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

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_alc33
_database_code_depnum_ccdc_archive 'CCDC 2008623'
loop_
_audit_author_name
_audit_author_address
'Frank Rominger'
;Heidelberg University
Germany
;
_audit_update_record             
;
2020-06-08 deposited with the CCDC.	2020-12-20 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            'DPrCuCl in manuscript'
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C41 H49 Cl6 Cu N2'
_chemical_formula_weight         846.06

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'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cu Cu 0.3201 1.2651 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

_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. 
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   10.6240(12)
_cell_length_b                   23.227(3)
_cell_length_c                   17.226(2)
_cell_angle_alpha                90
_cell_angle_beta                 97.340(3)
_cell_angle_gamma                90
_cell_volume                     4215.8(8)
_cell_formula_units_Z            4
_cell_measurement_temperature    200(2)
_cell_measurement_reflns_used    4197
_cell_measurement_theta_min      2.31
_cell_measurement_theta_max      20.23

_exptl_crystal_description       brick
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.333
_exptl_crystal_F_000             1760
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.084
_exptl_crystal_size_mid          0.064
_exptl_crystal_size_min          0.024
_exptl_absorpt_coefficient_mu    0.929
_shelx_estimated_absorpt_T_min   0.926
_shelx_estimated_absorpt_T_max   0.978
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.8493
_exptl_absorpt_correction_T_max  0.9579
_exptl_absorpt_process_details   
;
Sheldrick, G. M. (2008). SADABS. University of Göttingen, Germany.
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      200(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'ImuS microsource'
_diffrn_measurement_device_type  'Bruker APEX-II Quazar area detector'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            38755
_diffrn_reflns_av_unetI/netI     0.0756
_diffrn_reflns_av_R_equivalents  0.0983
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -27
_diffrn_reflns_limit_k_max       27
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         1.480
_diffrn_reflns_theta_max         25.096
_diffrn_reflns_theta_full        25.096
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measured_fraction_theta_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_point_group_measured_fraction_full 0.995
_reflns_number_total             7489
_reflns_number_gt                4749
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_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. 
;

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXT-2014 (Sheldrick 2014)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1147P)²+10.5389P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         7489
_refine_ls_number_parameters     459
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1245
_refine_ls_R_factor_gt           0.0755
_refine_ls_wR_factor_ref         0.2320
_refine_ls_wR_factor_gt          0.1998
_refine_ls_goodness_of_fit_ref   1.029
_refine_ls_restrained_S_all      1.029
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

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
Cu1 Cu 0.77110(7) 0.50662(3) 0.67353(4) 0.0290(2) Uani 1 1 d . . . . .
Cl1 Cl 0.72924(16) 0.59251(6) 0.63599(9) 0.0434(4) Uani 1 1 d . . . . .
C1 C 0.8070(5) 0.4324(2) 0.7160(3) 0.0243(12) Uani 1 1 d . . . . .
N2 N 0.8413(4) 0.42782(18) 0.7942(2) 0.0249(10) Uani 1 1 d . . . . .
C3 C 0.9223(5) 0.3817(2) 0.8347(3) 0.0307(13) Uani 1 1 d . . . . .
H3A H 0.990794 0.400248 0.870423 0.037 Uiso 1 1 calc R U . . .
H3B H 0.962928 0.360302 0.794863 0.037 Uiso 1 1 calc R U . . .
C4 C 0.7638(5) 0.3258(2) 0.7011(3) 0.0306(13) Uani 1 1 d . . . . .
H4A H 0.695718 0.309468 0.662921 0.037 Uiso 1 1 calc R U . . .
H4B H 0.727967 0.331255 0.750934 0.037 Uiso 1 1 calc R U . . .
N5 N 0.7967(4) 0.38380(18) 0.6722(2) 0.0243(10) Uani 1 1 d . . . . .
C11 C 0.8305(6) 0.4802(2) 0.8382(3) 0.0293(13) Uani 1 1 d . . . . .
C12 C 0.9364(6) 0.5175(2) 0.8515(3) 0.0324(13) Uani 1 1 d . . . . .
C13 C 0.9241(7) 0.5669(3) 0.8945(4) 0.0414(16) Uani 1 1 d . . . . .
H13 H 0.994481 0.592207 0.905234 0.050 Uiso 1 1 calc R U . . .
C14 C 0.8104(7) 0.5802(3) 0.9224(4) 0.0496(18) Uani 1 1 d . . . . .
H14 H 0.803037 0.614715 0.951050 0.060 Uiso 1 1 calc R U . . .
C15 C 0.7087(7) 0.5435(3) 0.9086(4) 0.0459(17) Uani 1 1 d . . . . .
H15 H 0.631809 0.552889 0.928452 0.055 Uiso 1 1 calc R U . . .
C16 C 0.7154(6) 0.4927(3) 0.8663(3) 0.0342(13) Uani 1 1 d . . . . .
C17 C 1.0609(6) 0.5060(3) 0.8190(4) 0.0373(14) Uani 1 1 d . . . . .
H17 H 1.050264 0.469916 0.787248 0.045 Uiso 1 1 calc R U . . .
C171 C 1.1708(7) 0.4966(3) 0.8845(4) 0.059(2) Uani 1 1 d . . . . .
H17A H 1.247201 0.485702 0.861661 0.088 Uiso 1 1 calc R U . . .
H17B H 1.148513 0.465839 0.919228 0.088 Uiso 1 1 calc R U . . .
H17C H 1.186842 0.532267 0.914574 0.088 Uiso 1 1 calc R U . . .
C172 C 1.0905(7) 0.5546(3) 0.7649(4) 0.0533(18) Uani 1 1 d . . . . .
H17D H 1.168948 0.545678 0.742963 0.080 Uiso 1 1 calc R U . . .
H17E H 1.101173 0.590612 0.794558 0.080 Uiso 1 1 calc R U . . .
H17F H 1.020493 0.558634 0.722349 0.080 Uiso 1 1 calc R U . . .
C19 C 0.5991(6) 0.4548(3) 0.8492(4) 0.0418(15) Uani 1 1 d . . . . .
H19 H 0.628251 0.416567 0.831498 0.050 Uiso 1 1 calc R U . . .
C191 C 0.5319(7) 0.4441(3) 0.9219(4) 0.0563(19) Uani 1 1 d . . . . .
H19A H 0.468905 0.413379 0.910723 0.084 Uiso 1 1 calc R U . . .
H19B H 0.489418 0.479469 0.935416 0.084 Uiso 1 1 calc R U . . .
H19C H 0.594572 0.432566 0.965933 0.084 Uiso 1 1 calc R U . . .
C192 C 0.5064(7) 0.4791(4) 0.7834(4) 0.058(2) Uani 1 1 d . . . . .
H19D H 0.434913 0.452495 0.771541 0.086 Uiso 1 1 calc R U . . .
H19E H 0.549251 0.484093 0.736685 0.086 Uiso 1 1 calc R U . . .
H19F H 0.475063 0.516415 0.799193 0.086 Uiso 1 1 calc R U . . .
C21 C 0.7761(5) 0.3923(2) 0.5879(3) 0.0252(12) Uani 1 1 d . . . . .
C22 C 0.6523(5) 0.3963(2) 0.5500(3) 0.0274(12) Uani 1 1 d . . . . .
C23 C 0.6351(6) 0.4059(2) 0.4703(3) 0.0350(14) Uani 1 1 d . . . . .
H23 H 0.551516 0.409328 0.443487 0.042 Uiso 1 1 calc R U . . .
C24 C 0.7374(6) 0.4105(2) 0.4291(3) 0.0384(15) Uani 1 1 d . . . . .
H24 H 0.724408 0.416921 0.374145 0.046 Uiso 1 1 calc R U . . .
C25 C 0.8584(6) 0.4058(3) 0.4677(4) 0.0384(15) Uani 1 1 d . . . . .
H25 H 0.928233 0.409456 0.438696 0.046 Uiso 1 1 calc R U . . .
C26 C 0.8819(5) 0.3961(2) 0.5475(3) 0.0298(13) Uani 1 1 d . . . . .
C27 C 0.5356(5) 0.3928(3) 0.5933(4) 0.0358(14) Uani 1 1 d . . . . .
H27 H 0.565161 0.390563 0.650657 0.043 Uiso 1 1 calc R U . . .
C271 C 0.4580(6) 0.3381(3) 0.5692(4) 0.0530(18) Uani 1 1 d . . . . .
H27A H 0.388558 0.334582 0.601245 0.080 Uiso 1 1 calc R U . . .
H27B H 0.513271 0.304300 0.577244 0.080 Uiso 1 1 calc R U . . .
H27C H 0.423033 0.340773 0.513869 0.080 Uiso 1 1 calc R U . . .
C272 C 0.4516(6) 0.4462(3) 0.5783(4) 0.0463(17) Uani 1 1 d . . . . .
H27D H 0.380503 0.443752 0.609193 0.069 Uiso 1 1 calc R U . . .
H27E H 0.418782 0.448405 0.522524 0.069 Uiso 1 1 calc R U . . .
H27F H 0.501732 0.480788 0.593480 0.069 Uiso 1 1 calc R U . . .
C29 C 1.0161(5) 0.3907(3) 0.5874(4) 0.0410(15) Uani 1 1 d . . . . .
H29 H 1.012393 0.373442 0.640211 0.049 Uiso 1 1 calc R U . . .
C291 C 1.0980(6) 0.3511(4) 0.5430(5) 0.060(2) Uani 1 1 d . . . . .
H29A H 1.177751 0.342596 0.576118 0.089 Uiso 1 1 calc R U . . .
H29B H 1.116240 0.370309 0.494987 0.089 Uiso 1 1 calc R U . . .
H29C H 1.052109 0.315142 0.529419 0.089 Uiso 1 1 calc R U . . .
C292 C 1.0784(7) 0.4501(3) 0.5996(5) 0.062(2) Uani 1 1 d . . . . .
H29D H 1.158622 0.446542 0.634224 0.093 Uiso 1 1 calc R U . . .
H29E H 1.021479 0.476148 0.623313 0.093 Uiso 1 1 calc R U . . .
H29F H 1.094804 0.465721 0.548955 0.093 Uiso 1 1 calc R U . . .
C31 C 0.8562(6) 0.3386(3) 0.8815(3) 0.0366(14) Uani 1 1 d . . . . .
C32 C 0.8482(6) 0.2800(3) 0.8588(4) 0.0408(16) Uani 1 1 d . . . . .
C33 C 0.7876(7) 0.2419(3) 0.9049(4) 0.057(2) Uani 1 1 d . . . . .
H33 H 0.781333 0.202410 0.890651 0.068 Uiso 1 1 calc R U . . .
C34 C 0.7374(8) 0.2600(4) 0.9698(5) 0.070(3) Uani 1 1 d . . . . .
H34 H 0.694612 0.233397 0.999105 0.084 Uiso 1 1 calc R U . . .
C35 C 0.7486(9) 0.3174(4) 0.9932(5) 0.072(3) Uani 1 1 d . . . . .
H35 H 0.714933 0.329923 1.038870 0.087 Uiso 1 1 calc R U . . .
C36 C 0.8093(7) 0.3558(3) 0.9493(4) 0.0486(17) Uani 1 1 d . . . . .
H36 H 0.819074 0.394714 0.965900 0.058 Uiso 1 1 calc R U . . .
C41 C 0.8693(6) 0.2815(2) 0.7151(3) 0.0342(14) Uani 1 1 d . . . . .
C42 C 0.9040(6) 0.2587(2) 0.7905(4) 0.0398(15) Uani 1 1 d . . . . .
C43 C 0.9933(7) 0.2144(3) 0.7995(5) 0.054(2) Uani 1 1 d . . . . .
H43 H 1.016075 0.198003 0.849825 0.065 Uiso 1 1 calc R U . . .
C44 C 1.0491(7) 0.1940(3) 0.7374(5) 0.058(2) Uani 1 1 d . . . . .
H44 H 1.110006 0.163949 0.744882 0.070 Uiso 1 1 calc R U . . .
C45 C 1.0164(7) 0.2173(3) 0.6648(5) 0.059(2) Uani 1 1 d . . . . .
H45 H 1.056258 0.203831 0.621874 0.070 Uiso 1 1 calc R U . . .
C46 C 0.9258(6) 0.2604(2) 0.6531(4) 0.0428(16) Uani 1 1 d . . . . .
H46 H 0.902326 0.275596 0.602034 0.051 Uiso 1 1 calc R U . . .
C51 C 0.2976(12) 0.2829(6) 0.8465(10) 0.154(7) Uani 1 1 d . . . . .
H51 H 0.267456 0.245090 0.823442 0.184 Uiso 1 1 calc R U . . .
Cl2 Cl 0.4545(4) 0.2816(2) 0.8660(4) 0.243(3) Uani 1 1 d . . . . .
Cl3 Cl 0.2192(5) 0.2974(2) 0.9280(3) 0.192(2) Uani 1 1 d . . . . .
Cl4 Cl 0.2492(4) 0.3395(2) 0.7770(3) 0.1702(18) Uani 1 1 d . . . . .
C52 C 0.5296(12) 0.6562(5) 0.7713(8) 0.116(4) Uani 1 1 d . . . . .
H52A H 0.568686 0.617603 0.778384 0.139 Uiso 1 1 calc R U . . .
H52B H 0.531565 0.667619 0.716046 0.139 Uiso 1 1 calc R U . . .
Cl5 Cl 0.6196(4) 0.70359(17) 0.8298(3) 0.1716(18) Uani 1 1 d . . . . .
Cl6 Cl 0.3748(3) 0.6514(2) 0.7878(2) 0.1579(17) 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
Cu1 C1 1.892(5) . ?
Cu1 Cl1 2.1267(16) . ?
C1 N5 1.354(7) . ?
C1 N2 1.354(7) . ?
N2 C11 1.446(7) . ?
N2 C3 1.491(7) . ?
C3 C31 1.513(8) . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C4 N5 1.492(7) . ?
C4 C41 1.519(8) . ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?
N5 C21 1.455(7) . ?
C11 C16 1.403(8) . ?
C11 C12 1.415(8) . ?
C12 C13 1.381(8) . ?
C12 C17 1.524(9) . ?
C13 C14 1.391(10) . ?
C13 H13 0.9500 . ?
C14 C15 1.374(10) . ?
C14 H14 0.9500 . ?
C15 C16 1.392(8) . ?
C15 H15 0.9500 . ?
C16 C19 1.516(9) . ?
C17 C172 1.520(9) . ?
C17 C171 1.532(9) . ?
C17 H17 1.0000 . ?
C171 H17A 0.9800 . ?
C171 H17B 0.9800 . ?
C171 H17C 0.9800 . ?
C172 H17D 0.9800 . ?
C172 H17E 0.9800 . ?
C172 H17F 0.9800 . ?
C19 C192 1.514(9) . ?
C19 C191 1.539(9) . ?
C19 H19 1.0000 . ?
C191 H19A 0.9800 . ?
C191 H19B 0.9800 . ?
C191 H19C 0.9800 . ?
C192 H19D 0.9800 . ?
C192 H19E 0.9800 . ?
C192 H19F 0.9800 . ?
C21 C22 1.395(7) . ?
C21 C26 1.397(8) . ?
C22 C23 1.381(8) . ?
C22 C27 1.528(8) . ?
C23 C24 1.376(9) . ?
C23 H23 0.9500 . ?
C24 C25 1.375(9) . ?
C24 H24 0.9500 . ?
C25 C26 1.384(8) . ?
C25 H25 0.9500 . ?
C26 C29 1.507(8) . ?
C27 C272 1.531(8) . ?
C27 C271 1.541(9) . ?
C27 H27 1.0000 . ?
C271 H27A 0.9800 . ?
C271 H27B 0.9800 . ?
C271 H27C 0.9800 . ?
C272 H27D 0.9800 . ?
C272 H27E 0.9800 . ?
C272 H27F 0.9800 . ?
C29 C292 1.533(9) . ?
C29 C291 1.536(9) . ?
C29 H29 1.0000 . ?
C291 H29A 0.9800 . ?
C291 H29B 0.9800 . ?
C291 H29C 0.9800 . ?
C292 H29D 0.9800 . ?
C292 H29E 0.9800 . ?
C292 H29F 0.9800 . ?
C31 C36 1.385(9) . ?
C31 C32 1.415(9) . ?
C32 C33 1.400(9) . ?
C32 C42 1.470(9) . ?
C33 C34 1.366(12) . ?
C33 H33 0.9500 . ?
C34 C35 1.392(13) . ?
C34 H34 0.9500 . ?
C35 C36 1.382(10) . ?
C35 H35 0.9500 . ?
C36 H36 0.9500 . ?
C41 C46 1.380(9) . ?
C41 C42 1.407(8) . ?
C42 C43 1.394(9) . ?
C43 C44 1.371(11) . ?
C43 H43 0.9500 . ?
C44 C45 1.367(11) . ?
C44 H44 0.9500 . ?
C45 C46 1.387(9) . ?
C45 H45 0.9500 . ?
C46 H46 0.9500 . ?
C51 Cl2 1.659(13) . ?
C51 Cl3 1.755(16) . ?
C51 Cl4 1.807(17) . ?
C51 H51 1.0000 . ?
C52 Cl5 1.701(12) . ?
C52 Cl6 1.708(12) . ?
C52 H52A 0.9900 . ?
C52 H52B 0.9900 . ?

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 Cu1 Cl1 174.96(17) . . ?
N5 C1 N2 118.7(5) . . ?
N5 C1 Cu1 123.2(4) . . ?
N2 C1 Cu1 118.1(4) . . ?
C1 N2 C11 115.2(4) . . ?
C1 N2 C3 126.1(4) . . ?
C11 N2 C3 116.0(4) . . ?
N2 C3 C31 116.5(5) . . ?
N2 C3 H3A 108.2 . . ?
C31 C3 H3A 108.2 . . ?
N2 C3 H3B 108.2 . . ?
C31 C3 H3B 108.2 . . ?
H3A C3 H3B 107.3 . . ?
N5 C4 C41 117.7(5) . . ?
N5 C4 H4A 107.9 . . ?
C41 C4 H4A 107.9 . . ?
N5 C4 H4B 107.9 . . ?
C41 C4 H4B 107.9 . . ?
H4A C4 H4B 107.2 . . ?
C1 N5 C21 115.7(4) . . ?
C1 N5 C4 124.9(4) . . ?
C21 N5 C4 116.4(4) . . ?
C16 C11 C12 121.8(5) . . ?
C16 C11 N2 119.1(5) . . ?
C12 C11 N2 119.0(5) . . ?
C13 C12 C11 117.9(6) . . ?
C13 C12 C17 119.2(6) . . ?
C11 C12 C17 122.9(5) . . ?
C12 C13 C14 121.0(6) . . ?
C12 C13 H13 119.5 . . ?
C14 C13 H13 119.5 . . ?
C15 C14 C13 120.1(6) . . ?
C15 C14 H14 119.9 . . ?
C13 C14 H14 119.9 . . ?
C14 C15 C16 121.6(6) . . ?
C14 C15 H15 119.2 . . ?
C16 C15 H15 119.2 . . ?
C15 C16 C11 117.5(6) . . ?
C15 C16 C19 119.9(6) . . ?
C11 C16 C19 122.5(5) . . ?
C172 C17 C12 110.7(5) . . ?
C172 C17 C171 111.1(6) . . ?
C12 C17 C171 111.7(5) . . ?
C172 C17 H17 107.7 . . ?
C12 C17 H17 107.7 . . ?
C171 C17 H17 107.7 . . ?
C17 C171 H17A 109.5 . . ?
C17 C171 H17B 109.5 . . ?
H17A C171 H17B 109.5 . . ?
C17 C171 H17C 109.5 . . ?
H17A C171 H17C 109.5 . . ?
H17B C171 H17C 109.5 . . ?
C17 C172 H17D 109.5 . . ?
C17 C172 H17E 109.5 . . ?
H17D C172 H17E 109.5 . . ?
C17 C172 H17F 109.5 . . ?
H17D C172 H17F 109.5 . . ?
H17E C172 H17F 109.5 . . ?
C192 C19 C16 111.4(6) . . ?
C192 C19 C191 110.2(6) . . ?
C16 C19 C191 112.8(5) . . ?
C192 C19 H19 107.4 . . ?
C16 C19 H19 107.4 . . ?
C191 C19 H19 107.4 . . ?
C19 C191 H19A 109.5 . . ?
C19 C191 H19B 109.5 . . ?
H19A C191 H19B 109.5 . . ?
C19 C191 H19C 109.5 . . ?
H19A C191 H19C 109.5 . . ?
H19B C191 H19C 109.5 . . ?
C19 C192 H19D 109.5 . . ?
C19 C192 H19E 109.5 . . ?
H19D C192 H19E 109.5 . . ?
C19 C192 H19F 109.5 . . ?
H19D C192 H19F 109.5 . . ?
H19E C192 H19F 109.5 . . ?
C22 C21 C26 122.3(5) . . ?
C22 C21 N5 119.2(5) . . ?
C26 C21 N5 118.5(5) . . ?
C23 C22 C21 118.2(5) . . ?
C23 C22 C27 118.7(5) . . ?
C21 C22 C27 123.0(5) . . ?
C24 C23 C22 120.9(6) . . ?
C24 C23 H23 119.6 . . ?
C22 C23 H23 119.6 . . ?
C25 C24 C23 119.7(6) . . ?
C25 C24 H24 120.2 . . ?
C23 C24 H24 120.2 . . ?
C24 C25 C26 122.2(6) . . ?
C24 C25 H25 118.9 . . ?
C26 C25 H25 118.9 . . ?
C25 C26 C21 116.7(5) . . ?
C25 C26 C29 120.4(5) . . ?
C21 C26 C29 122.8(5) . . ?
C22 C27 C272 111.5(5) . . ?
C22 C27 C271 110.6(5) . . ?
C272 C27 C271 110.0(5) . . ?
C22 C27 H27 108.2 . . ?
C272 C27 H27 108.2 . . ?
C271 C27 H27 108.2 . . ?
C27 C271 H27A 109.5 . . ?
C27 C271 H27B 109.5 . . ?
H27A C271 H27B 109.5 . . ?
C27 C271 H27C 109.5 . . ?
H27A C271 H27C 109.5 . . ?
H27B C271 H27C 109.5 . . ?
C27 C272 H27D 109.5 . . ?
C27 C272 H27E 109.5 . . ?
H27D C272 H27E 109.5 . . ?
C27 C272 H27F 109.5 . . ?
H27D C272 H27F 109.5 . . ?
H27E C272 H27F 109.5 . . ?
C26 C29 C292 110.8(6) . . ?
C26 C29 C291 112.7(5) . . ?
C292 C29 C291 110.2(5) . . ?
C26 C29 H29 107.6 . . ?
C292 C29 H29 107.6 . . ?
C291 C29 H29 107.6 . . ?
C29 C291 H29A 109.5 . . ?
C29 C291 H29B 109.5 . . ?
H29A C291 H29B 109.5 . . ?
C29 C291 H29C 109.5 . . ?
H29A C291 H29C 109.5 . . ?
H29B C291 H29C 109.5 . . ?
C29 C292 H29D 109.5 . . ?
C29 C292 H29E 109.5 . . ?
H29D C292 H29E 109.5 . . ?
C29 C292 H29F 109.5 . . ?
H29D C292 H29F 109.5 . . ?
H29E C292 H29F 109.5 . . ?
C36 C31 C32 119.7(6) . . ?
C36 C31 C3 120.0(6) . . ?
C32 C31 C3 120.2(6) . . ?
C33 C32 C31 117.8(7) . . ?
C33 C32 C42 120.1(6) . . ?
C31 C32 C42 122.0(5) . . ?
C34 C33 C32 121.7(7) . . ?
C34 C33 H33 119.1 . . ?
C32 C33 H33 119.1 . . ?
C33 C34 C35 120.3(7) . . ?
C33 C34 H34 119.9 . . ?
C35 C34 H34 119.9 . . ?
C36 C35 C34 119.2(8) . . ?
C36 C35 H35 120.4 . . ?
C34 C35 H35 120.4 . . ?
C35 C36 C31 121.2(7) . . ?
C35 C36 H36 119.4 . . ?
C31 C36 H36 119.4 . . ?
C46 C41 C42 119.5(6) . . ?
C46 C41 C4 120.2(5) . . ?
C42 C41 C4 120.2(6) . . ?
C43 C42 C41 118.4(7) . . ?
C43 C42 C32 119.9(6) . . ?
C41 C42 C32 121.8(5) . . ?
C44 C43 C42 121.6(7) . . ?
C44 C43 H43 119.2 . . ?
C42 C43 H43 119.2 . . ?
C45 C44 C43 119.5(7) . . ?
C45 C44 H44 120.2 . . ?
C43 C44 H44 120.2 . . ?
C44 C45 C46 120.6(8) . . ?
C44 C45 H45 119.7 . . ?
C46 C45 H45 119.7 . . ?
C41 C46 C45 120.4(6) . . ?
C41 C46 H46 119.8 . . ?
C45 C46 H46 119.8 . . ?
Cl2 C51 Cl3 114.1(9) . . ?
Cl2 C51 Cl4 109.9(10) . . ?
Cl3 C51 Cl4 105.5(6) . . ?
Cl2 C51 H51 109.0 . . ?
Cl3 C51 H51 109.0 . . ?
Cl4 C51 H51 109.0 . . ?
Cl5 C52 Cl6 115.1(7) . . ?
Cl5 C52 H52A 108.5 . . ?
Cl6 C52 H52A 108.5 . . ?
Cl5 C52 H52B 108.5 . . ?
Cl6 C52 H52B 108.5 . . ?
H52A C52 H52B 107.5 . . ?

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
N5 C1 N2 C11 -170.5(5) . . . . ?
Cu1 C1 N2 C11 7.8(6) . . . . ?
N5 C1 N2 C3 28.9(8) . . . . ?
Cu1 C1 N2 C3 -152.8(4) . . . . ?
C1 N2 C3 C31 -109.0(6) . . . . ?
C11 N2 C3 C31 90.6(6) . . . . ?
N2 C1 N5 C21 -172.2(4) . . . . ?
Cu1 C1 N5 C21 9.6(6) . . . . ?
N2 C1 N5 C4 28.4(7) . . . . ?
Cu1 C1 N5 C4 -149.8(4) . . . . ?
C41 C4 N5 C1 -106.5(6) . . . . ?
C41 C4 N5 C21 94.2(6) . . . . ?
C1 N2 C11 C16 88.8(6) . . . . ?
C3 N2 C11 C16 -108.6(6) . . . . ?
C1 N2 C11 C12 -91.0(6) . . . . ?
C3 N2 C11 C12 71.6(6) . . . . ?
C16 C11 C12 C13 1.0(8) . . . . ?
N2 C11 C12 C13 -179.2(5) . . . . ?
C16 C11 C12 C17 -177.6(5) . . . . ?
N2 C11 C12 C17 2.2(8) . . . . ?
C11 C12 C13 C14 -1.4(9) . . . . ?
C17 C12 C13 C14 177.3(6) . . . . ?
C12 C13 C14 C15 1.2(10) . . . . ?
C13 C14 C15 C16 -0.6(10) . . . . ?
C14 C15 C16 C11 0.2(9) . . . . ?
C14 C15 C16 C19 -177.2(6) . . . . ?
C12 C11 C16 C15 -0.4(8) . . . . ?
N2 C11 C16 C15 179.8(5) . . . . ?
C12 C11 C16 C19 177.0(5) . . . . ?
N2 C11 C16 C19 -2.9(8) . . . . ?
C13 C12 C17 C172 -59.2(7) . . . . ?
C11 C12 C17 C172 119.4(6) . . . . ?
C13 C12 C17 C171 65.1(7) . . . . ?
C11 C12 C17 C171 -116.3(6) . . . . ?
C15 C16 C19 C192 77.3(7) . . . . ?
C11 C16 C19 C192 -99.9(7) . . . . ?
C15 C16 C19 C191 -47.2(8) . . . . ?
C11 C16 C19 C191 135.6(6) . . . . ?
C1 N5 C21 C22 -89.8(6) . . . . ?
C4 N5 C21 C22 71.5(6) . . . . ?
C1 N5 C21 C26 90.4(6) . . . . ?
C4 N5 C21 C26 -108.3(5) . . . . ?
C26 C21 C22 C23 -1.9(8) . . . . ?
N5 C21 C22 C23 178.3(5) . . . . ?
C26 C21 C22 C27 -179.4(5) . . . . ?
N5 C21 C22 C27 0.7(8) . . . . ?
C21 C22 C23 C24 1.0(8) . . . . ?
C27 C22 C23 C24 178.7(5) . . . . ?
C22 C23 C24 C25 -0.3(9) . . . . ?
C23 C24 C25 C26 0.5(9) . . . . ?
C24 C25 C26 C21 -1.3(8) . . . . ?
C24 C25 C26 C29 179.5(6) . . . . ?
C22 C21 C26 C25 2.0(8) . . . . ?
N5 C21 C26 C25 -178.1(5) . . . . ?
C22 C21 C26 C29 -178.8(5) . . . . ?
N5 C21 C26 C29 1.0(8) . . . . ?
C23 C22 C27 C272 -54.4(7) . . . . ?
C21 C22 C27 C272 123.2(6) . . . . ?
C23 C22 C27 C271 68.4(7) . . . . ?
C21 C22 C27 C271 -114.0(6) . . . . ?
C25 C26 C29 C292 77.7(7) . . . . ?
C21 C26 C29 C292 -101.4(7) . . . . ?
C25 C26 C29 C291 -46.3(8) . . . . ?
C21 C26 C29 C291 134.6(6) . . . . ?
N2 C3 C31 C36 -68.5(7) . . . . ?
N2 C3 C31 C32 114.9(6) . . . . ?
C36 C31 C32 C33 2.5(9) . . . . ?
C3 C31 C32 C33 179.1(5) . . . . ?
C36 C31 C32 C42 -175.8(6) . . . . ?
C3 C31 C32 C42 0.8(8) . . . . ?
C31 C32 C33 C34 0.1(10) . . . . ?
C42 C32 C33 C34 178.5(6) . . . . ?
C32 C33 C34 C35 -1.9(12) . . . . ?
C33 C34 C35 C36 1.0(12) . . . . ?
C34 C35 C36 C31 1.6(11) . . . . ?
C32 C31 C36 C35 -3.4(10) . . . . ?
C3 C31 C36 C35 180.0(6) . . . . ?
N5 C4 C41 C46 -65.6(7) . . . . ?
N5 C4 C41 C42 118.9(6) . . . . ?
C46 C41 C42 C43 -1.1(9) . . . . ?
C4 C41 C42 C43 174.4(5) . . . . ?
C46 C41 C42 C32 179.1(6) . . . . ?
C4 C41 C42 C32 -5.4(8) . . . . ?
C33 C32 C42 C43 -55.6(8) . . . . ?
C31 C32 C42 C43 122.7(7) . . . . ?
C33 C32 C42 C41 124.2(7) . . . . ?
C31 C32 C42 C41 -57.5(8) . . . . ?
C41 C42 C43 C44 1.4(10) . . . . ?
C32 C42 C43 C44 -178.8(6) . . . . ?
C42 C43 C44 C45 -0.2(11) . . . . ?
C43 C44 C45 C46 -1.3(11) . . . . ?
C42 C41 C46 C45 -0.4(9) . . . . ?
C4 C41 C46 C45 -175.9(6) . . . . ?
C44 C45 C46 C41 1.6(11) . . . . ?

_refine_diff_density_max         1.683
_refine_diff_density_min         -1.067
_refine_diff_density_rms         0.101

####################################################################### 
# 
# 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_alc42
_database_code_depnum_ccdc_archive 'CCDC 2008624'
loop_
_audit_author_name
_audit_author_address
'Frank Rominger'
;Heidelberg University
Germany
;
_audit_update_record             
;
2020-06-08 deposited with the CCDC.	2020-12-20 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            'A8 in manuscript'
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C18 H16 O4'
_chemical_formula_weight         296.31

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'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_H-M_alt        'C 2/c'
_space_group_name_Hall           '-C 2yc'

_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. 
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z-1/2'

_cell_length_a                   33.614(6)
_cell_length_b                   6.0727(10)
_cell_length_c                   14.459(3)
_cell_angle_alpha                90
_cell_angle_beta                 93.236(3)
_cell_angle_gamma                90
_cell_volume                     2946.7(9)
_cell_formula_units_Z            8
_cell_measurement_temperature    200(2)
_cell_measurement_reflns_used    1258
_cell_measurement_theta_min      3.01
_cell_measurement_theta_max      21.90

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.336
_exptl_crystal_F_000             1248
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.107
_exptl_crystal_size_mid          0.075
_exptl_crystal_size_min          0.028
_exptl_absorpt_coefficient_mu    0.094
_shelx_estimated_absorpt_T_min   0.990
_shelx_estimated_absorpt_T_max   0.997
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.8613
_exptl_absorpt_correction_T_max  0.9578
_exptl_absorpt_process_details   
;
Sheldrick, G. M. (2008). SADABS. University of Göttingen, Germany.
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      200(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'ImuS microsource'
_diffrn_measurement_device_type  'Bruker APEX-II Quazar area detector'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            12678
_diffrn_reflns_av_unetI/netI     0.0663
_diffrn_reflns_av_R_equivalents  0.0843
_diffrn_reflns_limit_h_min       -39
_diffrn_reflns_limit_h_max       39
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         1.213
_diffrn_reflns_theta_max         24.836
_diffrn_reflns_theta_full        24.836
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measured_fraction_theta_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_point_group_measured_fraction_full 0.996
_reflns_number_total             2541
_reflns_number_gt                1483
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_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. 
;

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXT-2018/2 (Sheldrick 2015)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0566P)²+3.8443P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         2541
_refine_ls_number_parameters     199
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1147
_refine_ls_R_factor_gt           0.0593
_refine_ls_wR_factor_ref         0.1601
_refine_ls_wR_factor_gt          0.1334
_refine_ls_goodness_of_fit_ref   1.040
_refine_ls_restrained_S_all      1.040
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

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 0.70010(8) 0.7033(5) 0.5818(2) 0.0358(8) Uani 1 1 d . . . . .
H1A H 0.688878 0.821126 0.619891 0.043 Uiso 1 1 calc R U . . .
H1B H 0.701101 0.758350 0.517552 0.043 Uiso 1 1 calc R U . . .
O2 O 0.67548(6) 0.5140(4) 0.58318(15) 0.0423(6) Uani 1 1 d . . . . .
C3 C 0.64059(10) 0.5378(6) 0.5255(3) 0.0469(9) Uani 1 1 d . . . . .
H3A H 0.647552 0.565613 0.460922 0.056 Uiso 1 1 calc R U . . .
H3B H 0.624762 0.664042 0.546417 0.056 Uiso 1 1 calc R U . . .
C4 C 0.61684(10) 0.3288(6) 0.5305(2) 0.0469(9) Uani 1 1 d . . . . .
H4 H 0.628854 0.206398 0.561957 0.056 Uiso 1 1 calc R U . . .
C5 C 0.58101(10) 0.3060(6) 0.4943(2) 0.0414(9) Uani 1 1 d . . . . .
C6 C 0.55252(10) 0.1160(7) 0.4896(3) 0.0575(11) Uani 1 1 d . . . . .
H6A H 0.563928 -0.010907 0.457287 0.069 Uiso 1 1 calc R U . . .
H6B H 0.545805 0.069337 0.552461 0.069 Uiso 1 1 calc R U . . .
O7 O 0.51810(7) 0.2003(4) 0.43843(17) 0.0556(7) Uani 1 1 d . . . . .
C8 C 0.52397(10) 0.4120(7) 0.4174(2) 0.0473(9) Uani 1 1 d . . . . .
O8 O 0.50032(7) 0.5281(5) 0.3779(2) 0.0702(9) Uani 1 1 d . . . . .
O9 O 0.56116(7) 0.4780(4) 0.44725(17) 0.0492(7) Uani 1 1 d . . . . .
C11 C 0.74136(8) 0.6470(5) 0.6194(2) 0.0292(7) Uani 1 1 d . . . . .
C12 C 0.76388(9) 0.7987(5) 0.6714(2) 0.0320(8) Uani 1 1 d . . . . .
H12 H 0.752516 0.936572 0.686291 0.038 Uiso 1 1 calc R U . . .
C13 C 0.80272(9) 0.7517(5) 0.7018(2) 0.0322(8) Uani 1 1 d . . . . .
H13 H 0.817525 0.858136 0.737478 0.039 Uiso 1 1 calc R U . . .
C14 C 0.82058(9) 0.5524(5) 0.6815(2) 0.0290(7) Uani 1 1 d . . . . .
C15 C 0.79747(9) 0.3983(5) 0.6306(2) 0.0327(8) Uani 1 1 d . . . . .
H15 H 0.808757 0.260201 0.615760 0.039 Uiso 1 1 calc R U . . .
C16 C 0.75845(9) 0.4440(5) 0.6014(2) 0.0332(8) Uani 1 1 d . . . . .
H16 H 0.743078 0.335008 0.568620 0.040 Uiso 1 1 calc R U . . .
C21 C 0.86270(9) 0.5054(5) 0.7120(2) 0.0309(7) Uani 1 1 d . . . . .
C22 C 0.89173(9) 0.6679(6) 0.7102(2) 0.0380(8) Uani 1 1 d . . . . .
H22 H 0.884521 0.811061 0.688687 0.046 Uiso 1 1 calc R U . . .
C23 C 0.93102(10) 0.6255(6) 0.7392(2) 0.0445(9) Uani 1 1 d . . . . .
H23 H 0.950442 0.738872 0.737278 0.053 Uiso 1 1 calc R U . . .
C24 C 0.94187(10) 0.4183(6) 0.7709(2) 0.0449(9) Uani 1 1 d . . . . .
H24 H 0.968754 0.388286 0.790604 0.054 Uiso 1 1 calc R U . . .
C25 C 0.91359(10) 0.2564(6) 0.7736(3) 0.0477(9) Uani 1 1 d . . . . .
H25 H 0.920953 0.114328 0.796136 0.057 Uiso 1 1 calc R U . . .
C26 C 0.87466(10) 0.2970(5) 0.7441(2) 0.0409(9) Uani 1 1 d . . . . .
H26 H 0.855597 0.181736 0.745603 0.049 Uiso 1 1 calc R U . . .


_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 O2 1.418(3) . ?
C1 C11 1.500(4) . ?
C1 H1A 0.9900 . ?
C1 H1B 0.9900 . ?
O2 C3 1.407(4) . ?
C3 C4 1.503(5) . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C4 C5 1.293(4) . ?
C4 H4 0.9500 . ?
C5 O9 1.396(4) . ?
C5 C6 1.499(5) . ?
C6 O7 1.432(4) . ?
C6 H6A 0.9900 . ?
C6 H6B 0.9900 . ?
O7 C8 1.338(4) . ?
C8 O8 1.185(4) . ?
C8 O9 1.360(4) . ?
C11 C12 1.387(4) . ?
C11 C16 1.391(4) . ?
C12 C13 1.384(4) . ?
C12 H12 0.9500 . ?
C13 C14 1.390(4) . ?
C13 H13 0.9500 . ?
C14 C15 1.399(4) . ?
C14 C21 1.487(4) . ?
C15 C16 1.383(4) . ?
C15 H15 0.9500 . ?
C16 H16 0.9500 . ?
C21 C22 1.389(4) . ?
C21 C26 1.400(4) . ?
C22 C23 1.387(4) . ?
C22 H22 0.9500 . ?
C23 C24 1.381(5) . ?
C23 H23 0.9500 . ?
C24 C25 1.370(5) . ?
C24 H24 0.9500 . ?
C25 C26 1.375(4) . ?
C25 H25 0.9500 . ?
C26 H26 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
O2 C1 C11 109.8(2) . . ?
O2 C1 H1A 109.7 . . ?
C11 C1 H1A 109.7 . . ?
O2 C1 H1B 109.7 . . ?
C11 C1 H1B 109.7 . . ?
H1A C1 H1B 108.2 . . ?
C3 O2 C1 112.1(2) . . ?
O2 C3 C4 108.2(3) . . ?
O2 C3 H3A 110.1 . . ?
C4 C3 H3A 110.1 . . ?
O2 C3 H3B 110.1 . . ?
C4 C3 H3B 110.1 . . ?
H3A C3 H3B 108.4 . . ?
C5 C4 C3 123.8(3) . . ?
C5 C4 H4 118.1 . . ?
C3 C4 H4 118.1 . . ?
C4 C5 O9 121.7(3) . . ?
C4 C5 C6 132.8(3) . . ?
O9 C5 C6 105.5(3) . . ?
O7 C6 C5 104.1(3) . . ?
O7 C6 H6A 110.9 . . ?
C5 C6 H6A 110.9 . . ?
O7 C6 H6B 110.9 . . ?
C5 C6 H6B 110.9 . . ?
H6A C6 H6B 109.0 . . ?
C8 O7 C6 109.6(3) . . ?
O8 C8 O7 125.3(3) . . ?
O8 C8 O9 123.9(4) . . ?
O7 C8 O9 110.8(3) . . ?
C8 O9 C5 109.9(3) . . ?
C12 C11 C16 118.1(3) . . ?
C12 C11 C1 120.7(3) . . ?
C16 C11 C1 121.2(3) . . ?
C13 C12 C11 120.8(3) . . ?
C13 C12 H12 119.6 . . ?
C11 C12 H12 119.6 . . ?
C12 C13 C14 121.6(3) . . ?
C12 C13 H13 119.2 . . ?
C14 C13 H13 119.2 . . ?
C13 C14 C15 117.4(3) . . ?
C13 C14 C21 121.3(3) . . ?
C15 C14 C21 121.3(3) . . ?
C16 C15 C14 121.0(3) . . ?
C16 C15 H15 119.5 . . ?
C14 C15 H15 119.5 . . ?
C15 C16 C11 121.0(3) . . ?
C15 C16 H16 119.5 . . ?
C11 C16 H16 119.5 . . ?
C22 C21 C26 117.4(3) . . ?
C22 C21 C14 121.1(3) . . ?
C26 C21 C14 121.5(3) . . ?
C23 C22 C21 121.4(3) . . ?
C23 C22 H22 119.3 . . ?
C21 C22 H22 119.3 . . ?
C24 C23 C22 119.9(3) . . ?
C24 C23 H23 120.1 . . ?
C22 C23 H23 120.1 . . ?
C25 C24 C23 119.5(3) . . ?
C25 C24 H24 120.2 . . ?
C23 C24 H24 120.2 . . ?
C24 C25 C26 120.8(3) . . ?
C24 C25 H25 119.6 . . ?
C26 C25 H25 119.6 . . ?
C25 C26 C21 121.0(3) . . ?
C25 C26 H26 119.5 . . ?
C21 C26 H26 119.5 . . ?

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
C11 C1 O2 C3 -162.8(3) . . . . ?
C1 O2 C3 C4 179.2(3) . . . . ?
O2 C3 C4 C5 171.5(3) . . . . ?
C3 C4 C5 O9 -0.3(6) . . . . ?
C3 C4 C5 C6 179.0(4) . . . . ?
C4 C5 C6 O7 -179.2(4) . . . . ?
O9 C5 C6 O7 0.2(4) . . . . ?
C5 C6 O7 C8 -1.8(4) . . . . ?
C6 O7 C8 O8 -177.5(4) . . . . ?
C6 O7 C8 O9 2.8(4) . . . . ?
O8 C8 O9 C5 177.6(4) . . . . ?
O7 C8 O9 C5 -2.7(4) . . . . ?
C4 C5 O9 C8 -179.1(3) . . . . ?
C6 C5 O9 C8 1.4(4) . . . . ?
O2 C1 C11 C12 -144.7(3) . . . . ?
O2 C1 C11 C16 36.9(4) . . . . ?
C16 C11 C12 C13 2.1(4) . . . . ?
C1 C11 C12 C13 -176.4(3) . . . . ?
C11 C12 C13 C14 0.2(5) . . . . ?
C12 C13 C14 C15 -1.4(4) . . . . ?
C12 C13 C14 C21 178.2(3) . . . . ?
C13 C14 C15 C16 0.3(5) . . . . ?
C21 C14 C15 C16 -179.2(3) . . . . ?
C14 C15 C16 C11 2.0(5) . . . . ?
C12 C11 C16 C15 -3.2(4) . . . . ?
C1 C11 C16 C15 175.4(3) . . . . ?
C13 C14 C21 C22 -38.7(4) . . . . ?
C15 C14 C21 C22 140.8(3) . . . . ?
C13 C14 C21 C26 140.9(3) . . . . ?
C15 C14 C21 C26 -39.6(4) . . . . ?
C26 C21 C22 C23 0.0(5) . . . . ?
C14 C21 C22 C23 179.5(3) . . . . ?
C21 C22 C23 C24 -0.2(5) . . . . ?
C22 C23 C24 C25 -0.2(5) . . . . ?
C23 C24 C25 C26 0.8(5) . . . . ?
C24 C25 C26 C21 -1.1(6) . . . . ?
C22 C21 C26 C25 0.7(5) . . . . ?
C14 C21 C26 C25 -178.9(3) . . . . ?

_refine_diff_density_max         0.298
_refine_diff_density_min         -0.223
_refine_diff_density_rms         0.052

