# Electronic Supplementary Material (ESI) for CrystEngComm.
# This journal is © The Royal Society of Chemistry 2024

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
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# 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 
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data_cu_v4_21dfd1_0m
_database_code_depnum_ccdc_archive 'CCDC 2116481'
loop_
_audit_author_name
_audit_author_address
'Dumisani Vincent Kama'
;University Of The Free State
South Africa
;
_audit_update_record             
;
2023-03-09 deposited with the CCDC.	2024-01-18 downloaded from the CCDC.
;
_audit_creation_date             2023-03-09
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6408)
;
_shelx_SHELXL_version_number     2019/2
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C22 H24 Cl N O4'
_chemical_formula_sum            'C22 H24 Cl N O4'
_chemical_formula_weight         401.87
_chemical_absolute_configuration ?
_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      monoclinic
_space_group_IT_number           4
_space_group_name_H-M_alt        'P 1 21 1'
_space_group_name_Hall           'P 2yb'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z'

_cell_length_a                   15.207(2)
_cell_length_b                   5.1052(7)
_cell_length_c                   26.456(4)
_cell_angle_alpha                90
_cell_angle_beta                 99.547(5)
_cell_angle_gamma                90
_cell_volume                     2025.4(5)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9748
_cell_measurement_temperature    109.0
_cell_measurement_theta_max      53.45
_cell_measurement_theta_min      3.39
_shelx_estimated_absorpt_T_max   0.963
_shelx_estimated_absorpt_T_min   0.520
_exptl_absorpt_coefficient_mu    1.900
_exptl_absorpt_correction_T_max  0.7505
_exptl_absorpt_correction_T_min  0.5923
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016) was used for absorption correction.
wR2(int) was 0.1657 before and 0.0986 after correction.
The Ratio of minimum to maximum transmission is 0.7892.
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    1.318
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       Needle
_exptl_crystal_F_000             848
_exptl_crystal_size_max          0.396
_exptl_crystal_size_mid          0.077
_exptl_crystal_size_min          0.02
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0677
_diffrn_reflns_av_unetI/netI     0.0499
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_number            19172
_diffrn_reflns_point_group_measured_fraction_full 0.978
_diffrn_reflns_point_group_measured_fraction_max 0.978
_diffrn_reflns_theta_full        53.493
_diffrn_reflns_theta_max         53.493
_diffrn_reflns_theta_min         1.693
_diffrn_ambient_temperature      109.0
_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           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_source                   ?
_diffrn_source_current           1.2
_diffrn_source_power             0.06
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.720
_reflns_Friedel_fraction_full    0.952
_reflns_Friedel_fraction_max     0.951
_reflns_number_gt                4454
_reflns_number_total             4721
_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. Completness statistics refer to single and
 composite reflections containing twin component 1 only.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       ?
_computing_data_collection       ?
_computing_data_reduction        ?
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2019/2 (Sheldrick, 2015)'
_computing_structure_solution    'olex2.solve 1.3 (Bourhis et al., 2015)'
_refine_diff_density_max         0.210
_refine_diff_density_min         -0.291
_refine_diff_density_rms         0.046
_refine_ls_abs_structure_details 
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   0.15(2)
_refine_ls_extinction_coef       0.0041(4)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2019/2 (Sheldrick 2019)'
_refine_ls_goodness_of_fit_ref   1.043
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     541
_refine_ls_number_reflns         4721
_refine_ls_number_restraints     3
_refine_ls_R_factor_all          0.0429
_refine_ls_R_factor_gt           0.0389
_refine_ls_restrained_S_all      1.043
_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)+(0.0540P)²+1.1613P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1027
_refine_ls_wR_factor_ref         0.1061
_refine_special_details          
;
 Refined as a 2-component inversion twin.
;
_olex2_refinement_description    
;
1. Twinned data refinement
 Scales: 0.85(2)
 0.15(2)
2. 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
3. Restrained distances
 C23A-O6
 1.35 with sigma of 0.01
 C23-O6
 1.35 with sigma of 0.01
 C24-H24
 1 with sigma of 0.02
4. Uiso/Uaniso restraints and constraints
Uanis(C23A) = Uanis(O5A)
Uanis(C28) = Uanis(C29A)
Uanis(C23) = Uanis(O5)
Uanis(O6A) = Uanis(C23A)
Uanis(O6) = Uanis(C23)
Uanis(C30) = Uanis(C29)
Uanis(C28A) = Uanis(C27A)
5. Others
 Fixed Sof: O6(0.56) C23(0.56) C27(0.56) C29(0.56) H29A(0.56) H29B(0.56)
 H29C(0.56) C28(0.56) H28A(0.56) H28B(0.56) H28C(0.56) C30(0.56) H30A(0.56)
 H30B(0.56) H30C(0.56) O5(0.56) O5A(0.44) C28A(0.44) H28D(0.44) H28E(0.44)
 H28F(0.44) C27A(0.44) C30A(0.44) H30D(0.44) H30E(0.44) H30F(0.44) C29A(0.44)
 H29D(0.44) H29E(0.44) H29F(0.44) C23A(0.44) O6A(0.44)
6.a Ternary CH refined with riding coordinates:
 C32(H32), C10(H10), C2(H2A)
6.b Secondary CH2 refined with riding coordinates:
 C9(H9A,H9B), C31(H31A,H31B), C25(H25A,H25B), C3(H3A,H3B)
6.c Aromatic/amide H refined with riding coordinates:
 N1(H1), N2(H2), C12(H12), C21(H21), C34(H34), C36(H36), C35(H35), C15(H15),
 C43(H43), C18(H18), C20(H20), C40(H40), C14(H14), C19(H19), C13(H13), C42(H42),
  C37(H37), C41(H41)
6.d Idealised Me refined as rotating group:
 C8(H8A,H8B,H8C), C6(H6A,H6B,H6C), C7(H7A,H7B,H7C), C29(H29A,H29B,H29C),
 C28(H28A,H28B,H28C), C30(H30A,H30B,H30C), C28A(H28D,H28E,H28F), C30A(H30D,H30E,
 H30F), C29A(H29D,H29E,H29F)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     iterative
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Cl1 Cl 0.15286(9) 0.7918(3) 0.49983(5) 0.0435(4) Uani 1 1 d . . . . .
Cl2 Cl -0.13746(9) 1.0054(3) 0.75801(5) 0.0538(4) Uani 1 1 d . . . . .
O8 O 0.1250(2) 0.6375(6) 0.89316(11) 0.0263(8) Uani 1 1 d . . . . .
O4 O 0.3497(2) 0.5386(6) 0.66267(11) 0.0294(8) Uani 1 1 d . . . . .
O7 O 0.0785(2) 0.3059(7) 0.83843(12) 0.0334(8) Uani 1 1 d . . . . .
O3 O 0.3143(2) 0.2056(6) 0.60615(11) 0.0325(8) Uani 1 1 d . . . . .
O2 O 0.3482(2) 0.6359(6) 0.44534(11) 0.0315(8) Uani 1 1 d . . . . .
O1 O 0.3814(2) 0.9465(7) 0.50691(12) 0.0362(9) Uani 1 1 d . . . . .
O6 O 0.0045(8) 0.759(2) 0.6782(4) 0.0272(11) Uani 0.56 1 d D . P A 1
N1 N 0.3293(3) 0.6220(8) 0.57860(13) 0.0281(10) Uani 1 1 d . . . . .
H1 H 0.338642 0.787914 0.586777 0.034 Uiso 1 1 calc R U . . .
N2 N 0.0414(3) 0.7282(8) 0.81773(15) 0.0418(12) Uani 1 1 d . . . . .
H2 H 0.039695 0.890183 0.828889 0.050 Uiso 1 1 calc R U . . .
C4 C 0.3294(3) 0.4372(10) 0.61477(17) 0.0274(12) Uani 1 1 d . . . . .
C11 C 0.4854(3) 0.4838(9) 0.76013(15) 0.0252(11) Uani 1 1 d . . . . .
C38 C 0.2801(3) 0.3251(10) 1.04671(16) 0.0265(11) Uani 1 1 d . . . . .
C26 C 0.0808(3) 0.5383(10) 0.84833(17) 0.0273(11) Uani 1 1 d . . . . .
C33 C 0.2976(3) 0.3755(9) 0.99727(17) 0.0261(11) Uani 1 1 d . . . . .
C1 C 0.3525(3) 0.7333(10) 0.49239(18) 0.0308(12) Uani 1 1 d . . . . .
C12 C 0.5376(3) 0.6527(10) 0.73671(17) 0.0300(12) Uani 1 1 d . . . . .
H12 H 0.510535 0.779706 0.712826 0.036 Uiso 1 1 calc R U . . .
C32 C 0.2323(3) 0.5768(9) 0.97063(16) 0.0248(11) Uani 1 1 d . . . . .
H32 H 0.264536 0.734220 0.960583 0.030 Uiso 1 1 calc R U . . .
C16 C 0.5256(3) 0.2974(10) 0.79579(15) 0.0253(11) Uani 1 1 d . . . . .
C21 C 0.2953(3) 0.1594(11) 0.80794(16) 0.0302(12) Uani 1 1 d . . . . .
H21 H 0.238840 0.225968 0.792511 0.036 Uiso 1 1 calc R U . . .
C22 C 0.3728(3) 0.2574(9) 0.79458(16) 0.0257(11) Uani 1 1 d . . . . .
C34 C 0.3639(3) 0.2400(10) 0.97869(18) 0.0297(12) Uani 1 1 d . . . . .
H34 H 0.376441 0.274884 0.945329 0.036 Uiso 1 1 calc R U . . .
C10 C 0.3846(3) 0.4604(10) 0.75427(15) 0.0258(11) Uani 1 1 d . . . . .
H10 H 0.356749 0.631290 0.761192 0.031 Uiso 1 1 calc R U . . .
C17 C 0.4557(3) 0.1577(10) 0.81669(16) 0.0255(11) Uani 1 1 d . . . . .
C24 C 0.0019(3) 0.6610(11) 0.76626(19) 0.0347(12) Uani 1 1 d D . . . .
C39 C 0.2060(3) 0.4949(10) 1.05607(16) 0.0287(11) Uani 1 1 d . . . . .
C9 C 0.3423(3) 0.3483(10) 0.70252(16) 0.0284(11) Uani 1 1 d . . . . .
H9A H 0.372937 0.184041 0.695743 0.034 Uiso 1 1 calc R U . . .
H9B H 0.278712 0.307648 0.702799 0.034 Uiso 1 1 calc R U . . .
C36 C 0.3946(3) 0.0010(11) 1.05787(19) 0.0364(13) Uani 1 1 d . . . . .
H36 H 0.428407 -0.128548 1.078343 0.044 Uiso 1 1 calc R U . . .
C35 C 0.4120(3) 0.0523(10) 1.00944(19) 0.0356(13) Uani 1 1 d . . . . .
H35 H 0.457628 -0.042483 0.996903 0.043 Uiso 1 1 calc R U . . .
C44 C 0.1777(3) 0.6457(10) 1.01177(17) 0.0269(11) Uani 1 1 d . . . . .
C15 C 0.6176(3) 0.2750(11) 0.80679(17) 0.0332(12) Uani 1 1 d . . . . .
H15 H 0.644939 0.146259 0.830200 0.040 Uiso 1 1 calc R U . . .
C43 C 0.1089(3) 0.8219(10) 1.01084(17) 0.0298(11) Uani 1 1 d . . . . .
H43 H 0.088414 0.920602 0.980738 0.036 Uiso 1 1 calc R U . . .
C18 C 0.4612(3) -0.0431(10) 0.85339(17) 0.0306(12) Uani 1 1 d . . . . .
H18 H 0.517454 -0.111612 0.868707 0.037 Uiso 1 1 calc R U . . .
C2 C 0.3134(3) 0.5371(10) 0.52550(16) 0.0303(11) Uani 1 1 d . . . . .
H2A H 0.345308 0.367042 0.523573 0.036 Uiso 1 1 calc R U . . .
C31 C 0.1796(3) 0.4439(10) 0.92359(16) 0.0278(11) Uani 1 1 d . . . . .
H31A H 0.221071 0.362361 0.903021 0.033 Uiso 1 1 calc R U . . .
H31B H 0.141366 0.304579 0.934336 0.033 Uiso 1 1 calc R U . . .
C20 C 0.3014(3) -0.0379(11) 0.84428(17) 0.0349(13) Uani 1 1 d . . . . .
H20 H 0.248388 -0.105292 0.854018 0.042 Uiso 1 1 calc R U . . .
C40 C 0.1657(3) 0.5240(11) 1.09897(18) 0.0360(13) Uani 1 1 d . . . . .
H40 H 0.184646 0.421791 1.128804 0.043 Uiso 1 1 calc R U . . .
C14 C 0.6690(3) 0.4449(11) 0.78281(18) 0.0372(13) Uani 1 1 d . . . . .
H14 H 0.732116 0.431760 0.789958 0.045 Uiso 1 1 calc R U . . .
C19 C 0.3832(3) -0.1390(10) 0.86677(17) 0.0341(13) Uani 1 1 d . . . . .
H19 H 0.385695 -0.274962 0.891488 0.041 Uiso 1 1 calc R U . . .
C13 C 0.6295(3) 0.6341(11) 0.74850(18) 0.0374(13) Uani 1 1 d . . . . .
H13 H 0.665785 0.751096 0.733090 0.045 Uiso 1 1 calc R U . . .
C5 C 0.3669(4) 0.8035(10) 0.40214(17) 0.0340(12) Uani 1 1 d . . . . .
C42 C 0.0695(3) 0.8544(10) 1.05424(18) 0.0356(13) Uani 1 1 d . . . . .
H42 H 0.023323 0.979697 1.054156 0.043 Uiso 1 1 calc R U . . .
C37 C 0.3279(3) 0.1372(11) 1.07726(19) 0.0353(13) Uani 1 1 d . . . . .
H37 H 0.315709 0.101560 1.110650 0.042 Uiso 1 1 calc R U . . .
C8 C 0.2918(3) 1.0023(12) 0.39188(19) 0.0408(13) Uani 1 1 d . . . . .
H8A H 0.300273 1.136618 0.418713 0.061 Uiso 1 1 calc R U . . .
H8B H 0.234575 0.913843 0.391852 0.061 Uiso 1 1 calc R U . . .
H8C H 0.292011 1.084760 0.358451 0.061 Uiso 1 1 calc R U . . .
C41 C 0.0974(3) 0.7047(12) 1.09765(19) 0.0406(14) Uani 1 1 d . . . . .
H41 H 0.069296 0.726340 1.126886 0.049 Uiso 1 1 calc R U . . .
C25 C -0.0974(3) 0.6760(12) 0.75622(19) 0.0401(14) Uani 1 1 d . . . . .
H25A H -0.121409 0.570307 0.782194 0.048 Uiso 1 1 calc R U . . .
H25B H -0.119805 0.599539 0.722129 0.048 Uiso 1 1 calc R U . . .
C6 C 0.4579(4) 0.9248(13) 0.4137(2) 0.0464(14) Uani 1 1 d . . . . .
H6A H 0.472488 1.006353 0.382596 0.070 Uiso 1 1 calc R U . . .
H6B H 0.502076 0.789159 0.425682 0.070 Uiso 1 1 calc R U . . .
H6C H 0.458625 1.058249 0.440411 0.070 Uiso 1 1 calc R U . . .
C3 C 0.2155(3) 0.4907(11) 0.50529(17) 0.0366(12) Uani 1 1 d . . . . .
H3A H 0.190740 0.370107 0.528653 0.044 Uiso 1 1 calc R U . . .
H3B H 0.209248 0.406044 0.471214 0.044 Uiso 1 1 calc R U . . .
C7 C 0.3597(5) 0.6147(12) 0.35760(19) 0.0579(19) Uani 1 1 d . . . . .
H7A H 0.299943 0.536757 0.351473 0.087 Uiso 1 1 calc R U . . .
H7B H 0.404386 0.476143 0.365603 0.087 Uiso 1 1 calc R U . . .
H7C H 0.369940 0.708989 0.326837 0.087 Uiso 1 1 calc R U . . .
C23 C 0.0358(7) 0.8528(19) 0.7250(3) 0.0272(11) Uani 0.56 1 d D . P A 1
C27 C 0.0109(10) 0.915(2) 0.6304(6) 0.039(3) Uani 0.56 1 d . . P A 1
C29 C -0.0239(14) 0.730(3) 0.5881(6) 0.060(3) Uani 0.56 1 d . . P A 1
H29A H 0.015955 0.578147 0.589458 0.090 Uiso 0.56 1 calc R U P A 1
H29B H -0.026745 0.818464 0.555010 0.090 Uiso 0.56 1 calc R U P A 1
H29C H -0.083704 0.670977 0.592086 0.090 Uiso 0.56 1 calc R U P A 1
C28 C 0.1100(8) 0.978(3) 0.6299(4) 0.057(3) Uani 0.56 1 d . . P A 1
H28A H 0.130923 1.106896 0.656550 0.086 Uiso 0.56 1 calc R U P A 1
H28B H 0.116719 1.048636 0.596306 0.086 Uiso 0.56 1 calc R U P A 1
H28C H 0.145285 0.816945 0.636420 0.086 Uiso 0.56 1 calc R U P A 1
C30 C -0.0440(9) 1.156(2) 0.6325(4) 0.060(3) Uani 0.56 1 d . . P A 1
H30A H -0.104263 1.106286 0.637346 0.090 Uiso 0.56 1 calc R U P A 1
H30B H -0.047078 1.253689 0.600378 0.090 Uiso 0.56 1 calc R U P A 1
H30C H -0.016628 1.266097 0.661208 0.090 Uiso 0.56 1 calc R U P A 1
O5 O 0.0765(4) 1.0501(11) 0.73492(19) 0.0272(11) Uani 0.56 1 d . . P A 1
O5A O 0.1343(5) 0.834(2) 0.7513(3) 0.0472(18) Uani 0.44 1 d . . P A 2
C28A C 0.0859(9) 1.183(3) 0.6616(5) 0.049(3) Uani 0.44 1 d . . P A 2
H28D H 0.109074 1.271801 0.633643 0.074 Uiso 0.44 1 calc R U P A 2
H28E H 0.132055 1.180599 0.692223 0.074 Uiso 0.44 1 calc R U P A 2
H28F H 0.033530 1.277970 0.669150 0.074 Uiso 0.44 1 calc R U P A 2
C27A C 0.0602(14) 0.910(4) 0.6460(7) 0.049(3) Uani 0.44 1 d . . P A 2
C30A C -0.0115(12) 0.881(4) 0.5980(7) 0.061(7) Uani 0.44 1 d . . P A 2
H30D H -0.067256 0.960978 0.604376 0.092 Uiso 0.44 1 calc R U P A 2
H30E H -0.021472 0.695052 0.589971 0.092 Uiso 0.44 1 calc R U P A 2
H30F H 0.008461 0.969440 0.568999 0.092 Uiso 0.44 1 calc R U P A 2
C29A C 0.1438(10) 0.752(3) 0.6406(6) 0.057(3) Uani 0.44 1 d . . P A 2
H29D H 0.169285 0.819194 0.611472 0.086 Uiso 0.44 1 calc R U P A 2
H29E H 0.127943 0.567394 0.634898 0.086 Uiso 0.44 1 calc R U P A 2
H29F H 0.187728 0.769585 0.672037 0.086 Uiso 0.44 1 calc R U P A 2
C23A C 0.0558(10) 0.766(3) 0.7356(6) 0.0472(18) Uani 0.44 1 d . . P A 2
O6A O 0.0173(11) 0.786(4) 0.6860(6) 0.0472(18) Uani 0.44 1 d . . P A 2
H24 H 0.020(3) 0.479(6) 0.761(2) 0.047(15) Uiso 1 1 d 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 C3 1.801(6) . ?
Cl2 C25 1.792(6) . ?
O8 C26 1.361(6) . ?
O8 C31 1.447(6) . ?
O4 C4 1.356(6) . ?
O4 C9 1.452(5) . ?
O7 C26 1.214(6) . ?
O3 C4 1.219(6) . ?
O2 C1 1.332(6) . ?
O2 C5 1.492(6) . ?
O1 C1 1.212(6) . ?
O6 C23 1.340(11) . ?
O6 C27 1.513(18) . ?
N1 H1 0.8800 . ?
N1 C4 1.343(6) . ?
N1 C2 1.452(6) . ?
N2 H2 0.8800 . ?
N2 C26 1.339(6) . ?
N2 C24 1.436(6) . ?
C11 C12 1.385(7) . ?
C11 C16 1.407(7) . ?
C11 C10 1.520(6) . ?
C38 C33 1.401(6) . ?
C38 C39 1.476(7) . ?
C38 C37 1.381(7) . ?
C33 C32 1.519(6) . ?
C33 C34 1.379(7) . ?
C1 C2 1.516(7) . ?
C12 H12 0.9500 . ?
C12 C13 1.384(7) . ?
C32 H32 1.0000 . ?
C32 C44 1.516(6) . ?
C32 C31 1.523(6) . ?
C16 C17 1.463(7) . ?
C16 C15 1.385(7) . ?
C21 H21 0.9500 . ?
C21 C22 1.379(7) . ?
C21 C20 1.385(7) . ?
C22 C10 1.519(7) . ?
C22 C17 1.395(6) . ?
C34 H34 0.9500 . ?
C34 C35 1.384(7) . ?
C10 H10 1.0000 . ?
C10 C9 1.524(6) . ?
C17 C18 1.405(7) . ?
C24 C25 1.491(7) . ?
C24 C23 1.614(11) . ?
C24 C23A 1.357(17) . ?
C24 H24 0.99(3) . ?
C39 C44 1.408(7) . ?
C39 C40 1.384(7) . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C36 H36 0.9500 . ?
C36 C35 1.375(7) . ?
C36 C37 1.396(7) . ?
C35 H35 0.9500 . ?
C44 C43 1.377(7) . ?
C15 H15 0.9500 . ?
C15 C14 1.389(7) . ?
C43 H43 0.9500 . ?
C43 C42 1.390(7) . ?
C18 H18 0.9500 . ?
C18 C19 1.383(7) . ?
C2 H2A 1.0000 . ?
C2 C3 1.514(7) . ?
C31 H31A 0.9900 . ?
C31 H31B 0.9900 . ?
C20 H20 0.9500 . ?
C20 C19 1.387(7) . ?
C40 H40 0.9500 . ?
C40 C41 1.386(8) . ?
C14 H14 0.9500 . ?
C14 C13 1.392(8) . ?
C19 H19 0.9500 . ?
C13 H13 0.9500 . ?
C5 C8 1.519(7) . ?
C5 C6 1.501(8) . ?
C5 C7 1.512(7) . ?
C42 H42 0.9500 . ?
C42 C41 1.386(7) . ?
C37 H37 0.9500 . ?
C8 H8A 0.9800 . ?
C8 H8B 0.9800 . ?
C8 H8C 0.9800 . ?
C41 H41 0.9500 . ?
C25 H25A 0.9900 . ?
C25 H25B 0.9900 . ?
C6 H6A 0.9800 . ?
C6 H6B 0.9800 . ?
C6 H6C 0.9800 . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C7 H7A 0.9800 . ?
C7 H7B 0.9800 . ?
C7 H7C 0.9800 . ?
C23 O5 1.189(11) . ?
C27 C29 1.49(2) . ?
C27 C28 1.542(18) . ?
C27 C30 1.491(18) . ?
C29 H29A 0.9800 . ?
C29 H29B 0.9800 . ?
C29 H29C 0.9800 . ?
C28 H28A 0.9800 . ?
C28 H28B 0.9800 . ?
C28 H28C 0.9800 . ?
C30 H30A 0.9800 . ?
C30 H30B 0.9800 . ?
C30 H30C 0.9800 . ?
O5A C23A 1.247(17) . ?
C28A H28D 0.9800 . ?
C28A H28E 0.9800 . ?
C28A H28F 0.9800 . ?
C28A C27A 1.49(2) . ?
C27A C30A 1.54(2) . ?
C27A C29A 1.53(3) . ?
C27A O6A 1.47(3) . ?
C30A H30D 0.9800 . ?
C30A H30E 0.9800 . ?
C30A H30F 0.9800 . ?
C29A H29D 0.9800 . ?
C29A H29E 0.9800 . ?
C29A H29F 0.9800 . ?
C23A O6A 1.348(19) . ?

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
C26 O8 C31 112.7(4) . . ?
C4 O4 C9 112.9(4) . . ?
C1 O2 C5 121.0(4) . . ?
C23 O6 C27 121.4(10) . . ?
C4 N1 H1 121.3 . . ?
C4 N1 C2 117.4(4) . . ?
C2 N1 H1 121.3 . . ?
C26 N2 H2 120.8 . . ?
C26 N2 C24 118.4(4) . . ?
C24 N2 H2 120.8 . . ?
O3 C4 O4 123.5(4) . . ?
O3 C4 N1 124.8(4) . . ?
N1 C4 O4 111.8(4) . . ?
C12 C11 C16 120.2(4) . . ?
C12 C11 C10 130.2(4) . . ?
C16 C11 C10 109.5(4) . . ?
C33 C38 C39 108.5(4) . . ?
C37 C38 C33 120.7(4) . . ?
C37 C38 C39 130.7(4) . . ?
O7 C26 O8 123.0(4) . . ?
O7 C26 N2 125.6(4) . . ?
N2 C26 O8 111.4(4) . . ?
C38 C33 C32 110.3(4) . . ?
C34 C33 C38 120.3(4) . . ?
C34 C33 C32 129.4(4) . . ?
O2 C1 C2 109.3(4) . . ?
O1 C1 O2 126.2(4) . . ?
O1 C1 C2 124.5(4) . . ?
C11 C12 H12 120.4 . . ?
C13 C12 C11 119.2(5) . . ?
C13 C12 H12 120.4 . . ?
C33 C32 H32 110.8 . . ?
C33 C32 C31 107.0(4) . . ?
C44 C32 C33 102.6(3) . . ?
C44 C32 H32 110.8 . . ?
C44 C32 C31 114.4(4) . . ?
C31 C32 H32 110.8 . . ?
C11 C16 C17 108.7(4) . . ?
C15 C16 C11 120.6(4) . . ?
C15 C16 C17 130.7(4) . . ?
C22 C21 H21 120.6 . . ?
C22 C21 C20 118.7(5) . . ?
C20 C21 H21 120.6 . . ?
C21 C22 C10 129.3(4) . . ?
C21 C22 C17 120.8(4) . . ?
C17 C22 C10 109.8(4) . . ?
C33 C34 H34 120.5 . . ?
C33 C34 C35 118.9(5) . . ?
C35 C34 H34 120.5 . . ?
C11 C10 H10 111.3 . . ?
C11 C10 C9 112.9(4) . . ?
C22 C10 C11 102.5(4) . . ?
C22 C10 H10 111.3 . . ?
C22 C10 C9 107.0(4) . . ?
C9 C10 H10 111.3 . . ?
C22 C17 C16 109.1(4) . . ?
C22 C17 C18 120.2(4) . . ?
C18 C17 C16 130.7(4) . . ?
N2 C24 C25 114.1(4) . . ?
N2 C24 C23 111.5(5) . . ?
N2 C24 H24 105(3) . . ?
C25 C24 C23 106.0(5) . . ?
C25 C24 H24 109(3) . . ?
C23 C24 H24 111(3) . . ?
C23A C24 N2 105.9(7) . . ?
C23A C24 C25 124.6(7) . . ?
C23A C24 H24 95(3) . . ?
C44 C39 C38 108.5(4) . . ?
C40 C39 C38 130.9(4) . . ?
C40 C39 C44 120.6(4) . . ?
O4 C9 C10 109.2(4) . . ?
O4 C9 H9A 109.8 . . ?
O4 C9 H9B 109.8 . . ?
C10 C9 H9A 109.8 . . ?
C10 C9 H9B 109.8 . . ?
H9A C9 H9B 108.3 . . ?
C35 C36 H36 119.6 . . ?
C35 C36 C37 120.7(5) . . ?
C37 C36 H36 119.6 . . ?
C34 C35 H35 119.5 . . ?
C36 C35 C34 121.0(5) . . ?
C36 C35 H35 119.5 . . ?
C39 C44 C32 110.0(4) . . ?
C43 C44 C32 130.1(4) . . ?
C43 C44 C39 119.9(4) . . ?
C16 C15 H15 120.8 . . ?
C16 C15 C14 118.5(5) . . ?
C14 C15 H15 120.8 . . ?
C44 C43 H43 120.2 . . ?
C44 C43 C42 119.5(4) . . ?
C42 C43 H43 120.2 . . ?
C17 C18 H18 120.7 . . ?
C19 C18 C17 118.7(4) . . ?
C19 C18 H18 120.7 . . ?
N1 C2 C1 110.1(4) . . ?
N1 C2 H2A 107.7 . . ?
N1 C2 C3 112.7(4) . . ?
C1 C2 H2A 107.7 . . ?
C3 C2 C1 110.9(4) . . ?
C3 C2 H2A 107.7 . . ?
O8 C31 C32 109.0(4) . . ?
O8 C31 H31A 109.9 . . ?
O8 C31 H31B 109.9 . . ?
C32 C31 H31A 109.9 . . ?
C32 C31 H31B 109.9 . . ?
H31A C31 H31B 108.3 . . ?
C21 C20 H20 119.3 . . ?
C21 C20 C19 121.3(5) . . ?
C19 C20 H20 119.3 . . ?
C39 C40 H40 120.6 . . ?
C39 C40 C41 118.8(5) . . ?
C41 C40 H40 120.6 . . ?
C15 C14 H14 119.4 . . ?
C15 C14 C13 121.1(5) . . ?
C13 C14 H14 119.4 . . ?
C18 C19 C20 120.4(5) . . ?
C18 C19 H19 119.8 . . ?
C20 C19 H19 119.8 . . ?
C12 C13 C14 120.3(5) . . ?
C12 C13 H13 119.8 . . ?
C14 C13 H13 119.8 . . ?
O2 C5 C8 106.7(4) . . ?
O2 C5 C6 111.5(4) . . ?
O2 C5 C7 103.5(4) . . ?
C6 C5 C8 113.7(5) . . ?
C6 C5 C7 111.6(5) . . ?
C7 C5 C8 109.3(4) . . ?
C43 C42 H42 119.8 . . ?
C41 C42 C43 120.3(5) . . ?
C41 C42 H42 119.8 . . ?
C38 C37 C36 118.4(5) . . ?
C38 C37 H37 120.8 . . ?
C36 C37 H37 120.8 . . ?
C5 C8 H8A 109.5 . . ?
C5 C8 H8B 109.5 . . ?
C5 C8 H8C 109.5 . . ?
H8A C8 H8B 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
C40 C41 H41 119.6 . . ?
C42 C41 C40 120.9(4) . . ?
C42 C41 H41 119.6 . . ?
Cl2 C25 H25A 109.1 . . ?
Cl2 C25 H25B 109.1 . . ?
C24 C25 Cl2 112.5(4) . . ?
C24 C25 H25A 109.1 . . ?
C24 C25 H25B 109.1 . . ?
H25A C25 H25B 107.8 . . ?
C5 C6 H6A 109.5 . . ?
C5 C6 H6B 109.5 . . ?
C5 C6 H6C 109.5 . . ?
H6A C6 H6B 109.5 . . ?
H6A C6 H6C 109.5 . . ?
H6B C6 H6C 109.5 . . ?
Cl1 C3 H3A 109.3 . . ?
Cl1 C3 H3B 109.3 . . ?
C2 C3 Cl1 111.8(4) . . ?
C2 C3 H3A 109.3 . . ?
C2 C3 H3B 109.3 . . ?
H3A C3 H3B 107.9 . . ?
C5 C7 H7A 109.5 . . ?
C5 C7 H7B 109.5 . . ?
C5 C7 H7C 109.5 . . ?
H7A C7 H7B 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
O6 C23 C24 107.6(9) . . ?
O5 C23 O6 126.8(9) . . ?
O5 C23 C24 125.4(7) . . ?
O6 C27 C28 108.4(12) . . ?
C29 C27 O6 103.1(9) . . ?
C29 C27 C28 110.4(12) . . ?
C30 C27 O6 106.8(10) . . ?
C30 C27 C29 114.8(14) . . ?
C30 C27 C28 112.6(11) . . ?
C27 C29 H29A 109.5 . . ?
C27 C29 H29B 109.5 . . ?
C27 C29 H29C 109.5 . . ?
H29A C29 H29B 109.5 . . ?
H29A C29 H29C 109.5 . . ?
H29B C29 H29C 109.5 . . ?
C27 C28 H28A 109.5 . . ?
C27 C28 H28B 109.5 . . ?
C27 C28 H28C 109.5 . . ?
H28A C28 H28B 109.5 . . ?
H28A C28 H28C 109.5 . . ?
H28B C28 H28C 109.5 . . ?
C27 C30 H30A 109.5 . . ?
C27 C30 H30B 109.5 . . ?
C27 C30 H30C 109.5 . . ?
H30A C30 H30B 109.5 . . ?
H30A C30 H30C 109.5 . . ?
H30B C30 H30C 109.5 . . ?
H28D C28A H28E 109.5 . . ?
H28D C28A H28F 109.5 . . ?
H28E C28A H28F 109.5 . . ?
C27A C28A H28D 109.5 . . ?
C27A C28A H28E 109.5 . . ?
C27A C28A H28F 109.5 . . ?
C28A C27A C30A 115.7(17) . . ?
C28A C27A C29A 109.5(16) . . ?
C29A C27A C30A 111.1(14) . . ?
O6A C27A C28A 109.2(14) . . ?
O6A C27A C30A 102.4(16) . . ?
O6A C27A C29A 108.4(16) . . ?
C27A C30A H30D 109.5 . . ?
C27A C30A H30E 109.5 . . ?
C27A C30A H30F 109.5 . . ?
H30D C30A H30E 109.5 . . ?
H30D C30A H30F 109.5 . . ?
H30E C30A H30F 109.5 . . ?
C27A C29A H29D 109.5 . . ?
C27A C29A H29E 109.5 . . ?
C27A C29A H29F 109.5 . . ?
H29D C29A H29E 109.5 . . ?
H29D C29A H29F 109.5 . . ?
H29E C29A H29F 109.5 . . ?
O5A C23A C24 123.4(12) . . ?
O5A C23A O6A 122.7(14) . . ?
O6A C23A C24 113.8(13) . . ?
C23A O6A C27A 123.9(14) . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
N1 H1 O3 0.88 2.24 3.085(5) 161.4 1_565 yes
N2 H2 O7 0.88 2.21 3.035(6) 157.0 1_565 yes
C41 H41 O7 0.95 2.60 3.432(6) 147.0 2_557 yes

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
O2 C1 C2 N1 171.6(4) . . . . ?
O2 C1 C2 C3 -63.1(5) . . . . ?
O1 C1 C2 N1 -9.7(7) . . . . ?
O1 C1 C2 C3 115.7(5) . . . . ?
N1 C2 C3 Cl1 68.2(5) . . . . ?
N2 C24 C25 Cl2 68.1(6) . . . . ?
N2 C24 C23 O6 172.9(7) . . . . ?
N2 C24 C23 O5 -11.4(12) . . . . ?
N2 C24 C23A O5A 18.7(18) . . . . ?
N2 C24 C23A O6A -162.6(15) . . . . ?
C4 O4 C9 C10 168.2(4) . . . . ?
C4 N1 C2 C1 -156.3(4) . . . . ?
C4 N1 C2 C3 79.4(6) . . . . ?
C11 C12 C13 C14 1.1(7) . . . . ?
C11 C16 C17 C22 -0.5(5) . . . . ?
C11 C16 C17 C18 -179.5(5) . . . . ?
C11 C16 C15 C14 1.6(7) . . . . ?
C11 C10 C9 O4 -69.4(5) . . . . ?
C38 C33 C32 C44 2.5(5) . . . . ?
C38 C33 C32 C31 -118.2(4) . . . . ?
C38 C33 C34 C35 0.7(7) . . . . ?
C38 C39 C44 C32 0.8(5) . . . . ?
C38 C39 C44 C43 -179.8(4) . . . . ?
C38 C39 C40 C41 178.7(5) . . . . ?
C26 O8 C31 C32 175.4(3) . . . . ?
C26 N2 C24 C25 111.1(6) . . . . ?
C26 N2 C24 C23 -128.8(6) . . . . ?
C26 N2 C24 C23A -108.2(9) . . . . ?
C33 C38 C39 C44 0.9(5) . . . . ?
C33 C38 C39 C40 -178.1(5) . . . . ?
C33 C38 C37 C36 0.7(7) . . . . ?
C33 C32 C44 C39 -2.0(5) . . . . ?
C33 C32 C44 C43 178.6(5) . . . . ?
C33 C32 C31 O8 -172.3(3) . . . . ?
C33 C34 C35 C36 -0.2(7) . . . . ?
C1 O2 C5 C8 -67.7(5) . . . . ?
C1 O2 C5 C6 57.0(6) . . . . ?
C1 O2 C5 C7 177.0(5) . . . . ?
C1 C2 C3 Cl1 -55.7(5) . . . . ?
C12 C11 C16 C17 176.5(4) . . . . ?
C12 C11 C16 C15 -1.9(6) . . . . ?
C12 C11 C10 C22 -174.4(4) . . . . ?
C12 C11 C10 C9 70.7(6) . . . . ?
C32 C33 C34 C35 -176.0(5) . . . . ?
C32 C44 C43 C42 -178.9(5) . . . . ?
C16 C11 C12 C13 0.5(7) . . . . ?
C16 C11 C10 C22 5.3(5) . . . . ?
C16 C11 C10 C9 -109.5(4) . . . . ?
C16 C17 C18 C19 179.2(5) . . . . ?
C16 C15 C14 C13 0.0(7) . . . . ?
C21 C22 C10 C11 178.6(5) . . . . ?
C21 C22 C10 C9 -62.4(6) . . . . ?
C21 C22 C17 C16 -179.8(4) . . . . ?
C21 C22 C17 C18 -0.6(7) . . . . ?
C21 C20 C19 C18 0.3(7) . . . . ?
C22 C21 C20 C19 -0.7(7) . . . . ?
C22 C10 C9 O4 178.5(4) . . . . ?
C22 C17 C18 C19 0.2(7) . . . . ?
C34 C33 C32 C44 179.4(5) . . . . ?
C34 C33 C32 C31 58.7(6) . . . . ?
C10 C11 C12 C13 -179.7(4) . . . . ?
C10 C11 C16 C17 -3.2(5) . . . . ?
C10 C11 C16 C15 178.3(4) . . . . ?
C10 C22 C17 C16 4.0(5) . . . . ?
C10 C22 C17 C18 -176.9(4) . . . . ?
C17 C16 C15 C14 -176.5(5) . . . . ?
C17 C22 C10 C11 -5.6(5) . . . . ?
C17 C22 C10 C9 113.4(4) . . . . ?
C17 C18 C19 C20 -0.1(7) . . . . ?
C24 N2 C26 O8 171.8(4) . . . . ?
C24 N2 C26 O7 -8.2(8) . . . . ?
C24 C23A O6A C27A 176.0(15) . . . . ?
C39 C38 C33 C32 -2.2(5) . . . . ?
C39 C38 C33 C34 -179.4(4) . . . . ?
C39 C38 C37 C36 178.8(5) . . . . ?
C39 C44 C43 C42 1.7(7) . . . . ?
C39 C40 C41 C42 0.0(8) . . . . ?
C9 O4 C4 O3 -6.3(7) . . . . ?
C9 O4 C4 N1 174.7(4) . . . . ?
C35 C36 C37 C38 -0.2(8) . . . . ?
C44 C32 C31 O8 74.8(5) . . . . ?
C44 C39 C40 C41 -0.3(7) . . . . ?
C44 C43 C42 C41 -2.0(8) . . . . ?
C15 C16 C17 C22 177.8(5) . . . . ?
C15 C16 C17 C18 -1.2(8) . . . . ?
C15 C14 C13 C12 -1.4(7) . . . . ?
C43 C42 C41 C40 1.1(8) . . . . ?
C2 N1 C4 O4 176.7(4) . . . . ?
C2 N1 C4 O3 -2.3(7) . . . . ?
C31 O8 C26 O7 9.1(6) . . . . ?
C31 O8 C26 N2 -170.9(4) . . . . ?
C31 C32 C44 C39 113.5(4) . . . . ?
C31 C32 C44 C43 -65.9(7) . . . . ?
C20 C21 C22 C10 176.3(5) . . . . ?
C20 C21 C22 C17 0.8(7) . . . . ?
C40 C39 C44 C32 179.9(4) . . . . ?
C40 C39 C44 C43 -0.6(7) . . . . ?
C5 O2 C1 O1 -9.7(7) . . . . ?
C5 O2 C1 C2 169.1(4) . . . . ?
C37 C38 C33 C32 176.3(4) . . . . ?
C37 C38 C33 C34 -0.9(7) . . . . ?
C37 C38 C39 C44 -177.4(5) . . . . ?
C37 C38 C39 C40 3.5(9) . . . . ?
C37 C36 C35 C34 0.0(8) . . . . ?
C25 C24 C23 O6 -62.4(9) . . . . ?
C25 C24 C23 O5 113.3(9) . . . . ?
C25 C24 C23A O5A 154.1(12) . . . . ?
C25 C24 C23A O6A -27(2) . . . . ?
C23 O6 C27 C29 175.2(13) . . . . ?
C23 O6 C27 C28 58.1(15) . . . . ?
C23 O6 C27 C30 -63.5(15) . . . . ?
C23 C24 C25 Cl2 -55.0(6) . . . . ?
C27 O6 C23 C24 169.7(11) . . . . ?
C27 O6 C23 O5 -5.9(18) . . . . ?
O5A C23A O6A C27A -5(3) . . . . ?
C28A C27A O6A C23A -56(3) . . . . ?
C30A C27A O6A C23A -180(2) . . . . ?
C29A C27A O6A C23A 63(3) . . . . ?
C23A C24 C25 Cl2 -64.1(11) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
loop_
_twin_individual_id
_twin_individual_mass_fraction_refined
1 0.85(2)
2 0.15(2)

####################################################################### 
# 
# 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_cu_v4_21ffdb1_0m
_database_code_depnum_ccdc_archive 'CCDC 2116496'
loop_
_audit_author_name
_audit_author_address
'Francois Jacobs'
;University Of The Free State
South Africa
;
_audit_update_record             
;
2023-01-26 deposited with the CCDC.	2024-01-18 downloaded from the CCDC.
;
_audit_creation_date             2023-01-24
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6408)
;
_shelx_SHELXL_version_number     2019/2
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C9 H16 I N O4'
_chemical_formula_sum            'C9 H16 I N O4'
_chemical_formula_weight         329.13
_chemical_absolute_configuration ?
_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'
I I -0.3257 6.8362 '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, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'

_cell_length_a                   5.1261(9)
_cell_length_b                   8.7280(14)
_cell_length_c                   29.053(5)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1299.9(4)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9879
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      58.98
_cell_measurement_theta_min      3.04
_shelx_estimated_absorpt_T_max   0.527
_shelx_estimated_absorpt_T_min   0.296
_exptl_absorpt_coefficient_mu    19.359
_exptl_absorpt_correction_T_max  0.7516
_exptl_absorpt_correction_T_min  0.3989
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016) was used for absorption correction.
wR2(int) was 0.1768 before and 0.1292 after correction.
The Ratio of minimum to maximum transmission is 0.5307.
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    1.682
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       Plate
_exptl_crystal_F_000             648
_exptl_crystal_size_max          0.083
_exptl_crystal_size_mid          0.077
_exptl_crystal_size_min          0.038
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.1024
_diffrn_reflns_av_unetI/netI     0.0444
_diffrn_reflns_Laue_measured_fraction_full 0.992
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       32
_diffrn_reflns_limit_l_min       -32
_diffrn_reflns_number            19736
_diffrn_reflns_point_group_measured_fraction_full 0.990
_diffrn_reflns_point_group_measured_fraction_max 0.990
_diffrn_reflns_theta_full        59.312
_diffrn_reflns_theta_max         59.312
_diffrn_reflns_theta_min         3.042
_diffrn_ambient_temperature      100.0
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.992
_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_source_current           1.2
_diffrn_source_power             0.06
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.641
_reflns_Friedel_fraction_full    0.988
_reflns_Friedel_fraction_max     0.988
_reflns_number_gt                1769
_reflns_number_total             1872
_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. Completness statistics refer to single and
 composite reflections containing twin component 1 only.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       ?
_computing_data_collection       ?
_computing_data_reduction        ?
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2019/2 (Sheldrick, 2015)'
_computing_structure_solution    ?
_refine_diff_density_max         1.070
_refine_diff_density_min         -0.474
_refine_diff_density_rms         0.124
_refine_ls_abs_structure_details 
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   0.163(17)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.044
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     145
_refine_ls_number_reflns         1872
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0435
_refine_ls_R_factor_gt           0.0411
_refine_ls_restrained_S_all      1.044
_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)+(0.0755P)²+0.6581P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1063
_refine_ls_wR_factor_ref         0.1086
_refine_special_details          
;
 Refined as a 2-component inversion twin.
;
_olex2_refinement_description    
;
1. Twinned data refinement
 Scales: 0.837(17)
 0.163(17)
2. 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
3.a Ternary CH refined with riding coordinates:
 C2(H2)
3.b Secondary CH2 refined with riding coordinates:
 C3(H3A,H3B)
3.c Idealised Me refined as rotating group:
 C7(H7A,H7B,H7C), C9(H9A,H9B,H9C), C8(H8A,H8B,H8C), C5(H5A,H5B,H5C)
;
_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
I1 I -0.41888(16) -0.85289(8) -0.63505(2) 0.0530(3) Uani 1 1 d . . . . .
O3 O -0.8602(10) -0.4813(7) -0.60961(19) 0.0268(14) Uani 1 1 d . . . . .
O4 O -0.5672(10) -0.3701(7) -0.65778(17) 0.0260(12) Uani 1 1 d . . . . .
N1 N -0.4241(16) -0.4931(9) -0.5965(2) 0.0265(16) Uani 1 1 d . . . . .
O2 O -0.4682(18) -0.4232(11) -0.5028(3) 0.064(2) Uani 1 1 d . . . . .
C4 C -0.6341(15) -0.4505(10) -0.6210(3) 0.0245(19) Uani 1 1 d . . . . .
C7 C -0.9437(18) -0.1995(10) -0.6688(3) 0.0304(18) Uani 1 1 d . . . . .
H7A H -1.060016 -0.251204 -0.646956 0.046 Uiso 1 1 calc R U . . .
H7B H -1.047789 -0.148242 -0.692484 0.046 Uiso 1 1 calc R U . . .
H7C H -0.838157 -0.123459 -0.652351 0.046 Uiso 1 1 calc R U . . .
C2 C -0.4344(17) -0.6055(10) -0.5614(3) 0.0265(17) Uani 1 1 d . . . . .
H2 H -0.620591 -0.637459 -0.557774 0.032 Uiso 1 1 calc R U . . .
C3 C -0.2735(18) -0.7500(10) -0.5734(3) 0.0322(19) Uani 1 1 d . . . . .
H3A H -0.284348 -0.824417 -0.547739 0.039 Uiso 1 1 calc R U . . .
H3B H -0.088070 -0.721639 -0.577617 0.039 Uiso 1 1 calc R U . . .
C6 C -0.7669(15) -0.3158(11) -0.6910(3) 0.029(2) Uani 1 1 d . . . . .
O1 O -0.1752(19) -0.6062(12) -0.4918(3) 0.077(3) Uani 1 1 d . . . . .
C1 C -0.3390(19) -0.5450(12) -0.5146(3) 0.037(2) Uani 1 1 d . . . . .
C9 C -0.9120(19) -0.4508(11) -0.7117(3) 0.0335(19) Uani 1 1 d . . . . .
H9A H -0.788046 -0.533135 -0.718677 0.050 Uiso 1 1 calc R U . . .
H9B H -0.999151 -0.418464 -0.740127 0.050 Uiso 1 1 calc R U . . .
H9C H -1.042381 -0.488080 -0.689742 0.050 Uiso 1 1 calc R U . . .
C8 C -0.5973(18) -0.2372(12) -0.7276(3) 0.038(2) Uani 1 1 d . . . . .
H8A H -0.495443 -0.155141 -0.713175 0.057 Uiso 1 1 calc R U . . .
H8B H -0.709334 -0.193794 -0.751582 0.057 Uiso 1 1 calc R U . . .
H8C H -0.478678 -0.312511 -0.741288 0.057 Uiso 1 1 calc R U . . .
C5 C -0.408(3) -0.3527(17) -0.4583(4) 0.075(4) Uani 1 1 d . . . . .
H5A H -0.467011 -0.420115 -0.433388 0.113 Uiso 1 1 calc R U . . .
H5B H -0.496654 -0.253667 -0.455892 0.113 Uiso 1 1 calc R U . . .
H5C H -0.218844 -0.337315 -0.455707 0.113 Uiso 1 1 calc R U . . .
H1 H -0.32(2) -0.446(12) -0.601(3) 0.02(3) 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
I1 C3 2.138(9) . ?
O3 C4 1.235(10) . ?
O4 C4 1.323(10) . ?
O4 C6 1.485(9) . ?
N1 C4 1.343(12) . ?
N1 C2 1.417(11) . ?
N1 H1 0.69(10) . ?
O2 C1 1.299(14) . ?
O2 C5 1.466(13) . ?
C7 H7A 0.9800 . ?
C7 H7B 0.9800 . ?
C7 H7C 0.9800 . ?
C7 C6 1.506(13) . ?
C2 H2 1.0000 . ?
C2 C3 1.547(13) . ?
C2 C1 1.539(12) . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C6 C9 1.518(13) . ?
C6 C8 1.535(12) . ?
O1 C1 1.195(13) . ?
C9 H9A 0.9800 . ?
C9 H9B 0.9800 . ?
C9 H9C 0.9800 . ?
C8 H8A 0.9800 . ?
C8 H8B 0.9800 . ?
C8 H8C 0.9800 . ?
C5 H5A 0.9800 . ?
C5 H5B 0.9800 . ?
C5 H5C 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
C4 O4 C6 121.0(6) . . ?
C4 N1 C2 122.9(8) . . ?
C4 N1 H1 111(8) . . ?
C2 N1 H1 125(8) . . ?
C1 O2 C5 117.9(10) . . ?
O3 C4 O4 125.1(7) . . ?
O3 C4 N1 123.3(8) . . ?
O4 C4 N1 111.5(7) . . ?
H7A C7 H7B 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
C6 C7 H7A 109.5 . . ?
C6 C7 H7B 109.5 . . ?
C6 C7 H7C 109.5 . . ?
N1 C2 H2 107.8 . . ?
N1 C2 C3 112.5(7) . . ?
N1 C2 C1 112.8(7) . . ?
C3 C2 H2 107.8 . . ?
C1 C2 H2 107.8 . . ?
C1 C2 C3 108.0(7) . . ?
I1 C3 H3A 109.6 . . ?
I1 C3 H3B 109.6 . . ?
C2 C3 I1 110.2(5) . . ?
C2 C3 H3A 109.6 . . ?
C2 C3 H3B 109.6 . . ?
H3A C3 H3B 108.1 . . ?
O4 C6 C7 110.5(6) . . ?
O4 C6 C9 110.3(7) . . ?
O4 C6 C8 101.6(6) . . ?
C7 C6 C9 113.5(7) . . ?
C7 C6 C8 109.7(8) . . ?
C9 C6 C8 110.5(7) . . ?
O2 C1 C2 110.6(8) . . ?
O1 C1 O2 125.3(10) . . ?
O1 C1 C2 124.0(10) . . ?
C6 C9 H9A 109.5 . . ?
C6 C9 H9B 109.5 . . ?
C6 C9 H9C 109.5 . . ?
H9A C9 H9B 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 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 . . ?
O2 C5 H5A 109.5 . . ?
O2 C5 H5B 109.5 . . ?
O2 C5 H5C 109.5 . . ?
H5A C5 H5B 109.5 . . ?
H5A C5 H5C 109.5 . . ?
H5B C5 H5C 109.5 . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
C3 H3B O3 0.99 2.57 3.331(11) 133.2 1_655 yes
N1 H1 O3 0.69(10) 2.39(10) 2.917(10) 135(10) 1_655 yes

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
N1 C2 C3 I1 -60.1(8) . . . . ?
N1 C2 C1 O2 55.1(11) . . . . ?
N1 C2 C1 O1 -127.6(11) . . . . ?
C4 O4 C6 C7 66.1(10) . . . . ?
C4 O4 C6 C9 -60.3(9) . . . . ?
C4 O4 C6 C8 -177.6(7) . . . . ?
C4 N1 C2 C3 114.9(9) . . . . ?
C4 N1 C2 C1 -122.7(9) . . . . ?
C2 N1 C4 O3 14.8(13) . . . . ?
C2 N1 C4 O4 -166.4(7) . . . . ?
C3 C2 C1 O2 -179.9(8) . . . . ?
C3 C2 C1 O1 -2.6(13) . . . . ?
C6 O4 C4 O3 -3.7(13) . . . . ?
C6 O4 C4 N1 177.6(7) . . . . ?
C1 C2 C3 I1 174.7(5) . . . . ?
C5 O2 C1 C2 178.2(10) . . . . ?
C5 O2 C1 O1 0.9(17) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
loop_
_twin_individual_id
_twin_individual_mass_fraction_refined
1 0.837(17)
2 0.163(17)

####################################################################### 
# 
# 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_q1_22ffdb1_0m
_database_code_depnum_ccdc_archive 'CCDC 2238178'
loop_
_audit_author_name
_audit_author_address
'Francois Jacobs'
;University of the Free State
South Africa
;
_audit_update_record             
;
2023-01-26 deposited with the CCDC.	2024-01-18 downloaded from the CCDC.
;
_audit_creation_date             2023-01-24
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6408)
;
_shelx_SHELXL_version_number     2019/2
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C9 H16 Cl N O4'
_chemical_formula_sum            'C9 H16 Cl N O4'
_chemical_formula_weight         237.68
_chemical_absolute_configuration ?
_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           4
_space_group_name_H-M_alt        'P 1 21 1'
_space_group_name_Hall           'P 2yb'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z'

_cell_length_a                   9.2240(6)
_cell_length_b                   5.0773(3)
_cell_length_c                   13.2741(9)
_cell_angle_alpha                90
_cell_angle_beta                 107.467(2)
_cell_angle_gamma                90
_cell_volume                     593.00(7)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    9997
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      28.26
_cell_measurement_theta_min      3.19
_shelx_estimated_absorpt_T_max   0.967
_shelx_estimated_absorpt_T_min   0.861
_exptl_absorpt_coefficient_mu    0.317
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_correction_T_min  0.7042
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0573 before and 0.0464 after correction.
The Ratio of minimum to maximum transmission is 0.9443.
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    1.331
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       Needle
_exptl_crystal_F_000             252
_exptl_crystal_size_max          0.485
_exptl_crystal_size_mid          0.173
_exptl_crystal_size_min          0.107
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0189
_diffrn_reflns_av_unetI/netI     0.0177
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            12442
_diffrn_reflns_point_group_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.990
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.257
_diffrn_reflns_theta_min         3.191
_diffrn_ambient_temperature      100.0
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_device_type  
'Bruker D8 Quest Eco Chi Photon II CPAD diffractometer'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_source_current           20.0
_diffrn_source_power             1.0
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.792
_reflns_Friedel_fraction_full    0.994
_reflns_Friedel_fraction_max     0.985
_reflns_number_gt                2852
_reflns_number_total             2911
_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       ?
_computing_data_collection       ?
_computing_data_reduction        ?
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2019/2 (Sheldrick, 2015)'
_computing_structure_solution    'olex2.solve 1.3 (Bourhis et al., 2015)'
_refine_diff_density_max         0.221
_refine_diff_density_min         -0.165
_refine_diff_density_rms         0.031
_refine_ls_abs_structure_details 
;
 Flack x determined using 1226 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.027(11)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.075
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     144
_refine_ls_number_reflns         2911
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0219
_refine_ls_R_factor_gt           0.0212
_refine_ls_restrained_S_all      1.074
_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)+(0.0272P)²+0.0781P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0527
_refine_ls_wR_factor_ref         0.0531
_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:
 C2(H2)
2.b Secondary CH2 refined with riding coordinates:
 C3(H3A,H3B)
2.c Idealised Me refined as rotating group:
 C7(H7A,H7B,H7C), C5(H5A,H5B,H5C), C9(H9A,H9B,H9C), C8(H8A,H8B,H8C)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     iterative
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Cl1 Cl 0.93122(4) 0.21921(7) 0.22307(3) 0.02484(10) Uani 1 1 d . . . . .
O4 O 0.42369(11) 0.41886(19) 0.18011(8) 0.0162(2) Uani 1 1 d . . . . .
O2 O 0.67890(12) 0.5284(2) 0.49342(8) 0.0202(2) Uani 1 1 d . . . . .
O1 O 0.87520(11) 0.7652(2) 0.47520(8) 0.0186(2) Uani 1 1 d . . . . .
O3 O 0.58199(11) 0.7469(2) 0.26715(8) 0.0187(2) Uani 1 1 d . . . . .
N1 N 0.64366(14) 0.3171(2) 0.29707(10) 0.0141(2) Uani 1 1 d . . . . .
C2 C 0.79415(15) 0.3782(3) 0.36691(11) 0.0132(3) Uani 1 1 d . . . . .
H2 H 0.837732 0.212813 0.404999 0.016 Uiso 1 1 calc R U . . .
C4 C 0.55104(15) 0.5147(3) 0.24846(11) 0.0141(3) Uani 1 1 d . . . . .
C1 C 0.78809(16) 0.5837(3) 0.44971(11) 0.0145(3) Uani 1 1 d . . . . .
C3 C 0.90249(16) 0.4756(3) 0.30818(11) 0.0162(3) Uani 1 1 d . . . . .
H3A H 1.000948 0.525330 0.359390 0.019 Uiso 1 1 calc R U . . .
H3B H 0.859316 0.633132 0.265845 0.019 Uiso 1 1 calc R U . . .
C6 C 0.30656(16) 0.6028(3) 0.11711(11) 0.0156(3) Uani 1 1 d . . . . .
C7 C 0.37462(17) 0.7791(3) 0.05020(12) 0.0191(3) Uani 1 1 d . . . . .
H7A H 0.439388 0.912663 0.095275 0.029 Uiso 1 1 calc R U . . .
H7B H 0.292692 0.865819 -0.004307 0.029 Uiso 1 1 calc R U . . .
H7C H 0.435575 0.672181 0.016585 0.029 Uiso 1 1 calc R U . . .
C5 C 0.66449(17) 0.7167(4) 0.57173(12) 0.0267(3) Uani 1 1 d . . . . .
H5A H 0.756190 0.711568 0.632715 0.040 Uiso 1 1 calc R U . . .
H5B H 0.575746 0.672035 0.594429 0.040 Uiso 1 1 calc R U . . .
H5C H 0.651797 0.893873 0.541054 0.040 Uiso 1 1 calc R U . . .
C9 C 0.18961(17) 0.4186(3) 0.04661(13) 0.0233(3) Uani 1 1 d . . . . .
H9A H 0.234832 0.326147 -0.001414 0.035 Uiso 1 1 calc R U . . .
H9B H 0.101690 0.520924 0.005396 0.035 Uiso 1 1 calc R U . . .
H9C H 0.156847 0.289989 0.090355 0.035 Uiso 1 1 calc R U . . .
C8 C 0.23830(16) 0.7550(3) 0.19035(12) 0.0215(3) Uani 1 1 d . . . . .
H8A H 0.211947 0.632564 0.239185 0.032 Uiso 1 1 calc R U . . .
H8B H 0.146540 0.846942 0.148528 0.032 Uiso 1 1 calc R U . . .
H8C H 0.312370 0.883759 0.230595 0.032 Uiso 1 1 calc R U . . .
H1 H 0.622(2) 0.164(4) 0.2803(14) 0.016(5) 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 C3 1.7945(15) . ?
O4 C4 1.3418(16) . ?
O4 C6 1.4819(16) . ?
O2 C1 1.3345(17) . ?
O2 C5 1.4474(19) . ?
O1 C1 1.2027(18) . ?
O3 C4 1.2208(18) . ?
N1 C2 1.4527(17) . ?
N1 C4 1.3500(18) . ?
N1 H1 0.82(2) . ?
C2 H2 1.0000 . ?
C2 C1 1.5287(19) . ?
C2 C3 1.5227(19) . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C6 C7 1.523(2) . ?
C6 C9 1.519(2) . ?
C6 C8 1.519(2) . ?
C7 H7A 0.9800 . ?
C7 H7B 0.9800 . ?
C7 H7C 0.9800 . ?
C5 H5A 0.9800 . ?
C5 H5B 0.9800 . ?
C5 H5C 0.9800 . ?
C9 H9A 0.9800 . ?
C9 H9B 0.9800 . ?
C9 H9C 0.9800 . ?
C8 H8A 0.9800 . ?
C8 H8B 0.9800 . ?
C8 H8C 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
C4 O4 C6 119.67(11) . . ?
C1 O2 C5 114.66(12) . . ?
C2 N1 H1 119.2(13) . . ?
C4 N1 C2 119.52(12) . . ?
C4 N1 H1 120.5(13) . . ?
N1 C2 H2 107.8 . . ?
N1 C2 C1 111.74(11) . . ?
N1 C2 C3 113.01(11) . . ?
C1 C2 H2 107.8 . . ?
C3 C2 H2 107.8 . . ?
C3 C2 C1 108.52(11) . . ?
O4 C4 N1 110.70(12) . . ?
O3 C4 O4 126.27(13) . . ?
O3 C4 N1 123.02(13) . . ?
O2 C1 C2 111.36(12) . . ?
O1 C1 O2 124.52(13) . . ?
O1 C1 C2 124.05(13) . . ?
Cl1 C3 H3A 109.8 . . ?
Cl1 C3 H3B 109.8 . . ?
C2 C3 Cl1 109.29(10) . . ?
C2 C3 H3A 109.8 . . ?
C2 C3 H3B 109.8 . . ?
H3A C3 H3B 108.3 . . ?
O4 C6 C7 109.95(12) . . ?
O4 C6 C9 102.86(11) . . ?
O4 C6 C8 109.37(11) . . ?
C9 C6 C7 110.08(12) . . ?
C8 C6 C7 113.38(12) . . ?
C8 C6 C9 110.70(13) . . ?
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 . . ?
O2 C5 H5A 109.5 . . ?
O2 C5 H5B 109.5 . . ?
O2 C5 H5C 109.5 . . ?
H5A C5 H5B 109.5 . . ?
H5A C5 H5C 109.5 . . ?
H5B C5 H5C 109.5 . . ?
C6 C9 H9A 109.5 . . ?
C6 C9 H9B 109.5 . . ?
C6 C9 H9C 109.5 . . ?
H9A C9 H9B 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 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 . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
C2 H2 O1 1.00 2.66 3.1915(17) 113.3 2_746 yes
C3 H3A O1 0.99 2.52 3.1739(17) 123.1 2_746 yes
C7 H7A O3 0.98 2.42 2.9447(18) 113.2 . yes
C8 H8C O3 0.98 2.49 3.0250(18) 114.4 . yes
N1 H1 O3 0.82(2) 2.15(2) 2.9539(17) 169.3(17) 1_545 yes

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
N1 C2 C1 O2 45.74(15) . . . . ?
N1 C2 C1 O1 -137.29(14) . . . . ?
N1 C2 C3 Cl1 -63.15(13) . . . . ?
C2 N1 C4 O4 174.20(12) . . . . ?
C2 N1 C4 O3 -6.6(2) . . . . ?
C4 O4 C6 C7 59.20(16) . . . . ?
C4 O4 C6 C9 176.42(13) . . . . ?
C4 O4 C6 C8 -65.90(16) . . . . ?
C4 N1 C2 C1 51.72(17) . . . . ?
C4 N1 C2 C3 -71.03(16) . . . . ?
C1 C2 C3 Cl1 172.33(9) . . . . ?
C3 C2 C1 O2 171.00(11) . . . . ?
C3 C2 C1 O1 -12.02(18) . . . . ?
C6 O4 C4 O3 1.5(2) . . . . ?
C6 O4 C4 N1 -179.34(12) . . . . ?
C5 O2 C1 O1 3.9(2) . . . . ?
C5 O2 C1 C2 -179.13(12) . . . . ?

_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_cu_v3_22dfd1_b_0m
_database_code_depnum_ccdc_archive 'CCDC 2238182'
loop_
_audit_author_name
_audit_author_address
'Dumisani Vincent Kama'
;University Of The Free State
South Africa
;
_audit_update_record             
;
2023-01-26 deposited with the CCDC.	2024-01-18 downloaded from the CCDC.
;
_audit_creation_date             2023-01-24
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6408)
;
_shelx_SHELXL_version_number     2019/2
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C15 H20 Cl N O4'
_chemical_formula_sum            'C15 H20 Cl N O4'
_chemical_formula_weight         313.77
_chemical_absolute_configuration ?
_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, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'

_cell_length_a                   5.1069(15)
_cell_length_b                   11.791(3)
_cell_length_c                   26.327(8)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1585.3(8)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    2519
_cell_measurement_temperature    105(2)
_cell_measurement_theta_max      58.008
_cell_measurement_theta_min      3.357
_shelx_estimated_absorpt_T_max   0.956
_shelx_estimated_absorpt_T_min   0.639
_exptl_absorpt_coefficient_mu    2.268
_exptl_absorpt_correction_T_max  0.7528
_exptl_absorpt_correction_T_min  0.5166
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016) was used for absorption correction.
wR2(int) was 0.1530 before and 0.0906 after correction.
The Ratio of minimum to maximum transmission is 0.6862.
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    1.315
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             664
_exptl_crystal_size_max          0.217
_exptl_crystal_size_mid          0.021
_exptl_crystal_size_min          0.02
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0667
_diffrn_reflns_av_unetI/netI     0.0872
_diffrn_reflns_Laue_measured_fraction_full 0.813
_diffrn_reflns_Laue_measured_fraction_max 0.813
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_number            4985
_diffrn_reflns_point_group_measured_fraction_full 0.759
_diffrn_reflns_point_group_measured_fraction_max 0.759
_diffrn_reflns_theta_full        67.339
_diffrn_reflns_theta_max         67.339
_diffrn_reflns_theta_min         3.357
_diffrn_ambient_temperature      105.00
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.813
_diffrn_measured_fraction_theta_max 0.813
_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_source_current           1.2
_diffrn_source_power             0.06
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.566
_reflns_Friedel_fraction_full    0.679
_reflns_Friedel_fraction_max     0.679
_reflns_number_gt                1497
_reflns_number_total             2156
_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 V8.40B (?, 2016)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.40B (?, 2016)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2019/2 (Sheldrick, 2015)'
_computing_structure_solution    'olex2.solve 1.3 (Bourhis et al., 2015)'
_refine_diff_density_max         0.395
_refine_diff_density_min         -0.525
_refine_diff_density_rms         0.092
_refine_ls_abs_structure_details 
;
 Flack x determined using 439 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.07(2)
_refine_ls_extinction_coef       0.015(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2019/2 (Sheldrick 2019)'
_refine_ls_goodness_of_fit_ref   1.061
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     247
_refine_ls_number_reflns         2156
_refine_ls_number_restraints     97
_refine_ls_R_factor_all          0.1294
_refine_ls_R_factor_gt           0.0802
_refine_ls_restrained_S_all      1.040
_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)+(0.1255P)²+2.7844P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1981
_refine_ls_wR_factor_ref         0.2465
_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. Restrained distances
 H1-N1
 1 with sigma of 0.02
3. Rigid bond restraints
 C11, C6, C7, C8, C9, C10
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
 C10A, C11A, C6A, C7A, C8A, C9A
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
4. Uiso/Uaniso restraints and constraints
C11 \\sim C6 \\sim C7 \\sim C8 \\sim C9 \\sim C10: within 1.7A with sigma of
0.04 and sigma for terminal atoms of 0.08 within 1.7A
C10A \\sim C11A \\sim C6A \\sim C7A \\sim C8A \\sim C9A: within 1.7A with sigma
of 0.04 and sigma for terminal atoms of 0.08 within 1.7A
5. Others
 Sof(O2A)=Sof(C5A)=Sof(H5AA)=Sof(H5AB)=Sof(C10A)=Sof(H10A)=Sof(C11A)=Sof(H11A)=
 Sof(C6A)=Sof(C7A)=Sof(H7A)=Sof(C8A)=Sof(H8A)=Sof(C9A)=Sof(H9A)=1-FVAR(1)
 Sof(O2)=Sof(C5)=Sof(H5A)=Sof(H5B)=Sof(C11)=Sof(H11)=Sof(C6)=Sof(C7)=Sof(H7)=
 Sof(C8)=Sof(H8)=Sof(C9)=Sof(H9)=Sof(C10)=Sof(H10)=FVAR(1)
6.a Ternary CH refined with riding coordinates:
 C2(H2)
6.b Secondary CH2 refined with riding coordinates:
 C3(H3A,H3B), C5(H5A,H5B), C5A(H5AA,H5AB)
6.c Aromatic/amide H refined with riding coordinates:
 C11(H11), C7(H7), C8(H8), C9(H9), C10(H10), C10A(H10A), C11A(H11A), C7A(H7A),
 C8A(H8A), C9A(H9A)
6.d Fitted hexagon refined as free rotating group:
 C11(C6,C7,C8,C9,C10), C10A(C11A,C6A,C7A,C8A,C9A)
6.e Idealised Me refined as rotating group:
 C15(H15A,H15B,H15C), C14(H14A,H14B,H14C), C13(H13A,H13B,H13C)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     iterative
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Cl1 Cl 0.1416(6) 0.9302(2) 0.61660(10) 0.0690(11) Uani 1 1 d . . . . .
O4 O 0.3155(13) 0.5820(6) 0.7009(2) 0.0528(18) Uani 1 1 d . . . . .
O3 O 0.6387(14) 0.6463(6) 0.6493(2) 0.0494(17) Uani 1 1 d . . . . .
O1 O 0.6403(17) 0.6902(7) 0.5272(3) 0.065(2) Uani 1 1 d . . . . .
N1 N 0.2116(16) 0.6688(7) 0.6299(3) 0.049(2) Uani 1 1 d D . . . .
C4 C 0.407(2) 0.6328(8) 0.6600(3) 0.049(3) Uani 1 1 d . . . . .
C3 C 0.378(2) 0.8414(7) 0.5879(4) 0.046(2) Uani 1 1 d . . . . .
H3A H 0.425851 0.872060 0.554213 0.055 Uiso 1 1 calc R U . . .
H3B H 0.537374 0.839200 0.609219 0.055 Uiso 1 1 calc R U . . .
C2 C 0.2686(19) 0.7228(8) 0.5820(3) 0.044(2) Uani 1 1 d . . . . .
H2 H 0.100126 0.729006 0.562878 0.053 Uiso 1 1 calc R U . . .
C12 C 0.496(2) 0.5338(9) 0.7394(4) 0.053(3) Uani 1 1 d . . . . .
C15 C 0.666(2) 0.4454(8) 0.7155(4) 0.059(3) Uani 1 1 d . . . . .
H15A H 0.559678 0.396958 0.693463 0.088 Uiso 1 1 calc R U . . .
H15B H 0.747448 0.399134 0.742119 0.088 Uiso 1 1 calc R U . . .
H15C H 0.803174 0.482291 0.695310 0.088 Uiso 1 1 calc R U . . .
C1 C 0.456(2) 0.6515(9) 0.5499(4) 0.055(3) Uani 1 1 d . . . . .
C14 C 0.649(2) 0.6297(9) 0.7644(4) 0.060(3) Uani 1 1 d . . . . .
H14A H 0.775529 0.660840 0.740127 0.091 Uiso 1 1 calc R U . . .
H14B H 0.742544 0.600373 0.794170 0.091 Uiso 1 1 calc R U . . .
H14C H 0.527675 0.689460 0.775044 0.091 Uiso 1 1 calc R U . . .
C13 C 0.311(2) 0.4777(12) 0.7769(4) 0.077(4) Uani 1 1 d . . . . .
H13A H 0.187016 0.534213 0.789933 0.115 Uiso 1 1 calc R U . . .
H13B H 0.411071 0.445611 0.805145 0.115 Uiso 1 1 calc R U . . .
H13C H 0.213630 0.417016 0.759712 0.115 Uiso 1 1 calc R U . . .
O2 O 0.335(4) 0.5392(17) 0.5491(9) 0.050(6) Uani 0.54(2) 1 d . . P A 1
C5 C 0.463(9) 0.455(2) 0.5187(11) 0.093(12) Uani 0.54(2) 1 d . . P A 1
H5A H 0.581355 0.491070 0.493893 0.112 Uiso 0.54(2) 1 calc R U P A 1
H5B H 0.331293 0.409486 0.499810 0.112 Uiso 0.54(2) 1 calc R U P A 1
C11 C 0.853(3) 0.4135(11) 0.5756(7) 0.068(6) Uani 0.54(2) 1 d G U P A 1
H11 H 0.918158 0.487396 0.568606 0.082 Uiso 0.54(2) 1 calc R U P A 1
C6 C 0.618(3) 0.3780(11) 0.5542(6) 0.053(7) Uani 0.54(2) 1 d G U P A 1
C7 C 0.523(3) 0.2699(11) 0.5644(6) 0.063(6) Uani 0.54(2) 1 d G U P A 1
H7 H 0.362482 0.245581 0.549842 0.075 Uiso 0.54(2) 1 calc R U P A 1
C8 C 0.663(4) 0.1973(10) 0.5959(7) 0.061(6) Uani 0.54(2) 1 d G U P A 1
H8 H 0.598215 0.123433 0.602909 0.073 Uiso 0.54(2) 1 calc R U P A 1
C9 C 0.898(4) 0.2329(14) 0.6173(7) 0.071(7) Uani 0.54(2) 1 d G U P A 1
H9 H 0.993920 0.183265 0.638826 0.085 Uiso 0.54(2) 1 calc R U P A 1
C10 C 0.993(3) 0.3410(15) 0.6071(6) 0.076(7) Uani 0.54(2) 1 d G U P A 1
H10 H 1.153895 0.365246 0.621675 0.091 Uiso 0.54(2) 1 calc R U P A 1
O2A O 0.459(5) 0.5529(19) 0.5519(10) 0.048(7) Uani 0.46(2) 1 d . . P A 2
C5A C 0.643(7) 0.478(2) 0.5259(12) 0.059(8) Uani 0.46(2) 1 d . . P A 2
H5AA H 0.814886 0.516651 0.523398 0.071 Uiso 0.46(2) 1 calc R U P A 2
H5AB H 0.579548 0.463895 0.490950 0.071 Uiso 0.46(2) 1 calc R U P A 2
C10A C 0.848(6) 0.2508(17) 0.6185(10) 0.084(10) Uani 0.46(2) 1 d G U P A 2
H10A H 0.962802 0.239976 0.646502 0.101 Uiso 0.46(2) 1 calc R U P A 2
C11A C 0.844(5) 0.3541(14) 0.5931(9) 0.073(8) Uani 0.46(2) 1 d G U P A 2
H11A H 0.956109 0.413901 0.603717 0.088 Uiso 0.46(2) 1 calc R U P A 2
C6A C 0.676(5) 0.3699(14) 0.5521(8) 0.060(8) Uani 0.46(2) 1 d G U P A 2
C7A C 0.513(5) 0.2824(18) 0.5366(8) 0.087(10) Uani 0.46(2) 1 d G U P A 2
H7A H 0.397833 0.293202 0.508585 0.104 Uiso 0.46(2) 1 calc R U P A 2
C8A C 0.516(4) 0.1791(16) 0.5620(9) 0.089(9) Uani 0.46(2) 1 d G U P A 2
H8A H 0.404522 0.119278 0.551370 0.106 Uiso 0.46(2) 1 calc R U P A 2
C9A C 0.684(6) 0.1633(15) 0.6030(10) 0.082(10) Uani 0.46(2) 1 d G U P A 2
H9A H 0.687005 0.092663 0.620328 0.098 Uiso 0.46(2) 1 calc R U P A 2
H1 H 0.031(9) 0.656(8) 0.642(3) 0.05(3) Uiso 1 1 d 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 C3 1.766(10) . ?
O4 C4 1.319(12) . ?
O4 C12 1.484(12) . ?
O3 C4 1.225(12) . ?
O1 C1 1.205(13) . ?
N1 C4 1.343(12) . ?
N1 C2 1.442(11) . ?
N1 H1 0.99(3) . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C3 C2 1.514(13) . ?
C2 H2 1.0000 . ?
C2 C1 1.530(14) . ?
C12 C15 1.494(15) . ?
C12 C14 1.523(15) . ?
C12 C13 1.521(15) . ?
C15 H15A 0.9800 . ?
C15 H15B 0.9800 . ?
C15 H15C 0.9800 . ?
C1 O2 1.46(2) . ?
C1 O2A 1.16(2) . ?
C14 H14A 0.9800 . ?
C14 H14B 0.9800 . ?
C14 H14C 0.9800 . ?
C13 H13A 0.9800 . ?
C13 H13B 0.9800 . ?
C13 H13C 0.9800 . ?
O2 C5 1.44(4) . ?
C5 H5A 0.9900 . ?
C5 H5B 0.9900 . ?
C5 C6 1.52(4) . ?
C11 H11 0.9500 . ?
C11 C6 1.3900 . ?
C11 C10 1.3900 . ?
C6 C7 1.3900 . ?
C7 H7 0.9500 . ?
C7 C8 1.3900 . ?
C8 H8 0.9500 . ?
C8 C9 1.3900 . ?
C9 H9 0.9500 . ?
C9 C10 1.3900 . ?
C10 H10 0.9500 . ?
O2A C5A 1.46(4) . ?
C5A H5AA 0.9900 . ?
C5A H5AB 0.9900 . ?
C5A C6A 1.46(3) . ?
C10A H10A 0.9500 . ?
C10A C11A 1.3900 . ?
C10A C9A 1.3900 . ?
C11A H11A 0.9500 . ?
C11A C6A 1.3900 . ?
C6A C7A 1.3900 . ?
C7A H7A 0.9500 . ?
C7A C8A 1.3900 . ?
C8A H8A 0.9500 . ?
C8A C9A 1.3900 . ?
C9A H9A 0.9500 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C4 O4 C12 120.7(8) . . ?
C4 N1 C2 120.3(8) . . ?
C4 N1 H1 118(6) . . ?
C2 N1 H1 122(6) . . ?
O4 C4 N1 111.1(9) . . ?
O3 C4 O4 126.1(9) . . ?
O3 C4 N1 122.8(9) . . ?
Cl1 C3 H3A 109.7 . . ?
Cl1 C3 H3B 109.7 . . ?
H3A C3 H3B 108.2 . . ?
C2 C3 Cl1 109.9(7) . . ?
C2 C3 H3A 109.7 . . ?
C2 C3 H3B 109.7 . . ?
N1 C2 C3 113.1(8) . . ?
N1 C2 H2 107.5 . . ?
N1 C2 C1 111.5(8) . . ?
C3 C2 H2 107.5 . . ?
C3 C2 C1 109.5(8) . . ?
C1 C2 H2 107.5 . . ?
O4 C12 C15 110.0(8) . . ?
O4 C12 C14 109.2(8) . . ?
O4 C12 C13 102.7(8) . . ?
C15 C12 C14 113.7(9) . . ?
C15 C12 C13 109.4(9) . . ?
C13 C12 C14 111.2(9) . . ?
C12 C15 H15A 109.5 . . ?
C12 C15 H15B 109.5 . . ?
C12 C15 H15C 109.5 . . ?
H15A C15 H15B 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
O1 C1 C2 123.7(10) . . ?
O1 C1 O2 131.9(13) . . ?
O2 C1 C2 103.9(13) . . ?
O2A C1 O1 113.1(16) . . ?
O2A C1 C2 122.1(16) . . ?
C12 C14 H14A 109.5 . . ?
C12 C14 H14B 109.5 . . ?
C12 C14 H14C 109.5 . . ?
H14A C14 H14B 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C12 C13 H13A 109.5 . . ?
C12 C13 H13B 109.5 . . ?
C12 C13 H13C 109.5 . . ?
H13A C13 H13B 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
C5 O2 C1 116(2) . . ?
O2 C5 H5A 110.1 . . ?
O2 C5 H5B 110.1 . . ?
O2 C5 C6 108(2) . . ?
H5A C5 H5B 108.4 . . ?
C6 C5 H5A 110.1 . . ?
C6 C5 H5B 110.1 . . ?
C6 C11 H11 120.0 . . ?
C6 C11 C10 120.0 . . ?
C10 C11 H11 120.0 . . ?
C11 C6 C5 121.3(17) . . ?
C7 C6 C5 118.7(17) . . ?
C7 C6 C11 120.0 . . ?
C6 C7 H7 120.0 . . ?
C8 C7 C6 120.0 . . ?
C8 C7 H7 120.0 . . ?
C7 C8 H8 120.0 . . ?
C7 C8 C9 120.0 . . ?
C9 C8 H8 120.0 . . ?
C8 C9 H9 120.0 . . ?
C10 C9 C8 120.0 . . ?
C10 C9 H9 120.0 . . ?
C11 C10 H10 120.0 . . ?
C9 C10 C11 120.0 . . ?
C9 C10 H10 120.0 . . ?
C1 O2A C5A 126(2) . . ?
O2A C5A H5AA 109.1 . . ?
O2A C5A H5AB 109.1 . . ?
O2A C5A C6A 112(2) . . ?
H5AA C5A H5AB 107.9 . . ?
C6A C5A H5AA 109.1 . . ?
C6A C5A H5AB 109.1 . . ?
C11A C10A H10A 120.0 . . ?
C11A C10A C9A 120.0 . . ?
C9A C10A H10A 120.0 . . ?
C10A C11A H11A 120.0 . . ?
C6A C11A C10A 120.0 . . ?
C6A C11A H11A 120.0 . . ?
C11A C6A C5A 124(2) . . ?
C7A C6A C5A 116(2) . . ?
C7A C6A C11A 120.0 . . ?
C6A C7A H7A 120.0 . . ?
C8A C7A C6A 120.0 . . ?
C8A C7A H7A 120.0 . . ?
C7A C8A H8A 120.0 . . ?
C7A C8A C9A 120.0 . . ?
C9A C8A H8A 120.0 . . ?
C10A C9A H9A 120.0 . . ?
C8A C9A C10A 120.0 . . ?
C8A C9A H9A 120.0 . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
C2 H2 O1 1.00 2.57 3.540(13) 163.2 1_455 yes
N1 H1 O3 0.99(3) 2.01(4) 2.982(11) 166(8) 1_455 yes

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 C3 C2 N1 -63.7(9) . . . . ?
Cl1 C3 C2 C1 171.2(6) . . . . ?
O1 C1 O2 C5 5(3) . . . . ?
O1 C1 O2A C5A -6(4) . . . . ?
N1 C2 C1 O1 -135.9(10) . . . . ?
N1 C2 C1 O2 51.6(13) . . . . ?
N1 C2 C1 O2A 31(2) . . . . ?
C4 O4 C12 C15 -59.7(11) . . . . ?
C4 O4 C12 C14 65.7(11) . . . . ?
C4 O4 C12 C13 -176.1(9) . . . . ?
C4 N1 C2 C3 -72.4(11) . . . . ?
C4 N1 C2 C1 51.6(12) . . . . ?
C3 C2 C1 O1 -9.9(13) . . . . ?
C3 C2 C1 O2 177.6(11) . . . . ?
C3 C2 C1 O2A 157.4(19) . . . . ?
C2 N1 C4 O4 -177.5(8) . . . . ?
C2 N1 C4 O3 2.0(14) . . . . ?
C2 C1 O2 C5 176.5(19) . . . . ?
C2 C1 O2A C5A -175(2) . . . . ?
C12 O4 C4 O3 -0.3(15) . . . . ?
C12 O4 C4 N1 179.1(8) . . . . ?
C1 O2 C5 C6 102(2) . . . . ?
C1 O2A C5A C6A 154(3) . . . . ?
O2 C5 C6 C11 -76(3) . . . . ?
O2 C5 C6 C7 106(2) . . . . ?
C5 C6 C7 C8 179(2) . . . . ?
C11 C6 C7 C8 0.0 . . . . ?
C6 C11 C10 C9 0.0 . . . . ?
C6 C7 C8 C9 0.0 . . . . ?
C7 C8 C9 C10 0.0 . . . . ?
C8 C9 C10 C11 0.0 . . . . ?
C10 C11 C6 C5 -179(2) . . . . ?
C10 C11 C6 C7 0.0 . . . . ?
O2A C5A C6A C11A -83(3) . . . . ?
O2A C5A C6A C7A 92(3) . . . . ?
C5A C6A C7A C8A -175(3) . . . . ?
C10A C11A C6A C5A 175(3) . . . . ?
C10A C11A C6A C7A 0.0 . . . . ?
C11A C10A C9A C8A 0.0 . . . . ?
C11A C6A C7A C8A 0.0 . . . . ?
C6A C7A C8A C9A 0.0 . . . . ?
C7A C8A C9A C10A 0.0 . . . . ?
C9A C10A C11A C6A 0.0 . . . . ?

_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_mo_v1_22ffdb1_0m
_database_code_depnum_ccdc_archive 'CCDC 2238181'
loop_
_audit_author_name
_audit_author_address
'Francois Jacobs'
;University of the Free State
South Africa
;
_audit_update_record             
;
2023-01-26 deposited with the CCDC.	2024-01-18 downloaded from the CCDC.
;
_audit_creation_date             2023-01-24
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6408)
;
_shelx_SHELXL_version_number     2019/2
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         '2(C12 H22 Cl N O4)'
_chemical_formula_sum            'C24 H44 Cl2 N2 O8'
_chemical_formula_weight         559.51
_chemical_absolute_configuration ?
_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           4
_space_group_name_H-M_alt        'P 1 21 1'
_space_group_name_Hall           'P 2yb'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z'

_cell_length_a                   5.9666(5)
_cell_length_b                   9.8723(9)
_cell_length_c                   12.6022(11)
_cell_angle_alpha                90
_cell_angle_beta                 93.118(3)
_cell_angle_gamma                90
_cell_volume                     741.22(11)
_cell_formula_units_Z            1
_cell_measurement_reflns_used    9955
_cell_measurement_temperature    101(2)
_cell_measurement_theta_max      28.29
_cell_measurement_theta_min      2.62
_shelx_estimated_absorpt_T_max   0.942
_shelx_estimated_absorpt_T_min   0.900
_exptl_absorpt_coefficient_mu    0.264
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_correction_T_min  0.6535
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016) was used for absorption correction.
wR2(int) was 0.1092 before and 0.0507 after correction.
The Ratio of minimum to maximum transmission is 0.8764.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.253
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       Stout
_exptl_crystal_F_000             300
_exptl_crystal_size_max          0.408
_exptl_crystal_size_mid          0.351
_exptl_crystal_size_min          0.227
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0294
_diffrn_reflns_av_unetI/netI     0.0278
_diffrn_reflns_Laue_measured_fraction_full 0.974
_diffrn_reflns_Laue_measured_fraction_max 0.981
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            12661
_diffrn_reflns_point_group_measured_fraction_full 0.974
_diffrn_reflns_point_group_measured_fraction_max 0.980
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.303
_diffrn_reflns_theta_min         3.238
_diffrn_ambient_temperature      101.0
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.974
_diffrn_measured_fraction_theta_max 0.981
_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_source_current           1.4
_diffrn_source_power             0.07
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.893
_reflns_Friedel_fraction_full    0.975
_reflns_Friedel_fraction_max     0.980
_reflns_number_gt                3550
_reflns_number_total             3606
_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       ?
_computing_data_collection       ?
_computing_data_reduction        ?
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2019/2 (Sheldrick, 2015)'
_computing_structure_solution    ?
_refine_diff_density_max         0.208
_refine_diff_density_min         -0.143
_refine_diff_density_rms         0.027
_refine_ls_abs_structure_details 
;
 Flack x determined using 1645 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.012(14)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.046
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     173
_refine_ls_number_reflns         3606
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0234
_refine_ls_R_factor_gt           0.0231
_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)+(0.0314P)²+0.0701P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0615
_refine_ls_wR_factor_ref         0.0617
_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:
 C2(H2)
2.b Secondary CH2 refined with riding coordinates:
 C3(H3A,H3B)
2.c Idealised Me refined as rotating group:
 C11(H11A,H11B,H11C), C12(H12A,H12B,H12C), C10(H10A,H10B,H10C), C6(H6A,H6B,
 H6C), C7(H7A,H7B,H7C), C8(H8A,H8B,H8C)
;
_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 0.99802(7) 0.27990(4) 0.73466(4) 0.04292(13) Uani 1 1 d . . . . .
O4 O 0.41748(16) 0.54367(9) 0.90899(7) 0.01978(19) Uani 1 1 d . . . . .
O3 O 0.67742(18) 0.69285(10) 0.85087(8) 0.0269(2) Uani 1 1 d . . . . .
O2 O 0.80565(15) 0.45057(10) 0.51157(7) 0.02031(19) Uani 1 1 d . . . . .
O1 O 0.47160(17) 0.40133(12) 0.57935(9) 0.0290(2) Uani 1 1 d . . . . .
N1 N 0.6117(2) 0.48890(12) 0.77246(9) 0.0220(2) Uani 1 1 d . . . . .
C4 C 0.5775(2) 0.58609(13) 0.84586(10) 0.0186(2) Uani 1 1 d . . . . .
C1 C 0.6593(2) 0.44662(13) 0.58682(10) 0.0195(2) Uani 1 1 d . . . . .
C2 C 0.7617(2) 0.51008(13) 0.68840(10) 0.0192(2) Uani 1 1 d . . . . .
H2 H 0.771538 0.609939 0.676196 0.023 Uiso 1 1 calc R U . . .
C9 C 0.3517(2) 0.62604(13) 1.00024(10) 0.0189(2) Uani 1 1 d . . . . .
C11 C 0.2397(2) 0.75549(15) 0.96076(12) 0.0259(3) Uani 1 1 d . . . . .
H11A H 0.347642 0.810336 0.923598 0.039 Uiso 1 1 calc R U . . .
H11B H 0.187166 0.806641 1.021259 0.039 Uiso 1 1 calc R U . . .
H11C H 0.111603 0.733302 0.911846 0.039 Uiso 1 1 calc R U . . .
C12 C 0.5543(2) 0.65334(16) 1.07582(11) 0.0243(3) Uani 1 1 d . . . . .
H12A H 0.635842 0.568538 1.090132 0.036 Uiso 1 1 calc R U . . .
H12B H 0.503945 0.690419 1.142607 0.036 Uiso 1 1 calc R U . . .
H12C H 0.653671 0.718635 1.043375 0.036 Uiso 1 1 calc R U . . .
C10 C 0.1853(2) 0.53346(15) 1.05092(12) 0.0260(3) Uani 1 1 d . . . . .
H10A H 0.058647 0.515452 1.000067 0.039 Uiso 1 1 calc R U . . .
H10B H 0.130424 0.577190 1.114323 0.039 Uiso 1 1 calc R U . . .
H10C H 0.259147 0.447899 1.071116 0.039 Uiso 1 1 calc R U . . .
C5 C 0.7504(2) 0.39215(16) 0.40477(11) 0.0258(3) Uani 1 1 d . . . . .
C3 C 0.9979(2) 0.45902(16) 0.71577(11) 0.0263(3) Uani 1 1 d . . . . .
H3A H 1.058502 0.503859 0.781491 0.032 Uiso 1 1 calc R U . . .
H3B H 1.096123 0.482426 0.657661 0.032 Uiso 1 1 calc R U . . .
C6 C 0.6827(3) 0.24478(19) 0.41511(14) 0.0383(4) Uani 1 1 d . . . . .
H6A H 0.793527 0.197592 0.461946 0.057 Uiso 1 1 calc R U . . .
H6B H 0.675814 0.202046 0.344822 0.057 Uiso 1 1 calc R U . . .
H6C H 0.534931 0.239536 0.445250 0.057 Uiso 1 1 calc R U . . .
C7 C 0.5725(3) 0.4794(2) 0.34846(13) 0.0392(4) Uani 1 1 d . . . . .
H7A H 0.436513 0.478727 0.388688 0.059 Uiso 1 1 calc R U . . .
H7B H 0.537742 0.443421 0.276967 0.059 Uiso 1 1 calc R U . . .
H7C H 0.628123 0.572396 0.343264 0.059 Uiso 1 1 calc R U . . .
C8 C 0.9732(3) 0.4031(2) 0.35263(13) 0.0352(4) Uani 1 1 d . . . . .
H8A H 1.021937 0.497855 0.352823 0.053 Uiso 1 1 calc R U . . .
H8B H 0.955508 0.370383 0.279224 0.053 Uiso 1 1 calc R U . . .
H8C H 1.085929 0.347966 0.392200 0.053 Uiso 1 1 calc R U . . .
H1 H 0.523(4) 0.423(3) 0.7691(18) 0.039(6) 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 C3 1.7843(17) . ?
O4 C4 1.3424(16) . ?
O4 C9 1.4788(15) . ?
O3 C4 1.2109(17) . ?
O2 C1 1.3243(16) . ?
O2 C5 1.4848(16) . ?
O1 C1 1.2046(17) . ?
N1 C4 1.3559(17) . ?
N1 C2 1.4387(17) . ?
N1 H1 0.84(2) . ?
C1 C2 1.5229(18) . ?
C2 H2 1.0000 . ?
C2 C3 1.5186(18) . ?
C9 C11 1.5139(19) . ?
C9 C12 1.5217(18) . ?
C9 C10 1.5161(19) . ?
C11 H11A 0.9800 . ?
C11 H11B 0.9800 . ?
C11 H11C 0.9800 . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12C 0.9800 . ?
C10 H10A 0.9800 . ?
C10 H10B 0.9800 . ?
C10 H10C 0.9800 . ?
C5 C6 1.517(2) . ?
C5 C7 1.513(2) . ?
C5 C8 1.518(2) . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C6 H6A 0.9800 . ?
C6 H6B 0.9800 . ?
C6 H6C 0.9800 . ?
C7 H7A 0.9800 . ?
C7 H7B 0.9800 . ?
C7 H7C 0.9800 . ?
C8 H8A 0.9800 . ?
C8 H8B 0.9800 . ?
C8 H8C 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
C4 O4 C9 121.11(10) . . ?
C1 O2 C5 121.01(10) . . ?
C4 N1 C2 121.49(12) . . ?
C4 N1 H1 117.7(15) . . ?
C2 N1 H1 119.5(15) . . ?
O4 C4 N1 108.78(11) . . ?
O3 C4 O4 127.21(13) . . ?
O3 C4 N1 124.02(13) . . ?
O2 C1 C2 109.86(11) . . ?
O1 C1 O2 126.97(12) . . ?
O1 C1 C2 123.18(12) . . ?
N1 C2 C1 108.78(11) . . ?
N1 C2 H2 107.5 . . ?
N1 C2 C3 113.03(11) . . ?
C1 C2 H2 107.5 . . ?
C3 C2 C1 112.29(11) . . ?
C3 C2 H2 107.5 . . ?
O4 C9 C11 109.86(11) . . ?
O4 C9 C12 110.41(11) . . ?
O4 C9 C10 101.75(10) . . ?
C11 C9 C12 112.20(11) . . ?
C11 C9 C10 111.08(12) . . ?
C10 C9 C12 111.07(11) . . ?
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 . . ?
C9 C12 H12A 109.5 . . ?
C9 C12 H12B 109.5 . . ?
C9 C12 H12C 109.5 . . ?
H12A C12 H12B 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
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 . . ?
O2 C5 C6 109.97(12) . . ?
O2 C5 C7 108.64(13) . . ?
O2 C5 C8 102.03(11) . . ?
C6 C5 C8 110.41(14) . . ?
C7 C5 C6 113.74(14) . . ?
C7 C5 C8 111.41(14) . . ?
Cl1 C3 H3A 109.5 . . ?
Cl1 C3 H3B 109.5 . . ?
C2 C3 Cl1 110.67(10) . . ?
C2 C3 H3A 109.5 . . ?
C2 C3 H3B 109.5 . . ?
H3A C3 H3B 108.1 . . ?
C5 C6 H6A 109.5 . . ?
C5 C6 H6B 109.5 . . ?
C5 C6 H6C 109.5 . . ?
H6A C6 H6B 109.5 . . ?
H6A C6 H6C 109.5 . . ?
H6B C6 H6C 109.5 . . ?
C5 C7 H7A 109.5 . . ?
C5 C7 H7B 109.5 . . ?
C5 C7 H7C 109.5 . . ?
H7A C7 H7B 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
C5 C8 H8A 109.5 . . ?
C5 C8 H8B 109.5 . . ?
C5 C8 H8C 109.5 . . ?
H8A C8 H8B 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 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
O2 C1 C2 N1 -172.61(10) . . . . ?
O2 C1 C2 C3 -46.74(15) . . . . ?
O1 C1 C2 N1 7.73(18) . . . . ?
O1 C1 C2 C3 133.61(14) . . . . ?
N1 C2 C3 Cl1 63.48(13) . . . . ?
C4 O4 C9 C11 66.73(15) . . . . ?
C4 O4 C9 C12 -57.54(15) . . . . ?
C4 O4 C9 C10 -175.51(11) . . . . ?
C4 N1 C2 C1 -141.06(12) . . . . ?
C4 N1 C2 C3 93.50(15) . . . . ?
C1 O2 C5 C6 -55.62(17) . . . . ?
C1 O2 C5 C7 69.44(16) . . . . ?
C1 O2 C5 C8 -172.80(12) . . . . ?
C1 C2 C3 Cl1 -60.05(13) . . . . ?
C2 N1 C4 O4 175.08(11) . . . . ?
C2 N1 C4 O3 -4.6(2) . . . . ?
C9 O4 C4 O3 -3.3(2) . . . . ?
C9 O4 C4 N1 177.01(11) . . . . ?
C5 O2 C1 O1 -1.8(2) . . . . ?
C5 O2 C1 C2 178.52(11) . . . . ?

_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_q4_20dfd1_b_0m
_database_code_depnum_ccdc_archive 'CCDC 2116494'
loop_
_audit_author_name
_audit_author_address
'Dumisani Vincent Kama'
;University Of The Free State
South Africa
;
_audit_update_record             
;
2023-01-26 deposited with the CCDC.	2024-01-18 downloaded from the CCDC.
;
_audit_creation_date             2023-01-24
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6408)
;
_shelx_SHELXL_version_number     2019/2
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C12 H22 I N O4'
_chemical_formula_sum            'C12 H22 I N O4'
_chemical_formula_weight         371.20
_chemical_absolute_configuration ?
_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'
I I -0.4742 1.8119 '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      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, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'

_cell_length_a                   5.4467(8)
_cell_length_b                   11.4173(18)
_cell_length_c                   25.107(4)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1561.3(4)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9855
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      28.32
_cell_measurement_theta_min      3.02
_shelx_estimated_absorpt_T_max   0.937
_shelx_estimated_absorpt_T_min   0.722
_exptl_absorpt_coefficient_mu    2.058
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_correction_T_min  0.6306
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016) was used for absorption correction.
wR2(int) was 0.0828 before and 0.0650 after correction.
The Ratio of minimum to maximum transmission is 0.8456.
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    1.579
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       Plate
_exptl_crystal_F_000             744
_exptl_crystal_size_max          0.169
_exptl_crystal_size_mid          0.094
_exptl_crystal_size_min          0.032
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0408
_diffrn_reflns_av_unetI/netI     0.0245
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       33
_diffrn_reflns_limit_l_min       -33
_diffrn_reflns_number            26043
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.329
_diffrn_reflns_theta_min         3.018
_diffrn_ambient_temperature      100.0
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.997
_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_source_current           20.0
_diffrn_source_power             1.0
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.713
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     0.998
_reflns_number_gt                3783
_reflns_number_total             3883
_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       ?
_computing_data_collection       ?
_computing_data_reduction        ?
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2019/2 (Sheldrick, 2015)'
_computing_structure_solution    ?
_refine_diff_density_max         0.641
_refine_diff_density_min         -0.447
_refine_diff_density_rms         0.057
_refine_ls_abs_structure_details 
;
 Flack x determined using 1530 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.022(8)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.132
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     173
_refine_ls_number_reflns         3883
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0206
_refine_ls_R_factor_gt           0.0194
_refine_ls_restrained_S_all      1.136
_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)+(0.0074P)²+0.5353P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0393
_refine_ls_wR_factor_ref         0.0396
_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. Restrained distances
 H1-N1
 1 with sigma of 0.02
3.a Ternary CH refined with riding coordinates:
 C2(H2)
3.b Secondary CH2 refined with riding coordinates:
 C3(H3A,H3B)
3.c Idealised Me refined as rotating group:
 C7(H7A,H7B,H7C), C12(H12A,H12B,H12C), C8(H8A,H8B,H8C), C6(H6A,H6B,H6C),
 C10(H10A,H10B,H10C), C11(H11A,H11B,H11C)
;
_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
I1 I 0.79935(4) 0.67643(2) 0.45622(2) 0.02593(5) Uani 1 1 d . . . . .
O1 O 1.0497(4) 0.55681(17) 0.32876(8) 0.0229(4) Uani 1 1 d . . . . .
O2 O 0.7328(3) 0.67258(17) 0.30475(7) 0.0215(4) Uani 1 1 d . . . . .
O4 O 0.7385(4) 0.22904(16) 0.41109(8) 0.0214(4) Uani 1 1 d . . . . .
O3 O 0.3803(4) 0.3259(2) 0.39318(9) 0.0325(5) Uani 1 1 d . . . . .
N1 N 0.7525(4) 0.41259(19) 0.38369(9) 0.0199(5) Uani 1 1 d D . . . .
C3 C 0.5292(5) 0.5969(3) 0.40493(11) 0.0230(6) Uani 1 1 d . . . . .
H3A H 0.414724 0.549825 0.426831 0.028 Uiso 1 1 calc R U . . .
H3B H 0.432793 0.659334 0.387252 0.028 Uiso 1 1 calc R U . . .
C1 C 0.8367(5) 0.5834(2) 0.33012(10) 0.0175(6) Uani 1 1 d . . . . .
C2 C 0.6439(5) 0.5186(2) 0.36257(10) 0.0191(6) Uani 1 1 d . . . . .
H2 H 0.510034 0.494680 0.337565 0.023 Uiso 1 1 calc R U . . .
C4 C 0.6017(5) 0.3207(3) 0.39597(10) 0.0221(5) Uani 1 1 d . . . . .
C9 C 0.6163(6) 0.1189(2) 0.42735(12) 0.0231(6) Uani 1 1 d . . . . .
C5 C 0.8807(5) 0.7564(2) 0.27273(11) 0.0223(6) Uani 1 1 d . . . . .
C7 C 1.0530(6) 0.8214(3) 0.30936(12) 0.0301(6) Uani 1 1 d . . . . .
H7A H 0.961837 0.849976 0.340388 0.045 Uiso 1 1 calc R U . . .
H7B H 1.125368 0.887851 0.290311 0.045 Uiso 1 1 calc R U . . .
H7C H 1.183729 0.768400 0.321165 0.045 Uiso 1 1 calc R U . . .
C12 C 0.4487(6) 0.1405(3) 0.47421(12) 0.0286(7) Uani 1 1 d . . . . .
H12A H 0.540287 0.180380 0.502508 0.043 Uiso 1 1 calc R U . . .
H12B H 0.386432 0.065575 0.487566 0.043 Uiso 1 1 calc R U . . .
H12C H 0.310669 0.189731 0.462968 0.043 Uiso 1 1 calc R U . . .
C8 C 0.6880(7) 0.8377(3) 0.25025(14) 0.0383(8) Uani 1 1 d . . . . .
H8A H 0.572386 0.792742 0.228440 0.057 Uiso 1 1 calc R U . . .
H8B H 0.767318 0.897617 0.228210 0.057 Uiso 1 1 calc R U . . .
H8C H 0.599297 0.875569 0.279530 0.057 Uiso 1 1 calc R U . . .
C6 C 1.0151(7) 0.6915(3) 0.22860(12) 0.0356(8) Uani 1 1 d . . . . .
H6A H 1.149310 0.645434 0.243999 0.053 Uiso 1 1 calc R U . . .
H6B H 1.082199 0.748118 0.203127 0.053 Uiso 1 1 calc R U . . .
H6C H 0.900416 0.639117 0.210247 0.053 Uiso 1 1 calc R U . . .
C10 C 0.8292(6) 0.0430(3) 0.44453(17) 0.0443(10) Uani 1 1 d . . . . .
H10A H 0.944834 0.034549 0.414879 0.066 Uiso 1 1 calc R U . . .
H10B H 0.768127 -0.034317 0.455037 0.066 Uiso 1 1 calc R U . . .
H10C H 0.912737 0.079676 0.474824 0.066 Uiso 1 1 calc R U . . .
C11 C 0.4821(8) 0.0669(3) 0.38002(14) 0.0389(8) Uani 1 1 d . . . . .
H11A H 0.342882 0.117129 0.370576 0.058 Uiso 1 1 calc R U . . .
H11B H 0.422135 -0.011453 0.389239 0.058 Uiso 1 1 calc R U . . .
H11C H 0.594629 0.061368 0.349666 0.058 Uiso 1 1 calc R U . . .
H1 H 0.916(4) 0.403(2) 0.3850(10) 0.004(7) Uiso 1 1 d 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
I1 C3 2.156(3) . ?
O1 C1 1.200(3) . ?
O2 C1 1.328(3) . ?
O2 C5 1.488(3) . ?
O4 C4 1.340(4) . ?
O4 C9 1.480(3) . ?
O3 C4 1.210(3) . ?
N1 C2 1.448(3) . ?
N1 C4 1.367(4) . ?
N1 H1 0.90(2) . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C3 C2 1.524(4) . ?
C1 C2 1.521(4) . ?
C2 H2 1.0000 . ?
C9 C12 1.509(4) . ?
C9 C10 1.510(4) . ?
C9 C11 1.516(4) . ?
C5 C7 1.508(4) . ?
C5 C8 1.510(4) . ?
C5 C6 1.521(4) . ?
C7 H7A 0.9800 . ?
C7 H7B 0.9800 . ?
C7 H7C 0.9800 . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12C 0.9800 . ?
C8 H8A 0.9800 . ?
C8 H8B 0.9800 . ?
C8 H8C 0.9800 . ?
C6 H6A 0.9800 . ?
C6 H6B 0.9800 . ?
C6 H6C 0.9800 . ?
C10 H10A 0.9800 . ?
C10 H10B 0.9800 . ?
C10 H10C 0.9800 . ?
C11 H11A 0.9800 . ?
C11 H11B 0.9800 . ?
C11 H11C 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 O2 C5 121.5(2) . . ?
C4 O4 C9 119.5(2) . . ?
C2 N1 H1 121.2(17) . . ?
C4 N1 C2 118.6(2) . . ?
C4 N1 H1 119.8(18) . . ?
I1 C3 H3A 109.1 . . ?
I1 C3 H3B 109.1 . . ?
H3A C3 H3B 107.8 . . ?
C2 C3 I1 112.59(19) . . ?
C2 C3 H3A 109.1 . . ?
C2 C3 H3B 109.1 . . ?
O1 C1 O2 126.3(2) . . ?
O1 C1 C2 124.1(2) . . ?
O2 C1 C2 109.6(2) . . ?
N1 C2 C3 113.7(2) . . ?
N1 C2 C1 108.7(2) . . ?
N1 C2 H2 107.4 . . ?
C3 C2 H2 107.4 . . ?
C1 C2 C3 111.8(2) . . ?
C1 C2 H2 107.4 . . ?
O4 C4 N1 109.2(2) . . ?
O3 C4 O4 127.5(3) . . ?
O3 C4 N1 123.3(3) . . ?
O4 C9 C12 110.4(2) . . ?
O4 C9 C10 102.8(2) . . ?
O4 C9 C11 109.5(2) . . ?
C12 C9 C10 109.6(3) . . ?
C12 C9 C11 112.5(3) . . ?
C10 C9 C11 111.7(3) . . ?
O2 C5 C7 108.9(2) . . ?
O2 C5 C8 102.8(2) . . ?
O2 C5 C6 109.9(2) . . ?
C7 C5 C8 111.0(3) . . ?
C7 C5 C6 112.6(3) . . ?
C8 C5 C6 111.2(3) . . ?
C5 C7 H7A 109.5 . . ?
C5 C7 H7B 109.5 . . ?
C5 C7 H7C 109.5 . . ?
H7A C7 H7B 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
C9 C12 H12A 109.5 . . ?
C9 C12 H12B 109.5 . . ?
C9 C12 H12C 109.5 . . ?
H12A C12 H12B 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C5 C8 H8A 109.5 . . ?
C5 C8 H8B 109.5 . . ?
C5 C8 H8C 109.5 . . ?
H8A C8 H8B 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
C5 C6 H6A 109.5 . . ?
C5 C6 H6B 109.5 . . ?
C5 C6 H6C 109.5 . . ?
H6A C6 H6B 109.5 . . ?
H6A C6 H6C 109.5 . . ?
H6B C6 H6C 109.5 . . ?
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 . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
C2 H2 O1 1.00 2.62 3.374(3) 132.7 1_455 yes
C8 H8B O1 0.98 2.52 3.498(4) 177.1 3_755 yes
N1 H1 O1 0.90(2) 2.36(3) 2.690(3) 101.3(19) . yes

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
I1 C3 C2 N1 69.2(3) . . . . ?
I1 C3 C2 C1 -54.4(3) . . . . ?
O1 C1 C2 N1 -8.8(4) . . . . ?
O1 C1 C2 C3 117.6(3) . . . . ?
O2 C1 C2 N1 171.9(2) . . . . ?
O2 C1 C2 C3 -61.7(3) . . . . ?
C1 O2 C5 C7 -64.3(3) . . . . ?
C1 O2 C5 C8 177.9(2) . . . . ?
C1 O2 C5 C6 59.5(3) . . . . ?
C2 N1 C4 O4 175.6(2) . . . . ?
C2 N1 C4 O3 -4.7(4) . . . . ?
C4 O4 C9 C12 -59.5(3) . . . . ?
C4 O4 C9 C10 -176.3(3) . . . . ?
C4 O4 C9 C11 64.9(3) . . . . ?
C4 N1 C2 C3 79.5(3) . . . . ?
C4 N1 C2 C1 -155.2(2) . . . . ?
C9 O4 C4 O3 -0.7(4) . . . . ?
C9 O4 C4 N1 179.0(2) . . . . ?
C5 O2 C1 O1 -3.4(4) . . . . ?
C5 O2 C1 C2 175.8(2) . . . . ?

_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_mo_v4_21ffdb3_0m
_database_code_depnum_ccdc_archive 'CCDC 2116497'
loop_
_audit_author_name
_audit_author_address
'Francois Jacobs'
;University Of The Free State
South Africa
;
_audit_update_record             
;
2023-01-26 deposited with the CCDC.	2024-01-18 downloaded from the CCDC.
;
_audit_creation_date             2023-01-24
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6408)
;
_shelx_SHELXL_version_number     2019/2
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C15 H20 I N O4'
_chemical_formula_sum            'C15 H20 I N O4'
_chemical_formula_weight         405.22
_chemical_absolute_configuration ?
_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'
I I -0.4742 1.8119 '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      trigonal
_space_group_IT_number           144
_space_group_name_H-M_alt        'P 31'
_space_group_name_Hall           'P 31'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-y, x-y, z+1/3'
'-x+y, -x, z+2/3'

_cell_length_a                   16.6588(11)
_cell_length_b                   16.6588(11)
_cell_length_c                   5.1740(5)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                120
_cell_volume                     1243.5(2)
_cell_formula_units_Z            3
_cell_measurement_reflns_used    9899
_cell_measurement_temperature    110.0
_cell_measurement_theta_max      28.31
_cell_measurement_theta_min      2.45
_shelx_estimated_absorpt_T_max   0.924
_shelx_estimated_absorpt_T_min   0.531
_exptl_absorpt_coefficient_mu    1.946
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_correction_T_min  0.6057
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1395 before and 0.0899 after correction.
The Ratio of minimum to maximum transmission is 0.8123.
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    1.623
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       Needle
_exptl_crystal_F_000             606
_exptl_crystal_size_max          0.373
_exptl_crystal_size_mid          0.043
_exptl_crystal_size_min          0.041
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0647
_diffrn_reflns_av_unetI/netI     0.0541
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_h_min       -22
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_l_max       6
_diffrn_reflns_limit_l_min       -6
_diffrn_reflns_number            16446
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.992
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.356
_diffrn_reflns_theta_min         2.445
_diffrn_ambient_temperature      110.0
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.997
_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_source_current           1.4
_diffrn_source_power             0.07
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.989
_reflns_Friedel_fraction_full    0.993
_reflns_Friedel_fraction_max     0.986
_reflns_number_gt                3967
_reflns_number_total             4125
_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       ?
_computing_data_collection       ?
_computing_data_reduction        ?
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2019/2 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT  (Sheldrick, 2015)'
_refine_diff_density_max         0.336
_refine_diff_density_min         -0.741
_refine_diff_density_rms         0.082
_refine_ls_abs_structure_details 
;
 Flack x determined using 1894 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.055(15)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.036
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     194
_refine_ls_number_reflns         4125
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0295
_refine_ls_R_factor_gt           0.0273
_refine_ls_restrained_S_all      1.036
_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)+(0.0179P)²+0.1229P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0641
_refine_ls_wR_factor_ref         0.0656
_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:
 C2(H2)
2.b Secondary CH2 refined with riding coordinates:
 C3(H3A,H3B), C5(H5A,H5B)
2.c Me refined with riding coordinates:
 C15(H15A,H15B,H15C), C13(H13A,H13B,H13C), C14(H14A,H14B,H14C)
2.d Aromatic/amide H refined with riding coordinates:
 C11(H11), C9(H9), C7(H7), C10(H10), C8(H8)
;
_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
I1 I -0.01575(2) 0.12947(2) 0.11347(4) 0.02232(9) Uani 1 1 d . . . . .
O2 O 0.2634(2) 0.2299(2) 0.6272(7) 0.0206(7) Uani 1 1 d . . . . .
O3 O 0.1444(2) 0.3633(2) 0.8454(6) 0.0214(6) Uani 1 1 d . . . . .
O1 O 0.3143(2) 0.3716(2) 0.4595(7) 0.0240(7) Uani 1 1 d . . . . .
O4 O 0.1173(2) 0.4505(2) 0.5570(6) 0.0215(6) Uani 1 1 d . . . . .
N1 N 0.1303(3) 0.3322(3) 0.4160(7) 0.0185(7) Uani 1 1 d . . . . .
C2 C 0.1501(3) 0.2581(3) 0.4504(8) 0.0156(8) Uani 1 1 d . . . . .
H2 H 0.112306 0.218218 0.597676 0.019 Uiso 1 1 calc R U . . .
C4 C 0.1319(3) 0.3819(3) 0.6277(9) 0.0177(8) Uani 1 1 d . . . . .
C3 C 0.1283(3) 0.1984(3) 0.2096(9) 0.0174(8) Uani 1 1 d . . . . .
H3A H 0.147401 0.151518 0.238048 0.021 Uiso 1 1 calc R U . . .
H3B H 0.164711 0.237879 0.062637 0.021 Uiso 1 1 calc R U . . .
C12 C 0.1152(3) 0.5139(3) 0.7538(9) 0.0200(9) Uani 1 1 d . . . . .
C11 C 0.3850(4) 0.1605(4) 0.3617(11) 0.0289(10) Uani 1 1 d . . . . .
H11 H 0.332410 0.106540 0.426956 0.035 Uiso 1 1 calc R U . . .
C15 C 0.0344(3) 0.4604(4) 0.9378(9) 0.0256(10) Uani 1 1 d . . . . .
H15A H 0.033444 0.502829 1.067347 0.038 Uiso 1 1 calc R U . . .
H15B H -0.023860 0.431897 0.840177 0.038 Uiso 1 1 calc R U . . .
H15C H 0.041378 0.411914 1.024284 0.038 Uiso 1 1 calc R U . . .
C6 C 0.4107(3) 0.2463(3) 0.4704(9) 0.0226(9) Uani 1 1 d . . . . .
C1 C 0.2530(3) 0.2960(3) 0.5097(8) 0.0156(9) Uani 1 1 d . . . . .
C9 C 0.5117(5) 0.2313(5) 0.0631(12) 0.0415(16) Uani 1 1 d . . . . .
H9 H 0.546453 0.226480 -0.075534 0.050 Uiso 1 1 calc R U . . .
C7 C 0.4868(4) 0.3245(4) 0.3711(12) 0.0306(11) Uani 1 1 d . . . . .
H7 H 0.504315 0.383631 0.441777 0.037 Uiso 1 1 calc R U . . .
C13 C 0.2073(3) 0.5649(3) 0.8922(11) 0.0260(10) Uani 1 1 d . . . . .
H13A H 0.204931 0.606615 1.021747 0.039 Uiso 1 1 calc R U . . .
H13B H 0.220175 0.520069 0.977762 0.039 Uiso 1 1 calc R U . . .
H13C H 0.256435 0.601099 0.766974 0.039 Uiso 1 1 calc R U . . .
C5 C 0.3577(3) 0.2548(4) 0.6954(10) 0.0236(9) Uani 1 1 d . . . . .
H5A H 0.355847 0.214027 0.837374 0.028 Uiso 1 1 calc R U . . .
H5B H 0.390805 0.319403 0.759652 0.028 Uiso 1 1 calc R U . . .
C14 C 0.0985(4) 0.5801(4) 0.5913(10) 0.0309(12) Uani 1 1 d . . . . .
H14A H 0.095878 0.626016 0.703951 0.046 Uiso 1 1 calc R U . . .
H14B H 0.149261 0.611801 0.466960 0.046 Uiso 1 1 calc R U . . .
H14C H 0.039747 0.545225 0.498151 0.046 Uiso 1 1 calc R U . . .
C10 C 0.4354(4) 0.1528(5) 0.1581(12) 0.0367(13) Uani 1 1 d . . . . .
H10 H 0.417353 0.093831 0.085063 0.044 Uiso 1 1 calc R U . . .
C8 C 0.5377(4) 0.3173(5) 0.1701(12) 0.0404(14) Uani 1 1 d . . . . .
H8 H 0.590367 0.371322 0.105221 0.048 Uiso 1 1 calc R U . . .
H1 H 0.137(4) 0.354(4) 0.233(13) 0.031(16) 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
I1 C3 2.138(4) . ?
O2 C1 1.342(5) . ?
O2 C5 1.454(5) . ?
O3 C4 1.214(6) . ?
O1 C1 1.188(6) . ?
O4 C4 1.333(5) . ?
O4 C12 1.481(5) . ?
N1 C2 1.440(5) . ?
N1 C4 1.365(6) . ?
N1 H1 1.00(6) . ?
C2 H2 1.0000 . ?
C2 C3 1.520(6) . ?
C2 C1 1.532(6) . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C12 C15 1.521(7) . ?
C12 C13 1.511(7) . ?
C12 C14 1.518(6) . ?
C11 H11 0.9500 . ?
C11 C6 1.388(7) . ?
C11 C10 1.393(8) . ?
C15 H15A 0.9800 . ?
C15 H15B 0.9800 . ?
C15 H15C 0.9800 . ?
C6 C7 1.385(7) . ?
C6 C5 1.510(7) . ?
C9 H9 0.9500 . ?
C9 C10 1.381(9) . ?
C9 C8 1.388(10) . ?
C7 H7 0.9500 . ?
C7 C8 1.384(9) . ?
C13 H13A 0.9800 . ?
C13 H13B 0.9800 . ?
C13 H13C 0.9800 . ?
C5 H5A 0.9900 . ?
C5 H5B 0.9900 . ?
C14 H14A 0.9800 . ?
C14 H14B 0.9800 . ?
C14 H14C 0.9800 . ?
C10 H10 0.9500 . ?
C8 H8 0.9500 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1 O2 C5 116.2(4) . . ?
C4 O4 C12 120.2(3) . . ?
C2 N1 H1 114(4) . . ?
C4 N1 C2 118.5(4) . . ?
C4 N1 H1 125(4) . . ?
N1 C2 H2 109.0 . . ?
N1 C2 C3 112.2(3) . . ?
N1 C2 C1 111.1(3) . . ?
C3 C2 H2 109.0 . . ?
C3 C2 C1 106.6(3) . . ?
C1 C2 H2 109.0 . . ?
O3 C4 O4 126.9(4) . . ?
O3 C4 N1 123.0(4) . . ?
O4 C4 N1 110.1(4) . . ?
I1 C3 H3A 109.2 . . ?
I1 C3 H3B 109.2 . . ?
C2 C3 I1 112.3(3) . . ?
C2 C3 H3A 109.2 . . ?
C2 C3 H3B 109.2 . . ?
H3A C3 H3B 107.9 . . ?
O4 C12 C15 110.0(4) . . ?
O4 C12 C13 110.3(4) . . ?
O4 C12 C14 102.5(4) . . ?
C13 C12 C15 112.7(4) . . ?
C13 C12 C14 110.9(4) . . ?
C14 C12 C15 110.0(4) . . ?
C6 C11 H11 119.6 . . ?
C6 C11 C10 120.8(5) . . ?
C10 C11 H11 119.6 . . ?
C12 C15 H15A 109.5 . . ?
C12 C15 H15B 109.5 . . ?
C12 C15 H15C 109.5 . . ?
H15A C15 H15B 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
C11 C6 C5 121.0(4) . . ?
C7 C6 C11 118.9(5) . . ?
C7 C6 C5 120.1(5) . . ?
O2 C1 C2 109.2(4) . . ?
O1 C1 O2 125.0(4) . . ?
O1 C1 C2 125.8(4) . . ?
C10 C9 H9 120.0 . . ?
C10 C9 C8 120.0(6) . . ?
C8 C9 H9 120.0 . . ?
C6 C7 H7 119.7 . . ?
C8 C7 C6 120.7(6) . . ?
C8 C7 H7 119.7 . . ?
C12 C13 H13A 109.5 . . ?
C12 C13 H13B 109.5 . . ?
C12 C13 H13C 109.5 . . ?
H13A C13 H13B 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
O2 C5 C6 112.6(4) . . ?
O2 C5 H5A 109.1 . . ?
O2 C5 H5B 109.1 . . ?
C6 C5 H5A 109.1 . . ?
C6 C5 H5B 109.1 . . ?
H5A C5 H5B 107.8 . . ?
C12 C14 H14A 109.5 . . ?
C12 C14 H14B 109.5 . . ?
C12 C14 H14C 109.5 . . ?
H14A C14 H14B 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C11 C10 H10 120.2 . . ?
C9 C10 C11 119.6(6) . . ?
C9 C10 H10 120.2 . . ?
C9 C8 H8 120.0 . . ?
C7 C8 C9 120.0(6) . . ?
C7 C8 H8 120.0 . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
N1 H1 O3 1.00(6) 2.01(6) 2.986(5) 164(5) 1_554 yes

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
N1 C2 C3 I1 -63.0(4) . . . . ?
N1 C2 C1 O2 158.5(4) . . . . ?
N1 C2 C1 O1 -21.7(6) . . . . ?
C2 N1 C4 O3 -4.0(7) . . . . ?
C2 N1 C4 O4 176.4(4) . . . . ?
C4 O4 C12 C15 -63.8(5) . . . . ?
C4 O4 C12 C13 61.1(5) . . . . ?
C4 O4 C12 C14 179.2(4) . . . . ?
C4 N1 C2 C3 169.3(4) . . . . ?
C4 N1 C2 C1 -71.4(5) . . . . ?
C3 C2 C1 O2 -79.0(4) . . . . ?
C3 C2 C1 O1 100.8(5) . . . . ?
C12 O4 C4 O3 0.1(7) . . . . ?
C12 O4 C4 N1 179.6(4) . . . . ?
C11 C6 C7 C8 -1.2(8) . . . . ?
C11 C6 C5 O2 -65.9(6) . . . . ?
C6 C11 C10 C9 -0.1(8) . . . . ?
C6 C7 C8 C9 1.0(9) . . . . ?
C1 O2 C5 C6 -81.6(5) . . . . ?
C1 C2 C3 I1 175.1(3) . . . . ?
C7 C6 C5 O2 114.9(5) . . . . ?
C5 O2 C1 O1 -0.1(6) . . . . ?
C5 O2 C1 C2 179.6(4) . . . . ?
C5 C6 C7 C8 178.0(5) . . . . ?
C10 C11 C6 C7 0.8(7) . . . . ?
C10 C11 C6 C5 -178.5(5) . . . . ?
C10 C9 C8 C7 -0.3(9) . . . . ?
C8 C9 C10 C11 -0.1(9) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
