# Electronic Supplementary Material (ESI) for Journal of Materials Chemistry A.
# 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_mo_20180716-kcw-02_0m
_database_code_depnum_ccdc_archive 'CCDC 1986753'
loop_
_audit_author_name
_audit_author_address
'Kangcai Wang'
;CAEP
China
;
_audit_update_record             
;
2020-02-27 deposited with the CCDC.	2020-07-01 downloaded from the CCDC.
;
_audit_creation_date             2018-07-13
_audit_creation_method           
;
Olex2 1.2-beta
(compiled 2016.07.08 svn.r3312 for OlexSys, GUI svn.r5203)
;
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'Cu I2, C14 H20 Fe N'
_chemical_formula_sum            'C14 H20 Cu Fe I2 N'
_chemical_formula_weight         575.50
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cu Cu 0.3201 1.2651 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Fe Fe 0.3463 0.8444 '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'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   11.0739(13)
_cell_length_b                   10.4449(12)
_cell_length_c                   15.2751(17)
_cell_angle_alpha                90
_cell_angle_beta                 94.194(3)
_cell_angle_gamma                90
_cell_volume                     1762.1(3)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    1746
_cell_measurement_temperature    173
_cell_measurement_theta_max      23.110
_cell_measurement_theta_min      2.364
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    5.521
_exptl_absorpt_correction_T_max  0.462
_exptl_absorpt_correction_T_min  0.385
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2014/5 (Bruker,2014/5) was used for absorption correction.
wR2(int) was 0.1490 before and 0.0552 after correction.
The Ratio of minimum to maximum transmission is 0.4453.
The λ/2 correction factor is 0.00150.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear yellowish yellow'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   yellowish
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    2.169
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1088
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.14
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0634
_diffrn_reflns_av_unetI/netI     0.0654
_diffrn_reflns_Laue_measured_fraction_full 0.988
_diffrn_reflns_Laue_measured_fraction_max 0.979
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            13455
_diffrn_reflns_point_group_measured_fraction_full 0.988
_diffrn_reflns_point_group_measured_fraction_max 0.979
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.548
_diffrn_reflns_theta_min         1.844
_diffrn_ambient_temperature      173
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.988
_diffrn_measured_fraction_theta_max 0.979
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2845
_reflns_number_total             3984
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT v8.34A (Bruker, 2013)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT v8.34A (Bruker, 2013)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.936
_refine_diff_density_min         -0.786
_refine_diff_density_rms         0.165
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.007
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     175
_refine_ls_number_reflns         3984
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0625
_refine_ls_R_factor_gt           0.0397
_refine_ls_restrained_S_all      1.007
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0180P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0694
_refine_ls_wR_factor_ref         0.0776
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C4(H4A,H4B)
2.b Aromatic/amide H refined with riding coordinates:
 C6(H6), C8(H8), C7(H7), C13(H13), C14(H14), C9(H9), C10(H10), C12(H12),
 C11(H11)
2.c Idealised Me refined as rotating group:
 C2(H2A,H2B,H2C), C3(H3A,H3B,H3C), C1(H1A,H1B,H1C)
;
_atom_sites_solution_hydrogens   geom
_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
I2 I 0.82140(4) 0.26401(4) 0.60416(2) 0.03858(12) Uani 1 1 d . . . . .
I1 I 0.88160(4) 0.00876(4) 0.37634(2) 0.04443(13) Uani 1 1 d . . . . .
Cu1 Cu 0.93596(7) 0.09041(7) 0.53276(4) 0.03600(19) Uani 1 1 d . . . . .
Fe1 Fe 0.61227(7) 0.70990(7) 0.15524(4) 0.02587(18) Uani 1 1 d . . . . .
N1 N 0.8361(4) 0.4691(4) 0.3469(2) 0.0254(10) Uani 1 1 d . . . . .
C5 C 0.6810(5) 0.5890(5) 0.2492(3) 0.0239(11) Uani 1 1 d . . . . .
C4 C 0.8107(5) 0.5503(5) 0.2644(3) 0.0268(12) Uani 1 1 d . . . . .
H4A H 0.8615 0.6283 0.2694 0.032 Uiso 1 1 calc R . . . .
H4B H 0.8344 0.5013 0.2129 0.032 Uiso 1 1 calc R . . . .
C6 C 0.5910(5) 0.5262(5) 0.1936(3) 0.0283(12) Uani 1 1 d . . . . .
H6 H 0.6032 0.4524 0.1590 0.034 Uiso 1 1 calc R . . . .
C2 C 0.7490(5) 0.3596(5) 0.3485(3) 0.0315(13) Uani 1 1 d . . . . .
H2A H 0.6665 0.3928 0.3505 0.047 Uiso 1 1 calc GR . . . .
H2B H 0.7693 0.3068 0.4006 0.047 Uiso 1 1 calc GR . . . .
H2C H 0.7542 0.3074 0.2956 0.047 Uiso 1 1 calc GR . . . .
C8 C 0.5010(6) 0.6949(6) 0.2566(4) 0.0425(16) Uani 1 1 d . . . . .
H8 H 0.4417 0.7550 0.2721 0.051 Uiso 1 1 calc R . . . .
C7 C 0.4804(5) 0.5924(6) 0.1988(4) 0.0413(15) Uani 1 1 d . . . . .
H7 H 0.4053 0.5709 0.1683 0.050 Uiso 1 1 calc R . . . .
C13 C 0.5912(6) 0.8860(6) 0.0959(4) 0.0432(16) Uani 1 1 d . . . . .
H13 H 0.5437 0.9553 0.1143 0.052 Uiso 1 1 calc R . . . .
C14 C 0.7128(6) 0.8631(6) 0.1224(4) 0.0425(15) Uani 1 1 d . . . . .
H14 H 0.7619 0.9144 0.1622 0.051 Uiso 1 1 calc R . . . .
C9 C 0.6236(5) 0.6951(5) 0.2883(3) 0.0328(13) Uani 1 1 d . . . . .
H9 H 0.6613 0.7549 0.3283 0.039 Uiso 1 1 calc R . . . .
C3 C 0.8238(5) 0.5515(5) 0.4268(3) 0.0347(14) Uani 1 1 d . . . . .
H3A H 0.8815 0.6226 0.4267 0.052 Uiso 1 1 calc GR . . . .
H3B H 0.8407 0.4999 0.4799 0.052 Uiso 1 1 calc GR . . . .
H3C H 0.7412 0.5854 0.4258 0.052 Uiso 1 1 calc GR . . . .
C1 C 0.9635(5) 0.4198(6) 0.3479(3) 0.0377(14) Uani 1 1 d . . . . .
H1A H 0.9721 0.3665 0.2959 0.057 Uiso 1 1 calc GR . . . .
H1B H 0.9818 0.3686 0.4010 0.057 Uiso 1 1 calc GR . . . .
H1C H 1.0198 0.4922 0.3475 0.057 Uiso 1 1 calc GR . . . .
C10 C 0.7510(6) 0.7506(6) 0.0802(4) 0.0448(16) Uani 1 1 d . . . . .
H10 H 0.8293 0.7133 0.0868 0.054 Uiso 1 1 calc R . . . .
C12 C 0.5512(6) 0.7879(6) 0.0371(3) 0.0457(17) Uani 1 1 d . . . . .
H12 H 0.4721 0.7790 0.0093 0.055 Uiso 1 1 calc R . . . .
C11 C 0.6514(7) 0.7047(6) 0.0269(3) 0.0467(17) Uani 1 1 d . . . . .
H11 H 0.6510 0.6310 -0.0096 0.056 Uiso 1 1 calc R . . . .


_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
I2 Cu1 2.5077(8) . ?
I1 Cu1 2.5831(8) 3_756 ?
I1 Cu1 2.5667(8) . ?
Cu1 I1 2.5831(8) 3_756 ?
Cu1 Cu1 2.6055(14) 3_756 ?
Fe1 C5 2.019(5) . ?
Fe1 C6 2.025(5) . ?
Fe1 C8 2.055(5) . ?
Fe1 C7 2.055(6) . ?
Fe1 C13 2.056(6) . ?
Fe1 C14 2.033(6) . ?
Fe1 C9 2.033(5) . ?
Fe1 C10 2.028(6) . ?
Fe1 C12 2.050(5) . ?
Fe1 C11 2.039(5) . ?
N1 C4 1.528(6) . ?
N1 C2 1.498(6) . ?
N1 C3 1.508(6) . ?
N1 C1 1.500(6) . ?
C5 C4 1.494(7) . ?
C5 C6 1.421(7) . ?
C5 C9 1.429(7) . ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?
C6 H6 0.9500 . ?
C6 C7 1.414(8) . ?
C2 H2A 0.9800 . ?
C2 H2B 0.9800 . ?
C2 H2C 0.9800 . ?
C8 H8 0.9500 . ?
C8 C7 1.397(8) . ?
C8 C9 1.407(8) . ?
C7 H7 0.9500 . ?
C13 H13 0.9500 . ?
C13 C14 1.399(8) . ?
C13 C12 1.413(8) . ?
C14 H14 0.9500 . ?
C14 C10 1.419(8) . ?
C9 H9 0.9500 . ?
C3 H3A 0.9800 . ?
C3 H3B 0.9800 . ?
C3 H3C 0.9800 . ?
C1 H1A 0.9800 . ?
C1 H1B 0.9800 . ?
C1 H1C 0.9800 . ?
C10 H10 0.9500 . ?
C10 C11 1.406(9) . ?
C12 H12 0.9500 . ?
C12 C11 1.427(9) . ?
C11 H11 0.9500 . ?

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 I1 Cu1 60.78(3) . 3_756 ?
I2 Cu1 I1 117.18(3) . 3_756 ?
I2 Cu1 I1 123.60(3) . . ?
I2 Cu1 Cu1 176.48(5) . 3_756 ?
I1 Cu1 I1 119.21(3) . 3_756 ?
I1 Cu1 Cu1 59.30(3) 3_756 3_756 ?
I1 Cu1 Cu1 59.92(3) . 3_756 ?
C5 Fe1 C6 41.15(19) . . ?
C5 Fe1 C8 68.4(2) . . ?
C5 Fe1 C7 68.7(2) . . ?
C5 Fe1 C13 153.9(2) . . ?
C5 Fe1 C14 118.9(2) . . ?
C5 Fe1 C9 41.31(19) . . ?
C5 Fe1 C10 105.8(2) . . ?
C5 Fe1 C12 163.3(2) . . ?
C5 Fe1 C11 124.9(2) . . ?
C6 Fe1 C8 67.7(2) . . ?
C6 Fe1 C7 40.5(2) . . ?
C6 Fe1 C13 164.4(2) . . ?
C6 Fe1 C14 153.4(2) . . ?
C6 Fe1 C9 68.8(2) . . ?
C6 Fe1 C10 118.1(2) . . ?
C6 Fe1 C12 126.4(2) . . ?
C6 Fe1 C11 106.9(2) . . ?
C8 Fe1 C7 39.7(2) . . ?
C8 Fe1 C13 110.2(2) . . ?
C7 Fe1 C13 128.1(2) . . ?
C14 Fe1 C8 128.0(3) . . ?
C14 Fe1 C7 164.8(3) . . ?
C14 Fe1 C13 40.0(2) . . ?
C14 Fe1 C12 67.8(2) . . ?
C14 Fe1 C11 68.0(3) . . ?
C9 Fe1 C8 40.3(2) . . ?
C9 Fe1 C7 67.9(2) . . ?
C9 Fe1 C13 120.4(2) . . ?
C9 Fe1 C14 108.1(2) . . ?
C9 Fe1 C12 154.6(2) . . ?
C9 Fe1 C11 163.2(3) . . ?
C10 Fe1 C8 164.4(3) . . ?
C10 Fe1 C7 153.4(3) . . ?
C10 Fe1 C13 68.3(2) . . ?
C10 Fe1 C14 40.9(2) . . ?
C10 Fe1 C9 126.0(3) . . ?
C10 Fe1 C12 68.5(3) . . ?
C10 Fe1 C11 40.5(3) . . ?
C12 Fe1 C8 121.1(3) . . ?
C12 Fe1 C7 109.0(2) . . ?
C12 Fe1 C13 40.3(2) . . ?
C11 Fe1 C8 154.7(3) . . ?
C11 Fe1 C7 120.1(3) . . ?
C11 Fe1 C13 68.0(2) . . ?
C11 Fe1 C12 40.8(2) . . ?
C2 N1 C4 111.0(4) . . ?
C2 N1 C3 109.0(4) . . ?
C2 N1 C1 110.1(4) . . ?
C3 N1 C4 109.2(4) . . ?
C1 N1 C4 108.4(4) . . ?
C1 N1 C3 109.2(4) . . ?
C4 C5 Fe1 126.0(3) . . ?
C6 C5 Fe1 69.7(3) . . ?
C6 C5 C4 126.3(5) . . ?
C6 C5 C9 107.1(5) . . ?
C9 C5 Fe1 69.9(3) . . ?
C9 C5 C4 126.7(5) . . ?
N1 C4 H4A 108.9 . . ?
N1 C4 H4B 108.9 . . ?
C5 C4 N1 113.3(4) . . ?
C5 C4 H4A 108.9 . . ?
C5 C4 H4B 108.9 . . ?
H4A C4 H4B 107.7 . . ?
Fe1 C6 H6 125.7 . . ?
C5 C6 Fe1 69.2(3) . . ?
C5 C6 H6 125.9 . . ?
C7 C6 Fe1 70.9(3) . . ?
C7 C6 C5 108.2(5) . . ?
C7 C6 H6 125.9 . . ?
N1 C2 H2A 109.5 . . ?
N1 C2 H2B 109.5 . . ?
N1 C2 H2C 109.5 . . ?
H2A C2 H2B 109.5 . . ?
H2A C2 H2C 109.5 . . ?
H2B C2 H2C 109.5 . . ?
Fe1 C8 H8 126.9 . . ?
C7 C8 Fe1 70.1(3) . . ?
C7 C8 H8 125.5 . . ?
C7 C8 C9 109.1(5) . . ?
C9 C8 Fe1 69.0(3) . . ?
C9 C8 H8 125.5 . . ?
Fe1 C7 H7 126.8 . . ?
C6 C7 Fe1 68.6(3) . . ?
C6 C7 H7 126.0 . . ?
C8 C7 Fe1 70.1(3) . . ?
C8 C7 C6 108.0(5) . . ?
C8 C7 H7 126.0 . . ?
Fe1 C13 H13 126.8 . . ?
C14 C13 Fe1 69.1(3) . . ?
C14 C13 H13 125.9 . . ?
C14 C13 C12 108.1(6) . . ?
C12 C13 Fe1 69.6(3) . . ?
C12 C13 H13 125.9 . . ?
Fe1 C14 H14 125.8 . . ?
C13 C14 Fe1 70.9(3) . . ?
C13 C14 H14 125.6 . . ?
C13 C14 C10 108.8(6) . . ?
C10 C14 Fe1 69.3(3) . . ?
C10 C14 H14 125.6 . . ?
Fe1 C9 H9 125.9 . . ?
C5 C9 Fe1 68.8(3) . . ?
C5 C9 H9 126.2 . . ?
C8 C9 Fe1 70.7(3) . . ?
C8 C9 C5 107.7(5) . . ?
C8 C9 H9 126.2 . . ?
N1 C3 H3A 109.5 . . ?
N1 C3 H3B 109.5 . . ?
N1 C3 H3C 109.5 . . ?
H3A C3 H3B 109.5 . . ?
H3A C3 H3C 109.5 . . ?
H3B C3 H3C 109.5 . . ?
N1 C1 H1A 109.5 . . ?
N1 C1 H1B 109.5 . . ?
N1 C1 H1C 109.5 . . ?
H1A C1 H1B 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
Fe1 C10 H10 125.3 . . ?
C14 C10 Fe1 69.7(3) . . ?
C14 C10 H10 126.3 . . ?
C11 C10 Fe1 70.2(3) . . ?
C11 C10 C14 107.4(6) . . ?
C11 C10 H10 126.3 . . ?
Fe1 C12 H12 126.0 . . ?
C13 C12 Fe1 70.1(3) . . ?
C13 C12 H12 126.2 . . ?
C13 C12 C11 107.5(6) . . ?
C11 C12 Fe1 69.2(3) . . ?
C11 C12 H12 126.2 . . ?
Fe1 C11 H11 126.4 . . ?
C10 C11 Fe1 69.3(3) . . ?
C10 C11 C12 108.2(6) . . ?
C10 C11 H11 125.9 . . ?
C12 C11 Fe1 70.0(3) . . ?
C12 C11 H11 125.9 . . ?

_shelx_SHELXL_version_number     2014/7
_olex2_submission_special_instructions 'No special instructions were received'
