# Electronic Supplementary Material (ESI) for CrystEngComm.
# This journal is © The Royal Society of Chemistry 2023

####################################################################### 
# 
# 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_dwb1001m
_database_code_depnum_ccdc_archive 'CCDC 2245333'
loop_
_audit_author_name
_audit_author_address
'Adrian C Whitwood'
;University of York
United Kingdom
;
_audit_update_record             
;
2023-02-28 deposited with the CCDC.	2023-04-20 downloaded from the CCDC.
;
_audit_creation_date             2023-02-28
_audit_creation_method           
;
Olex2 1.5
(compiled 2023.02.24 svn.rf166f9f3 for OlexSys, GUI svn.r6725)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C6 H4 Cl2 O, C21 H27 N O'
_chemical_formula_sum            'C27 H31 Cl2 N O2'
_chemical_formula_weight         472.43
_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'
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'
Cl Cl 0.1484 0.1585 '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      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   7.7755(10)
_cell_length_b                   9.6671(12)
_cell_length_c                   16.403(2)
_cell_angle_alpha                91.184(3)
_cell_angle_beta                 91.699(3)
_cell_angle_gamma                92.084(2)
_cell_volume                     1231.3(3)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    4432
_cell_measurement_temperature    110.15
_cell_measurement_theta_max      29.91
_cell_measurement_theta_min      2.42
_shelx_estimated_absorpt_T_max   0.947
_shelx_estimated_absorpt_T_min   0.932
_exptl_absorpt_coefficient_mu    0.288
_exptl_absorpt_correction_T_max  0.947
_exptl_absorpt_correction_T_min  0.809
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS v2.10 (Sheldrick)'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.274
_exptl_crystal_density_meas      .
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             500
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.21
_exptl_crystal_size_min          0.19
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0196
_diffrn_reflns_av_unetI/netI     0.0313
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.965
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            14040
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.965
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.988
_diffrn_reflns_theta_min         2.109
_diffrn_ambient_temperature      110.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.965
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                5612
_reflns_number_total             6920
_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       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXS-1997  (Sheldrick, 2008)'
_refine_diff_density_max         0.387
_refine_diff_density_min         -0.219
_refine_diff_density_rms         0.055
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.034
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     294
_refine_ls_number_reflns         6920
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0523
_refine_ls_R_factor_gt           0.0409
_refine_ls_restrained_S_all      1.034
_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)+(0.0607P)²+0.1810P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1043
_refine_ls_wR_factor_ref         0.1127
_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 Secondary CH2 refined with riding coordinates:
 C20(H20A,H20B), C21(H21A,H21B), C22(H22A,H22B), C23(H23A,H23B), C24(H24A,
 H24B), C25(H25A,H25B), C26(H26A,H26B)
2.b Aromatic/amide H refined with riding coordinates:
 C2(H2), C4(H4), C5(H5), C7(H7), C8(H8), C10(H10), C11(H11), C12(H12),
 C13(H13), C15(H15), C16(H16), C18(H18), C19(H19)
2.c Idealised Me refined as rotating group:
 C27(H27A,H27B,H27C)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.44114(15) 0.67007(12) 0.93516(8) 0.0209(2) Uani 1 1 d . . . . .
C2 C 0.48902(15) 0.66593(12) 0.85336(8) 0.0214(2) Uani 1 1 d . . . . .
H2 H 0.581732 0.723911 0.836179 0.026 Uiso 1 1 calc R U . . .
C3 C 0.40167(16) 0.57772(13) 0.79769(8) 0.0227(2) Uani 1 1 d . . . . .
C4 C 0.26463(17) 0.49095(13) 0.81923(9) 0.0268(3) Uani 1 1 d . . . . .
H4 H 0.204985 0.432021 0.779962 0.032 Uiso 1 1 calc R U . . .
C5 C 0.21823(17) 0.49373(13) 0.90045(9) 0.0266(3) Uani 1 1 d . . . . .
H5 H 0.126353 0.434591 0.917334 0.032 Uiso 1 1 calc R U . . .
C6 C 0.30398(15) 0.58137(12) 0.95698(8) 0.0220(2) Uani 1 1 d . . . . .
Cl1 Cl 0.46935(5) 0.57684(4) 0.69733(2) 0.03153(10) Uani 1 1 d . . . . .
Cl2 Cl 0.24190(4) 0.58400(3) 1.05786(2) 0.02855(9) Uani 1 1 d . . . . .
O1 O 0.51944(12) 0.75403(10) 0.99170(6) 0.0275(2) Uani 1 1 d . . . . .
H1 H 0.611(3) 0.802(2) 0.9692(13) 0.068(7) Uiso 1 1 d . . . . .
C7 C 1.18223(16) 0.98011(13) 0.07324(7) 0.0228(2) Uani 1 1 d . . . . .
H7 H 1.269112 0.922628 0.053530 0.027 Uiso 1 1 calc R U . . .
C8 C 1.03347(16) 0.91819(13) 0.10223(8) 0.0223(2) Uani 1 1 d . . . . .
H8 H 1.019371 0.820129 0.100935 0.027 Uiso 1 1 calc R U . . .
C9 C 0.90412(15) 0.99848(12) 0.13331(7) 0.0204(2) Uani 1 1 d . . . . .
C10 C 0.93379(16) 1.14280(13) 0.13307(8) 0.0234(3) Uani 1 1 d . . . . .
H10 H 0.851113 1.202886 0.154179 0.028 Uiso 1 1 calc R U . . .
C11 C 1.08449(17) 1.19609(13) 0.10181(8) 0.0250(3) Uani 1 1 d . . . . .
H11 H 1.101546 1.293885 0.101425 0.030 Uiso 1 1 calc R U . . .
C12 C 0.74590(16) 0.93189(13) 0.16269(8) 0.0229(2) Uani 1 1 d . . . . .
H12 H 0.725495 0.836460 0.149430 0.028 Uiso 1 1 calc R U . . .
C13 C 0.62799(16) 0.99458(13) 0.20662(8) 0.0225(2) Uani 1 1 d . . . . .
H13 H 0.650564 1.089883 0.219557 0.027 Uiso 1 1 calc R U . . .
C14 C 0.46813(16) 0.93310(13) 0.23705(7) 0.0215(2) Uani 1 1 d . . . . .
C15 C 0.35992(17) 1.01473(13) 0.28219(8) 0.0241(3) Uani 1 1 d . . . . .
H15 H 0.392387 1.109221 0.292792 0.029 Uiso 1 1 calc R U . . .
C16 C 0.20571(17) 0.96237(13) 0.31230(8) 0.0243(3) Uani 1 1 d . . . . .
H16 H 0.134057 1.020600 0.342633 0.029 Uiso 1 1 calc R U . . .
C17 C 0.15766(16) 0.82381(13) 0.29749(8) 0.0229(2) Uani 1 1 d . . . . .
C18 C 0.26503(17) 0.73952(13) 0.25288(8) 0.0246(3) Uani 1 1 d . . . . .
H18 H 0.233362 0.644601 0.243320 0.030 Uiso 1 1 calc R U . . .
C19 C 0.41655(16) 0.79317(13) 0.22266(8) 0.0242(3) Uani 1 1 d . . . . .
H19 H 0.487144 0.735001 0.191712 0.029 Uiso 1 1 calc R U . . .
C20 C -0.10055(16) 0.84001(13) 0.37374(8) 0.0240(3) Uani 1 1 d . . . . .
H20A H -0.141675 0.921306 0.344164 0.029 Uiso 1 1 calc R U . . .
H20B H -0.037215 0.873068 0.424081 0.029 Uiso 1 1 calc R U . . .
C21 C -0.25073(16) 0.74478(13) 0.39450(8) 0.0253(3) Uani 1 1 d . . . . .
H21A H -0.206224 0.662831 0.422249 0.030 Uiso 1 1 calc R U . . .
H21B H -0.310878 0.711986 0.343277 0.030 Uiso 1 1 calc R U . . .
C22 C -0.38019(16) 0.81353(13) 0.44928(8) 0.0244(3) Uani 1 1 d . . . . .
H22A H -0.320995 0.845500 0.500900 0.029 Uiso 1 1 calc R U . . .
H22B H -0.424989 0.895675 0.421841 0.029 Uiso 1 1 calc R U . . .
C23 C -0.53037(16) 0.71484(13) 0.46846(8) 0.0246(3) Uani 1 1 d . . . . .
H23A H -0.586668 0.680778 0.416576 0.030 Uiso 1 1 calc R U . . .
H23B H -0.485077 0.633908 0.496957 0.030 Uiso 1 1 calc R U . . .
C24 C -0.66464(16) 0.78080(13) 0.52107(8) 0.0241(3) Uani 1 1 d . . . . .
H24A H -0.709096 0.862322 0.492856 0.029 Uiso 1 1 calc R U . . .
H24B H -0.608683 0.813920 0.573218 0.029 Uiso 1 1 calc R U . . .
C25 C -0.81595(16) 0.68207(13) 0.53943(8) 0.0244(3) Uani 1 1 d . . . . .
H25A H -0.882309 0.659690 0.488114 0.029 Uiso 1 1 calc R U . . .
H25B H -0.770792 0.594739 0.560339 0.029 Uiso 1 1 calc R U . . .
C26 C -0.93632(18) 0.74213(15) 0.60170(9) 0.0320(3) Uani 1 1 d . . . . .
H26A H -0.867726 0.771841 0.651210 0.038 Uiso 1 1 calc R U . . .
H26B H -0.988333 0.825367 0.578737 0.038 Uiso 1 1 calc R U . . .
C27 C -1.0799(2) 0.64156(18) 0.62606(11) 0.0426(4) Uani 1 1 d . . . . .
H27A H -1.153175 0.616172 0.578060 0.064 Uiso 1 1 calc R U . . .
H27B H -1.149108 0.685547 0.667560 0.064 Uiso 1 1 calc R U . . .
H27C H -1.029788 0.558191 0.648266 0.064 Uiso 1 1 calc R U . . .
N1 N 1.20880(13) 1.11802(11) 0.07182(7) 0.0238(2) Uani 1 1 d . . . . .
O2 O 0.00938(12) 0.76076(9) 0.32313(6) 0.0272(2) Uani 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
C1 C2 1.4033(17) . ?
C1 C6 1.4034(17) . ?
C1 O1 1.3374(15) . ?
C2 H2 0.9500 . ?
C2 C3 1.3824(17) . ?
C3 C4 1.3905(18) . ?
C3 Cl1 1.7429(13) . ?
C4 H4 0.9500 . ?
C4 C5 1.390(2) . ?
C5 H5 0.9500 . ?
C5 C6 1.3827(19) . ?
C6 Cl2 1.7374(13) . ?
O1 H1 0.92(2) . ?
C7 H7 0.9500 . ?
C7 C8 1.3843(17) . ?
C7 N1 1.3424(16) . ?
C8 H8 0.9500 . ?
C8 C9 1.3946(17) . ?
C9 C10 1.4059(17) . ?
C9 C12 1.4664(17) . ?
C10 H10 0.9500 . ?
C10 C11 1.3799(18) . ?
C11 H11 0.9500 . ?
C11 N1 1.3460(17) . ?
C12 H12 0.9500 . ?
C12 C13 1.3375(18) . ?
C13 H13 0.9500 . ?
C13 C14 1.4639(17) . ?
C14 C15 1.3928(17) . ?
C14 C19 1.4099(17) . ?
C15 H15 0.9500 . ?
C15 C16 1.3925(18) . ?
C16 H16 0.9500 . ?
C16 C17 1.3919(18) . ?
C17 C18 1.3991(17) . ?
C17 O2 1.3660(15) . ?
C18 H18 0.9500 . ?
C18 C19 1.3797(18) . ?
C19 H19 0.9500 . ?
C20 H20A 0.9900 . ?
C20 H20B 0.9900 . ?
C20 C21 1.5117(18) . ?
C20 O2 1.4388(15) . ?
C21 H21A 0.9900 . ?
C21 H21B 0.9900 . ?
C21 C22 1.5297(17) . ?
C22 H22A 0.9900 . ?
C22 H22B 0.9900 . ?
C22 C23 1.5251(18) . ?
C23 H23A 0.9900 . ?
C23 H23B 0.9900 . ?
C23 C24 1.5233(17) . ?
C24 H24A 0.9900 . ?
C24 H24B 0.9900 . ?
C24 C25 1.5287(18) . ?
C25 H25A 0.9900 . ?
C25 H25B 0.9900 . ?
C25 C26 1.5258(18) . ?
C26 H26A 0.9900 . ?
C26 H26B 0.9900 . ?
C26 C27 1.521(2) . ?
C27 H27A 0.9800 . ?
C27 H27B 0.9800 . ?
C27 H27C 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
C2 C1 C6 117.28(11) . . ?
O1 C1 C2 123.03(11) . . ?
O1 C1 C6 119.69(11) . . ?
C1 C2 H2 119.9 . . ?
C3 C2 C1 120.20(11) . . ?
C3 C2 H2 119.9 . . ?
C2 C3 C4 122.44(12) . . ?
C2 C3 Cl1 117.73(10) . . ?
C4 C3 Cl1 119.83(10) . . ?
C3 C4 H4 121.3 . . ?
C3 C4 C5 117.46(12) . . ?
C5 C4 H4 121.3 . . ?
C4 C5 H5 119.5 . . ?
C6 C5 C4 120.91(12) . . ?
C6 C5 H5 119.5 . . ?
C1 C6 Cl2 118.35(10) . . ?
C5 C6 C1 121.70(12) . . ?
C5 C6 Cl2 119.95(10) . . ?
C1 O1 H1 110.0(13) . . ?
C8 C7 H7 118.6 . . ?
N1 C7 H7 118.6 . . ?
N1 C7 C8 122.72(11) . . ?
C7 C8 H8 119.7 . . ?
C7 C8 C9 120.58(11) . . ?
C9 C8 H8 119.7 . . ?
C8 C9 C10 116.51(11) . . ?
C8 C9 C12 120.13(11) . . ?
C10 C9 C12 123.35(11) . . ?
C9 C10 H10 120.4 . . ?
C11 C10 C9 119.18(12) . . ?
C11 C10 H10 120.4 . . ?
C10 C11 H11 118.0 . . ?
N1 C11 C10 124.02(12) . . ?
N1 C11 H11 118.0 . . ?
C9 C12 H12 117.3 . . ?
C13 C12 C9 125.31(11) . . ?
C13 C12 H12 117.3 . . ?
C12 C13 H13 116.3 . . ?
C12 C13 C14 127.41(12) . . ?
C14 C13 H13 116.3 . . ?
C15 C14 C13 119.52(11) . . ?
C15 C14 C19 117.51(11) . . ?
C19 C14 C13 122.97(11) . . ?
C14 C15 H15 118.9 . . ?
C16 C15 C14 122.16(11) . . ?
C16 C15 H15 118.9 . . ?
C15 C16 H16 120.3 . . ?
C17 C16 C15 119.30(11) . . ?
C17 C16 H16 120.3 . . ?
C16 C17 C18 119.55(12) . . ?
O2 C17 C16 124.82(11) . . ?
O2 C17 C18 115.63(11) . . ?
C17 C18 H18 119.7 . . ?
C19 C18 C17 120.51(12) . . ?
C19 C18 H18 119.7 . . ?
C14 C19 H19 119.5 . . ?
C18 C19 C14 120.96(12) . . ?
C18 C19 H19 119.5 . . ?
H20A C20 H20B 108.6 . . ?
C21 C20 H20A 110.4 . . ?
C21 C20 H20B 110.4 . . ?
O2 C20 H20A 110.4 . . ?
O2 C20 H20B 110.4 . . ?
O2 C20 C21 106.76(10) . . ?
C20 C21 H21A 108.9 . . ?
C20 C21 H21B 108.9 . . ?
C20 C21 C22 113.39(10) . . ?
H21A C21 H21B 107.7 . . ?
C22 C21 H21A 108.9 . . ?
C22 C21 H21B 108.9 . . ?
C21 C22 H22A 109.2 . . ?
C21 C22 H22B 109.2 . . ?
H22A C22 H22B 107.9 . . ?
C23 C22 C21 111.93(10) . . ?
C23 C22 H22A 109.2 . . ?
C23 C22 H22B 109.2 . . ?
C22 C23 H23A 108.9 . . ?
C22 C23 H23B 108.9 . . ?
H23A C23 H23B 107.7 . . ?
C24 C23 C22 113.48(11) . . ?
C24 C23 H23A 108.9 . . ?
C24 C23 H23B 108.9 . . ?
C23 C24 H24A 108.9 . . ?
C23 C24 H24B 108.9 . . ?
C23 C24 C25 113.35(10) . . ?
H24A C24 H24B 107.7 . . ?
C25 C24 H24A 108.9 . . ?
C25 C24 H24B 108.9 . . ?
C24 C25 H25A 109.0 . . ?
C24 C25 H25B 109.0 . . ?
H25A C25 H25B 107.8 . . ?
C26 C25 C24 112.90(11) . . ?
C26 C25 H25A 109.0 . . ?
C26 C25 H25B 109.0 . . ?
C25 C26 H26A 108.8 . . ?
C25 C26 H26B 108.8 . . ?
H26A C26 H26B 107.7 . . ?
C27 C26 C25 113.88(12) . . ?
C27 C26 H26A 108.8 . . ?
C27 C26 H26B 108.8 . . ?
C26 C27 H27A 109.5 . . ?
C26 C27 H27B 109.5 . . ?
C26 C27 H27C 109.5 . . ?
H27A C27 H27B 109.5 . . ?
H27A C27 H27C 109.5 . . ?
H27B C27 H27C 109.5 . . ?
C7 N1 C11 116.97(11) . . ?
C17 O2 C20 118.03(10) . . ?

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
O1 H1 N1 0.92(2) 1.74(2) 2.6598(14) 176(2) 2_776 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
C1 C2 C3 C4 0.26(19) . . . . ?
C1 C2 C3 Cl1 -179.42(9) . . . . ?
C2 C1 C6 C5 -0.35(18) . . . . ?
C2 C1 C6 Cl2 179.92(9) . . . . ?
C2 C3 C4 C5 -0.97(19) . . . . ?
C3 C4 C5 C6 1.0(2) . . . . ?
C4 C5 C6 C1 -0.4(2) . . . . ?
C4 C5 C6 Cl2 179.35(10) . . . . ?
C6 C1 C2 C3 0.41(18) . . . . ?
Cl1 C3 C4 C5 178.70(10) . . . . ?
O1 C1 C2 C3 -179.34(11) . . . . ?
O1 C1 C6 C5 179.41(12) . . . . ?
O1 C1 C6 Cl2 -0.32(16) . . . . ?
C7 C8 C9 C10 0.16(18) . . . . ?
C7 C8 C9 C12 179.05(11) . . . . ?
C8 C7 N1 C11 1.36(18) . . . . ?
C8 C9 C10 C11 0.89(18) . . . . ?
C8 C9 C12 C13 167.31(13) . . . . ?
C9 C10 C11 N1 -0.9(2) . . . . ?
C9 C12 C13 C14 179.74(12) . . . . ?
C10 C9 C12 C13 -13.9(2) . . . . ?
C10 C11 N1 C7 -0.23(19) . . . . ?
C12 C9 C10 C11 -177.96(12) . . . . ?
C12 C13 C14 C15 179.98(13) . . . . ?
C12 C13 C14 C19 -0.2(2) . . . . ?
C13 C14 C15 C16 179.58(12) . . . . ?
C13 C14 C19 C18 179.71(12) . . . . ?
C14 C15 C16 C17 0.4(2) . . . . ?
C15 C14 C19 C18 -0.48(19) . . . . ?
C15 C16 C17 C18 0.17(19) . . . . ?
C15 C16 C17 O2 -179.45(12) . . . . ?
C16 C17 C18 C19 -0.9(2) . . . . ?
C16 C17 O2 C20 -4.32(19) . . . . ?
C17 C18 C19 C14 1.0(2) . . . . ?
C18 C17 O2 C20 176.05(11) . . . . ?
C19 C14 C15 C16 -0.24(19) . . . . ?
C20 C21 C22 C23 179.61(11) . . . . ?
C21 C20 O2 C17 -178.61(11) . . . . ?
C21 C22 C23 C24 -178.45(11) . . . . ?
C22 C23 C24 C25 179.39(11) . . . . ?
C23 C24 C25 C26 171.85(12) . . . . ?
C24 C25 C26 C27 -175.38(13) . . . . ?
N1 C7 C8 C9 -1.35(19) . . . . ?
O2 C17 C18 C19 178.77(11) . . . . ?
O2 C20 C21 C22 179.45(11) . . . . ?

__computing_molecular_graphics   'Olex2 1.5 (Dolomanov et al., 2009)'
_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_dwb1007m
_database_code_depnum_ccdc_archive 'CCDC 2245334'
loop_
_audit_author_name
_audit_author_address
'Adrian C Whitwood'
;University of York
United Kingdom
;
_audit_update_record             
;
2023-02-28 deposited with the CCDC.	2023-04-20 downloaded from the CCDC.
;
_audit_creation_date             2023-02-28
_audit_creation_method           
;
Olex2 1.5
(compiled 2023.02.24 svn.rf166f9f3 for OlexSys, GUI svn.r6725)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C6 H4 Cl2 O, C21 H27 N O'
_chemical_formula_sum            'C27 H31 Cl2 N O2'
_chemical_formula_weight         472.43
_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'
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'
Cl Cl 0.1484 0.1585 '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      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   7.8919(15)
_cell_length_b                   11.242(2)
_cell_length_c                   14.800(3)
_cell_angle_alpha                76.592(4)
_cell_angle_beta                 81.917(4)
_cell_angle_gamma                76.998(4)
_cell_volume                     1239.1(4)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    3186
_cell_measurement_temperature    110.15
_cell_measurement_theta_max      28.24
_cell_measurement_theta_min      2.60
_shelx_estimated_absorpt_T_max   0.986
_shelx_estimated_absorpt_T_min   0.929
_exptl_absorpt_coefficient_mu    0.286
_exptl_absorpt_correction_T_max  0.986
_exptl_absorpt_correction_T_min  0.840
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS v2.10; (Sheldrick)'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear yellow'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   .
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.266
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             500
_exptl_crystal_size_max          0.26
_exptl_crystal_size_mid          0.06
_exptl_crystal_size_min          0.05
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0238
_diffrn_reflns_av_unetI/netI     0.0368
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.986
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            12899
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.986
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.382
_diffrn_reflns_theta_min         1.901
_diffrn_ambient_temperature      110.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.986
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'fine-focus sealed tube'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                4675
_reflns_number_total             6116
_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 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXS-1997  (Sheldrick, 2008)'
_refine_diff_density_max         0.318
_refine_diff_density_min         -0.308
_refine_diff_density_rms         0.050
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.015
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     294
_refine_ls_number_reflns         6116
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0602
_refine_ls_R_factor_gt           0.0427
_refine_ls_restrained_S_all      1.015
_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)+(0.0502P)²+0.2519P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0978
_refine_ls_wR_factor_ref         0.1073
_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 Secondary CH2 refined with riding coordinates:
 C20(H20A,H20B), C21(H21A,H21B), C22(H22A,H22B), C23(H23A,H23B), C24(H24A,
 H24B), C25(H25A,H25B), C26(H26A,H26B)
2.b Aromatic/amide H refined with riding coordinates:
 C2(H2), C4(H4), C6(H6), C7(H7), C8(H8), C10(H10), C11(H11), C12(H12),
 C13(H13), C15(H15), C16(H16), C18(H18), C19(H19)
2.c Idealised Me refined as rotating group:
 C27(H27A,H27B,H27C)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C -0.07599(19) 0.94295(14) 0.16379(10) 0.0258(3) Uani 1 1 d . . . . .
C2 C 0.01086(19) 1.04276(14) 0.14106(10) 0.0255(3) Uani 1 1 d . . . . .
H2 H -0.037559 1.118061 0.162073 0.031 Uiso 1 1 calc R U . . .
C3 C 0.1690(2) 1.02919(14) 0.08723(11) 0.0268(3) Uani 1 1 d . . . . .
C4 C 0.2461(2) 0.92152(14) 0.05529(10) 0.0286(3) Uani 1 1 d . . . . .
H4 H 0.355110 0.914509 0.018308 0.034 Uiso 1 1 calc R U . . .
C5 C 0.1562(2) 0.82440(14) 0.08004(10) 0.0268(3) Uani 1 1 d . . . . .
C6 C -0.0019(2) 0.83242(14) 0.13362(10) 0.0265(3) Uani 1 1 d . . . . .
H6 H -0.059503 0.763704 0.149730 0.032 Uiso 1 1 calc R U . . .
Cl1 Cl 0.24441(6) 0.68671(4) 0.04060(3) 0.03797(12) Uani 1 1 d . . . . .
Cl2 Cl 0.27685(6) 1.15403(4) 0.05808(3) 0.04000(13) Uani 1 1 d . . . . .
O1 O -0.23270(15) 0.94865(11) 0.21432(8) 0.0338(3) Uani 1 1 d . . . . .
H1 H -0.279(3) 1.028(2) 0.2315(17) 0.077(8) Uiso 1 1 d . . . . .
C7 C -0.5297(2) 0.74719(16) 0.79101(12) 0.0323(4) Uani 1 1 d . . . . .
H7 H -0.546093 0.752856 0.854823 0.039 Uiso 1 1 calc R U . . .
C8 C -0.4176(2) 0.64400(15) 0.76619(11) 0.0307(3) Uani 1 1 d . . . . .
H8 H -0.359538 0.580673 0.812555 0.037 Uiso 1 1 calc R U . . .
C9 C -0.38944(19) 0.63271(14) 0.67315(11) 0.0256(3) Uani 1 1 d . . . . .
C10 C -0.4798(2) 0.72983(14) 0.60941(11) 0.0286(3) Uani 1 1 d . . . . .
H10 H -0.465181 0.727343 0.545016 0.034 Uiso 1 1 calc R U . . .
C11 C -0.5902(2) 0.82933(15) 0.64007(12) 0.0300(3) Uani 1 1 d . . . . .
H11 H -0.650737 0.893988 0.595465 0.036 Uiso 1 1 calc R U . . .
C12 C -0.2716(2) 0.52263(14) 0.64720(11) 0.0286(3) Uani 1 1 d . . . . .
H12 H -0.208782 0.465898 0.695114 0.034 Uiso 1 1 calc R U . . .
C13 C -0.24385(19) 0.49412(14) 0.56337(11) 0.0271(3) Uani 1 1 d . . . . .
H13 H -0.305104 0.551622 0.515191 0.032 Uiso 1 1 calc R U . . .
C14 C -0.12876(19) 0.38342(13) 0.53785(11) 0.0247(3) Uani 1 1 d . . . . .
C15 C -0.1263(2) 0.35897(14) 0.44981(11) 0.0269(3) Uani 1 1 d . . . . .
H15 H -0.199352 0.416106 0.406491 0.032 Uiso 1 1 calc R U . . .
C16 C -0.0205(2) 0.25370(14) 0.42281(11) 0.0267(3) Uani 1 1 d . . . . .
H16 H -0.022133 0.239219 0.362234 0.032 Uiso 1 1 calc R U . . .
C17 C 0.08730(19) 0.17029(14) 0.48543(11) 0.0252(3) Uani 1 1 d . . . . .
C18 C 0.0890(2) 0.19374(14) 0.57386(11) 0.0271(3) Uani 1 1 d . . . . .
H18 H 0.163631 0.137183 0.616704 0.033 Uiso 1 1 calc R U . . .
C19 C -0.01622(19) 0.29784(14) 0.59930(11) 0.0267(3) Uani 1 1 d . . . . .
H19 H -0.013059 0.312469 0.659683 0.032 Uiso 1 1 calc R U . . .
C20 C 0.2097(2) 0.03299(14) 0.37864(11) 0.0264(3) Uani 1 1 d . . . . .
H20A H 0.250327 0.099506 0.329564 0.032 Uiso 1 1 calc R U . . .
H20B H 0.095253 0.023189 0.364515 0.032 Uiso 1 1 calc R U . . .
C21 C 0.3411(2) -0.08838(14) 0.38373(11) 0.0267(3) Uani 1 1 d . . . . .
H21A H 0.296469 -0.153092 0.432877 0.032 Uiso 1 1 calc R U . . .
H21B H 0.451265 -0.077417 0.402462 0.032 Uiso 1 1 calc R U . . .
C22 C 0.3806(2) -0.13453(14) 0.29269(11) 0.0267(3) Uani 1 1 d . . . . .
H22A H 0.423495 -0.069811 0.242845 0.032 Uiso 1 1 calc R U . . .
H22B H 0.271763 -0.148592 0.274528 0.032 Uiso 1 1 calc R U . . .
C23 C 0.51708(19) -0.25535(14) 0.30167(10) 0.0255(3) Uani 1 1 d . . . . .
H23A H 0.622782 -0.241741 0.323519 0.031 Uiso 1 1 calc R U . . .
H23B H 0.470984 -0.320357 0.349858 0.031 Uiso 1 1 calc R U . . .
C24 C 0.5690(2) -0.30322(14) 0.21192(11) 0.0276(3) Uani 1 1 d . . . . .
H24A H 0.610612 -0.237168 0.162778 0.033 Uiso 1 1 calc R U . . .
H24B H 0.464804 -0.321040 0.191508 0.033 Uiso 1 1 calc R U . . .
C25 C 0.7114(2) -0.42076(14) 0.22202(11) 0.0273(3) Uani 1 1 d . . . . .
H25A H 0.810299 -0.405000 0.248871 0.033 Uiso 1 1 calc R U . . .
H25B H 0.665039 -0.488571 0.266996 0.033 Uiso 1 1 calc R U . . .
C26 C 0.7805(2) -0.46555(15) 0.13187(11) 0.0305(3) Uani 1 1 d . . . . .
H26A H 0.826129 -0.397977 0.086199 0.037 Uiso 1 1 calc R U . . .
H26B H 0.683075 -0.483863 0.105416 0.037 Uiso 1 1 calc R U . . .
C27 C 0.9247(2) -0.58178(17) 0.14621(14) 0.0417(4) Uani 1 1 d . . . . .
H27A H 1.019600 -0.565221 0.174653 0.063 Uiso 1 1 calc R U . . .
H27B H 0.969605 -0.603943 0.085847 0.063 Uiso 1 1 calc R U . . .
H27C H 0.877717 -0.650982 0.187377 0.063 Uiso 1 1 calc R U . . .
N1 N -0.61623(17) 0.83932(13) 0.72972(10) 0.0306(3) Uani 1 1 d . . . . .
O2 O 0.19574(14) 0.06318(10) 0.46918(7) 0.0284(2) Uani 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
C1 C2 1.396(2) . ?
C1 C6 1.394(2) . ?
C1 O1 1.3488(18) . ?
C2 H2 0.9500 . ?
C2 C3 1.380(2) . ?
C3 C4 1.383(2) . ?
C3 Cl2 1.7419(16) . ?
C4 H4 0.9500 . ?
C4 C5 1.386(2) . ?
C5 C6 1.378(2) . ?
C5 Cl1 1.7439(16) . ?
C6 H6 0.9500 . ?
O1 H1 0.96(2) . ?
C7 H7 0.9500 . ?
C7 C8 1.381(2) . ?
C7 N1 1.335(2) . ?
C8 H8 0.9500 . ?
C8 C9 1.394(2) . ?
C9 C10 1.397(2) . ?
C9 C12 1.465(2) . ?
C10 H10 0.9500 . ?
C10 C11 1.379(2) . ?
C11 H11 0.9500 . ?
C11 N1 1.341(2) . ?
C12 H12 0.9500 . ?
C12 C13 1.329(2) . ?
C13 H13 0.9500 . ?
C13 C14 1.459(2) . ?
C14 C15 1.389(2) . ?
C14 C19 1.407(2) . ?
C15 H15 0.9500 . ?
C15 C16 1.392(2) . ?
C16 H16 0.9500 . ?
C16 C17 1.386(2) . ?
C17 C18 1.396(2) . ?
C17 O2 1.3612(18) . ?
C18 H18 0.9500 . ?
C18 C19 1.371(2) . ?
C19 H19 0.9500 . ?
C20 H20A 0.9900 . ?
C20 H20B 0.9900 . ?
C20 C21 1.510(2) . ?
C20 O2 1.4406(18) . ?
C21 H21A 0.9900 . ?
C21 H21B 0.9900 . ?
C21 C22 1.522(2) . ?
C22 H22A 0.9900 . ?
C22 H22B 0.9900 . ?
C22 C23 1.524(2) . ?
C23 H23A 0.9900 . ?
C23 H23B 0.9900 . ?
C23 C24 1.517(2) . ?
C24 H24A 0.9900 . ?
C24 H24B 0.9900 . ?
C24 C25 1.523(2) . ?
C25 H25A 0.9900 . ?
C25 H25B 0.9900 . ?
C25 C26 1.521(2) . ?
C26 H26A 0.9900 . ?
C26 H26B 0.9900 . ?
C26 C27 1.522(2) . ?
C27 H27A 0.9800 . ?
C27 H27B 0.9800 . ?
C27 H27C 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
C6 C1 C2 120.15(14) . . ?
O1 C1 C2 122.43(14) . . ?
O1 C1 C6 117.42(14) . . ?
C1 C2 H2 120.9 . . ?
C3 C2 C1 118.26(14) . . ?
C3 C2 H2 120.9 . . ?
C2 C3 C4 123.36(14) . . ?
C2 C3 Cl2 118.34(12) . . ?
C4 C3 Cl2 118.30(12) . . ?
C3 C4 H4 121.7 . . ?
C3 C4 C5 116.51(14) . . ?
C5 C4 H4 121.7 . . ?
C4 C5 Cl1 118.93(12) . . ?
C6 C5 C4 122.76(14) . . ?
C6 C5 Cl1 118.30(12) . . ?
C1 C6 H6 120.5 . . ?
C5 C6 C1 118.95(14) . . ?
C5 C6 H6 120.5 . . ?
C1 O1 H1 113.5(15) . . ?
C8 C7 H7 118.4 . . ?
N1 C7 H7 118.4 . . ?
N1 C7 C8 123.21(15) . . ?
C7 C8 H8 120.0 . . ?
C7 C8 C9 120.06(15) . . ?
C9 C8 H8 120.0 . . ?
C8 C9 C10 116.36(14) . . ?
C8 C9 C12 119.91(14) . . ?
C10 C9 C12 123.73(14) . . ?
C9 C10 H10 120.0 . . ?
C11 C10 C9 119.93(15) . . ?
C11 C10 H10 120.0 . . ?
C10 C11 H11 118.4 . . ?
N1 C11 C10 123.24(15) . . ?
N1 C11 H11 118.4 . . ?
C9 C12 H12 116.7 . . ?
C13 C12 C9 126.55(15) . . ?
C13 C12 H12 116.7 . . ?
C12 C13 H13 116.7 . . ?
C12 C13 C14 126.58(15) . . ?
C14 C13 H13 116.7 . . ?
C15 C14 C13 120.30(14) . . ?
C15 C14 C19 117.09(14) . . ?
C19 C14 C13 122.61(14) . . ?
C14 C15 H15 118.8 . . ?
C14 C15 C16 122.33(14) . . ?
C16 C15 H15 118.8 . . ?
C15 C16 H16 120.4 . . ?
C17 C16 C15 119.18(14) . . ?
C17 C16 H16 120.4 . . ?
C16 C17 C18 119.57(14) . . ?
O2 C17 C16 125.65(14) . . ?
O2 C17 C18 114.78(13) . . ?
C17 C18 H18 119.8 . . ?
C19 C18 C17 120.45(14) . . ?
C19 C18 H18 119.8 . . ?
C14 C19 H19 119.3 . . ?
C18 C19 C14 121.37(14) . . ?
C18 C19 H19 119.3 . . ?
H20A C20 H20B 108.7 . . ?
C21 C20 H20A 110.6 . . ?
C21 C20 H20B 110.6 . . ?
O2 C20 H20A 110.6 . . ?
O2 C20 H20B 110.6 . . ?
O2 C20 C21 105.66(12) . . ?
C20 C21 H21A 108.7 . . ?
C20 C21 H21B 108.7 . . ?
C20 C21 C22 114.07(13) . . ?
H21A C21 H21B 107.6 . . ?
C22 C21 H21A 108.7 . . ?
C22 C21 H21B 108.7 . . ?
C21 C22 H22A 109.3 . . ?
C21 C22 H22B 109.3 . . ?
C21 C22 C23 111.52(13) . . ?
H22A C22 H22B 108.0 . . ?
C23 C22 H22A 109.3 . . ?
C23 C22 H22B 109.3 . . ?
C22 C23 H23A 108.7 . . ?
C22 C23 H23B 108.7 . . ?
H23A C23 H23B 107.6 . . ?
C24 C23 C22 114.23(13) . . ?
C24 C23 H23A 108.7 . . ?
C24 C23 H23B 108.7 . . ?
C23 C24 H24A 109.0 . . ?
C23 C24 H24B 109.0 . . ?
C23 C24 C25 113.00(13) . . ?
H24A C24 H24B 107.8 . . ?
C25 C24 H24A 109.0 . . ?
C25 C24 H24B 109.0 . . ?
C24 C25 H25A 108.5 . . ?
C24 C25 H25B 108.5 . . ?
H25A C25 H25B 107.5 . . ?
C26 C25 C24 115.06(13) . . ?
C26 C25 H25A 108.5 . . ?
C26 C25 H25B 108.5 . . ?
C25 C26 H26A 109.1 . . ?
C25 C26 H26B 109.1 . . ?
C25 C26 C27 112.55(14) . . ?
H26A C26 H26B 107.8 . . ?
C27 C26 H26A 109.1 . . ?
C27 C26 H26B 109.1 . . ?
C26 C27 H27A 109.5 . . ?
C26 C27 H27B 109.5 . . ?
C26 C27 H27C 109.5 . . ?
H27A C27 H27B 109.5 . . ?
H27A C27 H27C 109.5 . . ?
H27B C27 H27C 109.5 . . ?
C7 N1 C11 117.20(14) . . ?
C17 O2 C20 119.25(12) . . ?

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
O1 H1 N1 0.96(2) 1.72(3) 2.6736(18) 172(2) 2_476 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
C1 C2 C3 C4 -0.5(2) . . . . ?
C1 C2 C3 Cl2 179.56(11) . . . . ?
C2 C1 C6 C5 -1.0(2) . . . . ?
C2 C3 C4 C5 0.0(2) . . . . ?
C3 C4 C5 C6 0.0(2) . . . . ?
C3 C4 C5 Cl1 179.01(11) . . . . ?
C4 C5 C6 C1 0.5(2) . . . . ?
C6 C1 C2 C3 1.0(2) . . . . ?
Cl1 C5 C6 C1 -178.49(11) . . . . ?
Cl2 C3 C4 C5 179.96(11) . . . . ?
O1 C1 C2 C3 -178.55(14) . . . . ?
O1 C1 C6 C5 178.54(13) . . . . ?
C7 C8 C9 C10 0.0(2) . . . . ?
C7 C8 C9 C12 -179.45(14) . . . . ?
C8 C7 N1 C11 -0.3(2) . . . . ?
C8 C9 C10 C11 -0.3(2) . . . . ?
C8 C9 C12 C13 173.86(15) . . . . ?
C9 C10 C11 N1 0.4(2) . . . . ?
C9 C12 C13 C14 -178.89(14) . . . . ?
C10 C9 C12 C13 -5.5(2) . . . . ?
C10 C11 N1 C7 -0.1(2) . . . . ?
C12 C9 C10 C11 179.07(14) . . . . ?
C12 C13 C14 C15 173.17(15) . . . . ?
C12 C13 C14 C19 -7.1(2) . . . . ?
C13 C14 C15 C16 -179.09(13) . . . . ?
C13 C14 C19 C18 179.19(14) . . . . ?
C14 C15 C16 C17 -0.4(2) . . . . ?
C15 C14 C19 C18 -1.1(2) . . . . ?
C15 C16 C17 C18 -0.6(2) . . . . ?
C15 C16 C17 O2 179.19(13) . . . . ?
C16 C17 C18 C19 0.6(2) . . . . ?
C16 C17 O2 C20 3.0(2) . . . . ?
C17 C18 C19 C14 0.2(2) . . . . ?
C18 C17 O2 C20 -177.27(13) . . . . ?
C19 C14 C15 C16 1.2(2) . . . . ?
C20 C21 C22 C23 178.57(13) . . . . ?
C21 C20 O2 C17 178.96(12) . . . . ?
C21 C22 C23 C24 -177.18(12) . . . . ?
C22 C23 C24 C25 177.41(13) . . . . ?
C23 C24 C25 C26 -174.42(13) . . . . ?
C24 C25 C26 C27 178.92(14) . . . . ?
N1 C7 C8 C9 0.4(2) . . . . ?
O2 C17 C18 C19 -179.13(13) . . . . ?
O2 C20 C21 C22 -177.69(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_dwb1008m
_database_code_depnum_ccdc_archive 'CCDC 2245335'
loop_
_audit_author_name
_audit_author_address
'Adrian C Whitwood'
;University of York
United Kingdom
;
_audit_update_record             
;
2023-02-28 deposited with the CCDC.	2023-04-20 downloaded from the CCDC.
;
_audit_creation_date             2023-02-28
_audit_creation_method           
;
Olex2 1.5
(compiled 2023.02.24 svn.rf166f9f3 for OlexSys, GUI svn.r6725)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C6 H3 Cl3 O, C21 H27 N O'
_chemical_formula_sum            'C27 H30 Cl3 N O2'
_chemical_formula_weight         506.87
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
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'
Cl Cl 0.1484 0.1585 '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      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   7.8166(16)
_cell_length_b                   9.981(2)
_cell_length_c                   16.223(3)
_cell_angle_alpha                87.546(4)
_cell_angle_beta                 89.183(4)
_cell_angle_gamma                88.641(4)
_cell_volume                     1264.0(4)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    5812
_cell_measurement_temperature    110.15
_cell_measurement_theta_max      28.36
_cell_measurement_theta_min      2.35
_shelx_estimated_absorpt_T_max   0.959
_shelx_estimated_absorpt_T_min   0.906
_exptl_absorpt_coefficient_mu    0.387
_exptl_absorpt_correction_T_max  0.958
_exptl_absorpt_correction_T_min  0.785
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS v2.10; (Sheldrick)'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.332
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             532
_exptl_crystal_size_max          0.26
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.11
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0195
_diffrn_reflns_av_unetI/netI     0.0256
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.982
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            13040
_diffrn_reflns_point_group_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.982
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.363
_diffrn_reflns_theta_min         2.043
_diffrn_ambient_temperature      110.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.982
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'fine-focus sealed tube'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                5373
_reflns_number_total             6216
_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 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXS  (Sheldrick, 2008)'
_refine_diff_density_max         0.460
_refine_diff_density_min         -0.214
_refine_diff_density_rms         0.056
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.034
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     302
_refine_ls_number_reflns         6216
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0423
_refine_ls_R_factor_gt           0.0357
_refine_ls_restrained_S_all      1.034
_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)+(0.0581P)²+0.3089P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0952
_refine_ls_wR_factor_ref         0.1005
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All O(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C20(H20A,H20B), C21(H21A,H21B), C22(H22A,H22B), C23(H23A,H23B), C24(H24A,
 H24B), C25(H25A,H25B), C26(H26A,H26B)
2.b Aromatic/amide H refined with riding coordinates:
 C3(H3), C6(H6), C7(H7), C8(H8), C10(H10), C11(H11), C12(H12), C13(H13),
 C15(H15), C16(H16), C18(H18), C19(H19)
2.c Idealised Me refined as rotating group:
 C27(H27A,H27B,H27C)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.44179(16) 0.82295(13) 0.54418(8) 0.0209(3) Uani 1 1 d . . . . .
C2 C 0.30383(16) 0.90397(13) 0.51576(8) 0.0199(2) Uani 1 1 d . . . . .
C3 C 0.21672(16) 0.99037(12) 0.56681(8) 0.0203(2) Uani 1 1 d . . . . .
H3 H 0.123767 1.044060 0.545958 0.024 Uiso 1 1 calc R U . . .
C4 C 0.26464(16) 0.99895(13) 0.64847(8) 0.0206(2) Uani 1 1 d . . . . .
C5 C 0.40322(17) 0.92189(13) 0.67748(8) 0.0211(3) Uani 1 1 d . . . . .
C6 C 0.48977(16) 0.83430(13) 0.62626(8) 0.0219(3) Uani 1 1 d . . . . .
H6 H 0.583074 0.781253 0.647340 0.026 Uiso 1 1 calc R U . . .
Cl1 Cl 0.23945(4) 0.89317(3) 0.41453(2) 0.02488(9) Uani 1 1 d . . . . .
Cl2 Cl 0.15039(4) 1.10386(3) 0.71244(2) 0.02582(9) Uani 1 1 d . . . . .
Cl3 Cl 0.47249(5) 0.93261(4) 0.77767(2) 0.02921(10) Uani 1 1 d . . . . .
O1 O 0.52041(13) 0.73889(10) 0.49272(6) 0.0263(2) Uani 1 1 d . . . . .
H1 H 0.591(2) 0.7037(18) 0.5144(11) 0.032 Uiso 1 1 d . U . . .
C7 C 1.18130(17) 0.50845(14) 0.42535(8) 0.0228(3) Uani 1 1 d . . . . .
H7 H 1.267001 0.566162 0.443205 0.027 Uiso 1 1 calc R U . . .
C8 C 1.03217(17) 0.56515(13) 0.39300(8) 0.0222(3) Uani 1 1 d . . . . .
H8 H 1.017061 0.659940 0.389466 0.027 Uiso 1 1 calc R U . . .
C9 C 0.90354(16) 0.48343(13) 0.36548(8) 0.0206(3) Uani 1 1 d . . . . .
C10 C 0.93588(17) 0.34424(13) 0.37143(8) 0.0229(3) Uani 1 1 d . . . . .
H10 H 0.854352 0.283974 0.352428 0.027 Uiso 1 1 calc R U . . .
C11 C 1.08703(18) 0.29636(13) 0.40510(9) 0.0244(3) Uani 1 1 d . . . . .
H11 H 1.106114 0.201970 0.409283 0.029 Uiso 1 1 calc R U . . .
C12 C 0.74454(17) 0.54406(13) 0.33332(8) 0.0231(3) Uani 1 1 d . . . . .
H12 H 0.721835 0.635447 0.344600 0.028 Uiso 1 1 calc R U . . .
C13 C 0.62813(17) 0.48282(13) 0.28951(8) 0.0225(3) Uani 1 1 d . . . . .
H13 H 0.649822 0.390892 0.279341 0.027 Uiso 1 1 calc R U . . .
C14 C 0.47041(17) 0.54375(13) 0.25567(8) 0.0207(3) Uani 1 1 d . . . . .
C15 C 0.42754(17) 0.68102(13) 0.26221(8) 0.0225(3) Uani 1 1 d . . . . .
H15 H 0.502334 0.737049 0.290007 0.027 Uiso 1 1 calc R U . . .
C16 C 0.27896(17) 0.73496(13) 0.22890(8) 0.0230(3) Uani 1 1 d . . . . .
H16 H 0.253066 0.827883 0.233291 0.028 Uiso 1 1 calc R U . . .
C17 C 0.16574(17) 0.65406(13) 0.18863(8) 0.0212(3) Uani 1 1 d . . . . .
C18 C 0.20453(18) 0.51805(14) 0.18164(8) 0.0249(3) Uani 1 1 d . . . . .
H18 H 0.128441 0.462115 0.154564 0.030 Uiso 1 1 calc R U . . .
C19 C 0.35613(18) 0.46510(13) 0.21480(8) 0.0238(3) Uani 1 1 d . . . . .
H19 H 0.382686 0.372476 0.209443 0.029 Uiso 1 1 calc R U . . .
C20 C -0.09910(17) 0.64424(14) 0.11451(8) 0.0242(3) Uani 1 1 d . . . . .
H20A H -0.144030 0.569327 0.149801 0.029 Uiso 1 1 calc R U . . .
H20B H -0.044485 0.606946 0.064780 0.029 Uiso 1 1 calc R U . . .
C21 C -0.24186(18) 0.74257(14) 0.09046(9) 0.0259(3) Uani 1 1 d . . . . .
H21A H -0.192348 0.819556 0.058703 0.031 Uiso 1 1 calc R U . . .
H21B H -0.295345 0.777195 0.141223 0.031 Uiso 1 1 calc R U . . .
C22 C -0.38036(17) 0.68212(14) 0.03896(8) 0.0247(3) Uani 1 1 d . . . . .
H22A H -0.327991 0.648375 -0.012299 0.030 Uiso 1 1 calc R U . . .
H22B H -0.430499 0.605048 0.070372 0.030 Uiso 1 1 calc R U . . .
C23 C -0.52200(17) 0.78464(14) 0.01666(8) 0.0249(3) Uani 1 1 d . . . . .
H23A H -0.571422 0.819925 0.068138 0.030 Uiso 1 1 calc R U . . .
H23B H -0.471245 0.860718 -0.015460 0.030 Uiso 1 1 calc R U . . .
C24 C -0.66534(18) 0.72811(14) -0.03320(9) 0.0260(3) Uani 1 1 d . . . . .
H24A H -0.616894 0.696686 -0.085875 0.031 Uiso 1 1 calc R U . . .
H24B H -0.712651 0.649455 -0.002233 0.031 Uiso 1 1 calc R U . . .
C25 C -0.81017(17) 0.82907(14) -0.05197(9) 0.0259(3) Uani 1 1 d . . . . .
H25A H -0.868085 0.852140 0.000384 0.031 Uiso 1 1 calc R U . . .
H25B H -0.761346 0.912197 -0.076954 0.031 Uiso 1 1 calc R U . . .
C26 C -0.9416(2) 0.77699(17) -0.11006(10) 0.0365(4) Uani 1 1 d . . . . .
H26A H -0.990377 0.694161 -0.084662 0.044 Uiso 1 1 calc R U . . .
H26B H -0.882679 0.752729 -0.161950 0.044 Uiso 1 1 calc R U . . .
C27 C -1.0873(2) 0.8758(2) -0.13089(12) 0.0448(4) Uani 1 1 d . . . . .
H27A H -1.149213 0.898165 -0.080178 0.067 Uiso 1 1 calc R U . . .
H27B H -1.165749 0.835267 -0.168735 0.067 Uiso 1 1 calc R U . . .
H27C H -1.040767 0.957578 -0.157186 0.067 Uiso 1 1 calc R U . . .
N1 N 1.20995(14) 0.37551(11) 0.43256(7) 0.0236(2) Uani 1 1 d . . . . .
O2 O 0.02208(12) 0.71859(10) 0.15898(6) 0.0262(2) Uani 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
C1 C2 1.4037(18) . ?
C1 C6 1.3984(19) . ?
C1 O1 1.3414(16) . ?
C2 C3 1.3821(18) . ?
C2 Cl1 1.7329(13) . ?
C3 H3 0.9500 . ?
C3 C4 1.3885(18) . ?
C4 C5 1.3894(18) . ?
C4 Cl2 1.7301(13) . ?
C5 C6 1.3894(19) . ?
C5 Cl3 1.7289(14) . ?
C6 H6 0.9500 . ?
O1 H1 0.732(19) . ?
C7 H7 0.9500 . ?
C7 C8 1.3839(19) . ?
C7 N1 1.3408(17) . ?
C8 H8 0.9500 . ?
C8 C9 1.3995(18) . ?
C9 C10 1.4056(18) . ?
C9 C12 1.4625(18) . ?
C10 H10 0.9500 . ?
C10 C11 1.3755(19) . ?
C11 H11 0.9500 . ?
C11 N1 1.3505(18) . ?
C12 H12 0.9500 . ?
C12 C13 1.3375(19) . ?
C13 H13 0.9500 . ?
C13 C14 1.4650(18) . ?
C14 C15 1.4107(18) . ?
C14 C19 1.3959(19) . ?
C15 H15 0.9500 . ?
C15 C16 1.3761(19) . ?
C16 H16 0.9500 . ?
C16 C17 1.3991(19) . ?
C17 C18 1.3929(19) . ?
C17 O2 1.3645(16) . ?
C18 H18 0.9500 . ?
C18 C19 1.3918(19) . ?
C19 H19 0.9500 . ?
C20 H20A 0.9900 . ?
C20 H20B 0.9900 . ?
C20 C21 1.5127(19) . ?
C20 O2 1.4377(16) . ?
C21 H21A 0.9900 . ?
C21 H21B 0.9900 . ?
C21 C22 1.5278(18) . ?
C22 H22A 0.9900 . ?
C22 H22B 0.9900 . ?
C22 C23 1.5262(19) . ?
C23 H23A 0.9900 . ?
C23 H23B 0.9900 . ?
C23 C24 1.5241(18) . ?
C24 H24A 0.9900 . ?
C24 H24B 0.9900 . ?
C24 C25 1.5229(19) . ?
C25 H25A 0.9900 . ?
C25 H25B 0.9900 . ?
C25 C26 1.519(2) . ?
C26 H26A 0.9900 . ?
C26 H26B 0.9900 . ?
C26 C27 1.521(2) . ?
C27 H27A 0.9800 . ?
C27 H27B 0.9800 . ?
C27 H27C 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
C6 C1 C2 117.34(12) . . ?
O1 C1 C2 119.48(12) . . ?
O1 C1 C6 123.18(12) . . ?
C1 C2 Cl1 119.01(10) . . ?
C3 C2 C1 121.65(12) . . ?
C3 C2 Cl1 119.33(10) . . ?
C2 C3 H3 119.9 . . ?
C2 C3 C4 120.21(12) . . ?
C4 C3 H3 119.9 . . ?
C3 C4 C5 119.15(12) . . ?
C3 C4 Cl2 119.67(10) . . ?
C5 C4 Cl2 121.17(10) . . ?
C4 C5 C6 120.53(12) . . ?
C4 C5 Cl3 121.06(10) . . ?
C6 C5 Cl3 118.41(10) . . ?
C1 C6 H6 119.5 . . ?
C5 C6 C1 121.09(12) . . ?
C5 C6 H6 119.5 . . ?
C1 O1 H1 109.0(15) . . ?
C8 C7 H7 118.6 . . ?
N1 C7 H7 118.6 . . ?
N1 C7 C8 122.78(12) . . ?
C7 C8 H8 119.9 . . ?
C7 C8 C9 120.27(12) . . ?
C9 C8 H8 119.9 . . ?
C8 C9 C10 116.71(12) . . ?
C8 C9 C12 119.91(12) . . ?
C10 C9 C12 123.37(12) . . ?
C9 C10 H10 120.4 . . ?
C11 C10 C9 119.18(12) . . ?
C11 C10 H10 120.4 . . ?
C10 C11 H11 118.0 . . ?
N1 C11 C10 123.92(12) . . ?
N1 C11 H11 118.0 . . ?
C9 C12 H12 117.0 . . ?
C13 C12 C9 126.06(12) . . ?
C13 C12 H12 117.0 . . ?
C12 C13 H13 116.8 . . ?
C12 C13 C14 126.32(13) . . ?
C14 C13 H13 116.8 . . ?
C15 C14 C13 122.64(12) . . ?
C19 C14 C13 119.85(12) . . ?
C19 C14 C15 117.52(12) . . ?
C14 C15 H15 119.5 . . ?
C16 C15 C14 120.97(12) . . ?
C16 C15 H15 119.5 . . ?
C15 C16 H16 119.7 . . ?
C15 C16 C17 120.54(12) . . ?
C17 C16 H16 119.7 . . ?
C18 C17 C16 119.68(12) . . ?
O2 C17 C16 115.15(12) . . ?
O2 C17 C18 125.17(12) . . ?
C17 C18 H18 120.4 . . ?
C19 C18 C17 119.19(12) . . ?
C19 C18 H18 120.4 . . ?
C14 C19 H19 118.9 . . ?
C18 C19 C14 122.10(12) . . ?
C18 C19 H19 118.9 . . ?
H20A C20 H20B 108.7 . . ?
C21 C20 H20A 110.5 . . ?
C21 C20 H20B 110.5 . . ?
O2 C20 H20A 110.5 . . ?
O2 C20 H20B 110.5 . . ?
O2 C20 C21 106.20(11) . . ?
C20 C21 H21A 108.8 . . ?
C20 C21 H21B 108.8 . . ?
C20 C21 C22 113.65(12) . . ?
H21A C21 H21B 107.7 . . ?
C22 C21 H21A 108.8 . . ?
C22 C21 H21B 108.8 . . ?
C21 C22 H22A 109.3 . . ?
C21 C22 H22B 109.3 . . ?
H22A C22 H22B 107.9 . . ?
C23 C22 C21 111.76(11) . . ?
C23 C22 H22A 109.3 . . ?
C23 C22 H22B 109.3 . . ?
C22 C23 H23A 108.8 . . ?
C22 C23 H23B 108.8 . . ?
H23A C23 H23B 107.7 . . ?
C24 C23 C22 113.71(11) . . ?
C24 C23 H23A 108.8 . . ?
C24 C23 H23B 108.8 . . ?
C23 C24 H24A 108.9 . . ?
C23 C24 H24B 108.9 . . ?
H24A C24 H24B 107.7 . . ?
C25 C24 C23 113.49(11) . . ?
C25 C24 H24A 108.9 . . ?
C25 C24 H24B 108.9 . . ?
C24 C25 H25A 109.0 . . ?
C24 C25 H25B 109.0 . . ?
H25A C25 H25B 107.8 . . ?
C26 C25 C24 112.92(12) . . ?
C26 C25 H25A 109.0 . . ?
C26 C25 H25B 109.0 . . ?
C25 C26 H26A 108.7 . . ?
C25 C26 H26B 108.7 . . ?
C25 C26 C27 114.38(14) . . ?
H26A C26 H26B 107.6 . . ?
C27 C26 H26A 108.7 . . ?
C27 C26 H26B 108.7 . . ?
C26 C27 H27A 109.5 . . ?
C26 C27 H27B 109.5 . . ?
C26 C27 H27C 109.5 . . ?
H27A C27 H27B 109.5 . . ?
H27A C27 H27C 109.5 . . ?
H27B C27 H27C 109.5 . . ?
C7 N1 C11 117.11(12) . . ?
C17 O2 C20 119.01(10) . . ?

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
O1 H1 N1 0.732(19) 1.927(19) 2.6562(16) 175(2) 2_766 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
C1 C2 C3 C4 0.02(19) . . . . ?
C2 C1 C6 C5 0.37(19) . . . . ?
C2 C3 C4 C5 1.39(19) . . . . ?
C2 C3 C4 Cl2 -178.09(10) . . . . ?
C3 C4 C5 C6 -1.91(19) . . . . ?
C3 C4 C5 Cl3 177.95(10) . . . . ?
C4 C5 C6 C1 1.0(2) . . . . ?
C6 C1 C2 C3 -0.89(19) . . . . ?
C6 C1 C2 Cl1 -179.88(10) . . . . ?
Cl1 C2 C3 C4 179.00(10) . . . . ?
Cl2 C4 C5 C6 177.56(10) . . . . ?
Cl2 C4 C5 Cl3 -2.58(16) . . . . ?
Cl3 C5 C6 C1 -178.83(10) . . . . ?
O1 C1 C2 C3 178.81(12) . . . . ?
O1 C1 C2 Cl1 -0.18(17) . . . . ?
O1 C1 C6 C5 -179.32(12) . . . . ?
C7 C8 C9 C10 -0.97(19) . . . . ?
C7 C8 C9 C12 178.45(12) . . . . ?
C8 C7 N1 C11 1.29(19) . . . . ?
C8 C9 C10 C11 1.56(19) . . . . ?
C8 C9 C12 C13 164.86(13) . . . . ?
C9 C10 C11 N1 -0.8(2) . . . . ?
C9 C12 C13 C14 -178.64(12) . . . . ?
C10 C9 C12 C13 -15.8(2) . . . . ?
C10 C11 N1 C7 -0.6(2) . . . . ?
C12 C9 C10 C11 -177.84(13) . . . . ?
C12 C13 C14 C15 3.7(2) . . . . ?
C12 C13 C14 C19 -176.56(13) . . . . ?
C13 C14 C15 C16 179.34(12) . . . . ?
C13 C14 C19 C18 179.93(12) . . . . ?
C14 C15 C16 C17 0.8(2) . . . . ?
C15 C14 C19 C18 -0.3(2) . . . . ?
C15 C16 C17 C18 -0.5(2) . . . . ?
C15 C16 C17 O2 179.33(12) . . . . ?
C16 C17 C18 C19 -0.2(2) . . . . ?
C16 C17 O2 C20 178.15(11) . . . . ?
C17 C18 C19 C14 0.6(2) . . . . ?
C18 C17 O2 C20 -2.00(19) . . . . ?
C19 C14 C15 C16 -0.43(19) . . . . ?
C20 C21 C22 C23 179.63(11) . . . . ?
C21 C20 O2 C17 179.87(11) . . . . ?
C21 C22 C23 C24 -178.73(12) . . . . ?
C22 C23 C24 C25 177.41(11) . . . . ?
C23 C24 C25 C26 173.19(13) . . . . ?
C24 C25 C26 C27 -179.41(13) . . . . ?
N1 C7 C8 C9 -0.5(2) . . . . ?
O2 C17 C18 C19 179.97(13) . . . . ?
O2 C20 C21 C22 177.53(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_dwb1009m
_database_code_depnum_ccdc_archive 'CCDC 2245336'
loop_
_audit_author_name
_audit_author_address
'Adrian C Whitwood'
;University of York
United Kingdom
;
_audit_update_record             
;
2023-02-28 deposited with the CCDC.	2023-04-20 downloaded from the CCDC.
;
_audit_creation_date             2023-02-28
_audit_creation_method           
;
Olex2 1.5
(compiled 2023.02.24 svn.rf166f9f3 for OlexSys, GUI svn.r6725)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C6 H Cl5 O, C21 H27 N O'
_chemical_formula_sum            'C27 H28 Cl5 N O2'
_chemical_formula_weight         575.75
_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'
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'
Cl Cl 0.1484 0.1585 '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      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   7.938(9)
_cell_length_b                   11.115(13)
_cell_length_c                   15.689(18)
_cell_angle_alpha                74.87(2)
_cell_angle_beta                 87.11(2)
_cell_angle_gamma                83.09(2)
_cell_volume                     1326(3)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    2410
_cell_measurement_temperature    110.15
_cell_measurement_theta_max      25.14
_cell_measurement_theta_min      2.59
_shelx_estimated_absorpt_T_max   0.989
_shelx_estimated_absorpt_T_min   0.889
_exptl_absorpt_coefficient_mu    0.573
_exptl_absorpt_correction_T_max  0.9886
_exptl_absorpt_correction_T_min  0.8891
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS v2.10; (Sheldrick)'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear yellow'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.442
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             596
_exptl_crystal_size_max          0.21
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.02
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0437
_diffrn_reflns_av_unetI/netI     0.0685
_diffrn_reflns_Laue_measured_fraction_full 0.942
_diffrn_reflns_Laue_measured_fraction_max 0.942
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            7464
_diffrn_reflns_point_group_measured_fraction_full 0.942
_diffrn_reflns_point_group_measured_fraction_max 0.942
_diffrn_reflns_theta_full        25.202
_diffrn_reflns_theta_max         25.202
_diffrn_reflns_theta_min         1.910
_diffrn_ambient_temperature      110.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.942
_diffrn_measured_fraction_theta_max 0.942
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       ?
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3378
_reflns_number_total             4519
_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 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXS-1997  (Sheldrick, 2008)'
_refine_diff_density_max         0.580
_refine_diff_density_min         -0.420
_refine_diff_density_rms         0.091
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.021
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     321
_refine_ls_number_reflns         4519
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0735
_refine_ls_R_factor_gt           0.0541
_refine_ls_restrained_S_all      1.021
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0966P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1418
_refine_ls_wR_factor_ref         0.1578
_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 Secondary CH2 refined with riding coordinates:
 C20(H20A,H20B), C21(H21A,H21B), C22(H22A,H22B), C23(H23A,H23B), C24(H24A,
 H24B), C25(H25A,H25B), C26(H26A,H26B)
2.b Aromatic/amide H refined with riding coordinates:
 C7(H7), C8(H8), C10(H10), C11(H11), C12(H12), C13(H13), C15(H15), C16(H16),
 C18(H18), C19(H19)
2.c Idealised Me refined as rotating group:
 C27(H27A,H27B,H27C)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.6620(4) 0.0632(3) 0.1317(2) 0.0240(7) Uani 1 1 d . . . . .
C2 C 0.8092(4) 0.0029(3) 0.1762(2) 0.0244(7) Uani 1 1 d . . . . .
C3 C 0.8150(4) -0.0302(3) 0.2675(2) 0.0254(7) Uani 1 1 d . . . . .
C4 C 0.6733(4) -0.0041(3) 0.3176(2) 0.0270(7) Uani 1 1 d . . . . .
C5 C 0.5248(4) 0.0540(3) 0.2744(2) 0.0254(7) Uani 1 1 d . . . . .
C6 C 0.5215(4) 0.0889(3) 0.1827(2) 0.0243(7) Uani 1 1 d . . . . .
Cl1 Cl 0.98456(9) -0.02809(8) 0.11296(5) 0.0327(2) Uani 1 1 d . . . . .
Cl2 Cl 0.99945(10) -0.10159(8) 0.31947(6) 0.0376(3) Uani 1 1 d . . . . .
Cl3 Cl 0.67909(11) -0.04277(8) 0.43103(5) 0.0346(2) Uani 1 1 d . . . . .
Cl4 Cl 0.34609(10) 0.08483(9) 0.33506(6) 0.0376(3) Uani 1 1 d . . . . .
Cl5 Cl 0.33825(10) 0.16312(8) 0.12959(5) 0.0346(2) Uani 1 1 d . . . . .
O1 O 0.6693(3) 0.0926(2) 0.04411(15) 0.0291(5) Uani 1 1 d . . . . .
C7 C 0.5706(4) 0.1857(3) 0.8490(2) 0.0282(7) Uani 1 1 d . . . . .
H7 H 0.681297 0.143304 0.861677 0.034 Uiso 1 1 calc R U . . .
C8 C 0.5307(4) 0.2363(3) 0.7623(2) 0.0263(7) Uani 1 1 d . . . . .
H8 H 0.612345 0.229241 0.717013 0.032 Uiso 1 1 calc R U . . .
C9 C 0.3679(4) 0.2988(3) 0.7408(2) 0.0232(7) Uani 1 1 d . . . . .
C10 C 0.2570(4) 0.3031(3) 0.8120(2) 0.0293(7) Uani 1 1 d . . . . .
H10 H 0.144629 0.343254 0.801580 0.035 Uiso 1 1 calc R U . . .
C11 C 0.3091(4) 0.2495(3) 0.8973(2) 0.0273(7) Uani 1 1 d . . . . .
H11 H 0.230357 0.254050 0.944292 0.033 Uiso 1 1 calc R U . . .
C12 C 0.3147(4) 0.3571(3) 0.6511(2) 0.0257(7) Uani 1 1 d . . . . .
H12 H 0.210689 0.410417 0.644131 0.031 Uiso 1 1 calc R U . . .
C13 C 0.3963(4) 0.3438(3) 0.5774(2) 0.0242(7) Uani 1 1 d . . . . .
H13 H 0.499450 0.289473 0.584408 0.029 Uiso 1 1 calc R U . . .
C14 C 0.3444(4) 0.4036(3) 0.4871(2) 0.0243(7) Uani 1 1 d . . . . .
C15 C 0.2166(4) 0.5052(3) 0.4661(2) 0.0266(7) Uani 1 1 d . . . . .
H15 H 0.162806 0.537828 0.512069 0.032 Uiso 1 1 calc R U . . .
C16 C 0.1683(4) 0.5580(3) 0.3806(2) 0.0270(7) Uani 1 1 d . . . . .
H16 H 0.082220 0.627020 0.367901 0.032 Uiso 1 1 calc R U . . .
C17 C 0.2447(4) 0.5112(3) 0.3126(2) 0.0260(7) Uani 1 1 d . . . . .
C18 C 0.3743(4) 0.4132(3) 0.3307(2) 0.0272(7) Uani 1 1 d . . . . .
H18 H 0.429735 0.382508 0.284269 0.033 Uiso 1 1 calc R U . . .
C19 C 0.4220(4) 0.3604(3) 0.4178(2) 0.0261(7) Uani 1 1 d . . . . .
H19 H 0.510232 0.292847 0.430220 0.031 Uiso 1 1 calc R U . . .
C20 C 0.2654(4) 0.5358(3) 0.1553(2) 0.0287(7) Uani 1 1 d . . . . .
H20A H 0.266436 0.444851 0.161343 0.034 Uiso 1 1 calc R U . . .
H20B H 0.384005 0.556607 0.149202 0.034 Uiso 1 1 calc R U . . .
C21 C 0.1641(4) 0.6108(3) 0.0761(2) 0.0280(7) Uani 1 1 d . . . . .
H21A H 0.157814 0.700953 0.074362 0.034 Uiso 1 1 calc R U . . .
H21B H 0.046941 0.587169 0.083510 0.034 Uiso 1 1 calc R U . . .
C22 C 0.2376(4) 0.5920(3) -0.0116(2) 0.0282(7) Uani 1 1 d . . . . .
H22A H 0.349015 0.625350 -0.023084 0.034 Uiso 1 1 calc R U . . .
H22B H 0.256079 0.501115 -0.008140 0.034 Uiso 1 1 calc R U . . .
C23 C 0.1210(4) 0.6571(3) -0.0872(2) 0.0280(7) Uani 1 1 d . . . . .
H23A H 0.092766 0.745809 -0.085948 0.034 Uiso 1 1 calc R U . . .
H23B H 0.013927 0.617563 -0.077970 0.034 Uiso 1 1 calc R U . . .
C24 C 0.1941(4) 0.6532(3) -0.1781(2) 0.0289(7) Uani 1 1 d . . . . .
H24A H 0.296914 0.697899 -0.189094 0.035 Uiso 1 1 calc R U . . .
H24B H 0.229477 0.564777 -0.178203 0.035 Uiso 1 1 calc R U . . .
C25 C 0.0719(4) 0.7113(3) -0.2530(2) 0.0290(7) Uani 1 1 d . . . . .
H25A H 0.026592 0.796731 -0.249020 0.035 Uiso 1 1 calc R U . . .
H25B H -0.024825 0.660818 -0.245855 0.035 Uiso 1 1 calc R U . . .
C26 C 0.1535(4) 0.7195(3) -0.3437(2) 0.0299(7) Uani 1 1 d . . . . .
H26A H 0.197297 0.633826 -0.347674 0.036 Uiso 1 1 calc R U . . .
H26B H 0.251638 0.768536 -0.350078 0.036 Uiso 1 1 calc R U . . .
C27 C 0.0344(4) 0.7795(3) -0.4202(2) 0.0355(8) Uani 1 1 d . . . . .
H27A H -0.062987 0.731328 -0.414923 0.053 Uiso 1 1 calc R U . . .
H27B H 0.095136 0.779794 -0.476230 0.053 Uiso 1 1 calc R U . . .
H27C H -0.005538 0.865829 -0.418715 0.053 Uiso 1 1 calc R U . . .
N1 N 0.4648(3) 0.1916(2) 0.91725(17) 0.0271(6) Uani 1 1 d . . . . .
O2 O 0.1836(3) 0.5692(2) 0.23037(14) 0.0285(5) Uani 1 1 d . . . . .
H1 H 0.584(6) 0.119(4) 0.014(3) 0.066(15) 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
C1 C2 1.397(4) . ?
C1 C6 1.385(4) . ?
C1 O1 1.327(4) . ?
C2 C3 1.384(5) . ?
C2 Cl1 1.722(3) . ?
C3 C4 1.385(4) . ?
C3 Cl2 1.715(3) . ?
C4 C5 1.391(5) . ?
C4 Cl3 1.719(4) . ?
C5 C6 1.389(5) . ?
C5 Cl4 1.718(3) . ?
C6 Cl5 1.722(3) . ?
O1 H1 0.83(4) . ?
C7 H7 0.9500 . ?
C7 C8 1.366(5) . ?
C7 N1 1.338(4) . ?
C8 H8 0.9500 . ?
C8 C9 1.404(4) . ?
C9 C10 1.393(4) . ?
C9 C12 1.448(5) . ?
C10 H10 0.9500 . ?
C10 C11 1.378(5) . ?
C11 H11 0.9500 . ?
C11 N1 1.334(4) . ?
C12 H12 0.9500 . ?
C12 C13 1.330(4) . ?
C13 H13 0.9500 . ?
C13 C14 1.456(4) . ?
C14 C15 1.406(4) . ?
C14 C19 1.387(4) . ?
C15 H15 0.9500 . ?
C15 C16 1.370(5) . ?
C16 H16 0.9500 . ?
C16 C17 1.389(4) . ?
C17 C18 1.387(4) . ?
C17 O2 1.367(4) . ?
C18 H18 0.9500 . ?
C18 C19 1.391(5) . ?
C19 H19 0.9500 . ?
C20 H20A 0.9900 . ?
C20 H20B 0.9900 . ?
C20 C21 1.511(5) . ?
C20 O2 1.427(4) . ?
C21 H21A 0.9900 . ?
C21 H21B 0.9900 . ?
C21 C22 1.524(5) . ?
C22 H22A 0.9900 . ?
C22 H22B 0.9900 . ?
C22 C23 1.513(5) . ?
C23 H23A 0.9900 . ?
C23 H23B 0.9900 . ?
C23 C24 1.520(5) . ?
C24 H24A 0.9900 . ?
C24 H24B 0.9900 . ?
C24 C25 1.519(5) . ?
C25 H25A 0.9900 . ?
C25 H25B 0.9900 . ?
C25 C26 1.520(4) . ?
C26 H26A 0.9900 . ?
C26 H26B 0.9900 . ?
C26 C27 1.524(5) . ?
C27 H27A 0.9800 . ?
C27 H27B 0.9800 . ?
C27 H27C 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
C6 C1 C2 117.2(3) . . ?
O1 C1 C2 117.3(3) . . ?
O1 C1 C6 125.5(3) . . ?
C1 C2 Cl1 117.3(2) . . ?
C3 C2 C1 121.6(3) . . ?
C3 C2 Cl1 121.0(2) . . ?
C2 C3 C4 120.5(3) . . ?
C2 C3 Cl2 120.1(2) . . ?
C4 C3 Cl2 119.4(2) . . ?
C3 C4 C5 118.7(3) . . ?
C3 C4 Cl3 121.1(2) . . ?
C5 C4 Cl3 120.3(2) . . ?
C4 C5 Cl4 119.6(3) . . ?
C6 C5 C4 120.3(3) . . ?
C6 C5 Cl4 120.1(2) . . ?
C1 C6 C5 121.7(3) . . ?
C1 C6 Cl5 118.2(2) . . ?
C5 C6 Cl5 120.1(2) . . ?
C1 O1 H1 122(3) . . ?
C8 C7 H7 117.7 . . ?
N1 C7 H7 117.7 . . ?
N1 C7 C8 124.6(3) . . ?
C7 C8 H8 120.3 . . ?
C7 C8 C9 119.5(3) . . ?
C9 C8 H8 120.3 . . ?
C8 C9 C12 123.5(3) . . ?
C10 C9 C8 115.8(3) . . ?
C10 C9 C12 120.7(3) . . ?
C9 C10 H10 119.7 . . ?
C11 C10 C9 120.5(3) . . ?
C11 C10 H10 119.7 . . ?
C10 C11 H11 118.4 . . ?
N1 C11 C10 123.3(3) . . ?
N1 C11 H11 118.4 . . ?
C9 C12 H12 116.6 . . ?
C13 C12 C9 126.8(3) . . ?
C13 C12 H12 116.6 . . ?
C12 C13 H13 116.5 . . ?
C12 C13 C14 126.9(3) . . ?
C14 C13 H13 116.5 . . ?
C15 C14 C13 122.6(3) . . ?
C19 C14 C13 119.9(3) . . ?
C19 C14 C15 117.5(3) . . ?
C14 C15 H15 119.4 . . ?
C16 C15 C14 121.3(3) . . ?
C16 C15 H15 119.4 . . ?
C15 C16 H16 119.9 . . ?
C15 C16 C17 120.3(3) . . ?
C17 C16 H16 119.9 . . ?
C18 C17 C16 119.9(3) . . ?
O2 C17 C16 115.2(3) . . ?
O2 C17 C18 124.9(3) . . ?
C17 C18 H18 120.4 . . ?
C17 C18 C19 119.2(3) . . ?
C19 C18 H18 120.4 . . ?
C14 C19 C18 121.8(3) . . ?
C14 C19 H19 119.1 . . ?
C18 C19 H19 119.1 . . ?
H20A C20 H20B 108.7 . . ?
C21 C20 H20A 110.5 . . ?
C21 C20 H20B 110.5 . . ?
O2 C20 H20A 110.5 . . ?
O2 C20 H20B 110.5 . . ?
O2 C20 C21 106.3(3) . . ?
C20 C21 H21A 108.8 . . ?
C20 C21 H21B 108.8 . . ?
C20 C21 C22 113.9(3) . . ?
H21A C21 H21B 107.7 . . ?
C22 C21 H21A 108.8 . . ?
C22 C21 H21B 108.8 . . ?
C21 C22 H22A 109.3 . . ?
C21 C22 H22B 109.3 . . ?
H22A C22 H22B 108.0 . . ?
C23 C22 C21 111.6(3) . . ?
C23 C22 H22A 109.3 . . ?
C23 C22 H22B 109.3 . . ?
C22 C23 H23A 108.6 . . ?
C22 C23 H23B 108.6 . . ?
C22 C23 C24 114.5(3) . . ?
H23A C23 H23B 107.6 . . ?
C24 C23 H23A 108.6 . . ?
C24 C23 H23B 108.6 . . ?
C23 C24 H24A 108.7 . . ?
C23 C24 H24B 108.7 . . ?
H24A C24 H24B 107.6 . . ?
C25 C24 C23 114.1(3) . . ?
C25 C24 H24A 108.7 . . ?
C25 C24 H24B 108.7 . . ?
C24 C25 H25A 109.0 . . ?
C24 C25 H25B 109.0 . . ?
C24 C25 C26 113.1(3) . . ?
H25A C25 H25B 107.8 . . ?
C26 C25 H25A 109.0 . . ?
C26 C25 H25B 109.0 . . ?
C25 C26 H26A 108.7 . . ?
C25 C26 H26B 108.7 . . ?
C25 C26 C27 114.3(3) . . ?
H26A C26 H26B 107.6 . . ?
C27 C26 H26A 108.7 . . ?
C27 C26 H26B 108.7 . . ?
C26 C27 H27A 109.5 . . ?
C26 C27 H27B 109.5 . . ?
C26 C27 H27C 109.5 . . ?
H27A C27 H27B 109.5 . . ?
H27A C27 H27C 109.5 . . ?
H27B C27 H27C 109.5 . . ?
C11 N1 C7 116.3(3) . . ?
C17 O2 C20 119.1(2) . . ?

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
O1 H1 N1 0.83(4) 1.78(4) 2.562(4) 157(4) 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
C1 C2 C3 C4 0.0(5) . . . . ?
C1 C2 C3 Cl2 -178.9(2) . . . . ?
C2 C1 C6 C5 -1.5(5) . . . . ?
C2 C1 C6 Cl5 -180.0(2) . . . . ?
C2 C3 C4 C5 1.1(5) . . . . ?
C2 C3 C4 Cl3 -179.2(2) . . . . ?
C3 C4 C5 C6 -2.3(5) . . . . ?
C3 C4 C5 Cl4 178.8(2) . . . . ?
C4 C5 C6 C1 2.6(5) . . . . ?
C4 C5 C6 Cl5 -178.9(2) . . . . ?
C6 C1 C2 C3 0.2(5) . . . . ?
C6 C1 C2 Cl1 -179.5(2) . . . . ?
Cl1 C2 C3 C4 179.6(2) . . . . ?
Cl1 C2 C3 Cl2 0.8(4) . . . . ?
Cl2 C3 C4 C5 179.9(2) . . . . ?
Cl2 C3 C4 Cl3 -0.4(4) . . . . ?
Cl3 C4 C5 C6 177.9(2) . . . . ?
Cl3 C4 C5 Cl4 -1.0(4) . . . . ?
Cl4 C5 C6 C1 -178.5(2) . . . . ?
Cl4 C5 C6 Cl5 0.0(4) . . . . ?
O1 C1 C2 C3 179.1(3) . . . . ?
O1 C1 C2 Cl1 -0.5(4) . . . . ?
O1 C1 C6 C5 179.7(3) . . . . ?
O1 C1 C6 Cl5 1.2(4) . . . . ?
C7 C8 C9 C10 -0.5(4) . . . . ?
C7 C8 C9 C12 179.0(3) . . . . ?
C8 C7 N1 C11 1.3(5) . . . . ?
C8 C9 C10 C11 0.8(5) . . . . ?
C8 C9 C12 C13 11.8(5) . . . . ?
C9 C10 C11 N1 0.0(5) . . . . ?
C9 C12 C13 C14 -179.1(3) . . . . ?
C10 C9 C12 C13 -168.7(3) . . . . ?
C10 C11 N1 C7 -1.0(5) . . . . ?
C12 C9 C10 C11 -178.8(3) . . . . ?
C12 C13 C14 C15 13.9(5) . . . . ?
C12 C13 C14 C19 -166.1(3) . . . . ?
C13 C14 C15 C16 -178.8(3) . . . . ?
C13 C14 C19 C18 178.8(3) . . . . ?
C14 C15 C16 C17 0.4(5) . . . . ?
C15 C14 C19 C18 -1.2(5) . . . . ?
C15 C16 C17 C18 -2.1(5) . . . . ?
C15 C16 C17 O2 178.5(3) . . . . ?
C16 C17 C18 C19 2.1(5) . . . . ?
C16 C17 O2 C20 173.9(3) . . . . ?
C17 C18 C19 C14 -0.4(5) . . . . ?
C18 C17 O2 C20 -5.5(4) . . . . ?
C19 C14 C15 C16 1.2(5) . . . . ?
C20 C21 C22 C23 173.4(3) . . . . ?
C21 C20 O2 C17 177.4(2) . . . . ?
C21 C22 C23 C24 174.2(3) . . . . ?
C22 C23 C24 C25 176.2(3) . . . . ?
C23 C24 C25 C26 173.7(3) . . . . ?
C24 C25 C26 C27 -179.0(3) . . . . ?
N1 C7 C8 C9 -0.5(5) . . . . ?
O2 C17 C18 C19 -178.5(3) . . . . ?
O2 C20 C21 C22 177.4(3) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'

###END
