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

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
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data_nl1_etoh_0m_a
_database_code_depnum_ccdc_archive 'CCDC 2040548'
loop_
_audit_author_name
_audit_author_address
'Bhaskar Biswas'
;University of North Bengal
India
;
_audit_update_record             
;
2020-10-24 deposited with the CCDC.	2021-06-14 downloaded from the CCDC.
;
_audit_creation_date             2019-09-06
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/1
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C22 H17 N3'
_chemical_formula_sum            'C22 H17 N3'
_chemical_formula_weight         323.38
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/n 1'
_space_group_name_Hall           '-P 2yn'
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                   14.0160(17)
_cell_length_b                   8.1673(10)
_cell_length_c                   14.8905(19)
_cell_angle_alpha                90
_cell_angle_beta                 94.665(2)
_cell_angle_gamma                90
_cell_volume                     1698.9(4)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    3364
_cell_measurement_temperature    296.0(2)
_cell_measurement_theta_max      24.86
_cell_measurement_theta_min      2.74
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.076
_exptl_absorpt_correction_T_max  0.7452
_exptl_absorpt_correction_T_min  0.6896
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.0559 before and 0.0357 after correction. The Ratio of minimum to maximum transmission is 0.9254. The λ/2 correction factor is Not present.'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.264
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             680
_exptl_crystal_size_max          0.42
_exptl_crystal_size_mid          0.4
_exptl_crystal_size_min          0.4
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0203
_diffrn_reflns_av_unetI/netI     0.0213
_diffrn_reflns_Laue_measured_fraction_full 0.984
_diffrn_reflns_Laue_measured_fraction_max 0.984
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            9458
_diffrn_reflns_point_group_measured_fraction_full 0.984
_diffrn_reflns_point_group_measured_fraction_max 0.984
_diffrn_reflns_theta_full        25.006
_diffrn_reflns_theta_max         25.006
_diffrn_reflns_theta_min         2.745
_diffrn_ambient_temperature      296.0(2)
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.984
_diffrn_measured_fraction_theta_max 0.984
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2437
_reflns_number_total             2955
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT V8.38A (?, 2016)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.38A (?, 2016)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         0.140
_refine_diff_density_min         -0.223
_refine_diff_density_rms         0.038
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.061
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     230
_refine_ls_number_reflns         2955
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0477
_refine_ls_R_factor_gt           0.0388
_refine_ls_restrained_S_all      1.061
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0551P)²+0.1789P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0965
_refine_ls_wR_factor_ref         0.1026
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C4(H4), C5(H5), C19(H19), C20(H20), C21(H21), C10(H10), C9(H9), C8(H8),
 C14(H14), C15(H15), C16(H16), C22(H22), C3(H3), C2(H2A), C12(H12), C11(H11)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
N1 N 0.55306(8) 0.70200(13) 0.55587(7) 0.0418(3) Uani 1 1 d . . . . .
N2 N 0.61669(8) 0.54268(13) 0.40313(7) 0.0362(3) Uani 1 1 d . . . . .
N3 N 0.73416(8) 0.76835(14) 0.33408(7) 0.0429(3) Uani 1 1 d . . . . .
C4 C 0.53487(11) 0.96858(18) 0.61821(9) 0.0490(4) Uani 1 1 d . . . . .
H4 H 0.500139 1.038745 0.652401 0.059 Uiso 1 1 calc R . . . .
C5 C 0.50635(11) 0.80964(18) 0.60363(9) 0.0486(4) Uani 1 1 d . . . . .
H5 H 0.451114 0.774625 0.628498 0.058 Uiso 1 1 calc R . . . .
C1 C 0.63309(9) 0.75405(15) 0.52148(8) 0.0354(3) Uani 1 1 d . . . . .
C6 C 0.68540(9) 0.62341(15) 0.46923(8) 0.0351(3) Uani 1 1 d . . . . .
C18 C 0.58124(10) 0.63802(15) 0.32973(8) 0.0361(3) Uani 1 1 d . . . . .
C19 C 0.48928(11) 0.61710(17) 0.28894(9) 0.0464(4) Uani 1 1 d . . . . .
H19 H 0.448166 0.542270 0.312784 0.056 Uiso 1 1 calc R . . . .
C20 C 0.45838(12) 0.7064(2) 0.21330(10) 0.0582(4) Uani 1 1 d . . . . .
H20 H 0.397167 0.689380 0.185908 0.070 Uiso 1 1 calc R . . . .
C21 C 0.51729(13) 0.8203(2) 0.17817(10) 0.0601(4) Uani 1 1 d . . . . .
H21 H 0.495720 0.880665 0.127587 0.072 Uiso 1 1 calc R . . . .
C10 C 0.83698(12) 0.2700(2) 0.64274(13) 0.0689(5) Uani 1 1 d . . . . .
H10 H 0.871780 0.195459 0.679490 0.083 Uiso 1 1 calc R . . . .
C9 C 0.79608(13) 0.4032(2) 0.67956(11) 0.0668(5) Uani 1 1 d . . . . .
H9 H 0.802123 0.417999 0.741686 0.080 Uiso 1 1 calc R . . . .
C8 C 0.74565(11) 0.5163(2) 0.62510(9) 0.0503(4) Uani 1 1 d . . . . .
H8 H 0.719434 0.607802 0.650992 0.060 Uiso 1 1 calc R . . . .
C7 C 0.73377(9) 0.49506(16) 0.53280(8) 0.0386(3) Uani 1 1 d . . . . .
C17 C 0.64091(10) 0.75246(16) 0.29231(8) 0.0393(3) Uani 1 1 d . . . . .
C13 C 0.76155(10) 0.69994(16) 0.41665(8) 0.0391(3) Uani 1 1 d . . . . .
C14 C 0.85558(11) 0.7321(2) 0.43616(11) 0.0560(4) Uani 1 1 d . . . . .
H14 H 0.892646 0.700380 0.487878 0.067 Uiso 1 1 calc R . . . .
C15 C 0.88706(13) 0.8227(2) 0.36339(12) 0.0700(5) Uani 1 1 d . . . . .
H15 H 0.948854 0.861563 0.358820 0.084 Uiso 1 1 calc R . . . .
C16 C 0.81245(12) 0.8432(2) 0.30192(11) 0.0611(5) Uani 1 1 d . . . . .
H16 H 0.813524 0.898164 0.247317 0.073 Uiso 1 1 calc R . . . .
C22 C 0.60827(12) 0.84463(19) 0.21804(9) 0.0524(4) Uani 1 1 d . . . . .
H22 H 0.647826 0.923010 0.195077 0.063 Uiso 1 1 calc R . . . .
C3 C 0.61522(12) 1.02141(17) 0.58149(9) 0.0513(4) Uani 1 1 d . . . . .
H3 H 0.635840 1.129072 0.589327 0.062 Uiso 1 1 calc R . . . .
C2 C 0.66549(11) 0.91280(17) 0.53254(9) 0.0461(4) Uani 1 1 d . . . . .
H2A H 0.720766 0.946229 0.507183 0.055 Uiso 1 1 calc R . . . .
C12 C 0.77422(11) 0.35728(18) 0.49688(10) 0.0519(4) Uani 1 1 d . . . . .
H12 H 0.766022 0.338936 0.435090 0.062 Uiso 1 1 calc R . . . .
C11 C 0.82646(12) 0.2468(2) 0.55116(13) 0.0642(5) Uani 1 1 d . . . . .
H11 H 0.854509 0.156677 0.525674 0.077 Uiso 1 1 calc R . . . .
H2 H 0.5683(11) 0.4979(17) 0.4303(9) 0.046(4) Uiso 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
N1 C5 1.3353(17) . ?
N1 C1 1.3397(16) . ?
N2 C6 1.4754(16) . ?
N2 C18 1.3998(16) . ?
N2 H2 0.895(15) . ?
N3 C17 1.4071(19) . ?
N3 C13 1.3763(17) . ?
N3 C16 1.3758(18) . ?
C4 H4 0.9300 . ?
C4 C5 1.370(2) . ?
C4 C3 1.361(2) . ?
C5 H5 0.9300 . ?
C1 C6 1.5407(17) . ?
C1 C2 1.3792(19) . ?
C6 C7 1.5330(18) . ?
C6 C13 1.5096(17) . ?
C18 C19 1.3900(19) . ?
C18 C17 1.3997(18) . ?
C19 H19 0.9300 . ?
C19 C20 1.382(2) . ?
C20 H20 0.9300 . ?
C20 C21 1.375(2) . ?
C21 H21 0.9300 . ?
C21 C22 1.377(2) . ?
C10 H10 0.9300 . ?
C10 C9 1.365(3) . ?
C10 C11 1.373(3) . ?
C9 H9 0.9300 . ?
C9 C8 1.385(2) . ?
C8 H8 0.9300 . ?
C8 C7 1.3820(19) . ?
C7 C12 1.3868(19) . ?
C17 C22 1.3845(19) . ?
C13 C14 1.352(2) . ?
C14 H14 0.9300 . ?
C14 C15 1.412(2) . ?
C15 H15 0.9300 . ?
C15 C16 1.343(2) . ?
C16 H16 0.9300 . ?
C22 H22 0.9300 . ?
C3 H3 0.9300 . ?
C3 C2 1.378(2) . ?
C2 H2A 0.9300 . ?
C12 H12 0.9300 . ?
C12 C11 1.381(2) . ?
C11 H11 0.9300 . ?

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 N1 C1 117.18(12) . . ?
C6 N2 H2 111.0(9) . . ?
C18 N2 C6 116.31(10) . . ?
C18 N2 H2 110.2(9) . . ?
C13 N3 C17 122.62(11) . . ?
C16 N3 C17 128.73(12) . . ?
C16 N3 C13 108.60(13) . . ?
C5 C4 H4 120.8 . . ?
C3 C4 H4 120.8 . . ?
C3 C4 C5 118.47(13) . . ?
N1 C5 C4 123.96(14) . . ?
N1 C5 H5 118.0 . . ?
C4 C5 H5 118.0 . . ?
N1 C1 C6 114.88(11) . . ?
N1 C1 C2 122.04(12) . . ?
C2 C1 C6 123.08(11) . . ?
N2 C6 C1 109.56(10) . . ?
N2 C6 C7 109.77(10) . . ?
N2 C6 C13 106.83(10) . . ?
C7 C6 C1 111.50(10) . . ?
C13 C6 C1 111.14(10) . . ?
C13 C6 C7 107.91(10) . . ?
C19 C18 N2 122.04(12) . . ?
C19 C18 C17 118.09(12) . . ?
C17 C18 N2 119.78(12) . . ?
C18 C19 H19 119.7 . . ?
C20 C19 C18 120.62(14) . . ?
C20 C19 H19 119.7 . . ?
C19 C20 H20 119.7 . . ?
C21 C20 C19 120.61(15) . . ?
C21 C20 H20 119.7 . . ?
C20 C21 H21 120.1 . . ?
C20 C21 C22 119.84(14) . . ?
C22 C21 H21 120.1 . . ?
C9 C10 H10 120.2 . . ?
C9 C10 C11 119.63(16) . . ?
C11 C10 H10 120.2 . . ?
C10 C9 H9 119.8 . . ?
C10 C9 C8 120.50(16) . . ?
C8 C9 H9 119.8 . . ?
C9 C8 H8 119.6 . . ?
C7 C8 C9 120.86(15) . . ?
C7 C8 H8 119.6 . . ?
C8 C7 C6 122.66(12) . . ?
C8 C7 C12 117.75(13) . . ?
C12 C7 C6 119.40(11) . . ?
C18 C17 N3 116.69(11) . . ?
C22 C17 N3 122.52(13) . . ?
C22 C17 C18 120.79(14) . . ?
N3 C13 C6 118.28(12) . . ?
C14 C13 N3 108.02(12) . . ?
C14 C13 C6 133.39(12) . . ?
C13 C14 H14 126.4 . . ?
C13 C14 C15 107.27(15) . . ?
C15 C14 H14 126.4 . . ?
C14 C15 H15 125.9 . . ?
C16 C15 C14 108.28(15) . . ?
C16 C15 H15 125.9 . . ?
N3 C16 H16 126.1 . . ?
C15 C16 N3 107.84(14) . . ?
C15 C16 H16 126.1 . . ?
C21 C22 C17 120.01(14) . . ?
C21 C22 H22 120.0 . . ?
C17 C22 H22 120.0 . . ?
C4 C3 H3 120.5 . . ?
C4 C3 C2 118.93(13) . . ?
C2 C3 H3 120.5 . . ?
C1 C2 H2A 120.3 . . ?
C3 C2 C1 119.40(13) . . ?
C3 C2 H2A 120.3 . . ?
C7 C12 H12 119.4 . . ?
C11 C12 C7 121.22(15) . . ?
C11 C12 H12 119.4 . . ?
C10 C11 C12 120.01(16) . . ?
C10 C11 H11 120.0 . . ?
C12 C11 H11 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
N1 C1 C6 N2 50.04(14) . . . . ?
N1 C1 C6 C7 -71.69(14) . . . . ?
N1 C1 C6 C13 167.87(11) . . . . ?
N1 C1 C2 C3 1.0(2) . . . . ?
N2 C6 C7 C8 -134.61(13) . . . . ?
N2 C6 C7 C12 50.55(15) . . . . ?
N2 C6 C13 N3 37.22(15) . . . . ?
N2 C6 C13 C14 -150.11(15) . . . . ?
N2 C18 C19 C20 -176.13(12) . . . . ?
N2 C18 C17 N3 -2.15(16) . . . . ?
N2 C18 C17 C22 178.06(11) . . . . ?
N3 C17 C22 C21 177.95(13) . . . . ?
N3 C13 C14 C15 -0.10(18) . . . . ?
C4 C3 C2 C1 0.4(2) . . . . ?
C5 N1 C1 C6 178.42(12) . . . . ?
C5 N1 C1 C2 -1.52(19) . . . . ?
C5 C4 C3 C2 -1.1(2) . . . . ?
C1 N1 C5 C4 0.8(2) . . . . ?
C1 C6 C7 C8 -13.01(17) . . . . ?
C1 C6 C7 C12 172.16(12) . . . . ?
C1 C6 C13 N3 -82.26(14) . . . . ?
C1 C6 C13 C14 90.41(18) . . . . ?
C6 N2 C18 C19 -147.81(11) . . . . ?
C6 N2 C18 C17 35.72(15) . . . . ?
C6 C1 C2 C3 -178.96(13) . . . . ?
C6 C7 C12 C11 173.66(14) . . . . ?
C6 C13 C14 C15 -173.31(15) . . . . ?
C18 N2 C6 C1 69.72(13) . . . . ?
C18 N2 C6 C7 -167.52(10) . . . . ?
C18 N2 C6 C13 -50.77(14) . . . . ?
C18 C19 C20 C21 -1.4(2) . . . . ?
C18 C17 C22 C21 -2.3(2) . . . . ?
C19 C18 C17 N3 -178.76(11) . . . . ?
C19 C18 C17 C22 1.45(18) . . . . ?
C19 C20 C21 C22 0.6(2) . . . . ?
C20 C21 C22 C17 1.2(2) . . . . ?
C10 C9 C8 C7 1.5(3) . . . . ?
C9 C10 C11 C12 -0.4(3) . . . . ?
C9 C8 C7 C6 -175.10(14) . . . . ?
C9 C8 C7 C12 -0.2(2) . . . . ?
C8 C7 C12 C11 -1.4(2) . . . . ?
C7 C6 C13 N3 155.20(11) . . . . ?
C7 C6 C13 C14 -32.1(2) . . . . ?
C7 C12 C11 C10 1.7(2) . . . . ?
C17 N3 C13 C6 -7.84(18) . . . . ?
C17 N3 C13 C14 177.75(12) . . . . ?
C17 N3 C16 C15 -177.62(14) . . . . ?
C17 C18 C19 C20 0.40(19) . . . . ?
C13 N3 C17 C18 -11.84(18) . . . . ?
C13 N3 C17 C22 167.94(12) . . . . ?
C13 N3 C16 C15 -0.34(19) . . . . ?
C13 C6 C7 C8 109.31(14) . . . . ?
C13 C6 C7 C12 -65.52(15) . . . . ?
C13 C14 C15 C16 -0.1(2) . . . . ?
C14 C15 C16 N3 0.3(2) . . . . ?
C16 N3 C17 C18 165.09(14) . . . . ?
C16 N3 C17 C22 -15.1(2) . . . . ?
C16 N3 C13 C6 174.68(12) . . . . ?
C16 N3 C13 C14 0.27(16) . . . . ?
C3 C4 C5 N1 0.5(2) . . . . ?
C2 C1 C6 N2 -130.02(13) . . . . ?
C2 C1 C6 C7 108.26(14) . . . . ?
C2 C1 C6 C13 -12.18(17) . . . . ?
C11 C10 C9 C8 -1.2(3) . . . . ?


_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_cuclo4_nl1_rt
_database_code_depnum_ccdc_archive 'CCDC 2040549'
loop_
_audit_author_name
_audit_author_address
'Angshuman Roy Choudhury'
;IISER Mohali
India
;
_audit_update_record             
;
2021-06-05 deposited with the CCDC.	2021-06-14 downloaded from the CCDC.
;
_audit_creation_date             2021-06-04
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6272)
;
_shelx_SHELXL_version_number     2017/1
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C24 H22 Cu N2 O4, 2(Cl O4)'
_chemical_formula_sum            'C24 H22 Cl2 Cu N2 O12'
_chemical_formula_weight         664.87
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
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'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/n 1'
_space_group_name_Hall           '-P 2yn'
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                   7.6654(4)
_cell_length_b                   12.3371(5)
_cell_length_c                   14.5545(7)
_cell_angle_alpha                90
_cell_angle_beta                 96.846(4)
_cell_angle_gamma                90
_cell_volume                     1366.59(11)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    1625
_cell_measurement_temperature    298.0(2)
_cell_measurement_theta_max      24.4880
_cell_measurement_theta_min      3.2620
_shelx_estimated_absorpt_T_max   0.866
_shelx_estimated_absorpt_T_min   0.741
_exptl_absorpt_coefficient_mu    1.062
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.97837
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.35c (Rigaku Oxford Diffraction, 2017)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light green'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    green
_exptl_crystal_density_diffrn    1.616
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             678
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.14
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0225
_diffrn_reflns_av_unetI/netI     0.0493
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.895
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -7
_diffrn_reflns_number            7341
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.895
_diffrn_reflns_theta_full        25.000
_diffrn_reflns_theta_max         32.711
_diffrn_reflns_theta_min         2.819
_diffrn_ambient_temperature      298.0(2)
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.895
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -64.00 118.00   0.50   10.00    --   29.89  54.00  90.00  364
  2  ω     -3.00  30.00   0.50   10.00    --   29.89  54.00-180.00   66
;
_diffrn_measurement_device       'two-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Mini (ROW)'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2648
_reflns_number_total             4500
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.39.35c (Rigaku OD, 2017)'
_computing_data_collection       'CrysAlisPro 1.171.39.35c (Rigaku OD, 2017)'
_computing_data_reduction        'CrysAlisPro 1.171.39.35c (Rigaku OD, 2017)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2017/1 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/4 (Sheldrick, 2014)'
_refine_diff_density_max         0.668
_refine_diff_density_min         -0.500
_refine_diff_density_rms         0.073
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.031
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     188
_refine_ls_number_reflns         4500
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0993
_refine_ls_R_factor_gt           0.0543
_refine_ls_restrained_S_all      1.031
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0826P)²+0.1707P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1398
_refine_ls_wR_factor_ref         0.1813
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All O(H,H) groups
2.a Rotating group:
 O2(H2A,H2B)
2.b Aromatic/amide H refined with riding coordinates:
 C1(H1), C8(H8), C4(H4), C12(H12), C9(H9), C3(H3), C10(H10), C2(H2), C11(H11)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Cu1 Cu 0.500000 0.500000 0.500000 0.04569(18) Uani 1 2 d S . P . .
O1 O 0.3798(3) 0.39712(15) 0.57946(14) 0.0503(5) Uani 1 1 d . . . . .
O2 O 0.3036(4) 0.4314(2) 0.37481(18) 0.0773(7) Uani 1 1 d . . . . .
H2A H 0.308671 0.362533 0.374599 0.116 Uiso 1 1 d R U . . .
H2B H 0.339600 0.450213 0.324149 0.116 Uiso 1 1 d R U . . .
N1 N 0.6635(3) 0.37740(17) 0.50097(16) 0.0424(5) Uani 1 1 d . . . . .
C1 C 0.8152(4) 0.3772(2) 0.4647(2) 0.0529(7) Uani 1 1 d . . . . .
H1 H 0.845057 0.437227 0.431197 0.064 Uiso 1 1 calc R U . . .
C2 C 0.9296(4) 0.2900(3) 0.4757(3) 0.0640(9) Uani 1 1 d . . . . .
H2 H 1.033409 0.290361 0.448516 0.077 Uiso 1 1 calc R U . . .
C3 C 0.8874(4) 0.2036(3) 0.5272(2) 0.0601(8) Uani 1 1 d . . . . .
H3 H 0.963243 0.144641 0.535894 0.072 Uiso 1 1 calc R U . . .
C4 C 0.7307(4) 0.2036(2) 0.5667(2) 0.0489(6) Uani 1 1 d . . . . .
H4 H 0.701861 0.146081 0.603301 0.059 Uiso 1 1 calc R U . . .
C5 C 0.6194(3) 0.2910(2) 0.55020(18) 0.0409(5) Uani 1 1 d . . . . .
C6 C 0.4470(3) 0.3051(2) 0.58663(18) 0.0412(6) Uani 1 1 d . . . . .
C7 C 0.3548(4) 0.2183(2) 0.62969(19) 0.0430(6) Uani 1 1 d . . . . .
C8 C 0.3636(4) 0.1096(2) 0.6044(2) 0.0503(7) Uani 1 1 d . . . . .
H8 H 0.434042 0.088861 0.559669 0.060 Uiso 1 1 calc R U . . .
C9 C 0.2681(5) 0.0328(3) 0.6457(3) 0.0628(9) Uani 1 1 d . . . . .
H9 H 0.272063 -0.039338 0.627475 0.075 Uiso 1 1 calc R U . . .
C10 C 0.1670(4) 0.0618(3) 0.7137(3) 0.0651(9) Uani 1 1 d . . . . .
H10 H 0.106099 0.009089 0.742679 0.078 Uiso 1 1 calc R U . . .
C11 C 0.1558(4) 0.1698(3) 0.7392(2) 0.0654(9) Uani 1 1 d . . . . .
H11 H 0.085771 0.189597 0.784400 0.078 Uiso 1 1 calc R U . . .
C12 C 0.2480(4) 0.2473(3) 0.6976(2) 0.0527(7) Uani 1 1 d . . . . .
H12 H 0.239628 0.319666 0.714542 0.063 Uiso 1 1 calc R U . . .
Cl1 Cl 0.27945(11) 0.13122(6) 0.32493(6) 0.0641(3) Uani 1 1 d . . . . .
O3 O 0.4087(5) 0.1876(3) 0.3832(2) 0.1155(13) Uani 1 1 d . . . . .
O4 O 0.1521(6) 0.2024(4) 0.2868(3) 0.1441(17) Uani 1 1 d . . . . .
O5 O 0.3610(5) 0.0887(4) 0.2482(3) 0.1455(18) Uani 1 1 d . . . . .
O6 O 0.2157(7) 0.0499(3) 0.3751(4) 0.164(2) Uani 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Cu1 O1 2.0128(19) 3_666 ?
Cu1 O1 2.0128(19) . ?
Cu1 O2 2.377(2) 3_666 ?
Cu1 O2 2.377(2) . ?
Cu1 N1 1.963(2) . ?
Cu1 N1 1.963(2) 3_666 ?
O1 C6 1.245(3) . ?
O2 H2A 0.8502 . ?
O2 H2B 0.8500 . ?
N1 C1 1.333(3) . ?
N1 C5 1.350(3) . ?
C1 H1 0.9300 . ?
C1 C2 1.385(4) . ?
C2 H2 0.9300 . ?
C3 C2 1.364(5) . ?
C3 H3 0.9300 . ?
C4 C3 1.392(4) . ?
C4 H4 0.9300 . ?
C5 C4 1.378(4) . ?
C5 C6 1.492(4) . ?
C6 C7 1.465(4) . ?
C7 C8 1.395(4) . ?
C7 C12 1.403(4) . ?
C8 H8 0.9300 . ?
C8 C9 1.379(4) . ?
C9 H9 0.9300 . ?
C9 C10 1.375(5) . ?
C10 H10 0.9300 . ?
C10 C11 1.388(5) . ?
C11 H11 0.9300 . ?
C12 C11 1.372(4) . ?
C12 H12 0.9300 . ?
Cl1 O3 1.408(3) . ?
Cl1 O4 1.380(3) . ?
Cl1 O5 1.442(4) . ?
Cl1 O6 1.366(4) . ?

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 O1 180.0 . 3_666 ?
O1 Cu1 O2 85.66(9) . . ?
O1 Cu1 O2 94.34(9) . 3_666 ?
O1 Cu1 O2 85.66(9) 3_666 3_666 ?
O1 Cu1 O2 94.34(9) 3_666 . ?
O2 Cu1 O2 180.0 . 3_666 ?
N1 Cu1 O1 98.88(8) . 3_666 ?
N1 Cu1 O1 81.12(8) 3_666 3_666 ?
N1 Cu1 O1 81.12(8) . . ?
N1 Cu1 O1 98.88(8) 3_666 . ?
N1 Cu1 O2 85.61(9) . 3_666 ?
N1 Cu1 O2 94.39(9) 3_666 3_666 ?
N1 Cu1 O2 85.61(9) 3_666 . ?
N1 Cu1 O2 94.39(9) . . ?
N1 Cu1 N1 180.0 3_666 . ?
C6 O1 Cu1 114.19(17) . . ?
Cu1 O2 H2A 109.5 . . ?
Cu1 O2 H2B 109.0 . . ?
H2A O2 H2B 104.5 . . ?
C1 N1 Cu1 125.78(19) . . ?
C1 N1 C5 119.6(2) . . ?
C5 N1 Cu1 114.34(18) . . ?
N1 C1 H1 119.1 . . ?
N1 C1 C2 121.7(3) . . ?
C2 C1 H1 119.1 . . ?
C1 C2 H2 120.6 . . ?
C3 C2 C1 118.8(3) . . ?
C3 C2 H2 120.6 . . ?
C2 C3 H3 120.0 . . ?
C2 C3 C4 120.0(3) . . ?
C4 C3 H3 120.0 . . ?
C3 C4 H4 120.8 . . ?
C5 C4 C3 118.4(3) . . ?
C5 C4 H4 120.8 . . ?
N1 C5 C4 121.4(3) . . ?
N1 C5 C6 112.6(2) . . ?
C4 C5 C6 125.9(3) . . ?
O1 C6 C5 116.9(2) . . ?
O1 C6 C7 119.1(2) . . ?
C7 C6 C5 124.0(2) . . ?
C8 C7 C6 123.3(3) . . ?
C8 C7 C12 118.8(3) . . ?
C12 C7 C6 117.8(2) . . ?
C7 C8 H8 120.0 . . ?
C9 C8 C7 120.1(3) . . ?
C9 C8 H8 120.0 . . ?
C8 C9 H9 119.7 . . ?
C10 C9 C8 120.6(3) . . ?
C10 C9 H9 119.7 . . ?
C9 C10 H10 120.0 . . ?
C9 C10 C11 120.0(3) . . ?
C11 C10 H10 120.0 . . ?
C10 C11 H11 120.0 . . ?
C12 C11 C10 120.0(3) . . ?
C12 C11 H11 120.0 . . ?
C7 C12 H12 119.8 . . ?
C11 C12 C7 120.5(3) . . ?
C11 C12 H12 119.8 . . ?
O3 Cl1 O5 107.9(2) . . ?
O4 Cl1 O3 109.9(3) . . ?
O4 Cl1 O5 105.8(3) . . ?
O6 Cl1 O3 108.2(2) . . ?
O6 Cl1 O4 113.7(3) . . ?
O6 Cl1 O5 111.2(3) . . ?

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
Cu1 O1 C6 C5 10.1(3) . . . . ?
Cu1 O1 C6 C7 -170.04(18) . . . . ?
Cu1 N1 C1 C2 174.3(3) . . . . ?
Cu1 N1 C5 C4 -172.3(2) . . . . ?
Cu1 N1 C5 C6 4.7(3) . . . . ?
O1 C6 C7 C8 148.1(3) . . . . ?
O1 C6 C7 C12 -29.8(4) . . . . ?
N1 C1 C2 C3 -1.8(5) . . . . ?
N1 C5 C4 C3 -3.3(4) . . . . ?
N1 C5 C6 O1 -10.0(3) . . . . ?
N1 C5 C6 C7 170.1(2) . . . . ?
C1 N1 C5 C4 2.3(4) . . . . ?
C1 N1 C5 C6 179.3(2) . . . . ?
C4 C3 C2 C1 0.7(5) . . . . ?
C4 C5 C6 O1 166.8(3) . . . . ?
C4 C5 C6 C7 -13.0(4) . . . . ?
C5 N1 C1 C2 0.4(5) . . . . ?
C5 C4 C3 C2 1.8(5) . . . . ?
C5 C6 C7 C8 -32.1(4) . . . . ?
C5 C6 C7 C12 150.1(3) . . . . ?
C6 C5 C4 C3 -179.9(3) . . . . ?
C6 C7 C8 C9 -177.6(3) . . . . ?
C6 C7 C12 C11 178.8(3) . . . . ?
C7 C8 C9 C10 -1.7(5) . . . . ?
C7 C12 C11 C10 -0.4(5) . . . . ?
C8 C7 C12 C11 0.8(4) . . . . ?
C8 C9 C10 C11 2.2(5) . . . . ?
C9 C10 C11 C12 -1.1(5) . . . . ?
C12 C7 C8 C9 0.2(4) . . . . ?


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