# Electronic Supplementary Material (ESI) for Journal of Materials Chemistry C.
# This journal is © The Royal Society of Chemistry 2018

####################################################################### 
# 
# 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_1D-CuBr(3-Br-py)
_database_code_depnum_ccdc_archive 'CCDC 1506741'
_audit_update_record             
;
2016-09-26 deposited with the CCDC.
2018-12-04 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C5 H4 Br2 Cu N'
_chemical_formula_sum            'C5 H4 Br2 Cu N'

_chemical_formula_weight         301.44

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'
Cu Cu 0.3201 1.2651 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   ' P 21/n'
_symmetry_space_group_name_Hall  ' -P 2yn'

loop_
_symmetry_equiv_pos_as_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                   8.720(9)
_cell_length_b                   3.933(4)
_cell_length_c                   21.11(2)
_cell_angle_alpha                90.00
_cell_angle_beta                 100.603(13)
_cell_angle_gamma                90.00
_cell_volume                     711.6(12)
_cell_formula_units_Z            4
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    4244
_cell_measurement_theta_min      1.96
_cell_measurement_theta_max      27.10

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.36
_exptl_crystal_size_mid          0.27
_exptl_crystal_size_min          0.01
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    2.814
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             560
_exptl_absorpt_coefficient_mu    14.198
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.34
_exptl_absorpt_correction_T_max  0.76
_exptl_absorpt_process_details   'Bruker SAINT (SADABS)'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      298(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker SMART APEX CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            4244
_diffrn_reflns_av_R_equivalents  0.0420
_diffrn_reflns_av_sigmaI/netI    0.0485
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_theta_min         1.96
_diffrn_reflns_theta_max         27.10
_reflns_number_total             1542
_reflns_number_gt                1285
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0728P)²+1.2615P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         1542
_refine_ls_number_parameters     82
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0608
_refine_ls_R_factor_gt           0.0479
_refine_ls_wR_factor_ref         0.1269
_refine_ls_wR_factor_gt          0.1207
_refine_ls_goodness_of_fit_ref   1.067
_refine_ls_restrained_S_all      1.067
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Br1 Br 0.32956(7) 0.40401(15) 0.17743(3) 0.0306(2) Uani 1 1 d . . .
Br2 Br -0.25136(9) 1.3343(2) -0.01778(4) 0.0446(3) Uani 1 1 d . . .
Cu1 Cu 0.18087(10) 0.8943(3) 0.20301(5) 0.0451(3) Uani 1 1 d . . .
N1 N -0.0401(6) 0.9608(15) 0.1566(3) 0.0317(12) Uani 1 1 d . . .
C4 C -0.3120(8) 0.9177(19) 0.1534(4) 0.0395(16) Uani 1 1 d . . .
H4 H -0.3933 0.8535 0.1738 0.047 Uiso 1 1 calc R . .
C1 C -0.0705(8) 1.0979(16) 0.0985(3) 0.0321(14) Uani 1 1 d . . .
H1 H 0.0126 1.1610 0.0790 0.039 Uiso 1 1 calc R . .
C2 C -0.2197(8) 1.1509(15) 0.0658(3) 0.0307(14) Uani 1 1 d . . .
C3 C -0.3429(8) 1.060(2) 0.0941(4) 0.0400(17) Uani 1 1 d . . .
H3 H -0.4452 1.0950 0.0731 0.048 Uiso 1 1 calc R . .
C5 C -0.1600(8) 0.8685(18) 0.1834(3) 0.0355(15) Uani 1 1 d . . .
H5 H -0.1403 0.7671 0.2239 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
Br1 0.0294(4) 0.0288(4) 0.0353(4) 0.0017(2) 0.0104(3) -0.0005(2)
Br2 0.0479(5) 0.0447(4) 0.0381(4) 0.0044(3) -0.0006(3) 0.0004(3)
Cu1 0.0289(5) 0.0526(6) 0.0525(6) 0.0063(4) 0.0047(4) 0.0044(4)
N1 0.021(3) 0.041(3) 0.032(3) 0.001(2) 0.002(2) 0.000(2)
C4 0.025(3) 0.050(4) 0.047(4) -0.007(3) 0.016(3) -0.007(3)
C1 0.027(3) 0.031(3) 0.041(4) 0.001(3) 0.013(3) -0.002(3)
C2 0.033(3) 0.027(3) 0.031(3) -0.006(2) 0.003(3) -0.001(3)
C3 0.025(3) 0.050(4) 0.043(4) -0.010(3) 0.002(3) -0.002(3)
C5 0.032(4) 0.042(4) 0.034(4) 0.002(3) 0.012(3) -0.005(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
Br1 Cu1 2.439(2) . ?
Br1 Cu1 2.500(2) 1_545 ?
Br1 Cu1 2.543(3) 2_545 ?
Br2 C2 1.879(7) . ?
Cu1 N1 2.012(5) . ?
Cu1 Br1 2.500(2) 1_565 ?
Cu1 Br1 2.543(3) 2 ?
Cu1 Cu1 2.894(2) 2 ?
Cu1 Cu1 2.894(2) 2_545 ?
N1 C1 1.320(9) . ?
N1 C5 1.329(8) . ?
C4 C3 1.352(11) . ?
C4 C5 1.374(10) . ?
C1 C2 1.373(9) . ?
C2 C3 1.370(10) . ?

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
Cu1 Br1 Cu1 105.55(8) . 1_545 ?
Cu1 Br1 Cu1 71.00(4) . 2_545 ?
Cu1 Br1 Cu1 70.05(4) 1_545 2_545 ?
N1 Cu1 Br1 119.69(18) . . ?
N1 Cu1 Br1 106.20(18) . 1_565 ?
Br1 Cu1 Br1 105.55(8) . 1_565 ?
N1 Cu1 Br1 106.02(17) . 2 ?
Br1 Cu1 Br1 110.43(4) . 2 ?
Br1 Cu1 Br1 108.49(5) 1_565 2 ?
N1 Cu1 Cu1 119.13(17) . 2 ?
Br1 Cu1 Cu1 121.17(7) . 2 ?
Br1 Cu1 Cu1 55.67(6) 1_565 2 ?
Br1 Cu1 Cu1 52.83(6) 2 2 ?
N1 Cu1 Cu1 131.55(17) . 2_545 ?
Br1 Cu1 Cu1 56.17(6) . 2_545 ?
Br1 Cu1 Cu1 121.71(7) 1_565 2_545 ?
Br1 Cu1 Cu1 54.28(6) 2 2_545 ?
Cu1 Cu1 Cu1 85.60(9) 2 2_545 ?
C1 N1 C5 117.9(6) . . ?
C1 N1 Cu1 121.1(5) . . ?
C5 N1 Cu1 121.0(5) . . ?
C3 C4 C5 119.8(7) . . ?
N1 C1 C2 122.6(6) . . ?
C3 C2 C1 119.2(6) . . ?
C3 C2 Br2 121.2(5) . . ?
C1 C2 Br2 119.5(5) . . ?
C4 C3 C2 118.2(7) . . ?
N1 C5 C4 122.2(7) . . ?

_diffrn_measured_fraction_theta_max 0.995
_diffrn_reflns_theta_full        27.10
_diffrn_measured_fraction_theta_full 0.995
_refine_diff_density_max         1.147
_refine_diff_density_min         -1.479
_refine_diff_density_rms         0.196
####################################################################### 
# 
# 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_1D-CuBr(3-Cl-py)
_database_code_depnum_ccdc_archive 'CCDC 1506742'
_audit_update_record             
;
2016-09-26 deposited with the CCDC.
2018-12-04 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C5 H4 Br Cl Cu N'
_chemical_formula_sum            'C5 H4 Br Cl Cu N'
_chemical_formula_weight         256.99

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cu Cu 0.3201 1.2651 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 21/n'
_symmetry_space_group_name_Hall  ' -P 2yn'

loop_
_symmetry_equiv_pos_as_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                   8.7438(19)
_cell_length_b                   3.9296(9)
_cell_length_c                   21.002(5)
_cell_angle_alpha                90.00
_cell_angle_beta                 100.837(3)
_cell_angle_gamma                90.00
_cell_volume                     708.7(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    7887
_cell_measurement_theta_min      1.97
_cell_measurement_theta_max      30.42

_exptl_crystal_description       needle
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.21
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.04
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    2.408
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             488
_exptl_absorpt_coefficient_mu    8.995
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.353
_exptl_absorpt_correction_T_max  0.698
_exptl_absorpt_process_details   'Bruker SAINT (SADABS)'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      298(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker SMART APEX CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            7887
_diffrn_reflns_av_R_equivalents  0.0326
_diffrn_reflns_av_sigmaI/netI    0.0287
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_l_min       -29
_diffrn_reflns_limit_l_max       29
_diffrn_reflns_theta_min         1.97
_diffrn_reflns_theta_max         30.42
_reflns_number_total             2159
_reflns_number_gt                1805
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0450P)²+0.3410P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         2159
_refine_ls_number_parameters     82
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0382
_refine_ls_R_factor_gt           0.0306
_refine_ls_wR_factor_ref         0.0852
_refine_ls_wR_factor_gt          0.0817
_refine_ls_goodness_of_fit_ref   1.040
_refine_ls_restrained_S_all      1.040
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Br1 Br 0.33032(3) 0.90307(6) 0.176337(13) 0.03437(10) Uani 1 1 d . . .
Cu1 Cu 0.18109(4) 1.39375(10) 0.20309(2) 0.04815(13) Uani 1 1 d . . .
Cl1 Cl -0.24895(11) 1.8249(3) -0.01422(4) 0.0588(2) Uani 1 1 d . . .
C1 C -0.0698(3) 1.5973(7) 0.09604(14) 0.0367(6) Uani 1 1 d . . .
H1 H 0.0132 1.6623 0.0768 0.044 Uiso 1 1 calc R . .
N1 N -0.0407(3) 1.4571(6) 0.15456(12) 0.0350(5) Uani 1 1 d . . .
C4 C 0.6862(4) 1.4160(8) 0.15116(17) 0.0453(7) Uani 1 1 d . . .
H4 H 0.6046 1.3499 0.1712 0.054 Uiso 1 1 calc R . .
C2 C -0.2204(3) 1.6493(7) 0.06278(14) 0.0385(6) Uani 1 1 d . . .
C3 C 0.6554(3) 1.5615(8) 0.09065(17) 0.0457(7) Uani 1 1 d . . .
H3 H 0.5536 1.5993 0.0693 0.055 Uiso 1 1 calc R . .
C5 C -0.1623(3) 1.3682(8) 0.18211(15) 0.0409(6) Uani 1 1 d . . .
H5 H -0.1431 1.2716 0.2233 0.049 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
Br1 0.03636(16) 0.03115(14) 0.03750(16) 0.00117(10) 0.01185(11) -0.00103(9)
Cu1 0.0359(2) 0.0517(2) 0.0556(3) 0.00664(17) 0.00559(18) 0.00371(15)
Cl1 0.0662(5) 0.0662(5) 0.0393(4) 0.0057(4) -0.0023(4) 0.0018(4)
C1 0.0320(13) 0.0412(14) 0.0379(14) -0.0007(11) 0.0092(11) -0.0011(10)
N1 0.0288(11) 0.0382(12) 0.0384(12) -0.0004(9) 0.0073(9) -0.0014(9)
C4 0.0324(14) 0.0531(18) 0.0529(18) -0.0055(14) 0.0147(13) -0.0088(12)
C2 0.0400(14) 0.0395(15) 0.0340(13) -0.0047(11) 0.0018(11) 0.0024(11)
C3 0.0298(13) 0.0545(19) 0.0502(18) -0.0110(14) 0.0003(12) -0.0018(12)
C5 0.0381(15) 0.0446(16) 0.0418(16) -0.0003(12) 0.0122(12) -0.0053(12)

_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
Br1 Cu1 2.4519(6) . ?
Br1 Cu1 2.5099(6) 1_545 ?
Br1 Cu1 2.5532(7) 2_545 ?
Cu1 N1 2.029(2) . ?
Cu1 Br1 2.5099(6) 1_565 ?
Cu1 Br1 2.5531(7) 2 ?
Cu1 Cu1 2.8814(7) 2 ?
Cu1 Cu1 2.8814(7) 2_545 ?
Cl1 C2 1.733(3) . ?
C1 N1 1.327(4) . ?
C1 C2 1.385(4) . ?
N1 C5 1.349(3) . ?
C4 C3 1.373(5) . ?
C4 C5 1.374(4) 1_655 ?
C2 C3 1.371(4) 1_455 ?
C3 C2 1.371(4) 1_655 ?
C5 C4 1.374(4) 1_455 ?

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
Cu1 Br1 Cu1 104.73(2) . 1_545 ?
Cu1 Br1 Cu1 70.264(15) . 2_545 ?
Cu1 Br1 Cu1 69.370(14) 1_545 2_545 ?
N1 Cu1 Br1 118.75(7) . . ?
N1 Cu1 Br1 106.12(7) . 1_565 ?
Br1 Cu1 Br1 104.74(2) . 1_565 ?
N1 Cu1 Br1 106.53(7) . 2 ?
Br1 Cu1 Br1 111.115(17) . 2 ?
Br1 Cu1 Br1 109.235(18) 1_565 2 ?
N1 Cu1 Cu1 119.81(7) . 2 ?
Br1 Cu1 Cu1 121.38(3) . 2 ?
Br1 Cu1 Cu1 56.022(16) 1_565 2 ?
Br1 Cu1 Cu1 53.221(19) 2 2 ?
N1 Cu1 Cu1 131.64(7) . 2_545 ?
Br1 Cu1 Cu1 56.515(16) . 2_545 ?
Br1 Cu1 Cu1 121.91(2) 1_565 2_545 ?
Br1 Cu1 Cu1 54.608(19) 2 2_545 ?
Cu1 Cu1 Cu1 85.98(3) 2 2_545 ?
N1 C1 C2 121.8(3) . . ?
C1 N1 C5 118.4(2) . . ?
C1 N1 Cu1 120.98(19) . . ?
C5 N1 Cu1 120.6(2) . . ?
C3 C4 C5 119.9(3) . 1_655 ?
C3 C2 C1 120.1(3) 1_455 . ?
C3 C2 Cl1 120.8(2) 1_455 . ?
C1 C2 Cl1 119.1(2) . . ?
C2 C3 C4 117.8(3) 1_655 . ?
N1 C5 C4 122.0(3) . 1_455 ?

_diffrn_measured_fraction_theta_max 1.000
_diffrn_reflns_theta_full        30.42
_diffrn_measured_fraction_theta_full 1.000
_refine_diff_density_max         0.671
_refine_diff_density_min         -1.109
_refine_diff_density_rms         0.149
####################################################################### 
# 
# 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_1D-CuBr(3,5-dimethyl-py)
_database_code_depnum_ccdc_archive 'CCDC 1506745'
_audit_update_record             
;
2016-09-26 deposited with the CCDC.
2018-12-04 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C7 H9 Br Cu N'
_chemical_formula_sum            'C7 H9 Br Cu N'

_chemical_formula_weight         250.60

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'
Cu Cu 0.3201 1.2651 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   ' C 2/c'
_symmetry_space_group_name_Hall  '-C 2yc'


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

_cell_length_a                   13.910(17)
_cell_length_b                   15.111(18)
_cell_length_c                   8.107(10)
_cell_angle_alpha                90.00
_cell_angle_beta                 99.455(17)
_cell_angle_gamma                90.00
_cell_volume                     1681(4)
_cell_formula_units_Z            8
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    9180
_cell_measurement_theta_min      2.00
_cell_measurement_theta_max      30.42

_exptl_crystal_description       needle
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.8
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_min          0.08
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.980
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             976
_exptl_absorpt_coefficient_mu    7.274
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.38
_exptl_absorpt_correction_T_max  0.74
_exptl_absorpt_process_details   'sADABS, Sheldrick (2008)'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      295(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker SMART APEX CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            9180
_diffrn_reflns_av_R_equivalents  0.0536
_diffrn_reflns_av_sigmaI/netI    0.0487
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_theta_min         2.00
_diffrn_reflns_theta_max         30.42
_reflns_number_total             2512
_reflns_number_gt                1734
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0592P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         2512
_refine_ls_number_parameters     91
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0614
_refine_ls_R_factor_gt           0.0396
_refine_ls_wR_factor_ref         0.1107
_refine_ls_wR_factor_gt          0.0973
_refine_ls_goodness_of_fit_ref   0.984
_refine_ls_restrained_S_all      0.984
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Br1 Br 0.12569(2) 0.45660(3) 0.92107(4) 0.03944(14) Uani 1 1 d . . .
Cu1 Cu 0.05525(4) 0.43372(4) 0.61254(6) 0.05320(18) Uani 1 1 d . . .
N1 N 0.0966(2) 0.3133(2) 0.5408(3) 0.0354(7) Uani 1 1 d . . .
C1 C 0.1105(2) 0.2991(3) 0.3821(4) 0.0379(8) Uani 1 1 d . . .
H1 H 0.1033 0.3468 0.3086 0.045 Uiso 1 1 calc R . .
C5 C 0.1324(3) 0.1591(3) 0.5987(4) 0.0405(8) Uani 1 1 d . . .
C4 C 0.1467(3) 0.1487(3) 0.4339(4) 0.0453(9) Uani 1 1 d . . .
H4 H 0.1647 0.0936 0.3980 0.054 Uiso 1 1 calc R . .
C7 C 0.1077(2) 0.2430(3) 0.6448(4) 0.0374(8) Uani 1 1 d . . .
H7 H 0.0980 0.2516 0.7545 0.045 Uiso 1 1 calc R . .
C2 C 0.1347(2) 0.2185(3) 0.3224(4) 0.0372(8) Uani 1 1 d . . .
C3 C 0.1477(3) 0.2083(3) 0.1412(4) 0.0551(11) Uani 1 1 d . . .
H3A H 0.1640 0.1480 0.1207 0.083 Uiso 1 1 calc R . .
H3B H 0.1991 0.2466 0.1188 0.083 Uiso 1 1 calc R . .
H3C H 0.0881 0.2239 0.0695 0.083 Uiso 1 1 calc R . .
C6 C 0.1449(4) 0.0838(3) 0.7215(5) 0.0662(13) Uani 1 1 d . . .
H6A H 0.1619 0.0311 0.6670 0.099 Uiso 1 1 calc R . .
H6B H 0.0850 0.0744 0.7632 0.099 Uiso 1 1 calc R . .
H6C H 0.1957 0.0979 0.8128 0.099 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
Br1 0.0442(2) 0.0408(3) 0.0340(2) -0.00525(15) 0.00838(14) 0.00205(15)
Cu1 0.0692(4) 0.0411(4) 0.0529(3) -0.0069(2) 0.0207(3) 0.0103(2)
N1 0.0428(15) 0.0292(18) 0.0356(14) -0.0065(12) 0.0099(12) 0.0020(12)
C1 0.0435(18) 0.041(2) 0.0300(16) 0.0005(15) 0.0078(13) 0.0044(16)
C5 0.0462(19) 0.036(2) 0.0377(18) -0.0004(16) 0.0038(14) 0.0054(16)
C4 0.054(2) 0.037(3) 0.045(2) -0.0128(17) 0.0068(16) 0.0101(18)
C7 0.0438(18) 0.040(2) 0.0296(16) -0.0028(15) 0.0088(13) 0.0038(16)
C2 0.0410(17) 0.038(2) 0.0320(16) -0.0088(15) 0.0048(13) 0.0027(15)
C3 0.073(3) 0.058(3) 0.0355(19) -0.0101(19) 0.0143(18) 0.011(2)
C6 0.097(3) 0.051(3) 0.053(3) 0.018(2) 0.018(2) 0.013(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
Br1 Cu1 2.511(3) 2_556 ?
Br1 Cu1 2.556(3) . ?
Br1 Cu1 2.572(2) 6_566 ?
Cu1 N1 2.022(4) . ?
Cu1 Br1 2.511(3) 2_556 ?
Cu1 Br1 2.572(2) 6_565 ?
Cu1 Cu1 2.908(3) 2_556 ?
Cu1 Cu1 2.964(2) 5_566 ?
N1 C7 1.349(5) . ?
N1 C1 1.350(4) . ?
C1 C2 1.373(6) . ?
C5 C7 1.383(5) . ?
C5 C4 1.392(5) . ?
C5 C6 1.502(6) . ?
C4 C2 1.381(5) . ?
C2 C3 1.517(5) . ?

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
Cu1 Br1 Cu1 70.05(4) 2_556 . ?
Cu1 Br1 Cu1 71.32(5) 2_556 6_566 ?
Cu1 Br1 Cu1 123.71(6) . 6_566 ?
N1 Cu1 Br1 114.85(8) . 2_556 ?
N1 Cu1 Br1 108.78(9) . . ?
Br1 Cu1 Br1 107.70(4) 2_556 . ?
N1 Cu1 Br1 104.56(11) . 6_565 ?
Br1 Cu1 Br1 108.68(5) 2_556 6_565 ?
Br1 Cu1 Br1 112.37(7) . 6_565 ?
N1 Cu1 Cu1 115.58(9) . 2_556 ?
Br1 Cu1 Cu1 55.70(5) 2_556 2_556 ?
Br1 Cu1 Cu1 54.25(8) . 2_556 ?
Br1 Cu1 Cu1 139.84(4) 6_565 2_556 ?
N1 Cu1 Cu1 125.04(11) . 5_566 ?
Br1 Cu1 Cu1 55.31(3) 2_556 5_566 ?
Br1 Cu1 Cu1 126.00(6) . 5_566 ?
Br1 Cu1 Cu1 53.37(7) 6_565 5_566 ?
Cu1 Cu1 Cu1 100.72(8) 2_556 5_566 ?
C7 N1 C1 116.8(3) . . ?
C7 N1 Cu1 122.5(2) . . ?
C1 N1 Cu1 120.6(3) . . ?
N1 C1 C2 124.0(4) . . ?
C7 C5 C4 116.4(4) . . ?
C7 C5 C6 121.5(3) . . ?
C4 C5 C6 122.2(4) . . ?
C2 C4 C5 121.4(4) . . ?
N1 C7 C5 124.2(3) . . ?
C1 C2 C4 117.2(3) . . ?
C1 C2 C3 120.4(4) . . ?
C4 C2 C3 122.4(4) . . ?

_diffrn_measured_fraction_theta_max 0.983
_diffrn_reflns_theta_full        30.42
_diffrn_measured_fraction_theta_full 0.983
_refine_diff_density_max         1.020
_refine_diff_density_min         -0.725
_refine_diff_density_rms         0.134
