7 . . ?
C29A C28 H28B 110.7 . . ?
C28 C29A H29A 109.7 . . ?
C28 C29A H29B 109.7 . . ?
H29A C29A H29B 108.2 . . ?
C21 C29A C28 109.9(4) . . ?
C21 C29A H29A 109.7 . . ?
C21 C29A H29B 109.7 . . ?
C29A C21 H21B 109.5 . . ?
C29A C21 H21C 109.5 . . ?
C29A C21 H21D 109.5 . . ?
H21B C21 H21C 109.5 . . ?
H21B C21 H21D 109.5 . . ?
H21C C21 H21D 109.5 . . ?
C28 C29B H29C 111.1 . . ?
C28 C29B H29D 111.1 . . ?
C28 C29B C30B 103.4(14) . . ?
H29C C29B H29D 109.0 . . ?
C30B C29B H29C 111.1 . . ?
C30B C29B H29D 111.1 . . ?
C29B C30B H30A 109.5 . . ?
C29B C30B H30B 109.5 . . ?
C29B C30B H30C 109.5 . . ?
H30A C30B H30B 109.5 . . ?
H30A C30B H30C 109.5 . . ?
H30B C30B H30C 109.5 . . ?
O4 C34 O5 125.6(5) . . ?
O4 C34 C33 119.0(5) . . ?
O5 C34 C33 115.4(5) . . ?
C34 C33 H33 118.2 . . ?
C33 C33 C34 123.7(7) 3_665 . ?
C33 C33 H33 118.2 3_665 . ?
O2 C31 C32 117.7(14) . . ?
O3 C31 O2 126.6(13) . . ?
O3 C31 C32 115.6(12) . . ?
C31 C32 H32 117.3 . . ?
C32 C32 C31 125.4(17) 3_665 . ?
C32 C32 H32 117.3 3_665 . ?
C21A O1A H1A 109.5 . . ?
C21B O1B H1B 109.5 . . ?
C22 C21B C13 118(2) . . ?
C22 C21B O1B 128(3) . . ?
O1B C21B C13 108.5(17) . . ?

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
Cl1 C1 C2 C3 179.5(2) . . . . ?
Cl1 C1 C6 C5 179.3(2) . . . . ?
Cl2 C11 C12 C13 177.25(19) . . . . ?
Cl3 C18 C19 C20 179.09(18) . . . . ?
N1 C22 C21B C13 174.4(14) . . . . ?
N1 C22 C21B O1B 24(3) . . . . ?
N1 C23 C24 C25 -176.7(3) . . . . ?
N1 C27 C28 C29A -177.7(3) . . . . ?
N1 C27 C28 C29B 147.4(8) . . . . ?
C1 C2 C3 C4 2.6(4) . . . . ?
C2 C1 C6 C5 -1.6(4) . . . . ?
C2 C3 C4 C5 -4.3(4) . . . . ?
C2 C3 C4 C7 178.7(2) . . . . ?
C3 C4 C5 C6 3.1(4) . . . . ?
C3 C4 C7 C8 -144.2(3) . . . . ?
C4 C5 C6 C1 -0.2(4) . . . . ?
C4 C7 C8 C9 2.2(5) . . . . ?
C4 C7 C8 C20 -174.2(2) . . . . ?
C5 C4 C7 C8 39.0(4) . . . . ?
C6 C1 C2 C3 0.4(4) . . . . ?
C7 C4 C5 C6 179.9(3) . . . . ?
C7 C8 C9 C10 14.2(5) . . . . ?
C7 C8 C9 C14 -169.6(3) . . . . ?
C7 C8 C20 C15 170.9(2) . . . . ?
C7 C8 C20 C19 -7.9(4) . . . . ?
C8 C9 C10 C11 179.2(2) . . . . ?
C8 C9 C14 C13 175.0(2) . . . . ?
C8 C9 C14 C15 -5.7(3) . . . . ?
C9 C8 C20 C15 -6.3(3) . . . . ?
C9 C8 C20 C19 174.8(2) . . . . ?
C9 C10 C11 Cl2 -178.44(18) . . . . ?
C9 C10 C11 C12 2.8(4) . . . . ?
C9 C14 C15 C16 -174.7(3) . . . . ?
C9 C14 C15 C20 1.6(3) . . . . ?
C10 C9 C14 C13 -8.2(4) . . . . ?
C10 C9 C14 C15 171.0(2) . . . . ?
C10 C11 C12 C13 -3.9(4) . . . . ?
C11 C12 C13 C14 -1.0(4) . . . . ?
C11 C12 C13 C21A 173.2(2) . . . . ?
C11 C12 C13 C21B -172.2(10) . . . . ?
C12 C13 C14 C9 7.0(4) . . . . ?
C12 C13 C14 C15 -172.1(2) . . . . ?
C12 C13 C21A C22 78.8(4) . . . . ?
C12 C13 C21A O1A -42.1(4) . . . . ?
C12 C13 C21B C22 73(3) . . . . ?
C12 C13 C21B O1B -131.0(15) . . . . ?
C13 C14 C15 C16 4.5(5) . . . . ?
C13 C14 C15 C20 -179.2(2) . . . . ?
C13 C21A C22 N1 174.8(3) . . . . ?
C14 C9 C10 C11 3.3(3) . . . . ?
C14 C13 C21A C22 -107.2(3) . . . . ?
C14 C13 C21A O1A 131.9(3) . . . . ?
C14 C13 C21B C22 -97(2) . . . . ?
C14 C13 C21B O1B 59(2) . . . . ?
C14 C15 C16 C17 176.8(3) . . . . ?
C14 C15 C20 C8 3.1(3) . . . . ?
C14 C15 C20 C19 -178.0(2) . . . . ?
C15 C16 C17 C18 -0.3(4) . . . . ?
C16 C15 C20 C8 180.0(2) . . . . ?
C16 C15 C20 C19 -1.1(4) . . . . ?
C16 C17 C18 Cl3 -179.4(2) . . . . ?
C16 C17 C18 C19 0.2(4) . . . . ?
C17 C18 C19 C20 -0.5(4) . . . . ?
C18 C19 C20 C8 179.6(2) . . . . ?
C18 C19 C20 C15 0.9(4) . . . . ?
C20 C8 C9 C10 -168.9(2) . . . . ?
C20 C8 C9 C14 7.3(3) . . . . ?
C20 C15 C16 C17 0.8(4) . . . . ?
C21A C13 C14 C9 -167.0(2) . . . . ?
C21A C13 C14 C15 14.0(4) . . . . ?
C22 N1 C23 C24 66.4(3) . . . . ?
C22 N1 C27 C28 -178.2(3) . . . . ?
C23 N1 C22 C21A 153.5(3) . . . . ?
C23 N1 C22 C21B 152.5(17) . . . . ?
C23 N1 C27 C28 -51.7(4) . . . . ?
C23 C24 C25 C26 179.7(4) . . . . ?
C27 N1 C22 C21A -76.8(4) . . . . ?
C27 N1 C22 C21B -77.8(18) . . . . ?
C27 N1 C23 C24 -59.6(3) . . . . ?
C27 C28 C29A C21 -177.5(4) . . . . ?
C27 C28 C29B C30B 66.0(18) . . . . ?
O4 C34 C33 C33 -8.1(8) . . . 3_665 ?
O5 C34 C33 C33 172.4(5) . . . 3_665 ?
O2 C31 C32 C32 -2(2) . . . 3_665 ?
O3 C31 C32 C32 -178.7(15) . . . 3_665 ?
O1A C21A C22 N1 -65.7(4) . . . . ?
C21B C13 C14 C9 177.0(11) . . . . ?
C21B C13 C14 C15 -2.1(12) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
