# Electronic Supplementary Material (ESI) for Polymer Chemistry.
# 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_20160728lmf_0m_a_sqd
_database_code_depnum_ccdc_archive 'CCDC 1509942'
_audit_update_record             
;
2016-10-14 deposited with the CCDC.
2018-03-14 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C21 H18 Cl N3'
_chemical_formula_weight         347.83

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      cubic
_space_group_IT_number           198
_space_group_name_H-M_alt        'P 21 3'
_space_group_name_Hall           'P 2ac 2ab 3'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

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

_cell_length_a                   13.4840(8)
_cell_length_b                   13.4840(8)
_cell_length_c                   13.4840(8)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2451.6(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    8242
_cell_measurement_theta_min      2.62
_cell_measurement_theta_max      28.28

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    0.942
_exptl_crystal_F_000             728
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.270
_exptl_crystal_size_mid          0.250
_exptl_crystal_size_min          0.220
_exptl_absorpt_coefficient_mu    0.161
_shelx_estimated_absorpt_T_min   0.958
_shelx_estimated_absorpt_T_max   0.965
_exptl_absorpt_correction_type   MULTI-SCAN
_exptl_absorpt_correction_T_min  0.9577
_exptl_absorpt_correction_T_max  0.9653
_exptl_absorpt_process_details   SADABS
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            23175
_diffrn_reflns_av_unetI/netI     0.0343
_diffrn_reflns_av_R_equivalents  0.0890
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         2.136
_diffrn_reflns_theta_max         28.319
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             2045
_reflns_number_gt                1846
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.788
_reflns_Friedel_fraction_max     0.999
_reflns_Friedel_fraction_full    0.998

_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.
;

loop_
_platon_squeeze_void_nr
_platon_squeeze_void_average_x
_platon_squeeze_void_average_y
_platon_squeeze_void_average_z
_platon_squeeze_void_volume
_platon_squeeze_void_count_electrons
_platon_squeeze_void_content
1 0.096 -0.118 0.590 963 355 ' '
_platon_squeeze_void_probe_radius 1.20

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          
;
 Refined as a 2-component inversion twin.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1820P)²+3.4136P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   0.2(3)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         2045
_refine_ls_number_parameters     86
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.1140
_refine_ls_R_factor_gt           0.1082
_refine_ls_wR_factor_ref         0.3135
_refine_ls_wR_factor_gt          0.3079
_refine_ls_goodness_of_fit_ref   1.140
_refine_ls_restrained_S_all      1.142
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
N1 N 0.9998(6) 0.8082(6) 0.3082(6) 0.0199(16) Uani 0.5 1 d . . P A 1
H1A H 0.9739 0.7614 0.3430 0.024 Uiso 1 1 d R U . A 1
N1' N 1.0581(10) 0.9392(9) 0.2521(8) 0.043(3) Uani 0.5 1 d . . P . 2
C1 C 0.9575(7) 0.9313(9) 0.1997(7) 0.083(4) Uani 1 1 d D . . B 1
H1 H 1.0000 0.9694 0.2385 0.099 Uiso 1 1 calc R U . B 1
C2 C 0.9060(8) 0.9729(8) 0.1245(9) 0.075(3) Uani 1 1 d . . . . .
H2 H 0.9196 1.0383 0.1074 0.090 Uiso 1 1 calc R U . B 1
C3 C 0.8358(6) 0.9238(7) 0.0731(7) 0.061(3) Uani 1 1 d . . . . .
H3 H 0.7954 0.9561 0.0274 0.073 Uiso 1 1 calc R U . . .
C4 C 0.8266(7) 0.8256(8) 0.0907(6) 0.057(2) Uani 1 1 d . . . . .
H4 H 0.7829 0.7883 0.0525 0.068 Uiso 1 1 calc R U . . .
C5 C 0.8804(8) 0.7799(7) 0.1637(8) 0.068(3) Uani 1 1 d . . . . .
H5 H 0.8720 0.7126 0.1762 0.081 Uiso 1 1 calc R U . . .
C6 C 0.9460(7) 0.8335(9) 0.2176(7) 0.080(4) Uani 1 1 d D . . . .
C7 C 1.0809(6) 0.8475(6) 0.3454(5) 0.0459(17) Uani 1 1 d . . . . .
Cl1 Cl 0.87595(11) 0.62405(11) 0.37595(11) 0.0298(6) Uani 1 3 d S T P C 1

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
N1 0.024(4) 0.023(4) 0.012(3) 0.003(3) 0.003(3) -0.002(3)
N1' 0.048(6) 0.048(6) 0.033(5) 0.018(5) -0.008(5) -0.012(5)
C1 0.065(5) 0.143(10) 0.040(4) 0.031(5) -0.009(4) -0.072(7)
C2 0.071(6) 0.066(5) 0.089(7) 0.018(5) 0.016(6) -0.035(5)
C3 0.041(4) 0.080(6) 0.060(5) 0.047(5) -0.014(3) -0.021(4)
C4 0.051(4) 0.083(6) 0.036(3) 0.004(4) -0.010(3) -0.026(4)
C5 0.073(6) 0.055(5) 0.075(6) 0.034(4) 0.011(5) -0.002(4)
C6 0.044(4) 0.142(10) 0.055(5) 0.060(6) -0.020(4) -0.031(5)
C7 0.054(4) 0.045(4) 0.039(3) -0.004(3) -0.004(3) -0.006(3)
Cl1 0.0298(6) 0.0298(6) 0.0298(6) -0.0093(5) 0.0093(5) -0.0093(5)

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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
N1 C7 1.315(11) . ?
N1 C6 1.461(11) . ?
N1 H1A 0.8600 . ?
N1' C7 1.791(13) . ?
N1' C7 1.849(14) 6_674 ?
C1 C6 1.350(11) . ?
C1 C2 1.351(15) . ?
C1 H1 0.9300 . ?
C2 C3 1.347(14) . ?
C2 H2 0.9300 . ?
C3 C4 1.351(13) . ?
C3 H3 0.9300 . ?
C4 C5 1.370(13) . ?
C4 H4 0.9300 . ?
C5 C6 1.354(15) . ?
C5 H5 0.9300 . ?
C7 C7 1.386(13) 11_756 ?
C7 C7 1.386(13) 6_674 ?
C7 N1' 1.849(14) 11_756 ?

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
C7 N1 C6 129.6(8) . . ?
C7 N1 H1A 115.1 . . ?
C6 N1 H1A 115.2 . . ?
C7 N1' C7 44.7(5) . 6_674 ?
C6 C1 C2 118.7(9) . . ?
C6 C1 H1 120.6 . . ?
C2 C1 H1 120.6 . . ?
C3 C2 C1 122.9(9) . . ?
C3 C2 H2 118.5 . . ?
C1 C2 H2 118.5 . . ?
C4 C3 C2 117.1(8) . . ?
C4 C3 H3 121.4 . . ?
C2 C3 H3 121.4 . . ?
C3 C4 C5 121.2(9) . . ?
C3 C4 H4 119.4 . . ?
C5 C4 H4 119.4 . . ?
C4 C5 C6 119.5(8) . . ?
C4 C5 H5 120.2 . . ?
C6 C5 H5 120.2 . . ?
C1 C6 C5 120.0(8) . . ?
C1 C6 N1 108.7(9) . . ?
C5 C6 N1 130.4(8) . . ?
N1 C7 C7 147.7(9) . 11_756 ?
N1 C7 C7 152.2(9) . 6_674 ?
C7 C7 C7 59.999(2) 11_756 6_674 ?
C7 C7 N1' 129.6(7) 11_756 . ?
C7 C7 N1' 69.8(7) 6_674 . ?
C7 C7 N1' 65.4(7) 11_756 11_756 ?
C7 C7 N1' 125.2(7) 6_674 11_756 ?
N1' C7 N1' 161.7(8) . 11_756 ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C6 C1 C2 C3 7.3(17) . . . . ?
C1 C2 C3 C4 -8.4(17) . . . . ?
C2 C3 C4 C5 5.5(15) . . . . ?
C3 C4 C5 C6 -1.8(16) . . . . ?
C2 C1 C6 C5 -3.2(16) . . . . ?
C2 C1 C6 N1 -173.7(10) . . . . ?
C4 C5 C6 C1 0.5(16) . . . . ?
C4 C5 C6 N1 168.8(11) . . . . ?
C7 N1 C6 C1 -31.0(14) . . . . ?
C7 N1 C6 C5 159.7(11) . . . . ?
C6 N1 C7 C7 -176.6(8) . . . 11_756 ?
C6 N1 C7 C7 8.9(18) . . . 6_674 ?
C7 N1' C7 C7 6.4(6) 6_674 . . 11_756 ?
C7 N1' C7 N1' 147(3) 6_674 . . 11_756 ?

_refine_diff_density_max         0.703
_refine_diff_density_min         -0.437
_refine_diff_density_rms         0.108

_shelx_res_file                  
;

    20160728lmf_0m_a_sqd.res created by SHELXL-2014/7

TITL 20160728LMF_0m_a.res in P2(1)2(1 New: P213
CELL  0.71073   13.4840   13.4840   13.4840    90.000    90.000    90.000
ZERR        4    0.0008    0.0008    0.0008     0.000     0.000     0.000
LATT -1
SYMM     0.50000 - X ,            - Y ,    0.50000 + Z
SYMM     0.50000 + X ,    0.50000 - Y ,            - Z
SYMM             - X ,    0.50000 + Y ,    0.50000 - Z
SYMM               Z ,              X ,              Y
SYMM     0.50000 - Z ,            - X ,    0.50000 + Y
SYMM     0.50000 + Z ,    0.50000 - X ,            - Y
SYMM             - Z ,    0.50000 + X ,    0.50000 - Y
SYMM               Y ,              Z ,              X
SYMM     0.50000 + Y ,    0.50000 - Z ,            - X
SYMM             - Y ,    0.50000 + Z ,    0.50000 - X
SYMM     0.50000 - Y ,            - Z ,    0.50000 + X
SFAC C  H  Cl N
UNIT 84 72 4 12
L.S. 20
ACTA
BOND $H
FMAP 2
PLAN 0
DFIX 1.38 .01 C1 C6
WGHT    0.182000    3.413600
BASF   0.19349
FVAR       6.54521
RESI 0
SIZE .27 .25 .22
TWIN
CONF
TEMP   23
PART 1
N1    4    0.999765    0.808200    0.308224    10.50000    0.02434    0.02325 =
         0.01201    0.00301    0.00341   -0.00245
AFIX   3
H1A   2    0.973925    0.761380    0.342974    11.00000   -1.20000
PART 2
AFIX   0
N1'   4    1.058055    0.939239    0.252149    10.50000    0.04762    0.04839 =
         0.03294    0.01785   -0.00780   -0.01241
PART 1
C1    1    0.957464    0.931319    0.199748    11.00000    0.06487    0.14261 =
         0.04039    0.03072   -0.00914   -0.07194
AFIX  43
H1    2    0.999953    0.969393    0.238503    11.00000   -1.20000
PART 0
AFIX   0
C2    1    0.905984    0.972881    0.124472    11.00000    0.07124    0.06554 =
         0.08930    0.01750    0.01560   -0.03467
AFIX  43
H2    2    0.919643    1.038292    0.107392    11.00000   -1.20000
AFIX   0
C3    1    0.835764    0.923810    0.073061    11.00000    0.04139    0.08032 =
         0.06040    0.04706   -0.01352   -0.02081
AFIX  43
H3    2    0.795378    0.956132    0.027441    11.00000   -1.20000
AFIX   0
C4    1    0.826561    0.825575    0.090665    11.00000    0.05133    0.08260 =
         0.03597    0.00408   -0.00974   -0.02612
AFIX  43
H4    2    0.782874    0.788285    0.052483    11.00000   -1.20000
AFIX   0
C5    1    0.880415    0.779915    0.163731    11.00000    0.07283    0.05527 =
         0.07520    0.03430    0.01140   -0.00236
AFIX  43
H5    2    0.871953    0.712615    0.176221    11.00000   -1.20000
AFIX   0
C6    1    0.946036    0.833487    0.217611    11.00000    0.04387    0.14172 =
         0.05545    0.05982   -0.01998   -0.03080
C7    1    1.080881    0.847470    0.345445    11.00000    0.05369    0.04477 =
         0.03928   -0.00415   -0.00449   -0.00631
PART 1
CL1   3    0.875949    0.624051    0.375949    10.33333    0.02984    0.02984 =
         0.02984   -0.00929    0.00929   -0.00929
PART 0
HKLF 4 1  0.0000  0.0000  1.0000  1.0000  0.0000  0.0000  0.0000  1.0000  0.0000

REM  20160728LMF_0m_a.res in P2(1)2(1 New: P213
REM R1 =  0.1082 for    1846 Fo > 4sig(Fo)  and  0.1140 for all    2045 data
REM     86 parameters refined using      1 restraints

END

WGHT      0.1839      3.8143

REM Highest difference peak  0.703,  deepest hole -0.437,  1-sigma level  0.108
Q1    1   1.1002  0.8971  0.3241  11.00000  0.05    0.70
Q2    1   0.9078  0.5840  0.3539  11.00000  0.05    0.50
Q3    1   0.8378  0.6446  0.3638  11.00000  0.05    0.50
Q4    1   0.7968  0.7032  0.2968  10.33333  0.05    0.45
Q5    1   0.8834  0.9299  0.1015  11.00000  0.05    0.44
Q6    1   0.6780  0.8165 -0.1702  11.00000  0.05    0.43
Q7    1   0.8421  0.8768  0.0957  11.00000  0.05    0.38
Q8    1   0.9670  0.8847  0.1989  11.00000  0.05    0.38
Q9    1   1.0360  1.0360  0.0360  10.33333  0.05    0.36
Q10   1   1.0655  0.7720  0.2399  11.00000  0.05    0.33
Q11   1   0.9074  0.8393  0.1785  11.00000  0.05    0.33
Q12   1   0.9246  0.9043  0.1478  11.00000  0.05    0.31
Q13   1   0.9488  0.9571  0.0604  11.00000  0.05    0.31
Q14   1   0.7735  0.7796  0.2097  11.00000  0.05    0.31
Q15   1   0.9018  1.1028  0.1475  11.00000  0.05    0.31
Q16   1   0.7317  0.7683  0.2317  10.33333  0.05    0.31
Q17   1   0.8977  0.6569  0.1480  11.00000  0.05    0.31
Q18   1   0.9847  0.9216  0.0635  11.00000  0.05    0.30
Q19   1   0.9342  0.9342 -0.0658  10.33333  0.05    0.29
Q20   1   0.9325  0.9554  0.0807  11.00000  0.05    0.29
;
_shelx_res_checksum              10707
