# Electronic Supplementary Material (ESI) for CrystEngComm.
# This journal is © The Royal Society of Chemistry 2020

####################################################################### 
# 
# 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_96-8-2_ref
_database_code_depnum_ccdc_archive 'CCDC 1914148'
loop_
_audit_author_name
_audit_author_address
'Giuseppe Cruciani'
;University of Ferrara
Italy
;
_audit_update_record             
;
2020-01-24 deposited with the CCDC.	2020-09-29 downloaded from the CCDC.
;
_audit_creation_date             2020-01-23
_audit_creation_method           
;
Olex2 1.3
(compiled Nov 21 2019 18:26:39 for OlexSys, GUI svn.r6003)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        'ethylenediammonium lead iodide chloride'
_chemical_formula_moiety         'I4 Pb, 2(Cl), 2(C2 H10 N2)'
_chemical_formula_sum            'C16 H80 Cl8 I16 N16 Pb4'
_chemical_formula_weight         3639.72
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
Pb Pb -3.3944 10.1111 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
I I -0.4742 1.8119 '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'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
C C 0.0033 0.0016 '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           57
_space_group_name_H-M_alt        'P b c m'
_space_group_name_Hall           '-P 2c 2b'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x, -y+1/2, -z'
'-x, -y, -z'
'x, y, -z-1/2'
'x, -y-1/2, z-1/2'
'-x, y-1/2, z'

_cell_length_a                   8.7590(4)
_cell_length_b                   9.4400(4)
_cell_length_c                   23.5450(8)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1946.82(14)
_cell_formula_units_Z            1
_cell_measurement_reflns_used    ?
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      ?
_cell_measurement_theta_min      ?
_shelx_estimated_absorpt_T_max   0.310
_shelx_estimated_absorpt_T_min   0.310
_exptl_absorpt_coefficient_mu    15.269
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'reddish orange'
_exptl_crystal_density_diffrn    3.104
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       ?
_exptl_crystal_F_000             1600
_exptl_crystal_size_max          0.1
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.1
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0609
_diffrn_reflns_av_unetI/netI     0.0375
_diffrn_reflns_Laue_measured_fraction_full 0.886
_diffrn_reflns_Laue_measured_fraction_max 0.892
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       30
_diffrn_reflns_limit_l_min       -30
_diffrn_reflns_number            10927
_diffrn_reflns_point_group_measured_fraction_full 0.886
_diffrn_reflns_point_group_measured_fraction_max 0.892
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.603
_diffrn_reflns_theta_min         3.289
_diffrn_ambient_temperature      296.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.886
_diffrn_measured_fraction_theta_max 0.892
_diffrn_measurement_device_type  ?
_diffrn_measurement_method       ?
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71075
_diffrn_source                   ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1165
_reflns_number_total             2071
_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       ?
_computing_data_collection       ?
_computing_data_reduction        ?
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         2.394
_refine_diff_density_min         -1.608
_refine_diff_density_rms         0.271
_refine_ls_extinction_coef       0.00068(12)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.063
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     88
_refine_ls_number_reflns         2071
_refine_ls_number_restraints     18
_refine_ls_R_factor_all          0.1083
_refine_ls_R_factor_gt           0.0676
_refine_ls_restrained_S_all      1.058
_refine_ls_shift/su_max          0.831
_refine_ls_shift/su_mean         0.063
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0530P)²+66.9166P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1527
_refine_ls_wR_factor_ref         0.1745
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H,H) groups
2. Restrained distances
 N0AA-H0AA = N0AA-H0AB = N0AA-H0AC
 0.85 with sigma of 0.02
 H0AA-H0AB = H0AA-H0AC = H0AB-H0AC
 1.4 with sigma of 0.02
 C02-H0AA = C02-H0AB = C02-H0AC
 1.9 with sigma of 0.02
 N03-H03A = N03-H03B = N03-H03C
 0.85 with sigma of 0.02
 H03A-H03B = H03A-H03C = H03B-H03C
 1.4 with sigma of 0.02
 C01-H03A = C01-H03B = C01-H03C
 1.9 with sigma of 0.02
3. Others
 Fixed Uiso: H0AA(0.19) H0AB(0.19) H0AC(0.19) H03A(0.19) H03B(0.19) H03C(0.19)
4.a Secondary CH2 refined with riding coordinates:
 C02(H02A,H02B), C01(H01A,H01B)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_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
Pb01 Pb 0.74988(14) 0.57534(8) 0.250000 0.0336(3) Uani 1 2 d S T P . .
I002 I 0.4959(2) 0.8140(3) 0.250000 0.0595(6) Uani 1 2 d S T P . .
I003 I 0.7507(3) 0.56627(15) 0.38327(5) 0.0654(5) Uani 1 1 d . . . . .
I004 I 1.0058(3) 0.8138(3) 0.250000 0.0726(7) Uani 1 2 d S T P . .
Cl05 Cl 0.4611(7) 0.750000 0.500000 0.0405(16) Uani 1 2 d S T P . .
Cl06 Cl 1.0315(8) 0.750000 0.500000 0.0509(19) Uani 1 2 d S T P . .
N0AA N 0.748(3) 0.9532(18) 0.4631(6) 0.069(5) Uani 1 1 d D . . . .
H0AA H 0.681(15) 0.91(3) 0.482(4) 0.190 Uiso 1 1 d D U . . .
H0AB H 0.830(18) 0.91(3) 0.461(2) 0.190 Uiso 1 1 d D U . . .
H0AC H 0.76(3) 1.034(4) 0.478(5) 0.190 Uiso 1 1 d D U . . .
C02 C 0.690(3) 0.974(3) 0.4061(9) 0.072(8) Uani 1 1 d D . . . .
H02A H 0.593245 1.023364 0.408759 0.086 Uiso 1 1 calc R U . . .
H02B H 0.668732 0.880946 0.390016 0.086 Uiso 1 1 calc R U . . .
N03 N 0.773(3) 1.202(3) 0.3786(13) 0.138(11) Uiso 1 1 d D . . . .
H03A H 0.78(3) 1.249(4) 0.348(2) 0.190 Uiso 1 1 d D U . . .
H03B H 0.686(13) 1.214(7) 0.394(11) 0.190 Uiso 1 1 d D U . . .
H03C H 0.844(19) 1.225(8) 0.402(9) 0.190 Uiso 1 1 d D U . . .
C01 C 0.789(3) 1.052(2) 0.3652(10) 0.070(8) Uani 1 1 d D . . . .
H01A H 0.894983 1.023162 0.369415 0.084 Uiso 1 1 calc R U . . .
H01B H 0.757567 1.034148 0.326457 0.084 Uiso 1 1 calc R U . . .

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
Pb01 0.0360(4) 0.0300(4) 0.0349(4) 0.000 0.000 -0.0006(5)
I002 0.0520(13) 0.0523(14) 0.0742(14) 0.000 0.000 0.0201(10)
I003 0.1060(11) 0.0611(8) 0.0292(6) -0.0012(5) -0.0030(9) -0.0015(11)
I004 0.0550(14) 0.0553(15) 0.1075(19) 0.000 0.000 -0.0329(11)
Cl05 0.036(3) 0.041(4) 0.044(4) -0.015(3) 0.000 0.000
Cl06 0.039(4) 0.044(5) 0.070(5) -0.017(4) 0.000 0.000
N0AA 0.111(15) 0.059(10) 0.037(8) 0.001(7) -0.001(12) -0.043(14)
C02 0.101(19) 0.056(15) 0.059(14) -0.007(11) 0.004(13) -0.039(14)
C01 0.09(2) 0.072(16) 0.048(12) -0.004(10) -0.005(11) -0.038(13)

_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
Pb01 I002 3.274(2) 3_645 ?
Pb01 I002 3.166(2) . ?
Pb01 I003 3.1391(11) 6_556 ?
Pb01 I003 3.1391(11) . ?
Pb01 I004 3.177(2) . ?
Pb01 I004 3.267(2) 3_745 ?
N0AA H0AA 0.853(19) . ?
N0AA H0AB 0.856(19) . ?
N0AA H0AC 0.849(19) . ?
N0AA C02 1.45(2) . ?
C02 H02A 0.9700 . ?
C02 H02B 0.9700 . ?
C02 C01 1.50(3) . ?
N03 H03A 0.852(19) . ?
N03 H03B 0.853(19) . ?
N03 H03C 0.850(19) . ?
N03 C01 1.45(3) . ?
C01 H01A 0.9700 . ?
C01 H01B 0.9700 . ?

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
I002 Pb01 I002 94.25(3) . 3_645 ?
I002 Pb01 I004 176.28(7) . 3_745 ?
I002 Pb01 I004 89.52(6) . . ?
I003 Pb01 I002 91.20(4) 6_556 . ?
I003 Pb01 I002 88.90(4) . 3_645 ?
I003 Pb01 I002 91.20(4) . . ?
I003 Pb01 I002 88.90(4) 6_556 3_645 ?
I003 Pb01 I003 176.86(6) . 6_556 ?
I003 Pb01 I004 91.02(4) . . ?
I003 Pb01 I004 91.02(4) 6_556 . ?
I003 Pb01 I004 88.74(4) . 3_745 ?
I003 Pb01 I004 88.74(4) 6_556 3_745 ?
I004 Pb01 I002 176.23(7) . 3_645 ?
I004 Pb01 I002 82.02(6) 3_745 3_645 ?
I004 Pb01 I004 94.20(3) . 3_745 ?
Pb01 I002 Pb01 176.46(9) . 3_655 ?
Pb01 I004 Pb01 176.04(10) . 3_755 ?
H0AA N0AA H0AB 110(3) . . ?
H0AA N0AA H0AC 111(3) . . ?
H0AB N0AA H0AC 110(3) . . ?
C02 N0AA H0AA 109(3) . . ?
C02 N0AA H0AB 108(3) . . ?
C02 N0AA H0AC 109(3) . . ?
N0AA C02 H02A 108.0 . . ?
N0AA C02 H02B 108.0 . . ?
N0AA C02 C01 117(2) . . ?
H02A C02 H02B 107.3 . . ?
C01 C02 H02A 107.9 . . ?
C01 C02 H02B 108.0 . . ?
H03A N03 H03B 111(3) . . ?
H03A N03 H03C 111(3) . . ?
H03B N03 H03C 111(3) . . ?
C01 N03 H03A 108(3) . . ?
C01 N03 H03B 108(3) . . ?
C01 N03 H03C 108(3) . . ?
C02 C01 H01A 110.1 . . ?
C02 C01 H01B 110.4 . . ?
N03 C01 C02 107(2) . . ?
N03 C01 H01A 111.1 . . ?
N03 C01 H01B 110.1 . . ?
H01A C01 H01B 108.5 . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
N0AA H0AA Cl05 0.853(19) 2.47(5) 3.275(19) 158(10) . yes
N0AA H0AB Cl06 0.856(19) 2.47(5) 3.26(2) 154(10) . yes
N0AA H0AC Cl05 0.849(19) 2.9(2) 3.46(2) 126(20) 5_676 yes
N0AA H0AC Cl06 0.849(19) 2.76(15) 3.514(17) 149(25) 5_776 yes
C02 H02A I003 0.97 3.10 3.99(3) 153.9 8_665 yes
C02 H02B I003 0.97 3.06 3.92(3) 148.1 . yes
N03 H03A I004 0.852(19) 3.03(15) 3.75(3) 143(20) 3_755 yes
N03 H03B Cl05 0.853(19) 2.83(17) 3.55(3) 142(23) 5_676 yes
N03 H03C Cl06 0.850(19) 2.57(12) 3.36(3) 155(24) 5_776 yes
C01 H01A I003 0.97 3.15 4.05(3) 155.2 8_765 yes

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
N0AA C02 C01 N03 -79(3) . . . . ?

_shelx_res_file                  
;
TITL 0.5(I8 Pb2), 2(Cl), 2(C2 H8 N2)
    96-8-2_ref.res
    created by SHELXL-2018/3 at 14:33:01 on 23-Jan-2020
CELL 0.71075 8.759 9.44 23.545 90 90 90
ZERR 1 0.0004 0.0004 0.0008 0 0 0
LATT 1
SYMM -X,-Y,0.5+Z
SYMM -X,0.5+Y,0.5-Z
SYMM +X,0.5-Y,-Z
SFAC Pb I Cl N H C
UNIT 4 16 8 16 80 16
EQIV $1 2-X,0.5+Y,0.5-Z
EQIV $2 1-X,2-Y,1-Z
EQIV $3 2-X,2-Y,1-Z
EQIV $4 1-X,0.5+Y,+Z
EQIV $5 2-X,0.5+Y,+Z
DFIX 0.85 N0AA H0Aa N0AA H0Ab N0AA H0Ac
DFIX 1.4 H0Aa H0Ab H0Aa H0Ac H0Ab H0Ac
DFIX 1.9 C02 H0Aa C02 H0Ab C02 H0Ac
DFIX 0.85 N03 H03a N03 H03b N03 H03c
DFIX 1.4 H03a H03b H03a H03c H03b H03c
DFIX 1.9 C01 H03a C01 H03b C01 H03c

L.S. 5
PLAN  8
SIZE 0.1 0.1 0.1
TEMP 23
CONF
HTAB N0AA Cl05
HTAB N0AA Cl06
HTAB N0AA Cl05_$2
HTAB N0AA Cl06_$3
HTAB C02 I003_$4
HTAB C02 I003
HTAB N03 I004_$1
HTAB N03 Cl05_$2
HTAB N03 Cl06_$3
HTAB C01 I003_$5
WPDB -2
HTAB
BOND $H
LIST 3
MORE -1
fmap 2
acta
SHEL 99999 0
OMIT 0 0 2
REM <olex2.extras>
REM <HklSrc "%.\\96-8-2_ref.hkl">
REM </olex2.extras>

WGHT    0.053000   66.916603
EXTI    0.000683
FVAR       0.13939
PB01  1    0.749882    0.575343    0.250000    10.50000    0.03600    0.02996 =
         0.03494    0.00000    0.00000   -0.00061
I002  2    0.495884    0.813985    0.250000    10.50000    0.05201    0.05234 =
         0.07421    0.00000    0.00000    0.02012
I003  2    0.750671    0.566265    0.383271    11.00000    0.10598    0.06110 =
         0.02924   -0.00121   -0.00300   -0.00148
I004  2    1.005787    0.813801    0.250000    10.50000    0.05504    0.05525 =
         0.10746    0.00000    0.00000   -0.03287
CL05  3    0.461131    0.750000    0.500000    10.50000    0.03554    0.04147 =
         0.04443   -0.01513    0.00000    0.00000
CL06  3    1.031497    0.750000    0.500000    10.50000    0.03895    0.04357 =
         0.07022   -0.01743    0.00000    0.00000
N0AA  4    0.747604    0.953180    0.463132    11.00000    0.11094    0.05869 =
         0.03740    0.00083   -0.00108   -0.04269
H0AA  5    0.681315    0.907368    0.482257    11.00000   10.19000
H0AB  5    0.830183    0.905061    0.460960    11.00000   10.19000
H0AC  5    0.764935    1.033638    0.477877    11.00000   10.19000
C02   6    0.689820    0.973523    0.406078    11.00000    0.10150    0.05590 =
         0.05880   -0.00685    0.00380   -0.03923
AFIX  23
H02A  5    0.593245    1.023364    0.408759    11.00000   -1.20000
H02B  5    0.668732    0.880946    0.390016    11.00000   -1.20000
AFIX   0
N03   4    0.773053    1.201714    0.378612    11.00000    0.13771
H03A  5    0.780477    1.248512    0.347801    11.00000   10.19000
H03B  5    0.685564    1.214302    0.393692    11.00000   10.19000
H03C  5    0.843598    1.224816    0.401632    11.00000   10.19000
C01   6    0.789421    1.052417    0.365228    11.00000    0.09079    0.07182 =
         0.04823   -0.00448   -0.00465   -0.03783
AFIX  23
H01A  5    0.894983    1.023162    0.369415    11.00000   -1.20000
H01B  5    0.757567    1.034148    0.326457    11.00000   -1.20000
AFIX   0
HKLF 4




REM  0.5(I8 Pb2), 2(Cl), 2(C2 H8 N2)
REM wR2 = 0.1745, GooF = S = 1.063, Restrained GooF = 1.058 for all data
REM R1 = 0.0676 for 1165 Fo > 4sig(Fo) and 0.1083 for all 2071 data
REM 88 parameters refined using 18 restraints

END

WGHT      0.0533     66.7174

REM Instructions for potential hydrogen bonds
EQIV $10 x, -y+3/2, -z+1
HTAB N0AA I003_$10
HTAB N0AA Cl05
HTAB N0AA Cl06
HTAB N0AA Cl05_$2
HTAB N0AA Cl06_$3
HTAB C02 I003_$4
HTAB C02 I003
HTAB N03 I004_$1
HTAB N03 Cl05_$2
HTAB N03 Cl06_$3
HTAB C01 I003_$5

REM Highest difference peak  2.394,  deepest hole -1.608,  1-sigma level  0.271
Q1    1   0.8547  0.5196  0.2500  10.50000  0.05    2.39
Q2    1   0.6406  0.5217  0.2500  10.50000  0.05    2.27
Q3    1   0.4870  0.7767  0.4835  11.00000  0.05    1.63
Q4    1   0.7502  0.4739  0.3803  11.00000  0.05    1.61
Q5    1   1.0043  0.7821  0.4887  11.00000  0.05    1.59
Q6    1   0.6627  0.6395  0.2500  10.50000  0.05    1.49
Q7    1   0.4382  0.7709  0.5088  11.00000  0.05    1.46
Q8    1   0.4211  0.7500  0.5000  10.50000  0.05    1.41
;
_shelx_res_checksum              26440
_olex2_submission_special_instructions 'No special instructions were received'
_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent'
_chemical_properties_physical    
Air-sensitive,Moisture-sensitive,Light-sensitive
