# Electronic Supplementary Material (ESI) for Chemical Science.
# 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_P21n_a
_audit_block_doi                 10.5517/ccdc.csd.cc23453k
_database_code_depnum_ccdc_archive 'CCDC 1940417'
loop_
_audit_author_name
_audit_author_address
'Jeffery A. Bertke'
;Georgetown University
United States of America
;
_audit_update_record             
;
2019-08-03 deposited with the CCDC.	2021-11-23 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2017/1
_shelx_SHELXL_version_number     2017/1
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C27 H38 Cu N2 O'
_chemical_formula_sum            'C27 H38 Cu N2 O'
_chemical_formula_weight         470.13

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'
Cu Cu 0.3201 1.2651 '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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/n'
_space_group_name_Hall           '-P 2yn'

_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+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   15.755(4)
_cell_length_b                   9.051(2)
_cell_length_c                   18.592(4)
_cell_angle_alpha                90
_cell_angle_beta                 101.785(3)
_cell_angle_gamma                90
_cell_volume                     2595.5(10)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    7383
_cell_measurement_theta_min      2.24
_cell_measurement_theta_max      25.49
_exptl_crystal_description       prism
_exptl_crystal_colour            ?
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.203
_exptl_crystal_F_000             1004
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.288
_exptl_crystal_size_mid          0.206
_exptl_crystal_size_min          0.121
_exptl_absorpt_coefficient_mu    0.861
_shelx_estimated_absorpt_T_min   0.790
_shelx_estimated_absorpt_T_max   0.903
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.4795
_exptl_absorpt_correction_T_max  0.7452
_exptl_absorpt_process_details   'SADABS V2016/2 (Bruker, 2016)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  'multilayer mirrors'
_diffrn_measurement_device       'Bruker APEX DUO/ApexII CCD'
_diffrn_measurement_method       'profile data from φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            27153
_diffrn_reflns_av_unetI/netI     0.0450
_diffrn_reflns_av_R_equivalents  0.0689
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_theta_min         1.897
_diffrn_reflns_theta_max         25.586
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             4841
_reflns_number_gt                3963
_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       'APEX3 V2016.5-0 (Bruker, 2016)'
_computing_cell_refinement       'SAINT V8.37A (Bruker, 2005)'
_computing_data_reduction        
; 
SAINT V8.37A, XPREP v2014/2, SADABS V2016/2 (Bruker, 2016) 
;
_computing_structure_solution    'SHELX-2014-5 (Sheldrick, 2015)'
_computing_structure_refinement  'SHELX-2018-1 (Sheldrick, 2015)'
_computing_molecular_graphics    'SHELXLE v932 (Hubschle, 2011)'
_computing_publication_material  'XCIF V2014-2 (Bruker, 2014)'

_refine_special_details          
; 
Structure was phased by intrinsic methods (Sheldrick, 2015).  Systematic 
conditions suggested the ambiguous space group.  The space group choice was 
confirmed by successful convergence of the full-matrix least-squares 
refinement on F².  The final map had no significant features.  A final 
analysis of variance between observed and calculated structure factors 
showed little dependence on amplitude and resolution. 
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0507P)²+2.0075P] 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         4841
_refine_ls_number_parameters     331
_refine_ls_number_restraints     109
_refine_ls_R_factor_all          0.0508
_refine_ls_R_factor_gt           0.0372
_refine_ls_wR_factor_ref         0.1031
_refine_ls_wR_factor_gt          0.0948
_refine_ls_goodness_of_fit_ref   1.042
_refine_ls_restrained_S_all      1.048
_refine_ls_shift/su_max          0.002
_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 0.50871(2) 0.66420(3) 0.71177(2) 0.01685(11) Uani 1 1 d . . . . .
O1 O 0.39698(10) 0.61887(18) 0.68016(9) 0.0212(4) Uani 1 1 d D . . . .
N1 N 0.61299(13) 0.6805(2) 0.67766(10) 0.0190(4) Uani 1 1 d . . . . .
N2 N 0.55871(12) 0.6808(2) 0.81311(10) 0.0192(4) Uani 1 1 d . . . . .
C1 C 0.69141(15) 0.6850(3) 0.72061(13) 0.0194(5) Uani 1 1 d . . . . .
C2 C 0.70539(15) 0.6786(3) 0.79696(13) 0.0208(5) Uani 1 1 d . . . . .
H2 H 0.764135 0.673180 0.822280 0.025 Uiso 1 1 calc R U . . .
C3 C 0.64336(15) 0.6791(3) 0.84036(13) 0.0203(5) Uani 1 1 d . . . . .
C4 C 0.76951(16) 0.7005(3) 0.68637(14) 0.0271(6) Uani 1 1 d . . . . .
H4A H 0.769104 0.621833 0.650067 0.041 Uiso 1 1 calc R U . . .
H4B H 0.822307 0.692792 0.724603 0.041 Uiso 1 1 calc R U . . .
H4C H 0.768047 0.796830 0.662131 0.041 Uiso 1 1 calc R U . . .
C5 C 0.67519(17) 0.6775(3) 0.92249(14) 0.0301(6) Uani 1 1 d . . . . .
H5A H 0.664504 0.774053 0.942774 0.045 Uiso 1 1 calc R U . . .
H5B H 0.737511 0.656409 0.933940 0.045 Uiso 1 1 calc R U . . .
H5C H 0.644258 0.600939 0.944176 0.045 Uiso 1 1 calc R U . . .
C6 C 0.60470(14) 0.6965(3) 0.59956(12) 0.0170(5) Uani 1 1 d . . . . .
C7 C 0.60610(14) 0.5724(3) 0.55563(12) 0.0189(5) Uani 1 1 d . . . . .
C8 C 0.59886(15) 0.5922(3) 0.48044(13) 0.0202(5) Uani 1 1 d . . . . .
H8 H 0.598971 0.508041 0.449928 0.024 Uiso 1 1 calc R U . . .
C9 C 0.59145(15) 0.7320(3) 0.44878(13) 0.0205(5) Uani 1 1 d . . . . .
C10 C 0.58900(15) 0.8534(3) 0.49397(13) 0.0192(5) Uani 1 1 d . . . . .
H10 H 0.583136 0.949396 0.472843 0.023 Uiso 1 1 calc R U . . .
C11 C 0.59487(14) 0.8385(3) 0.56923(12) 0.0175(5) Uani 1 1 d . . . . .
C12 C 0.61837(17) 0.4204(3) 0.58869(14) 0.0265(6) Uani 1 1 d . . . . .
H12A H 0.605284 0.346297 0.549575 0.040 Uiso 1 1 calc R U . . .
H12B H 0.579290 0.407090 0.622974 0.040 Uiso 1 1 calc R U . . .
H12C H 0.678544 0.408821 0.615068 0.040 Uiso 1 1 calc R U . . .
C13 C 0.58825(18) 0.7497(3) 0.36750(13) 0.0296(6) Uani 1 1 d . . . . .
H13A H 0.591087 0.652239 0.345168 0.044 Uiso 1 1 calc R U . . .
H13B H 0.637551 0.809689 0.360120 0.044 Uiso 1 1 calc R U . . .
H13C H 0.534024 0.798702 0.344462 0.044 Uiso 1 1 calc R U . . .
C14 C 0.59262(16) 0.9705(3) 0.61788(13) 0.0233(5) Uani 1 1 d . . . . .
H14A H 0.542587 0.962814 0.641499 0.035 Uiso 1 1 calc R U . . .
H14B H 0.587746 1.060791 0.588237 0.035 Uiso 1 1 calc R U . . .
H14C H 0.646044 0.973900 0.655606 0.035 Uiso 1 1 calc R U . . .
C15 C 0.50008(15) 0.6973(3) 0.86211(12) 0.0196(5) Uani 1 1 d . . . . .
C16 C 0.48390(16) 0.8385(3) 0.88630(13) 0.0242(5) Uani 1 1 d . . . . .
C17 C 0.42670(17) 0.8525(3) 0.93362(14) 0.0277(6) Uani 1 1 d . . . . .
H17 H 0.416219 0.947664 0.951508 0.033 Uiso 1 1 calc R U . . .
C18 C 0.38438(16) 0.7311(3) 0.95555(13) 0.0287(6) Uani 1 1 d . . . . .
C19 C 0.40073(15) 0.5933(3) 0.92907(13) 0.0256(6) Uani 1 1 d . . . . .
H19 H 0.371781 0.509592 0.943412 0.031 Uiso 1 1 calc R U . . .
C20 C 0.45798(15) 0.5734(3) 0.88232(12) 0.0217(5) Uani 1 1 d . . . . .
C21 C 0.52585(19) 0.9728(3) 0.86083(16) 0.0350(6) Uani 1 1 d . . . . .
H21A H 0.588883 0.966374 0.877577 0.053 Uiso 1 1 calc R U . . .
H21B H 0.504388 1.061830 0.881294 0.053 Uiso 1 1 calc R U . . .
H21C H 0.511569 0.977736 0.807055 0.053 Uiso 1 1 calc R U . . .
C22 C 0.32329(18) 0.7502(4) 1.00725(15) 0.0392(7) Uani 1 1 d . . . . .
H22A H 0.355482 0.740871 1.058036 0.059 Uiso 1 1 calc R U . . .
H22B H 0.278171 0.674123 0.997326 0.059 Uiso 1 1 calc R U . . .
H22C H 0.296382 0.848182 1.000098 0.059 Uiso 1 1 calc R U . . .
C23 C 0.47259(18) 0.4235(3) 0.85339(15) 0.0303(6) Uani 1 1 d . . . . .
H23A H 0.448904 0.348326 0.881725 0.045 Uiso 1 1 calc R U . . .
H23B H 0.534930 0.406983 0.857872 0.045 Uiso 1 1 calc R U . . .
H23C H 0.443534 0.416937 0.801590 0.045 Uiso 1 1 calc R U . . .
C24 C 0.3219(5) 0.7086(9) 0.6650(5) 0.020(2) Uani 0.508(15) 1 d D U P A 1
C25 C 0.3386(5) 0.8380(10) 0.6177(8) 0.053(3) Uani 0.508(15) 1 d D U P A 1
H25A H 0.387832 0.895703 0.644149 0.079 Uiso 0.508(15) 1 calc R U P A 1
H25B H 0.286922 0.900947 0.606802 0.079 Uiso 0.508(15) 1 calc R U P A 1
H25C H 0.351736 0.800859 0.571717 0.079 Uiso 0.508(15) 1 calc R U P A 1
C26 C 0.2497(8) 0.6163(12) 0.6204(6) 0.036(2) Uani 0.508(15) 1 d D U P A 1
H26A H 0.265925 0.585439 0.574523 0.054 Uiso 0.508(15) 1 calc R U P A 1
H26B H 0.196322 0.674964 0.609121 0.054 Uiso 0.508(15) 1 calc R U P A 1
H26C H 0.240042 0.528715 0.648691 0.054 Uiso 0.508(15) 1 calc R U P A 1
C27 C 0.2999(8) 0.7594(16) 0.7353(5) 0.058(3) Uani 0.508(15) 1 d D U P A 1
H27A H 0.292630 0.673538 0.765533 0.087 Uiso 0.508(15) 1 calc R U P A 1
H27B H 0.245752 0.816164 0.724625 0.087 Uiso 0.508(15) 1 calc R U P A 1
H27C H 0.346698 0.822033 0.761812 0.087 Uiso 0.508(15) 1 calc R U P A 1
C24B C 0.3214(5) 0.7069(9) 0.6731(5) 0.025(2) Uani 0.492(15) 1 d D U P A 2
C25B C 0.3433(6) 0.8676(9) 0.6619(9) 0.056(3) Uani 0.492(15) 1 d D U P A 2
H25D H 0.378016 0.907089 0.707671 0.083 Uiso 0.492(15) 1 calc R U P A 2
H25E H 0.289564 0.924699 0.648184 0.083 Uiso 0.492(15) 1 calc R U P A 2
H25F H 0.376322 0.874555 0.622783 0.083 Uiso 0.492(15) 1 calc R U P A 2
C26B C 0.2583(10) 0.6549(18) 0.6050(7) 0.059(4) Uani 0.492(15) 1 d D U P A 2
H26D H 0.283441 0.671616 0.561645 0.089 Uiso 0.492(15) 1 calc R U P A 2
H26E H 0.203943 0.710129 0.599928 0.089 Uiso 0.492(15) 1 calc R U P A 2
H26F H 0.246838 0.549199 0.609487 0.089 Uiso 0.492(15) 1 calc R U P A 2
C27B C 0.2825(7) 0.6904(15) 0.7396(5) 0.049(2) Uani 0.492(15) 1 d D U P A 2
H27D H 0.268358 0.586331 0.745784 0.073 Uiso 0.492(15) 1 calc R U P A 2
H27E H 0.229478 0.749862 0.733533 0.073 Uiso 0.492(15) 1 calc R U P A 2
H27F H 0.324015 0.724276 0.783118 0.073 Uiso 0.492(15) 1 calc R U P A 2


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

_exptl_special_details           
; 
One distinct cell was identified using APEX3 (Bruker, 2016).  Four 
frame series were integrated and filtered for statistical outliers 
using SAINT (Bruker, 2016) then corrected for absorption by integration 
using SAINT/SADABS v2014/2 (Bruker, 2016) to sort, merge, and scale 
the combined data.  No decay correction was applied.    
;

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 O1 1.7860(16) . ?
Cu1 N1 1.884(2) . ?
Cu1 N2 1.894(2) . ?
O1 C24 1.415(6) . ?
O1 C24B 1.416(6) . ?
N1 C1 1.328(3) . ?
N1 C6 1.438(3) . ?
N2 C3 1.326(3) . ?
N2 C15 1.431(3) . ?
C1 C2 1.393(3) . ?
C1 C4 1.503(3) . ?
C2 C3 1.389(3) . ?
C2 H2 0.9500 . ?
C3 C5 1.507(3) . ?
C4 H4A 0.9800 . ?
C4 H4B 0.9800 . ?
C4 H4C 0.9800 . ?
C5 H5A 0.9800 . ?
C5 H5B 0.9800 . ?
C5 H5C 0.9800 . ?
C6 C7 1.391(3) . ?
C6 C11 1.400(3) . ?
C7 C8 1.391(3) . ?
C7 C12 1.503(3) . ?
C8 C9 1.391(3) . ?
C8 H8 0.9500 . ?
C9 C10 1.389(3) . ?
C9 C13 1.510(3) . ?
C10 C11 1.390(3) . ?
C10 H10 0.9500 . ?
C11 C14 1.503(3) . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12C 0.9800 . ?
C13 H13A 0.9800 . ?
C13 H13B 0.9800 . ?
C13 H13C 0.9800 . ?
C14 H14A 0.9800 . ?
C14 H14B 0.9800 . ?
C14 H14C 0.9800 . ?
C15 C20 1.393(3) . ?
C15 C16 1.395(3) . ?
C16 C17 1.388(4) . ?
C16 C21 1.506(4) . ?
C17 C18 1.389(4) . ?
C17 H17 0.9500 . ?
C18 C19 1.384(4) . ?
C18 C22 1.503(4) . ?
C19 C20 1.386(3) . ?
C19 H19 0.9500 . ?
C20 C23 1.495(4) . ?
C21 H21A 0.9800 . ?
C21 H21B 0.9800 . ?
C21 H21C 0.9800 . ?
C22 H22A 0.9800 . ?
C22 H22B 0.9800 . ?
C22 H22C 0.9800 . ?
C23 H23A 0.9800 . ?
C23 H23B 0.9800 . ?
C23 H23C 0.9800 . ?
C24 C27 1.490(7) . ?
C24 C26 1.516(7) . ?
C24 C25 1.520(7) . ?
C25 H25A 0.9800 . ?
C25 H25B 0.9800 . ?
C25 H25C 0.9800 . ?
C26 H26A 0.9800 . ?
C26 H26B 0.9800 . ?
C26 H26C 0.9800 . ?
C27 H27A 0.9800 . ?
C27 H27B 0.9800 . ?
C27 H27C 0.9800 . ?
C24B C27B 1.496(8) . ?
C24B C26B 1.516(7) . ?
C24B C25B 1.519(7) . ?
C25B H25D 0.9800 . ?
C25B H25E 0.9800 . ?
C25B H25F 0.9800 . ?
C26B H26D 0.9800 . ?
C26B H26E 0.9800 . ?
C26B H26F 0.9800 . ?
C27B H27D 0.9800 . ?
C27B H27E 0.9800 . ?
C27B H27F 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
O1 Cu1 N1 140.89(8) . . ?
O1 Cu1 N2 121.82(8) . . ?
N1 Cu1 N2 96.58(8) . . ?
C24 O1 Cu1 131.4(4) . . ?
C24B O1 Cu1 130.9(4) . . ?
C1 N1 C6 119.05(19) . . ?
C1 N1 Cu1 124.63(16) . . ?
C6 N1 Cu1 116.24(14) . . ?
C3 N2 C15 119.17(19) . . ?
C3 N2 Cu1 124.08(16) . . ?
C15 N2 Cu1 116.75(15) . . ?
N1 C1 C2 123.1(2) . . ?
N1 C1 C4 119.3(2) . . ?
C2 C1 C4 117.6(2) . . ?
C3 C2 C1 127.5(2) . . ?
C3 C2 H2 116.3 . . ?
C1 C2 H2 116.3 . . ?
N2 C3 C2 123.4(2) . . ?
N2 C3 C5 119.2(2) . . ?
C2 C3 C5 117.4(2) . . ?
C1 C4 H4A 109.5 . . ?
C1 C4 H4B 109.5 . . ?
H4A C4 H4B 109.5 . . ?
C1 C4 H4C 109.5 . . ?
H4A C4 H4C 109.5 . . ?
H4B C4 H4C 109.5 . . ?
C3 C5 H5A 109.5 . . ?
C3 C5 H5B 109.5 . . ?
H5A C5 H5B 109.5 . . ?
C3 C5 H5C 109.5 . . ?
H5A C5 H5C 109.5 . . ?
H5B C5 H5C 109.5 . . ?
C7 C6 C11 121.2(2) . . ?
C7 C6 N1 120.2(2) . . ?
C11 C6 N1 118.6(2) . . ?
C8 C7 C6 118.6(2) . . ?
C8 C7 C12 120.4(2) . . ?
C6 C7 C12 121.0(2) . . ?
C9 C8 C7 121.7(2) . . ?
C9 C8 H8 119.2 . . ?
C7 C8 H8 119.2 . . ?
C10 C9 C8 118.3(2) . . ?
C10 C9 C13 121.5(2) . . ?
C8 C9 C13 120.2(2) . . ?
C9 C10 C11 121.9(2) . . ?
C9 C10 H10 119.1 . . ?
C11 C10 H10 119.1 . . ?
C10 C11 C6 118.3(2) . . ?
C10 C11 C14 121.6(2) . . ?
C6 C11 C14 120.1(2) . . ?
C7 C12 H12A 109.5 . . ?
C7 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
C7 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C9 C13 H13A 109.5 . . ?
C9 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
C9 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
C11 C14 H14A 109.5 . . ?
C11 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
C11 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C20 C15 C16 121.4(2) . . ?
C20 C15 N2 119.5(2) . . ?
C16 C15 N2 119.0(2) . . ?
C17 C16 C15 118.2(2) . . ?
C17 C16 C21 120.6(2) . . ?
C15 C16 C21 121.2(2) . . ?
C16 C17 C18 121.8(2) . . ?
C16 C17 H17 119.1 . . ?
C18 C17 H17 119.1 . . ?
C19 C18 C17 118.2(2) . . ?
C19 C18 C22 121.4(3) . . ?
C17 C18 C22 120.3(3) . . ?
C18 C19 C20 122.1(2) . . ?
C18 C19 H19 118.9 . . ?
C20 C19 H19 118.9 . . ?
C19 C20 C15 118.1(2) . . ?
C19 C20 C23 120.7(2) . . ?
C15 C20 C23 121.1(2) . . ?
C16 C21 H21A 109.5 . . ?
C16 C21 H21B 109.5 . . ?
H21A C21 H21B 109.5 . . ?
C16 C21 H21C 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
C18 C22 H22A 109.5 . . ?
C18 C22 H22B 109.5 . . ?
H22A C22 H22B 109.5 . . ?
C18 C22 H22C 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
C20 C23 H23A 109.5 . . ?
C20 C23 H23B 109.5 . . ?
H23A C23 H23B 109.5 . . ?
C20 C23 H23C 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 109.5 . . ?
O1 C24 C27 109.8(7) . . ?
O1 C24 C26 107.2(8) . . ?
C27 C24 C26 111.5(7) . . ?
O1 C24 C25 108.7(6) . . ?
C27 C24 C25 111.6(7) . . ?
C26 C24 C25 107.9(6) . . ?
C24 C25 H25A 109.5 . . ?
C24 C25 H25B 109.5 . . ?
H25A C25 H25B 109.5 . . ?
C24 C25 H25C 109.5 . . ?
H25A C25 H25C 109.5 . . ?
H25B C25 H25C 109.5 . . ?
C24 C26 H26A 109.5 . . ?
C24 C26 H26B 109.5 . . ?
H26A C26 H26B 109.5 . . ?
C24 C26 H26C 109.5 . . ?
H26A C26 H26C 109.5 . . ?
H26B C26 H26C 109.5 . . ?
C24 C27 H27A 109.5 . . ?
C24 C27 H27B 109.5 . . ?
H27A C27 H27B 109.5 . . ?
C24 C27 H27C 109.5 . . ?
H27A C27 H27C 109.5 . . ?
H27B C27 H27C 109.5 . . ?
O1 C24B C27B 110.3(7) . . ?
O1 C24B C26B 107.3(9) . . ?
C27B C24B C26B 110.5(7) . . ?
O1 C24B C25B 110.0(6) . . ?
C27B C24B C25B 110.6(7) . . ?
C26B C24B C25B 108.2(7) . . ?
C24B C25B H25D 109.5 . . ?
C24B C25B H25E 109.5 . . ?
H25D C25B H25E 109.5 . . ?
C24B C25B H25F 109.5 . . ?
H25D C25B H25F 109.5 . . ?
H25E C25B H25F 109.5 . . ?
C24B C26B H26D 109.5 . . ?
C24B C26B H26E 109.5 . . ?
H26D C26B H26E 109.5 . . ?
C24B C26B H26F 109.5 . . ?
H26D C26B H26F 109.5 . . ?
H26E C26B H26F 109.5 . . ?
C24B C27B H27D 109.5 . . ?
C24B C27B H27E 109.5 . . ?
H27D C27B H27E 109.5 . . ?
C24B C27B H27F 109.5 . . ?
H27D C27B H27F 109.5 . . ?
H27E C27B H27F 109.5 . . ?

_refine_diff_density_max         0.615
_refine_diff_density_min         -0.672
_refine_diff_density_rms         0.066

####################################################################### 
# 
# 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_Me3NNCu_NHCPh2_a
_audit_block_doi                 10.5517/ccdc.csd.cc23454l
_database_code_depnum_ccdc_archive 'CCDC 1940418'
loop_
_audit_author_name
_audit_author_address
'Jeffery A. Bertke'
;Georgetown University
United States of America
;
_audit_update_record             
;
2019-08-03 deposited with the CCDC.	2021-11-23 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2017/1
_shelx_SHELXL_version_number     2017/1
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C36 H40 Cu N3, C4 H8 O'
_chemical_formula_sum            'C40 H48 Cu N3 O'
_chemical_formula_weight         650.35

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'
Cu Cu 0.3201 1.2651 '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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/n'
_space_group_name_Hall           '-P 2yn'

_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+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   11.7832(11)
_cell_length_b                   12.9552(12)
_cell_length_c                   22.918(2)
_cell_angle_alpha                90
_cell_angle_beta                 94.780(3)
_cell_angle_gamma                90
_cell_volume                     3486.3(6)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    9645
_cell_measurement_theta_min      2.34
_cell_measurement_theta_max      30.31
_exptl_crystal_description       prism
_exptl_crystal_colour            red
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.239
_exptl_crystal_F_000             1384
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.361
_exptl_crystal_size_mid          0.306
_exptl_crystal_size_min          0.144
_exptl_absorpt_coefficient_mu    0.661
_shelx_estimated_absorpt_T_min   0.796
_shelx_estimated_absorpt_T_max   0.911
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.85285
_exptl_absorpt_correction_T_max  0.92752
_exptl_absorpt_process_details   'SADABS V2016/2 (Bruker, 2016)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'microfocus sealed tube'
_diffrn_radiation_monochromator  'multilayer mirrors'
_diffrn_measurement_device       'Bruker D8 Quest/Photon 100'
_diffrn_measurement_method       'profile data from φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            119401
_diffrn_reflns_av_unetI/netI     0.0356
_diffrn_reflns_av_R_equivalents  0.0785
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_l_min       -32
_diffrn_reflns_limit_l_max       32
_diffrn_reflns_theta_min         2.341
_diffrn_reflns_theta_max         30.684
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             10763
_reflns_number_gt                8417
_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       'APEX3 V2016.5-0 (Bruker, 2016)'
_computing_cell_refinement       'SAINT V8.37A (Bruker, 2005)'
_computing_data_reduction        
; 
SAINT V8.37A, XPREP v2014/2, SADABS V2016/2 (Bruker, 2016) 
;
_computing_structure_solution    'SHELX-2014-5 (Sheldrick, 2015)'
_computing_structure_refinement  'SHELX-2018-1 (Sheldrick, 2015)'
_computing_molecular_graphics    'SHELXLE v932 (Hubschle, 2011)'
_computing_publication_material  'XCIF V2014-2 (Bruker, 2014)'

_refine_special_details          
; 
Structure was phased by intrinsic methods (Sheldrick, 2015).  
Systematic conditions suggested the ambiguous space group.  The space 
group choice was confirmed by successful convergence of the 
full-matrix least-squares refinement on F².  The highest peaks in 
the final difference Fourier map were in the vicinity of the THF 
solvent; the final map had no other significant features.  A final 
analysis of variance between observed and calculated structure factors 
showed little dependence on amplitude and resolution. 
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0632P)²+2.4081P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         10763
_refine_ls_number_parameters     417
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0626
_refine_ls_R_factor_gt           0.0433
_refine_ls_wR_factor_ref         0.1236
_refine_ls_wR_factor_gt          0.1104
_refine_ls_goodness_of_fit_ref   1.039
_refine_ls_restrained_S_all      1.039
_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 0.34322(2) 0.24065(2) 0.60527(2) 0.01505(6) Uani 1 1 d . . . . .
N1 N 0.40651(12) 0.14686(11) 0.66846(6) 0.0163(3) Uani 1 1 d . . . . .
N2 N 0.19882(12) 0.17435(11) 0.59023(6) 0.0167(3) Uani 1 1 d . . . . .
N3 N 0.44530(12) 0.34974(11) 0.59257(6) 0.0158(3) Uani 1 1 d . . . . .
H3 H 0.4358(18) 0.4088(18) 0.6120(10) 0.024 Uiso 1 1 d . U . . .
C1 C 0.35137(14) 0.06477(12) 0.68500(7) 0.0162(3) Uani 1 1 d . . . . .
C2 C 0.24283(14) 0.03598(13) 0.65954(7) 0.0180(3) Uani 1 1 d . . . . .
H2 H 0.214635 -0.028019 0.672489 0.022 Uiso 1 1 calc R U . . .
C3 C 0.17062(14) 0.08873(13) 0.61770(7) 0.0173(3) Uani 1 1 d . . . . .
C4 C 0.40443(16) -0.00214(14) 0.73429(8) 0.0222(3) Uani 1 1 d . . . . .
H4A H 0.359580 -0.065422 0.736945 0.033 Uiso 1 1 calc R U . . .
H4B H 0.405466 0.035767 0.771336 0.033 Uiso 1 1 calc R U . . .
H4C H 0.482529 -0.020009 0.726440 0.033 Uiso 1 1 calc R U . . .
C5 C 0.05189(15) 0.04366(15) 0.60474(9) 0.0258(4) Uani 1 1 d . . . . .
H5A H 0.042570 -0.016039 0.630160 0.039 Uiso 1 1 calc R U . . .
H5B H 0.041832 0.021902 0.563676 0.039 Uiso 1 1 calc R U . . .
H5C H -0.005181 0.096104 0.612025 0.039 Uiso 1 1 calc R U . . .
C6 C 0.50847(13) 0.18068(12) 0.70025(7) 0.0155(3) Uani 1 1 d . . . . .
C7 C 0.61502(14) 0.15437(13) 0.68167(7) 0.0174(3) Uani 1 1 d . . . . .
C8 C 0.71276(15) 0.20034(14) 0.70914(8) 0.0224(3) Uani 1 1 d . . . . .
H8 H 0.785045 0.183010 0.696400 0.027 Uiso 1 1 calc R U . . .
C9 C 0.70692(16) 0.27065(14) 0.75453(9) 0.0240(4) Uani 1 1 d . . . . .
C10 C 0.60057(16) 0.29329(14) 0.77324(7) 0.0219(3) Uani 1 1 d . . . . .
H10 H 0.595627 0.339817 0.804972 0.026 Uiso 1 1 calc R U . . .
C11 C 0.50109(15) 0.24993(12) 0.74694(7) 0.0183(3) Uani 1 1 d . . . . .
C12 C 0.11656(14) 0.22171(13) 0.54901(7) 0.0171(3) Uani 1 1 d . . . . .
C13 C 0.05211(14) 0.30533(13) 0.56661(7) 0.0189(3) Uani 1 1 d . . . . .
C14 C -0.02171(14) 0.35578(14) 0.52522(8) 0.0212(3) Uani 1 1 d . . . . .
H14 H -0.064288 0.413213 0.537121 0.025 Uiso 1 1 calc R U . . .
C15 C -0.03474(14) 0.32431(14) 0.46694(8) 0.0206(3) Uani 1 1 d . . . . .
C16 C 0.02923(15) 0.24045(14) 0.45078(8) 0.0207(3) Uani 1 1 d . . . . .
H16 H 0.020545 0.217436 0.411302 0.025 Uiso 1 1 calc R U . . .
C17 C 0.10576(14) 0.18880(13) 0.49041(7) 0.0183(3) Uani 1 1 d . . . . .
C18 C 0.62325(15) 0.07765(14) 0.63307(8) 0.0218(3) Uani 1 1 d . . . . .
H18A H 0.702274 0.073604 0.622886 0.033 Uiso 1 1 calc R U . . .
H18B H 0.574139 0.099637 0.598703 0.033 Uiso 1 1 calc R U . . .
H18C H 0.598718 0.009646 0.645904 0.033 Uiso 1 1 calc R U . . .
C19 C 0.81279(19) 0.32209(19) 0.78283(11) 0.0406(5) Uani 1 1 d . . . . .
H19A H 0.796060 0.394420 0.791225 0.061 Uiso 1 1 calc R U . . .
H19B H 0.873580 0.318799 0.756190 0.061 Uiso 1 1 calc R U . . .
H19C H 0.837364 0.286376 0.819414 0.061 Uiso 1 1 calc R U . . .
C20 C 0.38642(16) 0.27715(15) 0.76693(8) 0.0248(4) Uani 1 1 d . . . . .
H20A H 0.396167 0.325757 0.799729 0.037 Uiso 1 1 calc R U . . .
H20B H 0.348981 0.214402 0.779562 0.037 Uiso 1 1 calc R U . . .
H20C H 0.339397 0.309012 0.734523 0.037 Uiso 1 1 calc R U . . .
C21 C 0.06375(18) 0.34140(16) 0.62914(8) 0.0280(4) Uani 1 1 d . . . . .
H21A H 0.011274 0.398912 0.633854 0.042 Uiso 1 1 calc R U . . .
H21B H 0.142119 0.364348 0.639435 0.042 Uiso 1 1 calc R U . . .
H21C H 0.045466 0.284462 0.654902 0.042 Uiso 1 1 calc R U . . .
C22 C -0.11365(17) 0.38041(16) 0.42257(9) 0.0293(4) Uani 1 1 d . . . . .
H22A H -0.071027 0.403192 0.389965 0.044 Uiso 1 1 calc R U . . .
H22B H -0.146122 0.440581 0.441053 0.044 Uiso 1 1 calc R U . . .
H22C H -0.175138 0.333955 0.407840 0.044 Uiso 1 1 calc R U . . .
C23 C 0.17773(16) 0.10176(15) 0.47041(8) 0.0257(4) Uani 1 1 d . . . . .
H23A H 0.174597 0.101444 0.427544 0.039 Uiso 1 1 calc R U . . .
H23B H 0.148722 0.035970 0.484147 0.039 Uiso 1 1 calc R U . . .
H23C H 0.256723 0.111211 0.486516 0.039 Uiso 1 1 calc R U . . .
C24 C 0.54013(13) 0.35348(12) 0.56811(7) 0.0154(3) Uani 1 1 d . . . . .
C25 C 0.57012(14) 0.27039(12) 0.52771(7) 0.0170(3) Uani 1 1 d . . . . .
C26 C 0.48461(15) 0.21177(14) 0.49797(7) 0.0207(3) Uani 1 1 d . . . . .
H26 H 0.406911 0.227652 0.501921 0.025 Uiso 1 1 calc R U . . .
C27 C 0.51266(18) 0.13019(15) 0.46255(8) 0.0272(4) Uani 1 1 d . . . . .
H27 H 0.454037 0.090200 0.442569 0.033 Uiso 1 1 calc R U . . .
C28 C 0.62597(19) 0.10682(15) 0.45622(9) 0.0297(4) Uani 1 1 d . . . . .
H28 H 0.644868 0.050304 0.432456 0.036 Uiso 1 1 calc R U . . .
C29 C 0.71137(17) 0.16613(14) 0.48464(9) 0.0271(4) Uani 1 1 d . . . . .
H29 H 0.788858 0.150800 0.479768 0.033 Uiso 1 1 calc R U . . .
C30 C 0.68443(15) 0.24808(13) 0.52029(8) 0.0211(3) Uani 1 1 d . . . . .
H30 H 0.743335 0.288731 0.539532 0.025 Uiso 1 1 calc R U . . .
C31 C 0.62266(13) 0.43891(12) 0.58148(7) 0.0163(3) Uani 1 1 d . . . . .
C32 C 0.65834(15) 0.46003(14) 0.63969(7) 0.0213(3) Uani 1 1 d . . . . .
H32 H 0.629844 0.420244 0.670079 0.026 Uiso 1 1 calc R U . . .
C33 C 0.73565(17) 0.53930(15) 0.65345(8) 0.0268(4) Uani 1 1 d . . . . .
H33 H 0.760392 0.553164 0.693193 0.032 Uiso 1 1 calc R U . . .
C34 C 0.77662(16) 0.59809(15) 0.60920(9) 0.0269(4) Uani 1 1 d . . . . .
H34 H 0.829000 0.652486 0.618701 0.032 Uiso 1 1 calc R U . . .
C35 C 0.74121(16) 0.57761(14) 0.55095(8) 0.0238(3) Uani 1 1 d . . . . .
H35 H 0.768971 0.618249 0.520708 0.029 Uiso 1 1 calc R U . . .
C36 C 0.66514(15) 0.49758(13) 0.53704(7) 0.0196(3) Uani 1 1 d . . . . .
H36 H 0.641997 0.482772 0.497215 0.024 Uiso 1 1 calc R U . . .
O1 O 0.39254(13) 0.54799(11) 0.64589(6) 0.0315(3) Uani 1 1 d . . . . .
C37 C 0.3858(3) 0.55274(19) 0.70682(11) 0.0491(7) Uani 1 1 d . . . . .
H37A H 0.438321 0.501711 0.726702 0.059 Uiso 1 1 calc R U . . .
H37B H 0.307417 0.536690 0.716465 0.059 Uiso 1 1 calc R U . . .
C38 C 0.4187(2) 0.66166(18) 0.72726(9) 0.0345(4) Uani 1 1 d . . . . .
H38A H 0.499026 0.664763 0.743717 0.041 Uiso 1 1 calc R U . . .
H38B H 0.368750 0.686800 0.756886 0.041 Uiso 1 1 calc R U . . .
C39 C 0.40057(16) 0.72350(15) 0.67018(8) 0.0240(3) Uani 1 1 d . . . . .
H39A H 0.320509 0.746445 0.662855 0.029 Uiso 1 1 calc R U . . .
H39B H 0.451394 0.784398 0.670716 0.029 Uiso 1 1 calc R U . . .
C40 C 0.43122(17) 0.64524(14) 0.62524(8) 0.0254(4) Uani 1 1 d . . . . .
H40A H 0.392838 0.661708 0.586281 0.030 Uiso 1 1 calc R U . . .
H40B H 0.514543 0.644003 0.622244 0.030 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.
;

_exptl_special_details           
; 
One distinct cell was identified using APEX3 (Bruker, 2016).  Eight 
frame series were integrated and filtered for statistical outliers 
using SAINT (Bruker, 2016) then corrected for absorption by 
integration using SAINT/SADABS v2014/2 (Bruker, 2016) to sort, merge, 
and scale the combined data.  No decay correction was applied.    
;

loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
1.00 1.00 -1.00 0.1070
1.00 0.00 1.00 0.1440
-1.00 0.00 -1.00 0.1290
1.00 0.00 -1.00 0.0720
-1.00 0.00 1.00 0.0660
2.00 0.00 -1.00 0.0840
0.00 -1.00 -2.00 0.1040
0.00 -1.00 -1.00 0.1190
-1.00 2.00 2.00 0.1540
-1.00 1.00 1.00 0.1130
0.00 -2.00 -1.00 0.1370
1.00 -2.00 -1.00 0.1450
1.00 0.00 -2.00 0.0740
-2.00 1.00 2.00 0.0880
0.00 1.00 0.00 0.1310
3.00 -1.00 1.00 0.0940
1.00 -2.00 3.00 0.1150
0.00 0.00 1.00 0.1820
1.00 -1.00 3.00 0.1170

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 N3 1.8940(14) . ?
Cu1 N2 1.9115(14) . ?
Cu1 N1 1.9874(14) . ?
N1 C1 1.318(2) . ?
N1 C6 1.421(2) . ?
N2 C3 1.331(2) . ?
N2 C12 1.434(2) . ?
N3 C24 1.292(2) . ?
N3 H3 0.90(2) . ?
C1 C2 1.411(2) . ?
C1 C4 1.517(2) . ?
C2 C3 1.405(2) . ?
C2 H2 0.9500 . ?
C3 C5 1.522(2) . ?
C4 H4A 0.9800 . ?
C4 H4B 0.9800 . ?
C4 H4C 0.9800 . ?
C5 H5A 0.9800 . ?
C5 H5B 0.9800 . ?
C5 H5C 0.9800 . ?
C6 C7 1.401(2) . ?
C6 C11 1.404(2) . ?
C7 C8 1.399(2) . ?
C7 C18 1.502(2) . ?
C8 C9 1.389(3) . ?
C8 H8 0.9500 . ?
C9 C10 1.389(3) . ?
C9 C19 1.512(3) . ?
C10 C11 1.391(2) . ?
C10 H10 0.9500 . ?
C11 C20 1.504(2) . ?
C12 C13 1.401(2) . ?
C12 C17 1.405(2) . ?
C13 C14 1.395(2) . ?
C13 C21 1.503(2) . ?
C14 C15 1.393(2) . ?
C14 H14 0.9500 . ?
C15 C16 1.390(3) . ?
C15 C22 1.506(2) . ?
C16 C17 1.396(2) . ?
C16 H16 0.9500 . ?
C17 C23 1.505(2) . ?
C18 H18A 0.9800 . ?
C18 H18B 0.9800 . ?
C18 H18C 0.9800 . ?
C19 H19A 0.9800 . ?
C19 H19B 0.9800 . ?
C19 H19C 0.9800 . ?
C20 H20A 0.9800 . ?
C20 H20B 0.9800 . ?
C20 H20C 0.9800 . ?
C21 H21A 0.9800 . ?
C21 H21B 0.9800 . ?
C21 H21C 0.9800 . ?
C22 H22A 0.9800 . ?
C22 H22B 0.9800 . ?
C22 H22C 0.9800 . ?
C23 H23A 0.9800 . ?
C23 H23B 0.9800 . ?
C23 H23C 0.9800 . ?
C24 C25 1.482(2) . ?
C24 C31 1.488(2) . ?
C25 C26 1.394(2) . ?
C25 C30 1.402(2) . ?
C26 C27 1.389(2) . ?
C26 H26 0.9500 . ?
C27 C28 1.388(3) . ?
C27 H27 0.9500 . ?
C28 C29 1.385(3) . ?
C28 H28 0.9500 . ?
C29 C30 1.392(2) . ?
C29 H29 0.9500 . ?
C30 H30 0.9500 . ?
C31 C32 1.392(2) . ?
C31 C36 1.397(2) . ?
C32 C33 1.392(2) . ?
C32 H32 0.9500 . ?
C33 C34 1.387(3) . ?
C33 H33 0.9500 . ?
C34 C35 1.391(3) . ?
C34 H34 0.9500 . ?
C35 C36 1.390(2) . ?
C35 H35 0.9500 . ?
C36 H36 0.9500 . ?
O1 C37 1.407(3) . ?
O1 C40 1.434(2) . ?
C37 C38 1.527(3) . ?
C37 H37A 0.9900 . ?
C37 H37B 0.9900 . ?
C38 C39 1.534(3) . ?
C38 H38A 0.9900 . ?
C38 H38B 0.9900 . ?
C39 C40 1.510(3) . ?
C39 H39A 0.9900 . ?
C39 H39B 0.9900 . ?
C40 H40A 0.9900 . ?
C40 H40B 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
N3 Cu1 N2 151.02(6) . . ?
N3 Cu1 N1 111.32(6) . . ?
N2 Cu1 N1 97.53(6) . . ?
C1 N1 C6 121.13(14) . . ?
C1 N1 Cu1 122.60(11) . . ?
C6 N1 Cu1 115.78(10) . . ?
C3 N2 C12 119.11(14) . . ?
C3 N2 Cu1 122.87(11) . . ?
C12 N2 Cu1 117.99(10) . . ?
C24 N3 Cu1 132.68(12) . . ?
C24 N3 H3 109.4(14) . . ?
Cu1 N3 H3 116.9(14) . . ?
N1 C1 C2 123.07(15) . . ?
N1 C1 C4 119.52(15) . . ?
C2 C1 C4 117.40(14) . . ?
C3 C2 C1 129.06(15) . . ?
C3 C2 H2 115.5 . . ?
C1 C2 H2 115.5 . . ?
N2 C3 C2 124.55(15) . . ?
N2 C3 C5 119.27(15) . . ?
C2 C3 C5 116.18(15) . . ?
C1 C4 H4A 109.5 . . ?
C1 C4 H4B 109.5 . . ?
H4A C4 H4B 109.5 . . ?
C1 C4 H4C 109.5 . . ?
H4A C4 H4C 109.5 . . ?
H4B C4 H4C 109.5 . . ?
C3 C5 H5A 109.5 . . ?
C3 C5 H5B 109.5 . . ?
H5A C5 H5B 109.5 . . ?
C3 C5 H5C 109.5 . . ?
H5A C5 H5C 109.5 . . ?
H5B C5 H5C 109.5 . . ?
C7 C6 C11 120.06(15) . . ?
C7 C6 N1 120.64(14) . . ?
C11 C6 N1 118.95(14) . . ?
C8 C7 C6 119.00(15) . . ?
C8 C7 C18 120.92(15) . . ?
C6 C7 C18 120.09(15) . . ?
C9 C8 C7 121.74(16) . . ?
C9 C8 H8 119.1 . . ?
C7 C8 H8 119.1 . . ?
C8 C9 C10 118.17(16) . . ?
C8 C9 C19 121.32(18) . . ?
C10 C9 C19 120.51(18) . . ?
C9 C10 C11 122.01(16) . . ?
C9 C10 H10 119.0 . . ?
C11 C10 H10 119.0 . . ?
C10 C11 C6 118.99(16) . . ?
C10 C11 C20 121.27(16) . . ?
C6 C11 C20 119.73(15) . . ?
C13 C12 C17 120.11(15) . . ?
C13 C12 N2 119.59(15) . . ?
C17 C12 N2 120.17(15) . . ?
C14 C13 C12 119.25(16) . . ?
C14 C13 C21 120.33(16) . . ?
C12 C13 C21 120.42(15) . . ?
C15 C14 C13 121.84(16) . . ?
C15 C14 H14 119.1 . . ?
C13 C14 H14 119.1 . . ?
C16 C15 C14 117.75(16) . . ?
C16 C15 C22 121.00(17) . . ?
C14 C15 C22 121.24(17) . . ?
C15 C16 C17 122.44(16) . . ?
C15 C16 H16 118.8 . . ?
C17 C16 H16 118.8 . . ?
C16 C17 C12 118.59(16) . . ?
C16 C17 C23 120.72(16) . . ?
C12 C17 C23 120.67(15) . . ?
C7 C18 H18A 109.5 . . ?
C7 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
C7 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
C9 C19 H19A 109.5 . . ?
C9 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
C9 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
C11 C20 H20A 109.5 . . ?
C11 C20 H20B 109.5 . . ?
H20A C20 H20B 109.5 . . ?
C11 C20 H20C 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
C13 C21 H21A 109.5 . . ?
C13 C21 H21B 109.5 . . ?
H21A C21 H21B 109.5 . . ?
C13 C21 H21C 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
C15 C22 H22A 109.5 . . ?
C15 C22 H22B 109.5 . . ?
H22A C22 H22B 109.5 . . ?
C15 C22 H22C 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
C17 C23 H23A 109.5 . . ?
C17 C23 H23B 109.5 . . ?
H23A C23 H23B 109.5 . . ?
C17 C23 H23C 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 109.5 . . ?
N3 C24 C25 120.25(14) . . ?
N3 C24 C31 120.83(14) . . ?
C25 C24 C31 118.89(14) . . ?
C26 C25 C30 119.43(16) . . ?
C26 C25 C24 120.08(15) . . ?
C30 C25 C24 120.47(15) . . ?
C27 C26 C25 120.18(17) . . ?
C27 C26 H26 119.9 . . ?
C25 C26 H26 119.9 . . ?
C28 C27 C26 120.31(18) . . ?
C28 C27 H27 119.8 . . ?
C26 C27 H27 119.8 . . ?
C29 C28 C27 119.82(17) . . ?
C29 C28 H28 120.1 . . ?
C27 C28 H28 120.1 . . ?
C28 C29 C30 120.45(18) . . ?
C28 C29 H29 119.8 . . ?
C30 C29 H29 119.8 . . ?
C29 C30 C25 119.78(17) . . ?
C29 C30 H30 120.1 . . ?
C25 C30 H30 120.1 . . ?
C32 C31 C36 119.60(15) . . ?
C32 C31 C24 118.92(14) . . ?
C36 C31 C24 121.49(15) . . ?
C33 C32 C31 120.14(16) . . ?
C33 C32 H32 119.9 . . ?
C31 C32 H32 119.9 . . ?
C34 C33 C32 120.05(17) . . ?
C34 C33 H33 120.0 . . ?
C32 C33 H33 120.0 . . ?
C33 C34 C35 120.15(17) . . ?
C33 C34 H34 119.9 . . ?
C35 C34 H34 119.9 . . ?
C36 C35 C34 119.92(16) . . ?
C36 C35 H35 120.0 . . ?
C34 C35 H35 120.0 . . ?
C35 C36 C31 120.13(16) . . ?
C35 C36 H36 119.9 . . ?
C31 C36 H36 119.9 . . ?
C37 O1 C40 109.56(16) . . ?
O1 C37 C38 108.14(18) . . ?
O1 C37 H37A 110.1 . . ?
C38 C37 H37A 110.1 . . ?
O1 C37 H37B 110.1 . . ?
C38 C37 H37B 110.1 . . ?
H37A C37 H37B 108.4 . . ?
C37 C38 C39 101.96(17) . . ?
C37 C38 H38A 111.4 . . ?
C39 C38 H38A 111.4 . . ?
C37 C38 H38B 111.4 . . ?
C39 C38 H38B 111.4 . . ?
H38A C38 H38B 109.2 . . ?
C40 C39 C38 101.93(16) . . ?
C40 C39 H39A 111.4 . . ?
C38 C39 H39A 111.4 . . ?
C40 C39 H39B 111.4 . . ?
C38 C39 H39B 111.4 . . ?
H39A C39 H39B 109.2 . . ?
O1 C40 C39 105.32(14) . . ?
O1 C40 H40A 110.7 . . ?
C39 C40 H40A 110.7 . . ?
O1 C40 H40B 110.7 . . ?
C39 C40 H40B 110.7 . . ?
H40A C40 H40B 108.8 . . ?

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
N3 H3 O1 0.90(2) 2.04(2) 2.933(2) 170(2) . yes

_refine_diff_density_max         0.979
_refine_diff_density_min         -0.903
_refine_diff_density_rms         0.082

####################################################################### 
# 
# 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_P21n_a_CCDC1
_audit_block_doi                 10.5517/ccdc.csd.cc239b1t
_database_code_depnum_ccdc_archive 'CCDC 1945375'
loop_
_audit_author_name
_audit_author_address
'Jeffery A. Bertke'
;Georgetown University
United States of America
;
_audit_update_record             
;
2019-08-03 deposited with the CCDC.	2021-11-23 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2017/1
_shelx_SHELXL_version_number     2017/1
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C30 H24 Cl4 Cu N3'
_chemical_formula_sum            'C30 H24 Cl4 Cu N3'
_chemical_formula_weight         631.86

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cu Cu 0.3201 1.2651 '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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/n'
_space_group_name_Hall           '-P 2yn'

_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+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   12.8807(5)
_cell_length_b                   15.5610(5)
_cell_length_c                   14.8263(6)
_cell_angle_alpha                90
_cell_angle_beta                 108.036(2)
_cell_angle_gamma                90
_cell_volume                     2825.71(19)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    9977
_cell_measurement_theta_min      2.25
_cell_measurement_theta_max      25.49
_exptl_crystal_description       prism
_exptl_crystal_colour            ?
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.485
_exptl_crystal_F_000             1288
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.310
_exptl_crystal_size_mid          0.276
_exptl_crystal_size_min          0.118
_exptl_absorpt_coefficient_mu    1.176
_shelx_estimated_absorpt_T_min   0.712
_shelx_estimated_absorpt_T_max   0.874
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.5892
_exptl_absorpt_correction_T_max  0.7452
_exptl_absorpt_process_details   'SADABS V2016/2 (Bruker, 2016)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  'multilayer mirrors'
_diffrn_measurement_device       'Bruker APEX DUO/ApexII CCD'
_diffrn_measurement_method       'profile data from φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            26800
_diffrn_reflns_av_unetI/netI     0.0210
_diffrn_reflns_av_R_equivalents  0.0285
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         1.834
_diffrn_reflns_theta_max         25.487
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.991
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             5209
_reflns_number_gt                4723
_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       'APEX3 V2016.5-0 (Bruker, 2016)'
_computing_cell_refinement       'SAINT V8.37A (Bruker, 2005)'
_computing_data_reduction        
; 
SAINT V8.37A, XPREP v2014/2, SADABS V2016/2 (Bruker, 2016) 
;
_computing_structure_solution    'SHELX-2014-5 (Sheldrick, 2015)'
_computing_structure_refinement  'SHELX-2018-1 (Sheldrick, 2015)'
_computing_molecular_graphics    'SHELXLE v932 (Hubschle, 2011)'
_computing_publication_material  'XCIF V2014-2 (Bruker, 2014)'

_refine_special_details          
; 
Structure was phased by intrinsic methods (Sheldrick, 2015).  Systematic 
conditions suggested the ambiguous space group.  The space group choice 
was confirmed by successful convergence of the full-matrix least-squares 
refinement on F².  The final map had no significant features.  A final 
analysis of variance between observed and calculated structure factors 
showed little dependence on amplitude and resolution. 
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0248P)²+1.6714P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         5209
_refine_ls_number_parameters     348
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0260
_refine_ls_R_factor_gt           0.0222
_refine_ls_wR_factor_ref         0.0570
_refine_ls_wR_factor_gt          0.0552
_refine_ls_goodness_of_fit_ref   1.038
_refine_ls_restrained_S_all      1.038
_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 0.28582(2) 0.74121(2) 0.53319(2) 0.01256(6) Uani 1 1 d . . . . .
Cl1 Cl 0.46318(3) 0.88426(3) 0.49832(3) 0.02622(11) Uani 1 1 d . . . . .
Cl2 Cl 0.06871(3) 0.80960(3) 0.24775(3) 0.02331(10) Uani 1 1 d . . . . .
Cl3 Cl 0.36636(3) 0.80349(3) 0.79083(3) 0.02336(10) Uani 1 1 d . . . . .
Cl4 Cl 0.05165(3) 0.59771(3) 0.57186(3) 0.02145(10) Uani 1 1 d . . . . .
N1 N 0.22754(11) 0.83894(8) 0.44555(9) 0.0127(3) Uani 1 1 d . . . . .
N2 N 0.19474(11) 0.75430(8) 0.61192(9) 0.0130(3) Uani 1 1 d . . . . .
N3 N 0.40245(12) 0.68141(8) 0.50895(10) 0.0144(3) Uani 1 1 d . . . . .
H3 H 0.4673(17) 0.6905(12) 0.5449(14) 0.022 Uiso 1 1 d . U . . .
C1 C 0.15253(13) 0.89126(10) 0.45849(11) 0.0131(3) Uani 1 1 d . . . . .
C2 C 0.10348(13) 0.87998(10) 0.53046(11) 0.0138(3) Uani 1 1 d . . . . .
H2 H 0.049423 0.921350 0.530949 0.017 Uiso 1 1 calc R U . . .
C3 C 0.12208(13) 0.81733(9) 0.60123(11) 0.0124(3) Uani 1 1 d . . . . .
C4 C 0.11660(14) 0.97066(10) 0.39769(12) 0.0194(4) Uani 1 1 d . . . . .
H4A H 0.158224 0.975179 0.352636 0.029 Uiso 1 1 calc R U . . .
H4B H 0.129783 1.021760 0.438305 0.029 Uiso 1 1 calc R U . . .
H4C H 0.038563 0.966403 0.362810 0.029 Uiso 1 1 calc R U . . .
C5 C 0.05642(14) 0.82354(10) 0.66947(12) 0.0175(3) Uani 1 1 d . . . . .
H5A H 0.014062 0.770685 0.666295 0.026 Uiso 1 1 calc R U . . .
H5B H 0.006659 0.872725 0.652321 0.026 Uiso 1 1 calc R U . . .
H5C H 0.105904 0.831232 0.734087 0.026 Uiso 1 1 calc R U . . .
C6 C 0.26867(13) 0.84799(9) 0.36897(11) 0.0133(3) Uani 1 1 d . . . . .
C7 C 0.38012(14) 0.86309(10) 0.38385(12) 0.0174(3) Uani 1 1 d . . . . .
C8 C 0.42658(15) 0.86367(11) 0.31147(14) 0.0251(4) Uani 1 1 d . . . . .
H8 H 0.502850 0.872600 0.325067 0.030 Uiso 1 1 calc R U . . .
C9 C 0.36140(17) 0.85121(12) 0.21948(14) 0.0299(4) Uani 1 1 d . . . . .
H9 H 0.392298 0.852694 0.169038 0.036 Uiso 1 1 calc R U . . .
C10 C 0.25135(16) 0.83659(12) 0.20069(13) 0.0262(4) Uani 1 1 d . . . . .
H10 H 0.206166 0.828318 0.137186 0.031 Uiso 1 1 calc R U . . .
C11 C 0.20640(14) 0.83393(10) 0.27430(11) 0.0172(3) Uani 1 1 d . . . . .
C12 C 0.21105(13) 0.69579(10) 0.68746(11) 0.0132(3) Uani 1 1 d . . . . .
C13 C 0.29240(13) 0.70850(10) 0.77412(11) 0.0167(3) Uani 1 1 d . . . . .
C14 C 0.31710(15) 0.64787(11) 0.84604(12) 0.0232(4) Uani 1 1 d . . . . .
H14 H 0.373718 0.658321 0.903668 0.028 Uiso 1 1 calc R U . . .
C15 C 0.25835(16) 0.57177(11) 0.83305(13) 0.0252(4) Uani 1 1 d . . . . .
H15 H 0.274852 0.529677 0.881851 0.030 Uiso 1 1 calc R U . . .
C16 C 0.17588(15) 0.55708(11) 0.74928(13) 0.0212(4) Uani 1 1 d . . . . .
H16 H 0.134883 0.505295 0.740491 0.025 Uiso 1 1 calc R U . . .
C17 C 0.15342(13) 0.61834(10) 0.67825(11) 0.0155(3) Uani 1 1 d . . . . .
C18 C 0.40523(13) 0.63854(10) 0.43504(11) 0.0137(3) Uani 1 1 d . . . . .
C19 C 0.30041(13) 0.61381(9) 0.36468(11) 0.0144(3) Uani 1 1 d . . . . .
C20 C 0.28857(14) 0.61174(11) 0.26795(12) 0.0193(4) Uani 1 1 d . . . . .
H20 H 0.349474 0.623375 0.246579 0.023 Uiso 1 1 calc R U . . .
C21 C 0.18820(15) 0.59275(11) 0.20313(12) 0.0240(4) Uani 1 1 d . . . . .
H21 H 0.180231 0.592146 0.137256 0.029 Uiso 1 1 calc R U . . .
C22 C 0.09940(15) 0.57464(11) 0.23357(13) 0.0240(4) Uani 1 1 d . . . . .
H22 H 0.030612 0.561778 0.188711 0.029 Uiso 1 1 calc R U . . .
C23 C 0.11089(14) 0.57528(11) 0.32952(13) 0.0215(4) Uani 1 1 d . . . . .
H23 H 0.050126 0.562120 0.350538 0.026 Uiso 1 1 calc R U . . .
C24 C 0.21037(14) 0.59499(10) 0.39474(12) 0.0174(3) Uani 1 1 d . . . . .
H24 H 0.217646 0.595756 0.460484 0.021 Uiso 1 1 calc R U . . .
C25 C 0.51014(13) 0.61389(10) 0.42054(11) 0.0144(3) Uani 1 1 d . . . . .
C26 C 0.59826(13) 0.67063(11) 0.44590(11) 0.0164(3) Uani 1 1 d . . . . .
H26 H 0.589321 0.726377 0.468547 0.020 Uiso 1 1 calc R U . . .
C27 C 0.69872(14) 0.64637(11) 0.43833(12) 0.0205(4) Uani 1 1 d . . . . .
H27 H 0.758412 0.685330 0.455904 0.025 Uiso 1 1 calc R U . . .
C28 C 0.71205(14) 0.56498(11) 0.40500(12) 0.0215(4) Uani 1 1 d . . . . .
H28 H 0.781327 0.547771 0.401191 0.026 Uiso 1 1 calc R U . . .
C29 C 0.62450(14) 0.50903(11) 0.37738(12) 0.0203(4) Uani 1 1 d . . . . .
H29 H 0.633418 0.453887 0.353295 0.024 Uiso 1 1 calc R U . . .
C30 C 0.52373(14) 0.53304(10) 0.38467(11) 0.0176(3) Uani 1 1 d . . . . .
H30 H 0.463775 0.494438 0.365230 0.021 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.
;

_exptl_special_details           
; 
One distinct cell was identified using APEX3 (Bruker, 2016).  Five 
frame series were integrated and filtered for statistical outliers 
using SAINT (Bruker, 2016) then corrected for absorption by integration 
using SAINT/SADABS v2014/2 (Bruker, 2016) to sort, merge, and scale 
the combined data.  No decay correction was applied.    
;

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 N3 1.8937(14) . ?
Cu1 N2 1.9049(13) . ?
Cu1 N1 1.9901(13) . ?
Cl1 C7 1.7346(17) . ?
Cl2 C11 1.7353(17) . ?
Cl3 C13 1.7344(17) . ?
Cl4 C17 1.7405(17) . ?
N1 C1 1.322(2) . ?
N1 C6 1.401(2) . ?
N2 C3 1.331(2) . ?
N2 C12 1.408(2) . ?
N3 C18 1.293(2) . ?
N3 H3 0.85(2) . ?
C1 C2 1.409(2) . ?
C1 C4 1.515(2) . ?
C2 C3 1.397(2) . ?
C2 H2 0.9500 . ?
C3 C5 1.509(2) . ?
C4 H4A 0.9800 . ?
C4 H4B 0.9800 . ?
C4 H4C 0.9800 . ?
C5 H5A 0.9800 . ?
C5 H5B 0.9800 . ?
C5 H5C 0.9800 . ?
C6 C11 1.401(2) . ?
C6 C7 1.403(2) . ?
C7 C8 1.381(2) . ?
C8 C9 1.376(3) . ?
C8 H8 0.9500 . ?
C9 C10 1.376(3) . ?
C9 H9 0.9500 . ?
C10 C11 1.385(2) . ?
C10 H10 0.9500 . ?
C12 C13 1.398(2) . ?
C12 C17 1.400(2) . ?
C13 C14 1.385(2) . ?
C14 C15 1.386(3) . ?
C14 H14 0.9500 . ?
C15 C16 1.381(3) . ?
C15 H15 0.9500 . ?
C16 C17 1.383(2) . ?
C16 H16 0.9500 . ?
C18 C19 1.479(2) . ?
C18 C25 1.483(2) . ?
C19 C20 1.395(2) . ?
C19 C24 1.396(2) . ?
C20 C21 1.383(2) . ?
C20 H20 0.9500 . ?
C21 C22 1.382(3) . ?
C21 H21 0.9500 . ?
C22 C23 1.384(3) . ?
C22 H22 0.9500 . ?
C23 C24 1.380(2) . ?
C23 H23 0.9500 . ?
C24 H24 0.9500 . ?
C25 C26 1.395(2) . ?
C25 C30 1.398(2) . ?
C26 C27 1.386(2) . ?
C26 H26 0.9500 . ?
C27 C28 1.389(2) . ?
C27 H27 0.9500 . ?
C28 C29 1.383(3) . ?
C28 H28 0.9500 . ?
C29 C30 1.387(2) . ?
C29 H29 0.9500 . ?
C30 H30 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
N3 Cu1 N2 147.58(6) . . ?
N3 Cu1 N1 114.37(6) . . ?
N2 Cu1 N1 97.98(5) . . ?
C1 N1 C6 122.17(13) . . ?
C1 N1 Cu1 121.39(11) . . ?
C6 N1 Cu1 116.43(10) . . ?
C3 N2 C12 119.85(13) . . ?
C3 N2 Cu1 123.35(11) . . ?
C12 N2 Cu1 116.73(10) . . ?
C18 N3 Cu1 130.25(12) . . ?
C18 N3 H3 109.7(13) . . ?
Cu1 N3 H3 118.8(13) . . ?
N1 C1 C2 123.52(14) . . ?
N1 C1 C4 121.22(14) . . ?
C2 C1 C4 115.23(14) . . ?
C3 C2 C1 129.98(15) . . ?
C3 C2 H2 115.0 . . ?
C1 C2 H2 115.0 . . ?
N2 C3 C2 123.66(14) . . ?
N2 C3 C5 119.12(14) . . ?
C2 C3 C5 117.21(14) . . ?
C1 C4 H4A 109.5 . . ?
C1 C4 H4B 109.5 . . ?
H4A C4 H4B 109.5 . . ?
C1 C4 H4C 109.5 . . ?
H4A C4 H4C 109.5 . . ?
H4B C4 H4C 109.5 . . ?
C3 C5 H5A 109.5 . . ?
C3 C5 H5B 109.5 . . ?
H5A C5 H5B 109.5 . . ?
C3 C5 H5C 109.5 . . ?
H5A C5 H5C 109.5 . . ?
H5B C5 H5C 109.5 . . ?
N1 C6 C11 123.59(14) . . ?
N1 C6 C7 120.98(14) . . ?
C11 C6 C7 115.09(15) . . ?
C8 C7 C6 123.18(16) . . ?
C8 C7 Cl1 118.34(14) . . ?
C6 C7 Cl1 118.47(13) . . ?
C9 C8 C7 119.41(17) . . ?
C9 C8 H8 120.3 . . ?
C7 C8 H8 120.3 . . ?
C8 C9 C10 119.86(17) . . ?
C8 C9 H9 120.1 . . ?
C10 C9 H9 120.1 . . ?
C9 C10 C11 120.07(17) . . ?
C9 C10 H10 120.0 . . ?
C11 C10 H10 120.0 . . ?
C10 C11 C6 122.35(16) . . ?
C10 C11 Cl2 118.35(14) . . ?
C6 C11 Cl2 119.28(13) . . ?
C13 C12 C17 115.81(14) . . ?
C13 C12 N2 121.63(14) . . ?
C17 C12 N2 122.36(14) . . ?
C14 C13 C12 122.64(16) . . ?
C14 C13 Cl3 119.04(13) . . ?
C12 C13 Cl3 118.31(12) . . ?
C13 C14 C15 119.31(16) . . ?
C13 C14 H14 120.3 . . ?
C15 C14 H14 120.3 . . ?
C16 C15 C14 120.08(16) . . ?
C16 C15 H15 120.0 . . ?
C14 C15 H15 120.0 . . ?
C15 C16 C17 119.48(16) . . ?
C15 C16 H16 120.3 . . ?
C17 C16 H16 120.3 . . ?
C16 C17 C12 122.66(15) . . ?
C16 C17 Cl4 118.96(13) . . ?
C12 C17 Cl4 118.37(12) . . ?
N3 C18 C19 118.26(14) . . ?
N3 C18 C25 121.46(15) . . ?
C19 C18 C25 120.28(14) . . ?
C20 C19 C24 119.09(15) . . ?
C20 C19 C18 121.11(15) . . ?
C24 C19 C18 119.77(14) . . ?
C21 C20 C19 120.03(16) . . ?
C21 C20 H20 120.0 . . ?
C19 C20 H20 120.0 . . ?
C22 C21 C20 120.44(17) . . ?
C22 C21 H21 119.8 . . ?
C20 C21 H21 119.8 . . ?
C21 C22 C23 119.88(16) . . ?
C21 C22 H22 120.1 . . ?
C23 C22 H22 120.1 . . ?
C24 C23 C22 120.16(16) . . ?
C24 C23 H23 119.9 . . ?
C22 C23 H23 119.9 . . ?
C23 C24 C19 120.39(16) . . ?
C23 C24 H24 119.8 . . ?
C19 C24 H24 119.8 . . ?
C26 C25 C30 119.01(15) . . ?
C26 C25 C18 119.95(14) . . ?
C30 C25 C18 121.00(15) . . ?
C27 C26 C25 120.55(15) . . ?
C27 C26 H26 119.7 . . ?
C25 C26 H26 119.7 . . ?
C26 C27 C28 119.90(16) . . ?
C26 C27 H27 120.0 . . ?
C28 C27 H27 120.0 . . ?
C29 C28 C27 120.01(16) . . ?
C29 C28 H28 120.0 . . ?
C27 C28 H28 120.0 . . ?
C28 C29 C30 120.30(16) . . ?
C28 C29 H29 119.8 . . ?
C30 C29 H29 119.8 . . ?
C29 C30 C25 120.18(16) . . ?
C29 C30 H30 119.9 . . ?
C25 C30 H30 119.9 . . ?

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
N3 H3 Cl2 0.85(2) 2.88(2) 3.5279(14) 133.8(16) 4_676 yes

_refine_diff_density_max         0.289
_refine_diff_density_min         -0.285
_refine_diff_density_rms         0.047

####################################################################### 
# 
# 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_twin5
_database_code_depnum_ccdc_archive 'CCDC 2035780'
loop_
_audit_author_name
_audit_author_address
'Jeffery A. Bertke'
;Georgetown University
United States of America
;
_audit_update_record             
;
2020-10-06 deposited with the CCDC.	2021-11-23 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        
'N-(1-(1,3,3-Trimethyl-2-oxabicyclo[2.2.2]octan-5-yl) benzophenone imine'
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C23 H27 N O'
_chemical_formula_sum            'C23 H27 N O'
_chemical_formula_weight         333.45

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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_H-M_alt        'P 21'
_space_group_name_Hall           'P 2yb'

_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'

_cell_length_a                   10.3648(10)
_cell_length_b                   8.5788(8)
_cell_length_c                   10.6319(9)
_cell_angle_alpha                90
_cell_angle_beta                 100.736(4)
_cell_angle_gamma                90
_cell_volume                     928.81(15)
_cell_formula_units_Z            2
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    5644
_cell_measurement_theta_min      2.52
_cell_measurement_theta_max      25.26
_exptl_crystal_description       prism
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.192
_exptl_crystal_F_000             360
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.210
_exptl_crystal_size_mid          0.205
_exptl_crystal_size_min          0.078
_exptl_absorpt_coefficient_mu    0.072
_shelx_estimated_absorpt_T_min   0.985
_shelx_estimated_absorpt_T_max   0.994
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.593114
_exptl_absorpt_correction_T_max  0.745210
_exptl_absorpt_process_details   'SADABS V2016/2 (Bruker, 2016)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'microfocus sealed tube'
_diffrn_radiation_monochromator  'multilayer mirrors'
_diffrn_measurement_device       'Bruker D8 Quest/Photon 100'
_diffrn_measurement_method       'profile data from φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            2935
_diffrn_reflns_av_unetI/netI     0.0548
_diffrn_reflns_av_R_equivalents  ?
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         2.000
_diffrn_reflns_theta_max         25.294
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.536
_diffrn_reflns_point_group_measured_fraction_full 0.536
_reflns_number_total             2935
_reflns_number_gt                2474
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     0.000
_reflns_Friedel_fraction_full    0.000

_reflns_special_details          
;
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences. Completness statistics refer to single and
 composite reflections containing twin component 1 only.
;

_computing_data_collection       'APEX3 V2016.5-0 (Bruker, 2016)'
_computing_cell_refinement       'SAINT V8.37A (Bruker, 2005)'
_computing_data_reduction        
; 
SAINT V8.37A, XPREP v2014/2, TWINABS V2012/1 (Bruker, 2016) 
;
_computing_structure_solution    'SHELX-2014-5 (Sheldrick, 2015)'
_computing_structure_refinement  'SHELX-2018-3 (Sheldrick, 2015)'
_computing_molecular_graphics    'SHELXLE v932 (Hubschle, 2011)'
_computing_publication_material  'XCIF V2014-2 (Bruker, 2014)'
_refine_special_details          
;Refined as a 2-component twin.

Structure was phased by intrinsic methods (Sheldrick, 2015).  Systematic 
conditions suggested the ambiguous space group.  The space group choice 
was confirmed by successful convergence of the full-matrix least-squares 
refinement on F².  The final map had no significant features.  A final 
analysis of variance between observed and calculated structure factors 
showed little dependence on amplitude and resolution.,Twin
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0173P)²+1.4074P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     intrinsic
_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_abs_structure_details 
;
No quotients, so Flack parameter determined by classical intensity fit
;
_refine_ls_abs_structure_Flack   2(3)
_chemical_absolute_configuration unk
_refine_ls_number_reflns         2935
_refine_ls_number_parameters     230
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0948
_refine_ls_R_factor_gt           0.0614
_refine_ls_wR_factor_ref         0.1428
_refine_ls_wR_factor_gt          0.1225
_refine_ls_goodness_of_fit_ref   1.153
_refine_ls_restrained_S_all      1.153
_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
O1 O 0.6383(4) 0.7676(5) 0.3528(4) 0.0200(10) Uani 1 1 d . . . . .
N1 N 0.3287(5) 0.4674(6) 0.2056(5) 0.0213(12) Uani 1 1 d . . . . .
C1 C 0.5780(6) 0.7946(8) 0.2193(5) 0.0216(14) Uani 1 1 d . . . . .
C2 C 0.5030(6) 0.6464(8) 0.1674(6) 0.0226(15) Uani 1 1 d . . . . .
H2 H 0.452124 0.665364 0.079123 0.027 Uiso 1 1 calc R U . . .
C3 C 0.4090(6) 0.6017(8) 0.2587(6) 0.0199(14) Uani 1 1 d . . . . .
H3 H 0.350589 0.692009 0.268330 0.024 Uiso 1 1 calc R U . . .
C4 C 0.4931(6) 0.5602(9) 0.3899(6) 0.0250(16) Uani 1 1 d . . . . .
H4A H 0.459003 0.615759 0.458546 0.030 Uiso 1 1 calc R U . . .
H4B H 0.487573 0.446779 0.405348 0.030 Uiso 1 1 calc R U . . .
C5 C 0.6351(6) 0.6061(8) 0.3930(6) 0.0235(16) Uani 1 1 d . . . . .
C6 C 0.6920(6) 0.5049(8) 0.2994(6) 0.0245(15) Uani 1 1 d . . . . .
H6A H 0.699964 0.395944 0.330584 0.029 Uiso 1 1 calc R U . . .
H6B H 0.780739 0.542721 0.292812 0.029 Uiso 1 1 calc R U . . .
C7 C 0.6012(6) 0.5111(9) 0.1659(6) 0.0247(16) Uani 1 1 d . . . . .
H7A H 0.653847 0.528931 0.098571 0.030 Uiso 1 1 calc R U . . .
H7B H 0.553324 0.411359 0.147850 0.030 Uiso 1 1 calc R U . . .
C8 C 0.6862(6) 0.8388(9) 0.1457(6) 0.0274(17) Uani 1 1 d . . . . .
H8A H 0.646958 0.861405 0.056409 0.041 Uiso 1 1 calc R U . . .
H8B H 0.748157 0.751967 0.148705 0.041 Uiso 1 1 calc R U . . .
H8C H 0.732738 0.931238 0.184821 0.041 Uiso 1 1 calc R U . . .
C9 C 0.4887(7) 0.9367(9) 0.2181(7) 0.0302(16) Uani 1 1 d . . . . .
H9A H 0.540875 1.026152 0.255687 0.045 Uiso 1 1 calc R U . . .
H9B H 0.420509 0.914008 0.268143 0.045 Uiso 1 1 calc R U . . .
H9C H 0.447422 0.961088 0.129681 0.045 Uiso 1 1 calc R U . . .
C10 C 0.7181(6) 0.6005(9) 0.5261(6) 0.0290(17) Uani 1 1 d . . . . .
H10A H 0.807954 0.632966 0.522492 0.044 Uiso 1 1 calc R U . . .
H10B H 0.719062 0.493892 0.559405 0.044 Uiso 1 1 calc R U . . .
H10C H 0.680914 0.670978 0.582547 0.044 Uiso 1 1 calc R U . . .
C11 C 0.2130(6) 0.4552(8) 0.2351(5) 0.0167(14) Uani 1 1 d . . . . .
C12 C 0.1316(6) 0.3183(8) 0.1833(6) 0.0182(13) Uani 1 1 d . . . . .
C13 C 0.1882(6) 0.1881(8) 0.1371(6) 0.0203(14) Uani 1 1 d . . . . .
H13 H 0.280245 0.185619 0.139366 0.024 Uiso 1 1 calc R U . . .
C14 C 0.1116(7) 0.0623(8) 0.0880(6) 0.0255(16) Uani 1 1 d . . . . .
H14 H 0.151693 -0.026055 0.057480 0.031 Uiso 1 1 calc R U . . .
C15 C -0.0240(6) 0.0637(9) 0.0828(6) 0.0250(15) Uani 1 1 d . . . . .
H15 H -0.076436 -0.022454 0.048168 0.030 Uiso 1 1 calc R U . . .
C16 C -0.0809(6) 0.1924(8) 0.1287(6) 0.0213(15) Uani 1 1 d . . . . .
H16 H -0.173144 0.195452 0.125267 0.026 Uiso 1 1 calc R U . . .
C17 C -0.0028(6) 0.3178(8) 0.1801(5) 0.0188(13) Uani 1 1 d . . . . .
H17 H -0.042433 0.404469 0.213505 0.023 Uiso 1 1 calc R U . . .
C18 C 0.1581(6) 0.5634(8) 0.3206(6) 0.0196(14) Uani 1 1 d . . . . .
C19 C 0.1861(6) 0.5400(8) 0.4532(6) 0.0199(14) Uani 1 1 d . . . . .
H19 H 0.240003 0.455207 0.488356 0.024 Uiso 1 1 calc R U . . .
C20 C 0.1349(6) 0.6412(7) 0.5332(6) 0.0198(14) Uani 1 1 d . . . . .
H20 H 0.153939 0.624790 0.623120 0.024 Uiso 1 1 calc R U . . .
C21 C 0.0563(6) 0.7657(8) 0.4839(6) 0.0243(15) Uani 1 1 d . . . . .
H21 H 0.021452 0.833932 0.539603 0.029 Uiso 1 1 calc R U . . .
C22 C 0.0291(6) 0.7898(8) 0.3536(6) 0.0234(14) Uani 1 1 d . . . . .
H22 H -0.024576 0.875317 0.319700 0.028 Uiso 1 1 calc R U . . .
C23 C 0.0792(6) 0.6907(8) 0.2712(6) 0.0223(14) Uani 1 1 d . . . . .
H23 H 0.060054 0.708846 0.181488 0.027 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.
;

_exptl_special_details           
; 
Two distinct cells were identified using APEX3 (Bruker, 2016) and Cell_Now 
(Sheldrick, 2008).  Four frame series were integrated and filtered for 
statistical outliers using SAINT (Bruker, 2016) then corrected for 
absorption by integration using SAINT/TWINABS v2014/2 (Bruker, 2016) to 
sort, merge, and scale the combined data.  Combined unit cell parameters 
were determined from both components using SAINT (Bruker, 2013).  The twin 
law by rows was (-1 0 0), (0 -1 0), (.38 0 1).  Non-overlapping 
reflections from the primary orientation were used for phasing.  Combined 
data with complete or no overlap were used for refinement. No decay 
correction was applied.    
;

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
O1 C5 1.452(8) . ?
O1 C1 1.459(7) . ?
N1 C11 1.299(8) . ?
N1 C3 1.471(8) . ?
C1 C8 1.530(9) . ?
C1 C9 1.530(10) . ?
C1 C2 1.538(9) . ?
C2 C7 1.546(9) . ?
C2 C3 1.546(9) . ?
C2 H2 1.0000 . ?
C3 C4 1.543(8) . ?
C3 H3 1.0000 . ?
C4 C5 1.518(9) . ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?
C5 C10 1.514(9) . ?
C5 C6 1.520(9) . ?
C6 C7 1.551(9) . ?
C6 H6A 0.9900 . ?
C6 H6B 0.9900 . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C8 H8A 0.9800 . ?
C8 H8B 0.9800 . ?
C8 H8C 0.9800 . ?
C9 H9A 0.9800 . ?
C9 H9B 0.9800 . ?
C9 H9C 0.9800 . ?
C10 H10A 0.9800 . ?
C10 H10B 0.9800 . ?
C10 H10C 0.9800 . ?
C11 C18 1.484(9) . ?
C11 C12 1.491(9) . ?
C12 C17 1.387(8) . ?
C12 C13 1.393(9) . ?
C13 C14 1.383(9) . ?
C13 H13 0.9500 . ?
C14 C15 1.397(9) . ?
C14 H14 0.9500 . ?
C15 C16 1.383(10) . ?
C15 H15 0.9500 . ?
C16 C17 1.395(9) . ?
C16 H16 0.9500 . ?
C17 H17 0.9500 . ?
C18 C19 1.401(8) . ?
C18 C23 1.406(9) . ?
C19 C20 1.388(8) . ?
C19 H19 0.9500 . ?
C20 C21 1.386(9) . ?
C20 H20 0.9500 . ?
C21 C22 1.377(9) . ?
C21 H21 0.9500 . ?
C22 C23 1.390(9) . ?
C22 H22 0.9500 . ?
C23 H23 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
C5 O1 C1 114.1(5) . . ?
C11 N1 C3 116.9(5) . . ?
O1 C1 C8 108.4(5) . . ?
O1 C1 C9 106.5(5) . . ?
C8 C1 C9 107.3(6) . . ?
O1 C1 C2 108.3(5) . . ?
C8 C1 C2 113.0(5) . . ?
C9 C1 C2 113.0(5) . . ?
C1 C2 C7 109.5(5) . . ?
C1 C2 C3 108.4(5) . . ?
C7 C2 C3 108.2(5) . . ?
C1 C2 H2 110.2 . . ?
C7 C2 H2 110.2 . . ?
C3 C2 H2 110.2 . . ?
N1 C3 C4 110.5(6) . . ?
N1 C3 C2 109.3(5) . . ?
C4 C3 C2 108.0(5) . . ?
N1 C3 H3 109.7 . . ?
C4 C3 H3 109.7 . . ?
C2 C3 H3 109.7 . . ?
C5 C4 C3 110.0(5) . . ?
C5 C4 H4A 109.7 . . ?
C3 C4 H4A 109.7 . . ?
C5 C4 H4B 109.7 . . ?
C3 C4 H4B 109.7 . . ?
H4A C4 H4B 108.2 . . ?
O1 C5 C10 105.4(5) . . ?
O1 C5 C4 108.4(6) . . ?
C10 C5 C4 113.1(5) . . ?
O1 C5 C6 108.6(5) . . ?
C10 C5 C6 111.8(6) . . ?
C4 C5 C6 109.3(5) . . ?
C5 C6 C7 109.6(5) . . ?
C5 C6 H6A 109.7 . . ?
C7 C6 H6A 109.7 . . ?
C5 C6 H6B 109.7 . . ?
C7 C6 H6B 109.7 . . ?
H6A C6 H6B 108.2 . . ?
C2 C7 C6 107.8(5) . . ?
C2 C7 H7A 110.1 . . ?
C6 C7 H7A 110.1 . . ?
C2 C7 H7B 110.1 . . ?
C6 C7 H7B 110.1 . . ?
H7A C7 H7B 108.5 . . ?
C1 C8 H8A 109.5 . . ?
C1 C8 H8B 109.5 . . ?
H8A C8 H8B 109.5 . . ?
C1 C8 H8C 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
C1 C9 H9A 109.5 . . ?
C1 C9 H9B 109.5 . . ?
H9A C9 H9B 109.5 . . ?
C1 C9 H9C 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
C5 C10 H10A 109.5 . . ?
C5 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
C5 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
N1 C11 C18 125.0(6) . . ?
N1 C11 C12 117.3(6) . . ?
C18 C11 C12 117.7(5) . . ?
C17 C12 C13 118.4(6) . . ?
C17 C12 C11 120.5(6) . . ?
C13 C12 C11 121.0(5) . . ?
C14 C13 C12 120.6(6) . . ?
C14 C13 H13 119.7 . . ?
C12 C13 H13 119.7 . . ?
C13 C14 C15 120.7(7) . . ?
C13 C14 H14 119.6 . . ?
C15 C14 H14 119.6 . . ?
C16 C15 C14 119.0(6) . . ?
C16 C15 H15 120.5 . . ?
C14 C15 H15 120.5 . . ?
C15 C16 C17 119.9(6) . . ?
C15 C16 H16 120.0 . . ?
C17 C16 H16 120.0 . . ?
C12 C17 C16 121.3(6) . . ?
C12 C17 H17 119.4 . . ?
C16 C17 H17 119.4 . . ?
C19 C18 C23 119.0(6) . . ?
C19 C18 C11 119.7(6) . . ?
C23 C18 C11 121.3(6) . . ?
C20 C19 C18 119.7(6) . . ?
C20 C19 H19 120.1 . . ?
C18 C19 H19 120.1 . . ?
C21 C20 C19 121.0(6) . . ?
C21 C20 H20 119.5 . . ?
C19 C20 H20 119.5 . . ?
C22 C21 C20 119.5(6) . . ?
C22 C21 H21 120.3 . . ?
C20 C21 H21 120.3 . . ?
C21 C22 C23 120.8(6) . . ?
C21 C22 H22 119.6 . . ?
C23 C22 H22 119.6 . . ?
C22 C23 C18 120.0(6) . . ?
C22 C23 H23 120.0 . . ?
C18 C23 H23 120.0 . . ?

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
C5 O1 C1 C8 -111.5(6) . . . . ?
C5 O1 C1 C9 133.3(5) . . . . ?
C5 O1 C1 C2 11.5(7) . . . . ?
O1 C1 C2 C7 -65.0(7) . . . . ?
C8 C1 C2 C7 55.1(7) . . . . ?
C9 C1 C2 C7 177.3(5) . . . . ?
O1 C1 C2 C3 52.9(7) . . . . ?
C8 C1 C2 C3 173.0(5) . . . . ?
C9 C1 C2 C3 -64.8(7) . . . . ?
C11 N1 C3 C4 89.7(6) . . . . ?
C11 N1 C3 C2 -151.5(6) . . . . ?
C1 C2 C3 N1 175.6(5) . . . . ?
C7 C2 C3 N1 -65.7(6) . . . . ?
C1 C2 C3 C4 -64.1(7) . . . . ?
C7 C2 C3 C4 54.6(7) . . . . ?
N1 C3 C4 C5 130.2(6) . . . . ?
C2 C3 C4 C5 10.7(8) . . . . ?
C1 O1 C5 C10 172.3(5) . . . . ?
C1 O1 C5 C4 -66.4(6) . . . . ?
C1 O1 C5 C6 52.3(7) . . . . ?
C3 C4 C5 O1 51.5(7) . . . . ?
C3 C4 C5 C10 168.0(6) . . . . ?
C3 C4 C5 C6 -66.7(7) . . . . ?
O1 C5 C6 C7 -65.8(7) . . . . ?
C10 C5 C6 C7 178.4(6) . . . . ?
C4 C5 C6 C7 52.4(7) . . . . ?
C1 C2 C7 C6 49.5(7) . . . . ?
C3 C2 C7 C6 -68.4(6) . . . . ?
C5 C6 C7 C2 12.8(7) . . . . ?
C3 N1 C11 C18 -1.8(9) . . . . ?
C3 N1 C11 C12 -179.2(5) . . . . ?
N1 C11 C12 C17 -162.3(6) . . . . ?
C18 C11 C12 C17 20.1(9) . . . . ?
N1 C11 C12 C13 17.7(9) . . . . ?
C18 C11 C12 C13 -159.8(6) . . . . ?
C17 C12 C13 C14 0.7(9) . . . . ?
C11 C12 C13 C14 -179.3(6) . . . . ?
C12 C13 C14 C15 0.5(10) . . . . ?
C13 C14 C15 C16 -0.6(10) . . . . ?
C14 C15 C16 C17 -0.4(10) . . . . ?
C13 C12 C17 C16 -1.8(10) . . . . ?
C11 C12 C17 C16 178.2(6) . . . . ?
C15 C16 C17 C12 1.7(10) . . . . ?
N1 C11 C18 C19 -85.4(8) . . . . ?
C12 C11 C18 C19 91.9(7) . . . . ?
N1 C11 C18 C23 94.0(8) . . . . ?
C12 C11 C18 C23 -88.7(8) . . . . ?
C23 C18 C19 C20 0.6(9) . . . . ?
C11 C18 C19 C20 180.0(6) . . . . ?
C18 C19 C20 C21 -0.1(9) . . . . ?
C19 C20 C21 C22 -0.3(10) . . . . ?
C20 C21 C22 C23 0.2(10) . . . . ?
C21 C22 C23 C18 0.3(10) . . . . ?
C19 C18 C23 C22 -0.7(10) . . . . ?
C11 C18 C23 C22 179.9(6) . . . . ?

_refine_diff_density_max         0.327
_refine_diff_density_min         -0.289
_refine_diff_density_rms         0.075


_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: Diethyl ether'
####################################################################### 
# 
# 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_14_a
_audit_block_doi                 10.5517/ccdc.csd.cc239b0s
_database_code_depnum_ccdc_archive 'CCDC 1945374'
loop_
_audit_author_name
_audit_author_address
'Jeffery A. Bertke'
;Georgetown University
United States of America
;
_audit_update_record             
;
2019-08-03 deposited with the CCDC.	2021-11-23 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C36 H39 Cu N3'
_chemical_formula_sum            'C36 H39 Cu N3'
_chemical_formula_weight         577.24

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'
Cu Cu 0.3201 1.2651 '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'

_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                   8.9066(6)
_cell_length_b                   14.0911(9)
_cell_length_c                   24.8477(19)
_cell_angle_alpha                90
_cell_angle_beta                 97.140(4)
_cell_angle_gamma                90
_cell_volume                     3094.3(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    7716
_cell_measurement_theta_min      2.19
_cell_measurement_theta_max      26.78
_exptl_crystal_description       prism
_exptl_crystal_colour            ?
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.239
_exptl_crystal_F_000             1220
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.120
_exptl_crystal_size_min          0.100
_exptl_absorpt_coefficient_mu    0.734
_shelx_estimated_absorpt_T_min   0.867
_shelx_estimated_absorpt_T_max   0.930
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.5341
_exptl_absorpt_correction_T_max  0.7455
_exptl_absorpt_process_details   'SADABS V2016/2 (Bruker, 2016)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  'multilayer mirrors'
_diffrn_measurement_device       'Bruker APEX DUO/ApexII CCD'
_diffrn_measurement_method       'profile data from φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            32868
_diffrn_reflns_av_unetI/netI     0.0525
_diffrn_reflns_av_R_equivalents  0.0730
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_l_min       -31
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_theta_min         1.652
_diffrn_reflns_theta_max         27.333
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.990
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.990
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.990
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             6923
_reflns_number_gt                5032
_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       'APEX3 V2016.5-0 (Bruker, 2016)'
_computing_cell_refinement       'SAINT V8.37A (Bruker, 2005)'
_computing_data_reduction        
; 
SAINT V8.37A, XPREP v2014/2, SADABS V2016/2 (Bruker, 2016) 
;
_computing_structure_solution    'SHELX-2014-5 (Sheldrick, 2015)'
_computing_structure_refinement  'SHELX-2018-3 (Sheldrick, 2015)'
_computing_molecular_graphics    'SHELXLE v932 (Hubschle, 2011)'
_computing_publication_material  'XCIF V2014-2 (Bruker, 2014)'

_refine_special_details          
; 
Structure was phased by intrinsic methods (Sheldrick, 2015).  Systematic 
conditions suggested the ambiguous space group.  The space group choice was 
confirmed by successful convergence of the full-matrix least-squares 
refinement on F².  The final map had no other significant features.  A 
final analysis of variance between observed and calculated structure factors 
showed some dependence on amplitude and little dependence on resolution. 
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0714P)²+2.0528P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     intrinsic
_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         6923
_refine_ls_number_parameters     369
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0733
_refine_ls_R_factor_gt           0.0456
_refine_ls_wR_factor_ref         0.1342
_refine_ls_wR_factor_gt          0.1181
_refine_ls_goodness_of_fit_ref   1.011
_refine_ls_restrained_S_all      1.011
_refine_ls_shift/su_max          0.002
_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 0.62318(4) 0.77524(2) 0.63101(2) 0.02150(11) Uani 1 1 d . . . . .
N1 N 0.4698(2) 0.86030(15) 0.64053(8) 0.0180(4) Uani 1 1 d . . . . .
C1 C 0.3770(3) 0.90271(17) 0.60174(10) 0.0183(5) Uani 1 1 d . . . . .
N2 N 0.6090(2) 0.79334(14) 0.55636(8) 0.0173(4) Uani 1 1 d . . . . .
C2 C 0.3901(3) 0.89172(18) 0.54662(10) 0.0196(5) Uani 1 1 d . . . . .
H2 H 0.314361 0.920515 0.521570 0.024 Uiso 1 1 calc R U . . .
N3 N 0.7359(3) 0.70543(15) 0.67483(9) 0.0227(5) Uani 1 1 d . . . . .
C3 C 0.5042(3) 0.84232(17) 0.52521(10) 0.0184(5) Uani 1 1 d . . . . .
C4 C 0.2525(3) 0.96568(19) 0.61764(11) 0.0238(6) Uani 1 1 d . . . . .
H4A H 0.176197 0.926621 0.632338 0.036 Uiso 1 1 calc R U . . .
H4B H 0.205402 1.000128 0.585655 0.036 Uiso 1 1 calc R U . . .
H4C H 0.295249 1.011146 0.645227 0.036 Uiso 1 1 calc R U . . .
C5 C 0.5097(3) 0.84689(19) 0.46487(10) 0.0232(5) Uani 1 1 d . . . . .
H5A H 0.597635 0.884347 0.457538 0.035 Uiso 1 1 calc R U . . .
H5B H 0.417066 0.876771 0.447242 0.035 Uiso 1 1 calc R U . . .
H5C H 0.518029 0.782513 0.450613 0.035 Uiso 1 1 calc R U . . .
C6 C 0.4506(3) 0.87912(17) 0.69638(10) 0.0183(5) Uani 1 1 d . . . . .
C7 C 0.5314(3) 0.95331(18) 0.72382(11) 0.0231(6) Uani 1 1 d . . . . .
C8 C 0.5114(3) 0.9692(2) 0.77766(11) 0.0278(6) Uani 1 1 d . . . . .
H8 H 0.565274 1.019626 0.796668 0.033 Uiso 1 1 calc R U . . .
C9 C 0.4155(3) 0.9140(2) 0.80470(11) 0.0291(6) Uani 1 1 d . . . . .
C10 C 0.3377(3) 0.8405(2) 0.77622(11) 0.0275(6) Uani 1 1 d . . . . .
H10 H 0.271511 0.802085 0.794087 0.033 Uiso 1 1 calc R U . . .
C11 C 0.3540(3) 0.82154(19) 0.72222(10) 0.0214(5) Uani 1 1 d . . . . .
C12 C 0.6359(3) 1.0143(2) 0.69545(12) 0.0310(6) Uani 1 1 d . . . . .
H12A H 0.715664 0.974698 0.683295 0.047 Uiso 1 1 calc R U . . .
H12B H 0.681744 1.062858 0.720553 0.047 Uiso 1 1 calc R U . . .
H12C H 0.578436 1.045074 0.664024 0.047 Uiso 1 1 calc R U . . .
C13 C 0.3967(4) 0.9332(3) 0.86326(12) 0.0428(8) Uani 1 1 d . . . . .
H13A H 0.488022 0.964151 0.881212 0.064 Uiso 1 1 calc R U . . .
H13B H 0.380647 0.873155 0.881595 0.064 Uiso 1 1 calc R U . . .
H13C H 0.309241 0.974798 0.864979 0.064 Uiso 1 1 calc R U . . .
C14 C 0.2694(4) 0.7410(2) 0.69233(12) 0.0318(7) Uani 1 1 d . . . . .
H14A H 0.207837 0.708389 0.716667 0.048 Uiso 1 1 calc R U . . .
H14B H 0.341759 0.696223 0.679835 0.048 Uiso 1 1 calc R U . . .
H14C H 0.203525 0.766114 0.661031 0.048 Uiso 1 1 calc R U . . .
C15 C 0.7417(3) 0.76081(18) 0.53431(9) 0.0171(5) Uani 1 1 d . . . . .
C16 C 0.7505(3) 0.66731(18) 0.51554(9) 0.0189(5) Uani 1 1 d . . . . .
C17 C 0.8847(3) 0.63804(19) 0.49737(10) 0.0222(5) Uani 1 1 d . . . . .
H17 H 0.891215 0.575087 0.484172 0.027 Uiso 1 1 calc R U . . .
C18 C 1.0096(3) 0.6973(2) 0.49777(11) 0.0236(6) Uani 1 1 d . . . . .
C19 C 0.9969(3) 0.78947(19) 0.51683(10) 0.0227(6) Uani 1 1 d . . . . .
H19 H 1.080943 0.831132 0.517438 0.027 Uiso 1 1 calc R U . . .
C20 C 0.8649(3) 0.82244(18) 0.53502(10) 0.0200(5) Uani 1 1 d . . . . .
C21 C 0.6186(3) 0.60111(19) 0.51582(11) 0.0255(6) Uani 1 1 d . . . . .
H21A H 0.645789 0.538409 0.502979 0.038 Uiso 1 1 calc R U . . .
H21B H 0.531809 0.626013 0.491856 0.038 Uiso 1 1 calc R U . . .
H21C H 0.591971 0.595686 0.552799 0.038 Uiso 1 1 calc R U . . .
C22 C 1.1535(3) 0.6638(2) 0.47749(13) 0.0344(7) Uani 1 1 d . . . . .
H22A H 1.143703 0.596507 0.467633 0.052 Uiso 1 1 calc R U . . .
H22B H 1.238696 0.672046 0.506093 0.052 Uiso 1 1 calc R U . . .
H22C H 1.171495 0.700948 0.445582 0.052 Uiso 1 1 calc R U . . .
C23 C 0.8551(3) 0.92215(19) 0.55663(11) 0.0260(6) Uani 1 1 d . . . . .
H23A H 0.862109 0.920292 0.596285 0.039 Uiso 1 1 calc R U . . .
H23B H 0.758440 0.950608 0.541737 0.039 Uiso 1 1 calc R U . . .
H23C H 0.938541 0.960236 0.545877 0.039 Uiso 1 1 calc R U . . .
C24 C 0.8220(3) 0.65453(17) 0.70797(10) 0.0191(5) Uani 1 1 d . . . . .
C25 C 0.8170(3) 0.66692(17) 0.76743(10) 0.0190(5) Uani 1 1 d . . . . .
C26 C 0.9475(3) 0.65633(18) 0.80478(10) 0.0214(5) Uani 1 1 d . . . . .
H26 H 1.038995 0.634874 0.792875 0.026 Uiso 1 1 calc R U . . .
C27 C 0.9429(3) 0.67731(19) 0.85941(11) 0.0253(6) Uani 1 1 d . . . . .
H27 H 1.031761 0.670394 0.884549 0.030 Uiso 1 1 calc R U . . .
C28 C 0.8109(3) 0.70795(18) 0.87725(11) 0.0251(6) Uani 1 1 d . . . . .
H28 H 0.808384 0.721952 0.914526 0.030 Uiso 1 1 calc R U . . .
C29 C 0.6811(3) 0.71826(19) 0.84034(11) 0.0253(6) Uani 1 1 d . . . . .
H29 H 0.589687 0.739298 0.852456 0.030 Uiso 1 1 calc R U . . .
C30 C 0.6847(3) 0.69804(18) 0.78612(10) 0.0228(6) Uani 1 1 d . . . . .
H30 H 0.595472 0.705494 0.761252 0.027 Uiso 1 1 calc R U . . .
C31 C 0.9275(3) 0.58510(17) 0.68742(10) 0.0190(5) Uani 1 1 d . . . . .
C32 C 0.9849(3) 0.60342(19) 0.63850(10) 0.0217(5) Uani 1 1 d . . . . .
H32 H 0.957584 0.660226 0.619119 0.026 Uiso 1 1 calc R U . . .
C33 C 1.0813(3) 0.5390(2) 0.61820(11) 0.0275(6) Uani 1 1 d . . . . .
H33 H 1.120386 0.552214 0.585119 0.033 Uiso 1 1 calc R U . . .
C34 C 1.1209(3) 0.4558(2) 0.64583(12) 0.0308(6) Uani 1 1 d . . . . .
H34 H 1.187943 0.412245 0.631970 0.037 Uiso 1 1 calc R U . . .
C35 C 1.0626(3) 0.43594(19) 0.69378(12) 0.0295(6) Uani 1 1 d . . . . .
H35 H 1.088199 0.378177 0.712406 0.035 Uiso 1 1 calc R U . . .
C36 C 0.9666(3) 0.50046(18) 0.71471(11) 0.0234(6) Uani 1 1 d . . . . .
H36 H 0.927536 0.486758 0.747734 0.028 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.
;

_exptl_special_details           
; 
One distinct cell was identified using APEX3 (Bruker, 2016).  Five frame 
series were integrated and filtered for statistical outliers using SAINT 
(Bruker, 2016) then corrected for absorption by integration using 
SAINT/SADABS v2014/2 (Bruker, 2016) to sort, merge, and scale the combined 
data.  No decay correction was applied.    
;

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 N3 1.700(2) . ?
Cu1 N1 1.855(2) . ?
Cu1 N2 1.861(2) . ?
N1 C1 1.331(3) . ?
N1 C6 1.444(3) . ?
C1 C2 1.397(3) . ?
C1 C4 1.510(3) . ?
N2 C3 1.329(3) . ?
N2 C15 1.438(3) . ?
C2 C3 1.391(4) . ?
C2 H2 0.9500 . ?
N3 C24 1.274(3) . ?
C3 C5 1.508(3) . ?
C4 H4A 0.9800 . ?
C4 H4B 0.9800 . ?
C4 H4C 0.9800 . ?
C5 H5A 0.9800 . ?
C5 H5B 0.9800 . ?
C5 H5C 0.9800 . ?
C6 C11 1.396(4) . ?
C6 C7 1.398(4) . ?
C7 C8 1.389(4) . ?
C7 C12 1.506(4) . ?
C8 C9 1.388(4) . ?
C8 H8 0.9500 . ?
C9 C10 1.390(4) . ?
C9 C13 1.510(4) . ?
C10 C11 1.393(4) . ?
C10 H10 0.9500 . ?
C11 C14 1.506(4) . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12C 0.9800 . ?
C13 H13A 0.9800 . ?
C13 H13B 0.9800 . ?
C13 H13C 0.9800 . ?
C14 H14A 0.9800 . ?
C14 H14B 0.9800 . ?
C14 H14C 0.9800 . ?
C15 C20 1.398(4) . ?
C15 C16 1.403(3) . ?
C16 C17 1.392(4) . ?
C16 C21 1.501(4) . ?
C17 C18 1.390(4) . ?
C17 H17 0.9500 . ?
C18 C19 1.391(4) . ?
C18 C22 1.510(4) . ?
C19 C20 1.390(4) . ?
C19 H19 0.9500 . ?
C20 C23 1.510(4) . ?
C21 H21A 0.9800 . ?
C21 H21B 0.9800 . ?
C21 H21C 0.9800 . ?
C22 H22A 0.9800 . ?
C22 H22B 0.9800 . ?
C22 H22C 0.9800 . ?
C23 H23A 0.9800 . ?
C23 H23B 0.9800 . ?
C23 H23C 0.9800 . ?
C24 C31 1.490(3) . ?
C24 C25 1.494(3) . ?
C25 C30 1.390(4) . ?
C25 C26 1.402(4) . ?
C26 C27 1.395(4) . ?
C26 H26 0.9500 . ?
C27 C28 1.377(4) . ?
C27 H27 0.9500 . ?
C28 C29 1.391(4) . ?
C28 H28 0.9500 . ?
C29 C30 1.381(4) . ?
C29 H29 0.9500 . ?
C30 H30 0.9500 . ?
C31 C36 1.395(4) . ?
C31 C32 1.400(4) . ?
C32 C33 1.387(4) . ?
C32 H32 0.9500 . ?
C33 C34 1.383(4) . ?
C33 H33 0.9500 . ?
C34 C35 1.386(4) . ?
C34 H34 0.9500 . ?
C35 C36 1.392(4) . ?
C35 H35 0.9500 . ?
C36 H36 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
N3 Cu1 N1 132.69(10) . . ?
N3 Cu1 N2 132.78(10) . . ?
N1 Cu1 N2 94.53(9) . . ?
C1 N1 C6 118.5(2) . . ?
C1 N1 Cu1 126.78(17) . . ?
C6 N1 Cu1 114.73(15) . . ?
N1 C1 C2 122.7(2) . . ?
N1 C1 C4 119.0(2) . . ?
C2 C1 C4 118.3(2) . . ?
C3 N2 C15 119.6(2) . . ?
C3 N2 Cu1 127.38(17) . . ?
C15 N2 Cu1 112.29(15) . . ?
C3 C2 C1 125.7(2) . . ?
C3 C2 H2 117.1 . . ?
C1 C2 H2 117.1 . . ?
C24 N3 Cu1 178.9(2) . . ?
N2 C3 C2 122.1(2) . . ?
N2 C3 C5 119.6(2) . . ?
C2 C3 C5 118.3(2) . . ?
C1 C4 H4A 109.5 . . ?
C1 C4 H4B 109.5 . . ?
H4A C4 H4B 109.5 . . ?
C1 C4 H4C 109.5 . . ?
H4A C4 H4C 109.5 . . ?
H4B C4 H4C 109.5 . . ?
C3 C5 H5A 109.5 . . ?
C3 C5 H5B 109.5 . . ?
H5A C5 H5B 109.5 . . ?
C3 C5 H5C 109.5 . . ?
H5A C5 H5C 109.5 . . ?
H5B C5 H5C 109.5 . . ?
C11 C6 C7 121.3(2) . . ?
C11 C6 N1 119.3(2) . . ?
C7 C6 N1 119.4(2) . . ?
C8 C7 C6 118.1(3) . . ?
C8 C7 C12 121.3(2) . . ?
C6 C7 C12 120.6(2) . . ?
C9 C8 C7 122.4(3) . . ?
C9 C8 H8 118.8 . . ?
C7 C8 H8 118.8 . . ?
C8 C9 C10 117.9(2) . . ?
C8 C9 C13 121.0(3) . . ?
C10 C9 C13 121.1(3) . . ?
C9 C10 C11 121.9(3) . . ?
C9 C10 H10 119.1 . . ?
C11 C10 H10 119.1 . . ?
C10 C11 C6 118.4(2) . . ?
C10 C11 C14 120.9(2) . . ?
C6 C11 C14 120.7(2) . . ?
C7 C12 H12A 109.5 . . ?
C7 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
C7 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C9 C13 H13A 109.5 . . ?
C9 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
C9 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
C11 C14 H14A 109.5 . . ?
C11 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
C11 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C20 C15 C16 120.7(2) . . ?
C20 C15 N2 118.6(2) . . ?
C16 C15 N2 120.6(2) . . ?
C17 C16 C15 118.2(2) . . ?
C17 C16 C21 121.4(2) . . ?
C15 C16 C21 120.4(2) . . ?
C18 C17 C16 122.6(2) . . ?
C18 C17 H17 118.7 . . ?
C16 C17 H17 118.7 . . ?
C17 C18 C19 117.7(2) . . ?
C17 C18 C22 121.4(3) . . ?
C19 C18 C22 120.9(3) . . ?
C20 C19 C18 122.0(2) . . ?
C20 C19 H19 119.0 . . ?
C18 C19 H19 119.0 . . ?
C19 C20 C15 118.8(2) . . ?
C19 C20 C23 121.0(2) . . ?
C15 C20 C23 120.1(2) . . ?
C16 C21 H21A 109.5 . . ?
C16 C21 H21B 109.5 . . ?
H21A C21 H21B 109.5 . . ?
C16 C21 H21C 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
C18 C22 H22A 109.5 . . ?
C18 C22 H22B 109.5 . . ?
H22A C22 H22B 109.5 . . ?
C18 C22 H22C 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
C20 C23 H23A 109.5 . . ?
C20 C23 H23B 109.5 . . ?
H23A C23 H23B 109.5 . . ?
C20 C23 H23C 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 109.5 . . ?
N3 C24 C31 120.2(2) . . ?
N3 C24 C25 118.9(2) . . ?
C31 C24 C25 120.9(2) . . ?
C30 C25 C26 118.7(2) . . ?
C30 C25 C24 119.9(2) . . ?
C26 C25 C24 121.2(2) . . ?
C27 C26 C25 120.0(2) . . ?
C27 C26 H26 120.0 . . ?
C25 C26 H26 120.0 . . ?
C28 C27 C26 120.6(3) . . ?
C28 C27 H27 119.7 . . ?
C26 C27 H27 119.7 . . ?
C27 C28 C29 119.6(2) . . ?
C27 C28 H28 120.2 . . ?
C29 C28 H28 120.2 . . ?
C30 C29 C28 120.2(3) . . ?
C30 C29 H29 119.9 . . ?
C28 C29 H29 119.9 . . ?
C29 C30 C25 121.0(3) . . ?
C29 C30 H30 119.5 . . ?
C25 C30 H30 119.5 . . ?
C36 C31 C32 118.9(2) . . ?
C36 C31 C24 121.7(2) . . ?
C32 C31 C24 119.4(2) . . ?
C33 C32 C31 120.3(3) . . ?
C33 C32 H32 119.8 . . ?
C31 C32 H32 119.8 . . ?
C34 C33 C32 120.4(3) . . ?
C34 C33 H33 119.8 . . ?
C32 C33 H33 119.8 . . ?
C33 C34 C35 119.9(3) . . ?
C33 C34 H34 120.1 . . ?
C35 C34 H34 120.1 . . ?
C34 C35 C36 120.2(3) . . ?
C34 C35 H35 119.9 . . ?
C36 C35 H35 119.9 . . ?
C35 C36 C31 120.3(3) . . ?
C35 C36 H36 119.9 . . ?
C31 C36 H36 119.9 . . ?

_refine_diff_density_max         0.637
_refine_diff_density_min         -0.896
_refine_diff_density_rms         0.078

####################################################################### 
# 
# 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_14_a_CCDC1
_audit_block_doi                 10.5517/ccdc.csd.cc23456n
_database_code_depnum_ccdc_archive 'CCDC 1940420'
loop_
_audit_author_name
_audit_author_address
'Jeffery A. Bertke'
;Georgetown University
United States of America
;
_audit_update_record             
;
2019-08-03 deposited with the CCDC.	2021-11-23 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2017/1
_shelx_SHELXL_version_number     2017/1
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C17 H17 N O2'
_chemical_formula_sum            'C17 H17 N O2'
_chemical_formula_weight         267.31

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'
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'

_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                   16.2558(13)
_cell_length_b                   7.4638(6)
_cell_length_c                   11.6496(10)
_cell_angle_alpha                90
_cell_angle_beta                 101.984(2)
_cell_angle_gamma                90
_cell_volume                     1382.6(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    2019
_cell_measurement_theta_min      3.01
_cell_measurement_theta_max      22.32
_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.284
_exptl_crystal_F_000             568
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.154
_exptl_crystal_size_mid          0.134
_exptl_crystal_size_min          0.068
_exptl_absorpt_coefficient_mu    0.084
_shelx_estimated_absorpt_T_min   0.987
_shelx_estimated_absorpt_T_max   0.994
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.99273
_exptl_absorpt_correction_T_max  0.99583
_exptl_absorpt_process_details   'SADABS V2016/2 (Bruker, 2016)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  'multilayer mirrors'
_diffrn_measurement_device       'Bruker APEX DUO/ApexII CCD'
_diffrn_measurement_method       'profile data from φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            18777
_diffrn_reflns_av_unetI/netI     0.0504
_diffrn_reflns_av_R_equivalents  0.0790
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         2.562
_diffrn_reflns_theta_max         25.340
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             2527
_reflns_number_gt                1742
_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       'APEX3 V2016.5-0 (Bruker, 2016)'
_computing_cell_refinement       'SAINT V8.37A (Bruker, 2005)'
_computing_data_reduction        
; 
SAINT V8.37A, XPREP v2014/2, SADABS V2016/2 (Bruker, 2016) 
;
_computing_structure_solution    'SHELX-2014-5 (Sheldrick, 2015)'
_computing_structure_refinement  'SHELX-2018-3 (Sheldrick, 2015)'
_computing_molecular_graphics    'SHELXLE v932 (Hubschle, 2011)'
_computing_publication_material  'XCIF V2014-2 (Bruker, 2014)'

_refine_special_details          
; 
Structure was phased by intrinsic methods (Sheldrick, 2015).  Systematic 
conditions suggested the ambiguous space group.  The space group choice was 
confirmed by successful convergence of the full-matrix least-squares 
refinement on F².  The final map had no significant features.  A final 
analysis of variance between observed and calculated structure factors 
showed little dependence on amplitude and resolution. 
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0410P)²+0.2390P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     intrinsic
_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         2527
_refine_ls_number_parameters     181
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0794
_refine_ls_R_factor_gt           0.0438
_refine_ls_wR_factor_ref         0.0952
_refine_ls_wR_factor_gt          0.0835
_refine_ls_goodness_of_fit_ref   1.023
_refine_ls_restrained_S_all      1.023
_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
O1 O 0.11012(7) 0.68032(15) 0.70004(10) 0.0197(3) Uani 1 1 d . . . . .
O2 O 0.00538(7) 0.75961(16) 0.47933(10) 0.0219(3) Uani 1 1 d . . . . .
N1 N 0.22759(9) 0.71986(19) 0.62190(13) 0.0193(4) Uani 1 1 d . . . . .
C1 C 0.14086(10) 0.6635(2) 0.59377(15) 0.0189(4) Uani 1 1 d . . . . .
H1 H 0.135725 0.537359 0.564203 0.023 Uiso 1 1 calc R U . . .
C2 C 0.02129(11) 0.6438(2) 0.67679(16) 0.0211(4) Uani 1 1 d . . . . .
H2A H 0.000109 0.656284 0.750165 0.025 Uiso 1 1 calc R U . . .
H2B H 0.010942 0.519173 0.648427 0.025 Uiso 1 1 calc R U . . .
C3 C -0.02499(11) 0.7715(2) 0.58597(16) 0.0219(4) Uani 1 1 d . . . . .
H3A H -0.085808 0.743234 0.569830 0.026 Uiso 1 1 calc R U . . .
H3B H -0.017572 0.895436 0.616620 0.026 Uiso 1 1 calc R U . . .
C4 C 0.09380(10) 0.7920(2) 0.50258(16) 0.0210(4) Uani 1 1 d . . . . .
H4A H 0.104981 0.916584 0.530776 0.025 Uiso 1 1 calc R U . . .
H4B H 0.114611 0.778876 0.428968 0.025 Uiso 1 1 calc R U . . .
C5 C 0.28182(11) 0.6431(2) 0.57239(15) 0.0167(4) Uani 1 1 d . . . . .
C6 C 0.26429(10) 0.4837(2) 0.49221(15) 0.0166(4) Uani 1 1 d . . . . .
C7 C 0.22902(11) 0.5019(2) 0.37322(16) 0.0201(4) Uani 1 1 d . . . . .
H7 H 0.215605 0.617524 0.340658 0.024 Uiso 1 1 calc R U . . .
C8 C 0.21341(11) 0.3511(3) 0.30200(16) 0.0243(5) Uani 1 1 d . . . . .
H8 H 0.189828 0.364243 0.220719 0.029 Uiso 1 1 calc R U . . .
C9 C 0.23201(11) 0.1821(2) 0.34881(17) 0.0255(5) Uani 1 1 d . . . . .
H9 H 0.220299 0.079310 0.300073 0.031 Uiso 1 1 calc R U . . .
C10 C 0.26771(11) 0.1630(2) 0.46675(17) 0.0243(5) Uani 1 1 d . . . . .
H10 H 0.280867 0.046864 0.498767 0.029 Uiso 1 1 calc R U . . .
C11 C 0.28440(11) 0.3127(2) 0.53850(16) 0.0193(4) Uani 1 1 d . . . . .
H11 H 0.309539 0.298943 0.619226 0.023 Uiso 1 1 calc R U . . .
C12 C 0.36891(11) 0.7171(2) 0.59686(15) 0.0166(4) Uani 1 1 d . . . . .
C13 C 0.42454(11) 0.6798(2) 0.52398(16) 0.0190(4) Uani 1 1 d . . . . .
H13 H 0.408036 0.600470 0.459554 0.023 Uiso 1 1 calc R U . . .
C14 C 0.50378(11) 0.7571(2) 0.54428(16) 0.0231(4) Uani 1 1 d . . . . .
H14 H 0.540920 0.731550 0.493315 0.028 Uiso 1 1 calc R U . . .
C15 C 0.52899(12) 0.8716(2) 0.63864(17) 0.0230(4) Uani 1 1 d . . . . .
H15 H 0.583421 0.924000 0.652864 0.028 Uiso 1 1 calc R U . . .
C16 C 0.47428(12) 0.9091(3) 0.71206(17) 0.0256(5) Uani 1 1 d . . . . .
H16 H 0.491596 0.986800 0.777172 0.031 Uiso 1 1 calc R U . . .
C17 C 0.39483(11) 0.8347(2) 0.69161(16) 0.0229(4) Uani 1 1 d . . . . .
H17 H 0.357534 0.863064 0.741846 0.027 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.
;

_exptl_special_details           
; 
One distinct cell was identified using APEX3 (Bruker, 2016).  Five 
frame series were integrated and filtered for statistical outliers 
using SAINT (Bruker, 2016) then corrected for absorption by integration 
using SAINT/SADABS v2014/2 (Bruker, 2016) to sort, merge, and scale 
the combined data.  No decay correction was applied.    
;

loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
0.00 1.00 1.00 0.0230
0.00 1.00 -1.00 0.0430
0.00 1.00 0.00 0.0300
1.00 -1.00 -1.00 0.0630
1.00 1.00 -1.00 0.0500
-2.00 -2.00 -1.00 0.0310
2.00 0.00 1.00 0.0200
-2.00 0.00 -1.00 0.0620
-2.00 2.00 1.00 0.0310
-2.00 0.00 1.00 0.0270
1.00 0.00 -1.00 0.0760
-1.00 0.00 2.00 0.0100

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
O1 C1 1.434(2) . ?
O1 C2 1.439(2) . ?
O2 C4 1.427(2) . ?
O2 C3 1.432(2) . ?
N1 C5 1.284(2) . ?
N1 C1 1.442(2) . ?
C1 C4 1.516(2) . ?
C1 H1 1.0000 . ?
C2 C3 1.504(2) . ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?
C5 C12 1.491(2) . ?
C5 C6 1.503(2) . ?
C6 C7 1.392(2) . ?
C6 C11 1.397(2) . ?
C7 C8 1.390(2) . ?
C7 H7 0.9500 . ?
C8 C9 1.382(3) . ?
C8 H8 0.9500 . ?
C9 C10 1.383(3) . ?
C9 H9 0.9500 . ?
C10 C11 1.388(2) . ?
C10 H10 0.9500 . ?
C11 H11 0.9500 . ?
C12 C13 1.391(2) . ?
C12 C17 1.404(2) . ?
C13 C14 1.386(2) . ?
C13 H13 0.9500 . ?
C14 C15 1.385(3) . ?
C14 H14 0.9500 . ?
C15 C16 1.384(3) . ?
C15 H15 0.9500 . ?
C16 C17 1.380(2) . ?
C16 H16 0.9500 . ?
C17 H17 0.9500 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1 O1 C2 109.70(13) . . ?
C4 O2 C3 109.87(13) . . ?
C5 N1 C1 119.83(15) . . ?
O1 C1 N1 106.13(13) . . ?
O1 C1 C4 109.51(14) . . ?
N1 C1 C4 107.58(14) . . ?
O1 C1 H1 111.1 . . ?
N1 C1 H1 111.1 . . ?
C4 C1 H1 111.1 . . ?
O1 C2 C3 110.39(14) . . ?
O1 C2 H2A 109.6 . . ?
C3 C2 H2A 109.6 . . ?
O1 C2 H2B 109.6 . . ?
C3 C2 H2B 109.6 . . ?
H2A C2 H2B 108.1 . . ?
O2 C3 C2 111.04(14) . . ?
O2 C3 H3A 109.4 . . ?
C2 C3 H3A 109.4 . . ?
O2 C3 H3B 109.4 . . ?
C2 C3 H3B 109.4 . . ?
H3A C3 H3B 108.0 . . ?
O2 C4 C1 111.57(14) . . ?
O2 C4 H4A 109.3 . . ?
C1 C4 H4A 109.3 . . ?
O2 C4 H4B 109.3 . . ?
C1 C4 H4B 109.3 . . ?
H4A C4 H4B 108.0 . . ?
N1 C5 C12 117.49(15) . . ?
N1 C5 C6 124.97(16) . . ?
C12 C5 C6 117.54(15) . . ?
C7 C6 C11 119.22(16) . . ?
C7 C6 C5 121.83(15) . . ?
C11 C6 C5 118.95(15) . . ?
C8 C7 C6 120.12(17) . . ?
C8 C7 H7 119.9 . . ?
C6 C7 H7 119.9 . . ?
C9 C8 C7 120.35(17) . . ?
C9 C8 H8 119.8 . . ?
C7 C8 H8 119.8 . . ?
C8 C9 C10 119.89(17) . . ?
C8 C9 H9 120.1 . . ?
C10 C9 H9 120.1 . . ?
C9 C10 C11 120.26(17) . . ?
C9 C10 H10 119.9 . . ?
C11 C10 H10 119.9 . . ?
C10 C11 C6 120.14(17) . . ?
C10 C11 H11 119.9 . . ?
C6 C11 H11 119.9 . . ?
C13 C12 C17 118.54(16) . . ?
C13 C12 C5 121.38(15) . . ?
C17 C12 C5 120.00(16) . . ?
C14 C13 C12 120.75(17) . . ?
C14 C13 H13 119.6 . . ?
C12 C13 H13 119.6 . . ?
C15 C14 C13 120.23(18) . . ?
C15 C14 H14 119.9 . . ?
C13 C14 H14 119.9 . . ?
C16 C15 C14 119.52(17) . . ?
C16 C15 H15 120.2 . . ?
C14 C15 H15 120.2 . . ?
C17 C16 C15 120.67(18) . . ?
C17 C16 H16 119.7 . . ?
C15 C16 H16 119.7 . . ?
C16 C17 C12 120.28(17) . . ?
C16 C17 H17 119.9 . . ?
C12 C17 H17 119.9 . . ?

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
C2 O1 C1 N1 174.21(12) . . . . ?
C2 O1 C1 C4 58.35(17) . . . . ?
C5 N1 C1 O1 145.11(15) . . . . ?
C5 N1 C1 C4 -97.73(18) . . . . ?
C1 O1 C2 C3 -58.87(18) . . . . ?
C4 O2 C3 C2 -56.45(18) . . . . ?
O1 C2 C3 O2 58.02(19) . . . . ?
C3 O2 C4 C1 56.77(18) . . . . ?
O1 C1 C4 O2 -58.19(18) . . . . ?
N1 C1 C4 O2 -173.12(14) . . . . ?
C1 N1 C5 C12 174.83(14) . . . . ?
C1 N1 C5 C6 -5.5(3) . . . . ?
N1 C5 C6 C7 83.6(2) . . . . ?
C12 C5 C6 C7 -96.8(2) . . . . ?
N1 C5 C6 C11 -96.8(2) . . . . ?
C12 C5 C6 C11 82.9(2) . . . . ?
C11 C6 C7 C8 0.6(3) . . . . ?
C5 C6 C7 C8 -179.72(16) . . . . ?
C6 C7 C8 C9 0.6(3) . . . . ?
C7 C8 C9 C10 -1.1(3) . . . . ?
C8 C9 C10 C11 0.5(3) . . . . ?
C9 C10 C11 C6 0.8(3) . . . . ?
C7 C6 C11 C10 -1.3(3) . . . . ?
C5 C6 C11 C10 179.04(16) . . . . ?
N1 C5 C12 C13 -161.19(16) . . . . ?
C6 C5 C12 C13 19.1(2) . . . . ?
N1 C5 C12 C17 15.5(2) . . . . ?
C6 C5 C12 C17 -164.24(15) . . . . ?
C17 C12 C13 C14 -0.1(2) . . . . ?
C5 C12 C13 C14 176.59(15) . . . . ?
C12 C13 C14 C15 0.7(3) . . . . ?
C13 C14 C15 C16 -0.4(3) . . . . ?
C14 C15 C16 C17 -0.5(3) . . . . ?
C15 C16 C17 C12 1.1(3) . . . . ?
C13 C12 C17 C16 -0.8(3) . . . . ?
C5 C12 C17 C16 -177.53(16) . . . . ?

_refine_diff_density_max         0.149
_refine_diff_density_min         -0.229
_refine_diff_density_rms         0.044

