# Electronic Supplementary Material (ESI) for Chemical Communications.
# This journal is © The Royal Society of Chemistry 2019

####################################################################### 
# 
# 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_cl-beta-150k
_database_code_depnum_ccdc_archive 'CCDC 1889441'
loop_
_audit_author_name
_audit_author_address
'Dan Li'
;Jinan University
China
;
_audit_update_record             
;
2019-02-16 deposited with the CCDC.	2019-03-21 downloaded from the CCDC.
;
_audit_creation_date             2019-02-15
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2016/6
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C9 H6 Cl3 Cu3 N6'
_chemical_formula_sum            'C9 H6 Cl3 Cu3 N6'
_chemical_formula_weight         495.17
_chemical_melting_point          ?
_chemical_oxdiff_formula         'Cu C H N Cl'
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.3639 0.7018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cu Cu -1.9646 0.5888 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      orthorhombic
_space_group_IT_number           61
_space_group_name_H-M_alt        'P b c a'
_space_group_name_Hall           '-P 2ac 2ab'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'x+1/2, -y+1/2, -z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'-x-1/2, y-1/2, z'
'x, -y-1/2, z-1/2'

_cell_length_a                   17.3175(5)
_cell_length_b                   8.5617(3)
_cell_length_c                   18.9646(6)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2811.82(15)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    6237
_cell_measurement_temperature    150.00(10)
_cell_measurement_theta_max      77.4790
_cell_measurement_theta_min      4.6110
_shelx_estimated_absorpt_T_max   0.391
_shelx_estimated_absorpt_T_min   0.301
_exptl_absorpt_coefficient_mu    10.522
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.58804
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.33c (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 colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    2.339
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             1920
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.13
_exptl_crystal_size_min          0.11
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0525
_diffrn_reflns_av_unetI/netI     0.0375
_diffrn_reflns_Laue_measured_fraction_full 0.992
_diffrn_reflns_Laue_measured_fraction_max 0.962
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            10541
_diffrn_reflns_point_group_measured_fraction_full 0.992
_diffrn_reflns_point_group_measured_fraction_max 0.962
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         77.831
_diffrn_reflns_theta_min         4.663
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      150.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.962
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     30.00  56.00   0.50    3.38    --   -0.90  59.00 118.00   52
  2  ω    -78.00 -29.00   0.50    3.38    --    0.90 -67.00-168.00   98
  3  ω     64.00  90.00   0.50    3.38    --    0.90  59.00 118.00   52
  4  ω     35.00  83.00   0.50   13.51    --  105.10 -67.00-168.00   96
  5  ω     62.00  90.00   0.50   13.51    --  105.10 -59.00 -21.00   56
  6  ω    132.00 157.00   0.50   13.51    --  105.10  67.00 -34.00   50
  7  ω    136.00 169.00   0.50   13.51    --  105.10  59.00 118.00   66
  8  ω    -37.00  25.00   0.50    3.38    --   -0.90 -82.00 150.00  124
  9  ω     -3.00  39.00   0.50    3.38    --    0.90  82.00-180.00   84
 10  ω     16.00 128.00   0.50   13.51    --  105.10 -38.00-180.00  224
 11  ω    120.00 160.00   0.50   13.51    --  105.10  82.00-150.00   80
 12  ω     16.00 139.00   0.50   13.51    --  105.10 -82.00 -30.00  246
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB AFC12 (RINC): Kappa single'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0357094000
_diffrn_orient_matrix_UB_12      -0.0332528000
_diffrn_orient_matrix_UB_13      -0.0728816000
_diffrn_orient_matrix_UB_21      0.0469185000
_diffrn_orient_matrix_UB_22      -0.1358333000
_diffrn_orient_matrix_UB_23      0.0317122000
_diffrn_orient_matrix_UB_31      -0.0666083000
_diffrn_orient_matrix_UB_32      -0.1132748000
_diffrn_orient_matrix_UB_33      -0.0167411000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'Rotating-anode X-ray tube (dual wavelength)'
_diffrn_source_type              'Rigaku (Cu) X-ray DW Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2446
_reflns_number_total             2890
_reflns_odcompleteness_completeness 99.41
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_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 1.171.39.33c (Rigaku OD, 2017)'
_computing_data_collection       'CrysAlisPro 1.171.39.33c (Rigaku OD, 2017)'
_computing_data_reduction        'CrysAlisPro 1.171.39.33c (Rigaku OD, 2017)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'XS (Sheldrick, 2008)'
_refine_diff_density_max         0.834
_refine_diff_density_min         -0.822
_refine_diff_density_rms         0.158
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.059
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     190
_refine_ls_number_reflns         2890
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0628
_refine_ls_R_factor_gt           0.0526
_refine_ls_restrained_S_all      1.059
_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)+(0.0838P)²+12.3765P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1459
_refine_ls_wR_factor_ref         0.1511
_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:
 C2(H2), C3(H3), C4(H4), C6(H6), C7(H7), C9(H9)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Cu1 Cu 0.11236(5) 0.01170(9) 0.51328(4) 0.0286(2) Uani 1 1 d . . . . .
Cu2 Cu -0.03068(4) 0.22970(9) 0.56537(4) 0.0287(2) Uani 1 1 d . . . . .
Cu3 Cu 0.03416(5) 0.27379(9) 0.40982(4) 0.0298(2) Uani 1 1 d . . . . .
Cl1 Cl 0.22685(7) -0.09038(18) 0.23670(7) 0.0355(3) Uani 1 1 d . . . . .
Cl2 Cl 0.09275(8) -0.05875(16) 0.80978(6) 0.0337(3) Uani 1 1 d . . . . .
Cl3 Cl -0.22313(8) 0.68586(17) 0.43835(8) 0.0385(3) Uani 1 1 d . . . . .
N1 N 0.1149(3) 0.1471(5) 0.3782(2) 0.0294(9) Uani 1 1 d . . . . .
N2 N 0.1440(3) 0.0302(5) 0.4199(2) 0.0269(9) Uani 1 1 d . . . . .
N3 N 0.0811(3) 0.0089(5) 0.6073(2) 0.0281(9) Uani 1 1 d . . . . .
N4 N 0.0257(2) 0.1113(6) 0.6306(2) 0.0277(9) Uani 1 1 d . . . . .
N5 N -0.0830(3) 0.3607(6) 0.5033(2) 0.0291(9) Uani 1 1 d . . . . .
N6 N -0.0519(3) 0.3902(5) 0.4385(2) 0.0272(9) Uani 1 1 d . . . . .
C1 C 0.1844(3) -0.0090(6) 0.3099(3) 0.0281(10) Uani 1 1 d . . . . .
C2 C 0.1862(3) -0.0650(6) 0.3783(3) 0.0271(10) Uani 1 1 d . . . . .
H2 H 0.212795 -0.155929 0.393520 0.032 Uiso 1 1 calc R . . . .
C3 C 0.1395(3) 0.1238(7) 0.3122(3) 0.0296(11) Uani 1 1 d . . . . .
H3 H 0.127822 0.188691 0.272933 0.036 Uiso 1 1 calc R . . . .
C4 C 0.1103(3) -0.0644(7) 0.6639(3) 0.0291(11) Uani 1 1 d . . . . .
H4 H 0.149551 -0.141913 0.663094 0.035 Uiso 1 1 calc R . . . .
C5 C 0.0739(3) -0.0081(6) 0.7237(3) 0.0257(10) Uani 1 1 d . . . . .
C6 C 0.0211(3) 0.0998(6) 0.7003(3) 0.0274(10) Uani 1 1 d . . . . .
H6 H -0.013242 0.157373 0.729396 0.033 Uiso 1 1 calc R . . . .
C7 C -0.1444(3) 0.4556(7) 0.5118(3) 0.0298(11) Uani 1 1 d . . . . .
H7 H -0.176465 0.459851 0.552389 0.036 Uiso 1 1 calc R . . . .
C8 C -0.1531(3) 0.5450(6) 0.4524(3) 0.0282(11) Uani 1 1 d . . . . .
C9 C -0.0945(3) 0.5014(6) 0.4071(3) 0.0301(11) Uani 1 1 d . . . . .
H9 H -0.085699 0.543044 0.361363 0.036 Uiso 1 1 calc R . . . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
Cu1 0.0339(4) 0.0315(4) 0.0204(4) -0.0010(3) 0.0002(3) -0.0006(3)
Cu2 0.0319(4) 0.0286(4) 0.0257(4) 0.0012(3) -0.0037(3) 0.0029(3)
Cu3 0.0334(4) 0.0262(4) 0.0297(4) -0.0014(3) 0.0025(3) 0.0024(3)
Cl1 0.0343(7) 0.0465(8) 0.0257(6) -0.0045(6) 0.0041(5) 0.0035(6)
Cl2 0.0431(7) 0.0365(7) 0.0217(6) 0.0038(5) -0.0002(5) -0.0030(6)
Cl3 0.0347(7) 0.0335(7) 0.0475(8) 0.0012(6) -0.0093(6) 0.0070(5)
N1 0.035(2) 0.026(2) 0.027(2) 0.0002(18) 0.0041(17) -0.0001(18)
N2 0.028(2) 0.027(2) 0.026(2) -0.0001(17) -0.0025(16) -0.0010(17)
N3 0.030(2) 0.030(2) 0.025(2) 0.0013(17) -0.0023(17) 0.0032(18)
N4 0.027(2) 0.031(2) 0.024(2) -0.0020(18) -0.0018(16) -0.0007(18)
N5 0.030(2) 0.033(2) 0.024(2) 0.0007(18) 0.0013(16) -0.0016(19)
N6 0.031(2) 0.023(2) 0.028(2) 0.0001(17) -0.0026(17) 0.0012(18)
C1 0.025(2) 0.033(3) 0.027(2) -0.001(2) 0.0011(19) -0.002(2)
C2 0.027(2) 0.030(3) 0.024(2) 0.000(2) -0.0006(19) 0.001(2)
C3 0.032(3) 0.031(3) 0.025(2) 0.004(2) 0.003(2) -0.003(2)
C4 0.031(3) 0.031(3) 0.025(2) 0.000(2) -0.0003(19) 0.002(2)
C5 0.029(2) 0.023(2) 0.026(2) -0.0012(19) -0.0011(19) -0.002(2)
C6 0.033(3) 0.024(3) 0.024(2) 0.0002(19) 0.0020(19) 0.001(2)
C7 0.027(3) 0.031(3) 0.031(3) -0.006(2) -0.001(2) 0.002(2)
C8 0.030(2) 0.019(2) 0.036(3) 0.001(2) -0.011(2) 0.000(2)
C9 0.030(3) 0.031(3) 0.029(3) 0.003(2) -0.001(2) -0.002(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.
;
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 Cu2 2.9150(11) 5_556 ?
Cu1 N2 1.860(4) . ?
Cu1 N3 1.864(5) . ?
Cu2 N4 1.873(5) . ?
Cu2 N5 1.861(5) . ?
Cu3 N1 1.868(5) . ?
Cu3 N6 1.873(4) . ?
Cl1 C1 1.718(5) . ?
Cl2 C5 1.720(5) . ?
Cl3 C8 1.731(5) . ?
N1 N2 1.372(6) . ?
N1 C3 1.338(7) . ?
N2 C2 1.350(7) . ?
N3 N4 1.373(6) . ?
N3 C4 1.342(7) . ?
N4 C6 1.327(7) . ?
N5 N6 1.366(6) . ?
N5 C7 1.347(7) . ?
N6 C9 1.343(7) . ?
C1 C2 1.383(7) . ?
C1 C3 1.379(8) . ?
C4 C5 1.385(7) . ?
C5 C6 1.373(7) . ?
C7 C8 1.370(8) . ?
C8 C9 1.382(8) . ?

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
N2 Cu1 Cu2 73.51(14) . 5_556 ?
N2 Cu1 N3 175.8(2) . . ?
N3 Cu1 Cu2 109.85(15) . 5_556 ?
N4 Cu2 Cu1 101.96(14) . 5_556 ?
N5 Cu2 Cu1 82.37(15) . 5_556 ?
N5 Cu2 N4 175.7(2) . . ?
N1 Cu3 N6 175.8(2) . . ?
N2 N1 Cu3 120.9(3) . . ?
C3 N1 Cu3 128.7(4) . . ?
C3 N1 N2 108.3(4) . . ?
N1 N2 Cu1 120.2(3) . . ?
C2 N2 Cu1 131.7(4) . . ?
C2 N2 N1 107.5(4) . . ?
N4 N3 Cu1 120.1(3) . . ?
C4 N3 Cu1 131.4(4) . . ?
C4 N3 N4 107.8(4) . . ?
N3 N4 Cu2 119.8(3) . . ?
C6 N4 Cu2 131.8(4) . . ?
C6 N4 N3 108.3(4) . . ?
N6 N5 Cu2 119.2(3) . . ?
C7 N5 Cu2 132.2(4) . . ?
C7 N5 N6 107.9(4) . . ?
N5 N6 Cu3 118.5(3) . . ?
C9 N6 Cu3 133.2(4) . . ?
C9 N6 N5 108.2(4) . . ?
C2 C1 Cl1 127.5(4) . . ?
C3 C1 Cl1 126.9(4) . . ?
C3 C1 C2 105.6(5) . . ?
N2 C2 C1 109.1(5) . . ?
N1 C3 C1 109.4(5) . . ?
N3 C4 C5 108.7(5) . . ?
C4 C5 Cl2 127.1(4) . . ?
C6 C5 Cl2 127.1(4) . . ?
C6 C5 C4 105.8(5) . . ?
N4 C6 C5 109.5(5) . . ?
N5 C7 C8 109.0(5) . . ?
C7 C8 Cl3 126.3(5) . . ?
C7 C8 C9 106.2(5) . . ?
C9 C8 Cl3 127.4(4) . . ?
N6 C9 C8 108.7(5) . . ?

_shelx_res_file                  
;
TITL Cl-beta-150K in Pbca #61
    cl-beta-150k.res
    created by SHELXL-2016/6 at 22:12:59 on 15-Feb-2019
REM reset to Pbca #61
CELL 1.54184 17.317493 8.561685 18.964567 90 90 90
ZERR 8 0.000508 0.00027 0.00056 0 0 0
LATT 1
SYMM 0.5-X,-Y,0.5+Z
SYMM 0.5+X,0.5-Y,-Z
SYMM -X,0.5+Y,0.5-Z
SFAC C H N Cl Cu
UNIT 72 48 48 24 24

L.S. 20 0 0
PLAN  1
SIZE 0.15 0.13 0.11
TEMP -123.15(10)
BOND
fmap 2 53
acta
OMIT 8 9 0
OMIT 11 7 11
OMIT 9 7 4
OMIT 8 9 1
OMIT 7 10 4
OMIT 5 10 5
OMIT 7 8 13
OMIT 3 10 4
OMIT 12 0 18
OMIT 10 9 0
OMIT 9 7 12
OMIT 3 10 3
OMIT 11 7 12
REM <olex2.extras>
REM <HklSrc "%.\\Cl-beta-150K.hkl">
REM </olex2.extras>

WGHT    0.083800   12.376499
FVAR       0.86412
CU1   5    0.112357    0.011701    0.513285    11.00000    0.03390    0.03155 =
         0.02035   -0.00104    0.00024   -0.00056
CU2   5   -0.030681    0.229696    0.565369    11.00000    0.03191    0.02857 =
         0.02573    0.00117   -0.00371    0.00292
CU3   5    0.034156    0.273791    0.409818    11.00000    0.03337    0.02624 =
         0.02972   -0.00138    0.00252    0.00242
CL1   4    0.226854   -0.090378    0.236696    11.00000    0.03432    0.04649 =
         0.02574   -0.00445    0.00407    0.00346
CL2   4    0.092751   -0.058748    0.809785    11.00000    0.04306    0.03651 =
         0.02165    0.00383   -0.00016   -0.00299
CL3   4   -0.223127    0.685859    0.438351    11.00000    0.03465    0.03350 =
         0.04745    0.00120   -0.00931    0.00695
N1    3    0.114888    0.147114    0.378198    11.00000    0.03474    0.02612 =
         0.02720    0.00018    0.00405   -0.00013
N2    3    0.143973    0.030219    0.419940    11.00000    0.02756    0.02667 =
         0.02642   -0.00011   -0.00246   -0.00102
N3    3    0.081091    0.008889    0.607349    11.00000    0.03035    0.02953 =
         0.02450    0.00129   -0.00226    0.00320
N4    3    0.025679    0.111338    0.630599    11.00000    0.02742    0.03138 =
         0.02422   -0.00197   -0.00178   -0.00075
N5    3   -0.083036    0.360668    0.503314    11.00000    0.02984    0.03313 =
         0.02435    0.00068    0.00134   -0.00162
N6    3   -0.051868    0.390228    0.438483    11.00000    0.03082    0.02301 =
         0.02777    0.00010   -0.00259    0.00124
C1    1    0.184437   -0.009048    0.309908    11.00000    0.02477    0.03278 =
         0.02663   -0.00106    0.00109   -0.00203
C2    1    0.186162   -0.064984    0.378283    11.00000    0.02734    0.03035 =
         0.02354    0.00011   -0.00063    0.00077
AFIX  43
H2    2    0.212795   -0.155929    0.393520    11.00000   -1.20000
AFIX   0
C3    1    0.139491    0.123826    0.312154    11.00000    0.03233    0.03128 =
         0.02531    0.00409    0.00250   -0.00282
AFIX  43
H3    2    0.127822    0.188691    0.272933    11.00000   -1.20000
AFIX   0
C4    1    0.110333   -0.064351    0.663932    11.00000    0.03142    0.03113 =
         0.02462   -0.00030   -0.00029    0.00195
AFIX  43
H4    2    0.149551   -0.141913    0.663094    11.00000   -1.20000
AFIX   0
C5    1    0.073852   -0.008100    0.723739    11.00000    0.02852    0.02279 =
         0.02587   -0.00124   -0.00108   -0.00215
C6    1    0.021149    0.099829    0.700271    11.00000    0.03342    0.02447 =
         0.02445    0.00020    0.00205    0.00131
AFIX  43
H6    2   -0.013242    0.157373    0.729396    11.00000   -1.20000
AFIX   0
C7    1   -0.144411    0.455579    0.511782    11.00000    0.02732    0.03126 =
         0.03072   -0.00562   -0.00075    0.00192
AFIX  43
H7    2   -0.176465    0.459851    0.552389    11.00000   -1.20000
AFIX   0
C8    1   -0.153126    0.544953    0.452359    11.00000    0.02954    0.01936 =
         0.03567    0.00107   -0.01064   -0.00047
C9    1   -0.094458    0.501352    0.407092    11.00000    0.03018    0.03085 =
         0.02930    0.00278   -0.00127   -0.00233
AFIX  43
H9    2   -0.085699    0.543044    0.361363    11.00000   -1.20000
AFIX   0
HKLF 4




REM  Cl-beta-150K in Pbca #61
REM R1 =  0.0526 for    2446 Fo > 4sig(Fo)  and  0.0628 for all    2890 data
REM    190 parameters refined using      0 restraints

END

WGHT      0.0838     12.3679

REM Highest difference peak  0.834,  deepest hole -0.822,  1-sigma level  0.158
Q1    1  -0.0386  0.2759  0.4995  11.00000  0.05    0.83
;
_shelx_res_checksum              30823
_olex2_submission_original_sample_id Cl-beta-150K
_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
;
_oxdiff_exptl_absorpt_empirical_full_max 3.900
_oxdiff_exptl_absorpt_empirical_full_min 0.539
####################################################################### 
# 
# 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_cl-beta-300k
_database_code_depnum_ccdc_archive 'CCDC 1889442'
loop_
_audit_author_name
_audit_author_address
'Dan Li'
;Jinan University
China
;
_audit_update_record             
;
2019-02-16 deposited with the CCDC.	2019-03-21 downloaded from the CCDC.
;
_audit_creation_date             2019-02-16
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2016/6
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C9 H6 Cl3 Cu3 N6'
_chemical_formula_sum            'C9 H6 Cl3 Cu3 N6'
_chemical_formula_weight         495.17
_chemical_melting_point          ?
_chemical_oxdiff_formula         'Cu C H N Cl'
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.3639 0.7018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cu Cu -1.9646 0.5888 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      orthorhombic
_space_group_IT_number           61
_space_group_name_H-M_alt        'P b c a'
_space_group_name_Hall           '-P 2ac 2ab'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'x+1/2, -y+1/2, -z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'-x-1/2, y-1/2, z'
'x, -y-1/2, z-1/2'

_cell_length_a                   17.5436(11)
_cell_length_b                   8.6121(6)
_cell_length_c                   19.0546(10)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2878.9(3)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    4509
_cell_measurement_temperature    300(1)
_cell_measurement_theta_max      76.3800
_cell_measurement_theta_min      5.0210
_shelx_estimated_absorpt_T_max   0.398
_shelx_estimated_absorpt_T_min   0.308
_exptl_absorpt_coefficient_mu    10.276
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.42035
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.33c (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 colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    2.285
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             1920
_exptl_crystal_preparation       ?
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.13
_exptl_crystal_size_min          0.11
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0456
_diffrn_reflns_av_unetI/netI     0.0385
_diffrn_reflns_Laue_measured_fraction_full 0.985
_diffrn_reflns_Laue_measured_fraction_max 0.947
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            9360
_diffrn_reflns_point_group_measured_fraction_full 0.985
_diffrn_reflns_point_group_measured_fraction_max 0.947
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         77.809
_diffrn_reflns_theta_min         4.641
_diffrn_ambient_environment      air
_diffrn_ambient_temperature      300(1)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.985
_diffrn_measured_fraction_theta_max 0.947
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω      6.00  31.00   0.50    4.21    --   -0.90  21.00 -47.00   50
  2  ω    -29.00  -4.00   0.50    4.21    --    0.90 -21.00 145.00   50
  3  ω     52.00  77.00   0.50   16.82    --  105.10 -21.00 145.00   50
  4  ω    108.00 180.00   0.50   16.82    --  105.10  21.00 -47.00  144
  5  ω    -31.00  39.00   0.50    4.21    --    0.90  82.00 -90.00  140
  6  ω     -8.00  39.00   0.50    4.21    --    0.90  82.00   0.00   94
  7  ω     16.00 138.00   0.50   16.82    --  105.10 -77.00  30.00  244
  8  ω     73.00 194.00   0.50   16.82    --  105.10  19.00  30.00  242
  9  ω    145.00 170.00   0.50   16.82    --  105.10  82.00-150.00   50
 10  ω     92.00 125.00   0.50   16.82    --  105.10 -57.00 -30.00   66
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB AFC12 (RINC): Kappa single'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0167205000
_diffrn_orient_matrix_UB_12      -0.0310724000
_diffrn_orient_matrix_UB_13      -0.0781024000
_diffrn_orient_matrix_UB_21      0.0836832000
_diffrn_orient_matrix_UB_22      -0.0357731000
_diffrn_orient_matrix_UB_23      0.0179811000
_diffrn_orient_matrix_UB_31      -0.0204404000
_diffrn_orient_matrix_UB_32      -0.1726093000
_diffrn_orient_matrix_UB_33      0.0104596000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'Rotating-anode X-ray tube (dual wavelength)'
_diffrn_source_type              'Rigaku (Cu) X-ray DW Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2123
_reflns_number_total             2916
_reflns_odcompleteness_completeness 98.57
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_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 1.171.39.33c (Rigaku OD, 2017)'
_computing_data_collection       'CrysAlisPro 1.171.39.33c (Rigaku OD, 2017)'
_computing_data_reduction        'CrysAlisPro 1.171.39.33c (Rigaku OD, 2017)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'XS (Sheldrick, 2008)'
_refine_diff_density_max         0.619
_refine_diff_density_min         -0.449
_refine_diff_density_rms         0.111
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.063
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     190
_refine_ls_number_reflns         2916
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0777
_refine_ls_R_factor_gt           0.0546
_refine_ls_restrained_S_all      1.063
_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)+(0.0834P)²+3.3182P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1442
_refine_ls_wR_factor_ref         0.1583
_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:
 C2(H2), C3(H3), C4(H4), C6(H6), C7(H7), C9(H9)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Cu1 Cu -0.02941(5) 0.72983(10) -0.06546(5) 0.0599(3) Uani 1 1 d . . . . .
Cu2 Cu 0.11219(5) 0.51511(10) -0.01354(4) 0.0587(3) Uani 1 1 d . . . . .
Cu3 Cu 0.03345(5) 0.77154(10) 0.08955(5) 0.0611(3) Uani 1 1 d . . . . .
Cl1 Cl -0.22133(9) 1.17761(18) 0.06141(10) 0.0770(5) Uani 1 1 d . . . . .
Cl2 Cl 0.22551(9) 0.4118(2) 0.26074(8) 0.0739(4) Uani 1 1 d . . . . .
Cl3 Cl 0.09179(9) 0.44234(18) -0.30802(7) 0.0681(4) Uani 1 1 d . . . . .
N1 N -0.0517(3) 0.8862(5) 0.0612(2) 0.0551(10) Uani 1 1 d . . . . .
N2 N -0.0816(3) 0.8588(5) -0.0035(3) 0.0577(11) Uani 1 1 d . . . . .
N3 N 0.0264(2) 0.6125(5) -0.1295(3) 0.0537(10) Uani 1 1 d . . . . .
N4 N 0.0816(3) 0.5127(5) -0.1075(2) 0.0535(10) Uani 1 1 d . . . . .
N5 N 0.1430(3) 0.5322(5) 0.0798(2) 0.0550(11) Uani 1 1 d . . . . .
N6 N 0.1137(3) 0.6469(5) 0.1204(3) 0.0573(11) Uani 1 1 d . . . . .
C1 C -0.1517(3) 1.0394(6) 0.0472(3) 0.0558(13) Uani 1 1 d . . . . .
C2 C -0.1426(3) 0.9529(6) -0.0118(3) 0.0581(13) Uani 1 1 d . . . . .
H2 H -0.173394 0.957557 -0.051422 0.070 Uiso 1 1 calc R . . . .
C3 C -0.0942(4) 0.9958(6) 0.0923(3) 0.0606(14) Uani 1 1 d . . . . .
H3 H -0.086277 1.035641 0.137104 0.073 Uiso 1 1 calc R . . . .
C4 C 0.0214(3) 0.6004(7) -0.1993(3) 0.0551(13) Uani 1 1 d . . . . .
H4 H -0.012264 0.655297 -0.227634 0.066 Uiso 1 1 calc R . . . .
C5 C 0.0739(3) 0.4939(6) -0.2223(3) 0.0522(12) Uani 1 1 d . . . . .
C6 C 0.1102(3) 0.4410(7) -0.1633(3) 0.0541(12) Uani 1 1 d . . . . .
H6 H 0.148668 0.366697 -0.162503 0.065 Uiso 1 1 calc R . . . .
C7 C 0.1846(3) 0.4396(7) 0.1203(3) 0.0541(12) Uani 1 1 d . . . . .
H7 H 0.210791 0.352103 0.104868 0.065 Uiso 1 1 calc R . . . .
C8 C 0.1834(3) 0.4922(6) 0.1882(3) 0.0536(12) Uani 1 1 d . . . . .
C9 C 0.1378(3) 0.6235(7) 0.1864(3) 0.0592(13) Uani 1 1 d . . . . .
H9 H 0.125841 0.685470 0.224848 0.071 Uiso 1 1 calc R . . . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
Cu1 0.0628(5) 0.0602(5) 0.0566(5) -0.0047(4) 0.0065(4) 0.0058(4)
Cu2 0.0682(6) 0.0639(5) 0.0442(4) 0.0011(4) -0.0009(4) -0.0011(4)
Cu3 0.0644(5) 0.0556(5) 0.0633(6) 0.0022(4) -0.0038(4) 0.0058(4)
Cl1 0.0666(9) 0.0666(9) 0.0977(12) -0.0036(8) 0.0169(8) 0.0136(7)
Cl2 0.0701(9) 0.0958(12) 0.0558(7) 0.0099(8) -0.0090(6) 0.0073(8)
Cl3 0.0862(10) 0.0728(9) 0.0453(7) -0.0099(6) -0.0003(6) -0.0048(7)
N1 0.062(3) 0.049(2) 0.054(3) 0.003(2) 0.006(2) 0.001(2)
N2 0.059(3) 0.054(3) 0.059(3) -0.003(2) 0.005(2) 0.001(2)
N3 0.059(2) 0.048(2) 0.054(3) -0.002(2) 0.002(2) -0.0003(19)
N4 0.059(3) 0.052(3) 0.049(2) 0.000(2) 0.002(2) 0.001(2)
N5 0.055(3) 0.061(3) 0.049(2) 0.001(2) 0.0008(19) 0.001(2)
N6 0.067(3) 0.050(2) 0.054(3) -0.004(2) -0.004(2) 0.000(2)
C1 0.050(3) 0.050(3) 0.067(3) 0.003(3) 0.012(2) 0.002(2)
C2 0.054(3) 0.059(3) 0.061(3) 0.003(3) -0.001(2) 0.007(2)
C3 0.067(3) 0.055(3) 0.060(3) -0.008(3) 0.010(3) -0.001(3)
C4 0.057(3) 0.062(3) 0.046(3) 0.005(3) -0.006(2) 0.001(2)
C5 0.056(3) 0.056(3) 0.045(3) -0.001(2) 0.000(2) -0.009(2)
C6 0.058(3) 0.058(3) 0.046(3) -0.003(2) 0.000(2) 0.008(2)
C7 0.054(3) 0.057(3) 0.051(3) 0.002(2) 0.002(2) 0.001(2)
C8 0.049(3) 0.062(3) 0.049(3) 0.001(2) -0.004(2) -0.004(2)
C9 0.063(3) 0.066(3) 0.048(3) -0.006(3) -0.002(2) 0.001(3)

_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 Cu2 2.9706(12) 5_565 ?
Cu1 N2 1.862(5) . ?
Cu1 N3 1.863(5) . ?
Cu2 N4 1.868(5) . ?
Cu2 N5 1.865(5) . ?
Cu3 N1 1.870(5) . ?
Cu3 N6 1.866(5) . ?
Cl1 C1 1.727(5) . ?
Cl2 C8 1.714(6) . ?
Cl3 C5 1.722(5) . ?
N1 N2 1.360(7) . ?
N1 C3 1.342(7) . ?
N2 C2 1.350(7) . ?
N3 N4 1.361(6) . ?
N3 C4 1.336(7) . ?
N4 C6 1.329(7) . ?
N5 N6 1.355(6) . ?
N5 C7 1.328(7) . ?
N6 C9 1.342(7) . ?
C1 C2 1.358(8) . ?
C1 C3 1.377(9) . ?
C4 C5 1.372(8) . ?
C5 C6 1.369(7) . ?
C7 C8 1.370(8) . ?
C8 C9 1.385(8) . ?

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
N2 Cu1 Cu2 82.06(15) . 5_565 ?
N2 Cu1 N3 176.1(2) . . ?
N3 Cu1 Cu2 101.77(14) . 5_565 ?
N4 Cu2 Cu1 109.72(14) . 5_565 ?
N5 Cu2 Cu1 73.39(15) . 5_565 ?
N5 Cu2 N4 176.1(2) . . ?
N6 Cu3 N1 176.0(2) . . ?
N2 N1 Cu3 118.6(4) . . ?
C3 N1 Cu3 133.4(5) . . ?
C3 N1 N2 107.9(5) . . ?
N1 N2 Cu1 119.2(4) . . ?
C2 N2 Cu1 132.4(4) . . ?
C2 N2 N1 107.9(5) . . ?
N4 N3 Cu1 121.0(4) . . ?
C4 N3 Cu1 131.2(4) . . ?
C4 N3 N4 107.7(4) . . ?
N3 N4 Cu2 119.5(3) . . ?
C6 N4 Cu2 131.6(4) . . ?
C6 N4 N3 108.4(4) . . ?
N6 N5 Cu2 119.5(4) . . ?
C7 N5 Cu2 131.7(4) . . ?
C7 N5 N6 108.3(5) . . ?
N5 N6 Cu3 121.6(4) . . ?
C9 N6 Cu3 128.3(4) . . ?
C9 N6 N5 107.8(5) . . ?
C2 C1 Cl1 126.2(5) . . ?
C2 C1 C3 106.3(5) . . ?
C3 C1 Cl1 127.4(5) . . ?
N2 C2 C1 109.0(5) . . ?
N1 C3 C1 108.8(6) . . ?
N3 C4 C5 109.0(5) . . ?
C4 C5 Cl3 126.7(4) . . ?
C6 C5 Cl3 127.5(4) . . ?
C6 C5 C4 105.8(5) . . ?
N4 C6 C5 109.1(5) . . ?
N5 C7 C8 109.9(5) . . ?
C7 C8 Cl2 128.4(5) . . ?
C7 C8 C9 104.9(5) . . ?
C9 C8 Cl2 126.7(5) . . ?
N6 C9 C8 109.1(5) . . ?

_shelx_res_file                  
;
TITL Cl-beta-300K in Pbca #61
    cl-beta-300k.res
    created by SHELXL-2016/6 at 11:57:02 on 16-Feb-2019
REM reset to Pbca #61
CELL 1.54184 17.543612 8.61209 19.054615 90 90 90
ZERR 8 0.001084 0.000556 0.001007 0 0 0
LATT 1
SYMM 0.5-X,-Y,0.5+Z
SYMM 0.5+X,0.5-Y,-Z
SYMM -X,0.5+Y,0.5-Z
SFAC C H N Cl Cu
UNIT 72 48 48 24 24

L.S. 20 0 0
PLAN  1
SIZE 0.15 0.13 0.11
TEMP 26.9(10)
BOND
fmap 2 53
acta
OMIT 0 10 0
OMIT 2 4 15
OMIT 1 9 12
OMIT 11 3 18
OMIT 0 2 11
OMIT 0 10 2
OMIT 2 9 13
OMIT 1 9 13
OMIT 18 2 12
OMIT 1 2 11
OMIT 8 8 12
OMIT 17 1 14
OMIT 19 2 10
OMIT 13 1 18
OMIT 17 2 14
OMIT 3 9 13
REM <olex2.extras>
REM <HklSrc "%.\\Cl-beta-300K.hkl">
REM </olex2.extras>

WGHT    0.083400    3.318200
FVAR       0.96061
CU1   5   -0.029409    0.729826   -0.065460    11.00000    0.06284    0.06022 =
         0.05661   -0.00471    0.00651    0.00578
CU2   5    0.112191    0.515105   -0.013541    11.00000    0.06815    0.06388 =
         0.04416    0.00111   -0.00087   -0.00106
CU3   5    0.033449    0.771538    0.089547    11.00000    0.06444    0.05555 =
         0.06325    0.00225   -0.00379    0.00576
CL1   4   -0.221326    1.177613    0.061405    11.00000    0.06657    0.06659 =
         0.09770   -0.00365    0.01693    0.01363
CL2   4    0.225507    0.411842    0.260742    11.00000    0.07010    0.09580 =
         0.05583    0.00992   -0.00899    0.00726
CL3   4    0.091792    0.442343   -0.308024    11.00000    0.08616    0.07275 =
         0.04533   -0.00990   -0.00033   -0.00482
N1    3   -0.051666    0.886238    0.061164    11.00000    0.06211    0.04885 =
         0.05423    0.00273    0.00631    0.00108
N2    3   -0.081650    0.858845   -0.003507    11.00000    0.05934    0.05437 =
         0.05937   -0.00334    0.00490    0.00068
N3    3    0.026436    0.612513   -0.129502    11.00000    0.05904    0.04788 =
         0.05421   -0.00181    0.00228   -0.00035
N4    3    0.081643    0.512708   -0.107473    11.00000    0.05940    0.05237 =
         0.04871   -0.00050    0.00240    0.00065
N5    3    0.142958    0.532190    0.079838    11.00000    0.05485    0.06098 =
         0.04920    0.00084    0.00085    0.00121
N6    3    0.113723    0.646859    0.120444    11.00000    0.06748    0.05043 =
         0.05397   -0.00380   -0.00397   -0.00001
C1    1   -0.151677    1.039434    0.047198    11.00000    0.04988    0.05024 =
         0.06734    0.00270    0.01235    0.00235
C2    1   -0.142599    0.952868   -0.011751    11.00000    0.05441    0.05941 =
         0.06061    0.00329   -0.00063    0.00721
AFIX  43
H2    2   -0.173394    0.957557   -0.051422    11.00000   -1.20000
AFIX   0
C3    1   -0.094245    0.995763    0.092344    11.00000    0.06667    0.05513 =
         0.05998   -0.00850    0.00982   -0.00072
AFIX  43
H3    2   -0.086277    1.035641    0.137104    11.00000   -1.20000
AFIX   0
C4    1    0.021410    0.600397   -0.199257    11.00000    0.05672    0.06213 =
         0.04640    0.00469   -0.00626    0.00143
AFIX  43
H4    2   -0.012264    0.655297   -0.227634    11.00000   -1.20000
AFIX   0
C5    1    0.073936    0.493903   -0.222276    11.00000    0.05605    0.05591 =
         0.04459   -0.00137   -0.00021   -0.00880
C6    1    0.110200    0.440976   -0.163323    11.00000    0.05824    0.05793 =
         0.04598   -0.00270   -0.00040    0.00752
AFIX  43
H6    2    0.148668    0.366697   -0.162503    11.00000   -1.20000
AFIX   0
C7    1    0.184637    0.439606    0.120302    11.00000    0.05373    0.05739 =
         0.05124    0.00189    0.00182    0.00078
AFIX  43
H7    2    0.210791    0.352103    0.104868    11.00000   -1.20000
AFIX   0
C8    1    0.183361    0.492220    0.188168    11.00000    0.04940    0.06238 =
         0.04887    0.00054   -0.00395   -0.00407
C9    1    0.137813    0.623474    0.186436    11.00000    0.06271    0.06649 =
         0.04826   -0.00641   -0.00250    0.00145
AFIX  43
H9    2    0.125841    0.685470    0.224848    11.00000   -1.20000
AFIX   0
HKLF 4




REM  Cl-beta-300K in Pbca #61
REM R1 =  0.0546 for    2123 Fo > 4sig(Fo)  and  0.0777 for all    2916 data
REM    190 parameters refined using      0 restraints

END

WGHT      0.0834      3.3183

REM Highest difference peak  0.619,  deepest hole -0.449,  1-sigma level  0.111
Q1    1   0.0392  0.6390  0.0861  11.00000  0.05    0.62
;
_shelx_res_checksum              20228
_olex2_submission_original_sample_id Cl-beta-300K
_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
;
_oxdiff_exptl_absorpt_empirical_full_max 2.758
_oxdiff_exptl_absorpt_empirical_full_min 0.534



####################################################################### 
# 
# 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_cl-alpha-150k
_database_code_depnum_ccdc_archive 'CCDC 1889444'
loop_
_audit_author_name
_audit_author_address
'Dan Li'
;Jinan University
China
;
_audit_update_record             
;
2019-02-16 deposited with the CCDC.	2019-03-21 downloaded from the CCDC.
;
_audit_creation_date             2019-02-15
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2016/6
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C9 H6 Cl3 Cu3 N6'
_chemical_formula_sum            'C9 H6 Cl3 Cu3 N6'
_chemical_formula_weight         495.17
_chemical_melting_point          ?
_chemical_oxdiff_formula         'Cu Cl C H N'
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.3639 0.7018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cu Cu -1.9646 0.5888 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      orthorhombic
_space_group_IT_number           60
_space_group_name_H-M_alt        'P b c n'
_space_group_name_Hall           '-P 2n 2ab'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y+1/2, z+1/2'
'x+1/2, -y+1/2, -z'
'-x, y, -z+1/2'
'-x, -y, -z'
'x-1/2, y-1/2, -z-1/2'
'-x-1/2, y-1/2, z'
'x, -y, z-1/2'

_cell_length_a                   16.3157(4)
_cell_length_b                   11.6083(3)
_cell_length_c                   7.6970(2)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1457.78(7)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    2076
_cell_measurement_temperature    150.00(10)
_cell_measurement_theta_max      76.2360
_cell_measurement_theta_min      4.6440
_shelx_estimated_absorpt_T_max   0.402
_shelx_estimated_absorpt_T_min   0.236
_exptl_absorpt_coefficient_mu    10.147
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.52819
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.33c (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 colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    2.256
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             960
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.11
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0557
_diffrn_reflns_av_unetI/netI     0.0531
_diffrn_reflns_Laue_measured_fraction_full 0.971
_diffrn_reflns_Laue_measured_fraction_max 0.930
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -5
_diffrn_reflns_number            4789
_diffrn_reflns_point_group_measured_fraction_full 0.971
_diffrn_reflns_point_group_measured_fraction_max 0.930
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         77.328
_diffrn_reflns_theta_min         4.675
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      150.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.971
_diffrn_measured_fraction_theta_max 0.930
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -74.00 -31.00   0.50    6.21    --   -0.90 -26.00  13.00   86
  2  ω      6.00  31.00   0.50    6.21    --   -0.90  26.00 176.00   50
  3  ω     72.00  99.00   0.50   24.85    --  105.10 -26.00  13.00   54
  4  ω    112.00 137.00   0.50   24.85    --  105.10  26.00 176.00   50
  5  ω    -32.00  16.00   0.50    6.21    --   -0.90  82.00-180.00   96
  6  ω    -32.00  34.00   0.50    6.21    --    0.90  82.00  90.00  132
  7  ω     18.00 132.00   0.50   24.85    --  105.10 -57.00   0.00  228
  8  ω     51.00 138.00   0.50   24.85    --  105.10 -77.00 -90.00  174
  9  ω    126.00 151.00   0.50   24.85    --  105.10  82.00-150.00   50
 10  ω     73.00 124.00   0.50   24.85    --  105.10 -38.00 150.00  102
 11  ω    162.00 187.00   0.50   24.85    --  105.10  82.00  30.00   50
 12  ω    107.00 132.00   0.50   24.85    --  105.10  82.00  30.00   50
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB AFC12 (RINC): Kappa single'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0395978000
_diffrn_orient_matrix_UB_12      -0.1204121000
_diffrn_orient_matrix_UB_13      0.0053951000
_diffrn_orient_matrix_UB_21      0.0801634000
_diffrn_orient_matrix_UB_22      -0.0535469000
_diffrn_orient_matrix_UB_23      -0.0681488000
_diffrn_orient_matrix_UB_31      0.0301983000
_diffrn_orient_matrix_UB_32      -0.0157683000
_diffrn_orient_matrix_UB_33      0.1882148000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'Rotating-anode X-ray tube (dual wavelength)'
_diffrn_source_type              'Rigaku (Cu) X-ray DW Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1096
_reflns_number_total             1444
_reflns_odcompleteness_completeness 99.28
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_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 1.171.39.33c (Rigaku OD, 2017)'
_computing_data_collection       'CrysAlisPro 1.171.39.33c (Rigaku OD, 2017)'
_computing_data_reduction        'CrysAlisPro 1.171.39.33c (Rigaku OD, 2017)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'XS (Sheldrick, 2008)'
_refine_diff_density_max         0.636
_refine_diff_density_min         -0.544
_refine_diff_density_rms         0.139
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.022
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     97
_refine_ls_number_reflns         1444
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0787
_refine_ls_R_factor_gt           0.0538
_refine_ls_restrained_S_all      1.022
_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)+(0.0964P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1316
_refine_ls_wR_factor_ref         0.1428
_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:
 C2(H2), C3(H3), C5(H5)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Cu1 Cu 0.41577(5) 0.82197(6) 0.13548(10) 0.0403(3) Uani 1 1 d . . . . .
Cu2 Cu 0.500000 1.06350(8) 0.250000 0.0389(3) Uani 1 2 d S T P . .
Cl1 Cl 0.500000 0.35414(13) 0.250000 0.0415(4) Uani 1 2 d S T P . .
Cl2 Cl 0.21690(8) 1.17840(10) -0.13931(19) 0.0481(4) Uani 1 1 d . . . . .
N1 N 0.4628(3) 0.6835(3) 0.2070(6) 0.0384(9) Uani 1 1 d . . . . .
N2 N 0.3704(2) 0.9614(3) 0.0652(6) 0.0365(9) Uani 1 1 d . . . . .
N3 N 0.4087(2) 1.0626(3) 0.1057(6) 0.0370(9) Uani 1 1 d . . . . .
C1 C 0.500000 0.5022(5) 0.250000 0.0335(13) Uani 1 2 d S T P . .
C2 C 0.4402(3) 0.5745(4) 0.1815(7) 0.0395(11) Uani 1 1 d . . . . .
H2 H 0.391199 0.550136 0.125693 0.047 Uiso 1 1 calc R . . . .
C3 C 0.3003(3) 0.9859(4) -0.0195(7) 0.0364(10) Uani 1 1 d . . . . .
H3 H 0.261834 0.931153 -0.061503 0.044 Uiso 1 1 calc R . . . .
C4 C 0.2940(3) 1.1043(4) -0.0351(6) 0.0357(10) Uani 1 1 d . . . . .
C5 C 0.3626(3) 1.1490(4) 0.0438(6) 0.0362(10) Uani 1 1 d . . . . .
H5 H 0.375341 1.228584 0.053105 0.043 Uiso 1 1 calc R . . . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
Cu1 0.0483(5) 0.0283(4) 0.0442(5) 0.0012(3) -0.0029(3) 0.0045(3)
Cu2 0.0376(5) 0.0372(6) 0.0419(7) 0.000 -0.0033(4) 0.000
Cl1 0.0457(8) 0.0269(7) 0.0519(10) 0.000 0.0013(7) 0.000
Cl2 0.0472(7) 0.0406(6) 0.0564(9) 0.0015(5) -0.0102(6) 0.0108(5)
N1 0.045(2) 0.0313(19) 0.039(2) 0.0027(16) -0.0032(18) -0.0001(16)
N2 0.042(2) 0.0316(18) 0.036(2) 0.0016(16) 0.0022(17) 0.0029(15)
N3 0.037(2) 0.036(2) 0.037(2) 0.0024(17) -0.0028(17) 0.0002(14)
C1 0.042(3) 0.024(3) 0.035(4) 0.000 0.001(3) 0.000
C2 0.043(3) 0.029(2) 0.046(3) -0.0034(19) -0.004(2) -0.0006(17)
C3 0.040(2) 0.031(2) 0.038(3) 0.0028(19) 0.0006(19) -0.0021(17)
C4 0.041(2) 0.0308(19) 0.035(3) 0.000(2) 0.0002(19) 0.0047(18)
C5 0.041(2) 0.030(2) 0.037(3) 0.001(2) 0.0007(19) 0.0020(17)

_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 N1 1.865(4) . ?
Cu1 N2 1.860(4) . ?
Cu2 N3 1.859(4) 4_655 ?
Cu2 N3 1.859(4) . ?
Cl1 C1 1.718(6) . ?
Cl2 C4 1.722(5) . ?
N1 N1 1.382(8) 4_655 ?
N1 C2 1.333(6) . ?
N2 N3 1.366(5) . ?
N2 C3 1.347(6) . ?
N3 C5 1.341(6) . ?
C1 C2 1.391(6) . ?
C1 C2 1.391(6) 4_655 ?
C3 C4 1.383(6) . ?
C4 C5 1.376(6) . ?

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
N2 Cu1 N1 179.03(19) . . ?
N3 Cu2 N3 179.4(3) . 4_655 ?
N1 N1 Cu1 120.20(13) 4_655 . ?
C2 N1 Cu1 131.4(4) . . ?
C2 N1 N1 108.3(3) . 4_655 ?
N3 N2 Cu1 120.0(3) . . ?
C3 N2 Cu1 131.5(3) . . ?
C3 N2 N3 108.5(4) . . ?
N2 N3 Cu2 120.5(3) . . ?
C5 N3 Cu2 131.1(3) . . ?
C5 N3 N2 107.8(4) . . ?
C2 C1 Cl1 127.1(3) . . ?
C2 C1 Cl1 127.1(3) 4_655 . ?
C2 C1 C2 105.8(6) . 4_655 ?
N1 C2 C1 108.8(4) . . ?
N2 C3 C4 108.4(4) . . ?
C3 C4 Cl2 126.3(4) . . ?
C5 C4 Cl2 127.7(4) . . ?
C5 C4 C3 106.0(4) . . ?
N3 C5 C4 109.3(4) . . ?

_shelx_res_file                  
;
TITL Cl-alpha-150K in Pbcn #60
    cl-alpha-150k.res
    created by SHELXL-2016/6 at 21:53:35 on 15-Feb-2019
REM reset to Pbcn #60
CELL 1.54184 16.315681 11.60825 7.696953 90 90 90
ZERR 4 0.000414 0.000299 0.00023 0 0 0
LATT 1
SYMM 0.5-X,0.5-Y,0.5+Z
SYMM 0.5+X,0.5-Y,-Z
SYMM -X,+Y,0.5-Z
SFAC C H N Cl Cu
UNIT 36 24 24 12 12

L.S. 10 0 0
PLAN  1
SIZE 0.2 0.15 0.11
TEMP -123.15(10)
BOND
fmap 2 53
acta
OMIT 1 5 9
OMIT 1 2 9
OMIT 1 1 9
OMIT 5 8 5
OMIT 0 2 9
OMIT 5 7 8
OMIT 0 8 0
OMIT 3 4 9
OMIT 2 4 9
OMIT 0 6 8
OMIT 0 4 9
OMIT 4 4 9
OMIT 2 1 9
OMIT 2 2 9
OMIT 3 10 7
OMIT 3 2 9
OMIT 3 8 8
OMIT 4 1 9
OMIT 7 1 0
OMIT 9 5 8
OMIT 1 1 5
OMIT 1 4 6
OMIT 1 7 5
OMIT 1 11 6
OMIT 6 7 4
OMIT 7 1 8
OMIT 5 11 1
OMIT 0 0 8
OMIT 1 0 8
OMIT 11 12 2
OMIT 0 8 2
OMIT 8 6 8
OMIT 0 2 8
OMIT 1 8 4
OMIT 13 3 7
OMIT 1 1 8
OMIT 9 10 3
OMIT 4 0 0
OMIT 10 2 8
OMIT 3 2 8
OMIT 6 7 6
OMIT 1 7 6
OMIT 0 8 8
OMIT 6 3 1
OMIT 10 0 2
OMIT 7 2 9
OMIT 18 0 4
OMIT 14 1 6
OMIT 3 1 9
OMIT 12 2 7
REM <olex2.extras>
REM <HklSrc "%.\\Cl-alpha-150K.hkl">
REM </olex2.extras>

WGHT    0.096400
FVAR       0.80621
CU1   5    0.415774    0.821967    0.135483    11.00000    0.04834    0.02833 =
         0.04422    0.00120   -0.00292    0.00453
CU2   5    0.500000    1.063496    0.250000    10.50000    0.03760    0.03716 =
         0.04193    0.00000   -0.00326    0.00000
CL1   4    0.500000    0.354138    0.250000    10.50000    0.04572    0.02689 =
         0.05190    0.00000    0.00135    0.00000
CL2   4    0.216897    1.178399   -0.139314    11.00000    0.04722    0.04057 =
         0.05641    0.00146   -0.01015    0.01079
N1    3    0.462835    0.683495    0.207019    11.00000    0.04537    0.03125 =
         0.03851    0.00268   -0.00320   -0.00013
N2    3    0.370436    0.961378    0.065250    11.00000    0.04193    0.03162 =
         0.03587    0.00164    0.00222    0.00290
N3    3    0.408679    1.062590    0.105658    11.00000    0.03733    0.03639 =
         0.03723    0.00241   -0.00276    0.00023
C1    1    0.500000    0.502164    0.250000    10.50000    0.04169    0.02406 =
         0.03462    0.00000    0.00100    0.00000
C2    1    0.440166    0.574464    0.181494    11.00000    0.04315    0.02942 =
         0.04589   -0.00337   -0.00441   -0.00063
AFIX  43
H2    2    0.391199    0.550136    0.125693    11.00000   -1.20000
AFIX   0
C3    1    0.300339    0.985876   -0.019546    11.00000    0.03986    0.03091 =
         0.03839    0.00285    0.00056   -0.00209
AFIX  43
H3    2    0.261834    0.931153   -0.061503    11.00000   -1.20000
AFIX   0
C4    1    0.293955    1.104259   -0.035144    11.00000    0.04109    0.03078 =
         0.03535   -0.00020    0.00024    0.00467
C5    1    0.362598    1.148967    0.043836    11.00000    0.04135    0.03015 =
         0.03709    0.00101    0.00067    0.00197
AFIX  43
H5    2    0.375341    1.228584    0.053105    11.00000   -1.20000
AFIX   0
HKLF 4




REM  Cl-alpha-150K in Pbcn #60
REM R1 =  0.0538 for    1096 Fo > 4sig(Fo)  and  0.0787 for all    1444 data
REM     97 parameters refined using      0 restraints

END

WGHT      0.0964      0.0000

REM Highest difference peak  0.636,  deepest hole -0.544,  1-sigma level  0.139
Q1    1   0.4461  1.0335  0.1661  11.00000  0.05    0.64
;
_shelx_res_checksum              5392
_olex2_submission_original_sample_id Cl-alpha-150K
_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
;
_oxdiff_exptl_absorpt_empirical_full_max 1.757
_oxdiff_exptl_absorpt_empirical_full_min 0.386
####################################################################### 
# 
# 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_cl-alpha-300k
_database_code_depnum_ccdc_archive 'CCDC 1889443'
loop_
_audit_author_name
_audit_author_address
'Dan Li'
;Jinan University
China
;
_audit_update_record             
;
2019-02-16 deposited with the CCDC.	2019-03-21 downloaded from the CCDC.
;
_audit_creation_date             2019-02-15
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2016/6
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C9 H6 Cl3 Cu3 N6'
_chemical_formula_sum            'C9 H6 Cl3 Cu3 N6'
_chemical_formula_weight         495.17
_chemical_melting_point          ?
_chemical_oxdiff_formula         'Cu C H N Cl'
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.3639 0.7018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cu Cu -1.9646 0.5888 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      orthorhombic
_space_group_IT_number           60
_space_group_name_H-M_alt        'P b c n'
_space_group_name_Hall           '-P 2n 2ab'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y+1/2, z+1/2'
'x+1/2, -y+1/2, -z'
'-x, y, -z+1/2'
'-x, -y, -z'
'x-1/2, y-1/2, -z-1/2'
'-x-1/2, y-1/2, z'
'x, -y, z-1/2'

_cell_length_a                   16.3471(15)
_cell_length_b                   11.6390(11)
_cell_length_c                   7.8446(15)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1492.6(3)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    1817
_cell_measurement_temperature    300(2)
_cell_measurement_theta_max      75.1160
_cell_measurement_theta_min      4.6130
_shelx_estimated_absorpt_T_max   0.409
_shelx_estimated_absorpt_T_min   0.242
_exptl_absorpt_coefficient_mu    9.911
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.79037
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.33c (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 colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    2.204
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             960
_exptl_crystal_preparation       ?
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.11
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0961
_diffrn_reflns_av_unetI/netI     0.0631
_diffrn_reflns_Laue_measured_fraction_full 0.965
_diffrn_reflns_Laue_measured_fraction_max 0.922
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            5341
_diffrn_reflns_point_group_measured_fraction_full 0.965
_diffrn_reflns_point_group_measured_fraction_max 0.922
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         78.961
_diffrn_reflns_theta_min         4.664
_diffrn_ambient_environment      air
_diffrn_ambient_temperature      300(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.965
_diffrn_measured_fraction_theta_max 0.922
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -58.00 -33.00   0.50    2.53    --   -0.90 -49.00 -23.00   50
  2  ω      4.00  29.00   0.50    2.53    --   -0.90  72.00 -50.00   50
  3  ω    -81.00 -56.00   0.50    2.53    --   -0.90 -72.00 179.00   50
  4  ω    -56.00 -31.00   0.50    2.53    --    0.90 -49.00 -23.00   50
  5  ω    113.00 138.00   0.50   10.11    --  105.10  49.00 124.00   50
  6  ω     49.00  74.00   0.50   10.11    --  105.10 -49.00 -23.00   50
  7  ω     76.00 101.00   0.50   10.11    --  105.10 -72.00 179.00   50
  8  ω     79.00 147.00   0.50   10.11    --  105.10  72.00 -50.00  136
  9  ω    -17.00  24.00   0.50    2.53    --    0.90  82.00-180.00   82
 10  ω    -39.00  22.00   0.50    2.53    --    0.90 -82.00 150.00  122
 11  ω     76.00 175.00   0.50   10.11    --  105.10  77.00 -30.00  198
 12  ω     19.00 137.00   0.50   10.11    --  105.10 -82.00  90.00  236
 13  ω    166.00 191.00   0.50   10.11    --  105.10  57.00-150.00   50
 14  ω    106.00 148.00   0.50   10.11    --  105.10  82.00 -90.00   84
 15  ω    113.00 152.00   0.50   10.11    --  105.10  57.00-150.00   78
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB AFC12 (RINC): Kappa single'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0852367000
_diffrn_orient_matrix_UB_12      0.0539814000
_diffrn_orient_matrix_UB_13      -0.0206161000
_diffrn_orient_matrix_UB_21      0.0343185000
_diffrn_orient_matrix_UB_22      0.1171156000
_diffrn_orient_matrix_UB_23      0.0569137000
_diffrn_orient_matrix_UB_31      0.0196767000
_diffrn_orient_matrix_UB_32      0.0295656000
_diffrn_orient_matrix_UB_33      -0.1874846000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'Rotating-anode X-ray tube (dual wavelength)'
_diffrn_source_type              'Rigaku (Cu) X-ray DW Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                888
_reflns_number_total             1488
_reflns_odcompleteness_completeness 94.97
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_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 1.171.39.33c (Rigaku OD, 2017)'
_computing_data_collection       'CrysAlisPro 1.171.39.33c (Rigaku OD, 2017)'
_computing_data_reduction        'CrysAlisPro 1.171.39.33c (Rigaku OD, 2017)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'XS (Sheldrick, 2008)'
_refine_diff_density_max         0.807
_refine_diff_density_min         -1.314
_refine_diff_density_rms         0.229
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.277
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     97
_refine_ls_number_reflns         1488
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1257
_refine_ls_R_factor_gt           0.0809
_refine_ls_restrained_S_all      1.277
_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)+(0.2000P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2536
_refine_ls_wR_factor_ref         0.3560
_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:
 C2(H2), C3(H3), C5(H5)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Cu1 Cu 0.58299(11) 0.67234(12) 0.1373(3) 0.0805(8) Uani 1 1 d . . . . .
Cu2 Cu 0.500000 0.43177(19) 0.250000 0.0797(9) Uani 1 2 d S T P . .
Cl1 Cl 0.500000 1.1379(3) 0.250000 0.0864(14) Uani 1 2 d S T P . .
Cl2 Cl 0.7790(2) 0.3183(3) -0.1363(5) 0.0972(12) Uani 1 1 d . . . . .
N1 N 0.5364(6) 0.8102(6) 0.2121(13) 0.070(2) Uani 1 1 d . . . . .
N2 N 0.6294(5) 0.5343(6) 0.0685(13) 0.069(2) Uani 1 1 d . . . . .
N3 N 0.5921(5) 0.4318(7) 0.1110(13) 0.075(3) Uani 1 1 d . . . . .
C1 C 0.500000 0.9903(12) 0.250000 0.075(4) Uani 1 2 d S T P . .
C2 C 0.5596(8) 0.9182(8) 0.1842(18) 0.080(3) Uani 1 1 d . . . . .
H2 H 0.607463 0.941277 0.129915 0.096 Uiso 1 1 calc R . . . .
C3 C 0.6971(6) 0.5097(8) -0.0149(15) 0.068(3) Uani 1 1 d . . . . .
H3 H 0.734419 0.563209 -0.055955 0.082 Uiso 1 1 calc R . . . .
C4 C 0.7039(6) 0.3926(8) -0.0318(17) 0.072(3) Uani 1 1 d . . . . .
C5 C 0.6369(6) 0.3485(8) 0.0459(15) 0.067(3) Uani 1 1 d . . . . .
H5 H 0.624396 0.270661 0.052422 0.081 Uiso 1 1 calc R . . . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
Cu1 0.0849(12) 0.0464(9) 0.1102(18) -0.0041(7) 0.0054(9) 0.0086(6)
Cu2 0.0664(13) 0.0617(13) 0.111(2) 0.000 0.0095(12) 0.000
Cl1 0.091(2) 0.0404(14) 0.128(4) 0.000 0.003(2) 0.000
Cl2 0.0865(19) 0.0700(16) 0.135(3) -0.0031(15) 0.0222(19) 0.0211(12)
N1 0.091(6) 0.046(3) 0.074(7) 0.005(3) 0.010(5) 0.002(3)
N2 0.067(4) 0.052(4) 0.087(6) 0.002(4) 0.004(4) -0.001(3)
N3 0.074(5) 0.049(4) 0.104(8) 0.005(4) -0.005(5) 0.007(3)
C1 0.079(9) 0.043(5) 0.104(13) 0.000 -0.001(8) 0.000
C2 0.076(6) 0.046(4) 0.118(9) 0.009(5) 0.017(7) 0.004(4)
C3 0.062(5) 0.060(5) 0.083(8) 0.006(5) -0.007(5) 0.003(4)
C4 0.065(5) 0.056(5) 0.094(9) -0.004(5) -0.008(5) 0.009(4)
C5 0.071(6) 0.050(4) 0.080(7) -0.006(5) 0.002(5) 0.006(4)

_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 N1 1.870(8) . ?
Cu1 N2 1.857(8) . ?
Cu2 N3 1.859(10) 4_655 ?
Cu2 N3 1.859(10) . ?
Cl1 C1 1.718(15) . ?
Cl2 C4 1.710(10) . ?
N1 N1 1.331(19) 4_655 ?
N1 C2 1.331(13) . ?
N2 N3 1.380(12) . ?
N2 C3 1.317(13) . ?
N3 C5 1.318(13) . ?
C1 C2 1.386(14) . ?
C1 C2 1.386(14) 4_655 ?
C3 C4 1.374(12) . ?
C4 C5 1.354(14) . ?

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
N2 Cu1 N1 178.6(5) . . ?
N3 Cu2 N3 180.0(5) 4_655 . ?
N1 N1 Cu1 120.3(3) 4_655 . ?
N1 N1 C2 109.2(6) 4_655 . ?
C2 N1 Cu1 130.0(8) . . ?
N3 N2 Cu1 119.8(7) . . ?
C3 N2 Cu1 132.5(7) . . ?
C3 N2 N3 107.6(8) . . ?
N2 N3 Cu2 120.0(7) . . ?
C5 N3 Cu2 132.6(8) . . ?
C5 N3 N2 107.3(9) . . ?
C2 C1 Cl1 127.3(7) 4_655 . ?
C2 C1 Cl1 127.3(7) . . ?
C2 C1 C2 105.5(13) 4_655 . ?
N1 C2 C1 108.1(10) . . ?
N2 C3 C4 109.4(9) . . ?
C3 C4 Cl2 127.3(9) . . ?
C5 C4 Cl2 127.2(8) . . ?
C5 C4 C3 105.5(9) . . ?
N3 C5 C4 110.2(9) . . ?

_shelx_res_file                  
;
TITL Cl-alpha-300k in Pbcn #60
    cl-alpha-300k.res
    created by SHELXL-2016/6 at 22:21:05 on 15-Feb-2019
REM reset to Pbcn #60
CELL 1.54184 16.347139 11.638998 7.844636 90 90 90
ZERR 4 0.001502 0.00114 0.001503 0 0 0
LATT 1
SYMM 0.5-X,0.5-Y,0.5+Z
SYMM 0.5+X,0.5-Y,-Z
SYMM -X,+Y,0.5-Z
SFAC C H N Cl Cu
UNIT 36 24 24 12 12

L.S. 20 0 0
PLAN  1
SIZE 0.2 0.15 0.11
TEMP 27(2)
BOND
fmap 2 53
acta
REM <olex2.extras>
REM <HklSrc "%.\\Cl-alpha-300k.hkl">
REM </olex2.extras>

WGHT    0.200000
FVAR       1.33806
CU1   5    0.582985    0.672339    0.137347    11.00000    0.08488    0.04641 =
         0.11024   -0.00409    0.00540    0.00859
CU2   5    0.500000    0.431773    0.250000    10.50000    0.06644    0.06172 =
         0.11086    0.00000    0.00952    0.00000
CL1   4    0.500000    1.137946    0.250000    10.50000    0.09076    0.04045 =
         0.12795    0.00000    0.00296    0.00000
CL2   4    0.778953    0.318303   -0.136290    11.00000    0.08653    0.06999 =
         0.13521   -0.00306    0.02216    0.02111
N1    3    0.536439    0.810209    0.212145    11.00000    0.09092    0.04577 =
         0.07393    0.00463    0.01043    0.00216
N2    3    0.629395    0.534258    0.068503    11.00000    0.06691    0.05158 =
         0.08749    0.00221    0.00391   -0.00060
N3    3    0.592123    0.431802    0.110982    11.00000    0.07352    0.04859 =
         0.10360    0.00548   -0.00507    0.00654
C1    1    0.500000    0.990318    0.250000    10.50000    0.07919    0.04325 =
         0.10403    0.00000   -0.00147    0.00000
C2    1    0.559616    0.918223    0.184168    11.00000    0.07577    0.04565 =
         0.11793    0.00862    0.01664    0.00377
AFIX  43
H2    2    0.607463    0.941277    0.129915    11.00000   -1.20000
AFIX   0
C3    1    0.697068    0.509668   -0.014891    11.00000    0.06159    0.05981 =
         0.08343    0.00560   -0.00733    0.00334
AFIX  43
H3    2    0.734419    0.563209   -0.055955    11.00000   -1.20000
AFIX   0
C4    1    0.703889    0.392581   -0.031771    11.00000    0.06454    0.05577 =
         0.09425   -0.00381   -0.00756    0.00948
C5    1    0.636948    0.348472    0.045905    11.00000    0.07134    0.05040 =
         0.07959   -0.00643    0.00181    0.00642
AFIX  43
H5    2    0.624396    0.270661    0.052422    11.00000   -1.20000
AFIX   0
HKLF 4




REM  Cl-alpha-300k in Pbcn #60
REM R1 =  0.0809 for     888 Fo > 4sig(Fo)  and  0.1257 for all    1488 data
REM     97 parameters refined using      0 restraints

END

WGHT      0.2000      0.0000

REM Highest difference peak  0.807,  deepest hole -1.314,  1-sigma level  0.229
Q1    1   0.5000  0.6819  0.2500  10.50000  0.05    0.81
;
_shelx_res_checksum              59275
_olex2_submission_original_sample_id Cl-alpha-
_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
;
_oxdiff_exptl_absorpt_empirical_full_max 2.047
_oxdiff_exptl_absorpt_empirical_full_min 0.430
