#------------------------------------------------------------------------------
#$Date: 2023-05-05 04:53:52 +0300 (Fri, 05 May 2023) $
#$Revision: 283269 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/71/19/7711972.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_7711972
loop_
_publ_author_name
'Teri, Gele'
'Jia, Qiang-Qiang'
'Ni, Hao-Fei'
'Wang, Jun-Qin'
'Fu, Da-Wei'
'Guo, Qiang'
_publ_section_title
;
 Halogen engineering of organic-inorganic hybrid perovskites displaying
 nonlinear optical, fluorescence properties and phase transition.
;
_journal_issue                   4
_journal_name_full
'Dalton transactions (Cambridge, England : 2003)'
_journal_page_first              1074
_journal_page_last               1081
_journal_paper_doi               10.1039/d2dt04014j
_journal_volume                  52
_journal_year                    2023
_chemical_formula_moiety         'I4 Zn, 2(C8 H12 N O)'
_chemical_formula_sum            'C16 H24 I4 N2 O2 Zn'
_chemical_formula_weight         849.34
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_date             2022-09-29
_audit_creation_method
;
Olex2 1.5
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6498)
;
_audit_update_record
;
2022-10-11 deposited with the CCDC.	2022-12-19 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 102.4590(10)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   17.3830(7)
_cell_length_b                   8.2623(4)
_cell_length_c                   18.0124(7)
_cell_measurement_reflns_used    7422
_cell_measurement_temperature    300.00
_cell_measurement_theta_max      25.83
_cell_measurement_theta_min      2.72
_cell_volume                     2526.08(19)
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      300.00
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.1113
_diffrn_reflns_av_unetI/netI     0.0504
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_h_min       -22
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            59207
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.524
_diffrn_reflns_theta_min         1.838
_diffrn_source_current           1.4
_diffrn_source_power             0.07
_diffrn_source_voltage           50.0
_exptl_absorpt_coefficient_mu    5.872
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6366
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016) was used for absorption correction.
wR2(int) was 0.1473 before and 0.0787 after correction.
The Ratio of minimum to maximum transmission is 0.8538.
The λ/2 correction factor is Not present.
;
_exptl_crystal_density_diffrn    2.233
_exptl_crystal_description       needle
_exptl_crystal_F_000             1568
_refine_diff_density_max         1.001
_refine_diff_density_min         -1.136
_refine_diff_density_rms         0.140
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.050
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     230
_refine_ls_number_reflns         5807
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.050
_refine_ls_R_factor_all          0.0627
_refine_ls_R_factor_gt           0.0353
_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)+(0.0056P)²+4.5239P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0615
_refine_ls_wR_factor_ref         0.0749
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4058
_reflns_number_total             5807
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d2dt04014j2.cif
_cod_data_source_block           mo_2022_1_0m_a
_cod_depositor_comments
'Adding full bibliography for 7711970--7711972.cif.'
_cod_database_code               7711972
_shelx_shelxl_version_number     2018/3
_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.
;
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H,H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C16(H16A,H16B), C1(H1D,H1E)
2.b Aromatic/amide H refined with riding coordinates:
 C6(H6), C4(H4), C11(H11), C13(H13), C7(H7), C3(H3), C10(H10), C14(H14)
2.c Idealised Me refined as rotating group:
 N2(H2A,H2B,H2C), N1(H1A,H1B,H1C), C8(H8A,H8B,H8C), C9(H9A,H9B,H9C)
;
_olex2_submission_special_instructions 'No special instructions were received'
loop_
_space_group_symop_operation_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'
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
I1 I -0.12516(2) -0.00119(4) 0.28691(2) 0.05241(11) Uani 1 1 d . . . . .
I3 I -0.10457(2) 0.50766(4) 0.26839(2) 0.05324(11) Uani 1 1 d . . . . .
I2 I -0.20758(2) 0.31125(5) 0.44082(2) 0.05486(11) Uani 1 1 d . . . . .
I4 I 0.04349(2) 0.25539(6) 0.45146(3) 0.07429(15) Uani 1 1 d . . . . .
Zn1 Zn -0.09815(4) 0.26773(7) 0.36396(4) 0.04720(16) Uani 1 1 d . . . . .
O1 O 0.4007(2) 0.8099(6) 0.3296(3) 0.0712(12) Uani 1 1 d . . . . .
N2 N 0.7498(3) 0.7209(5) 0.3656(3) 0.0631(14) Uani 1 1 d . . . . .
H2A H 0.703744 0.705247 0.333565 0.076 Uiso 1 1 calc R U . . .
H2B H 0.767204 0.627363 0.387497 0.076 Uiso 1 1 calc R U . . .
H2C H 0.784539 0.759072 0.340180 0.076 Uiso 1 1 calc R U . . .
O2 O 0.5274(3) 0.6422(6) 0.6040(3) 0.0853(14) Uani 1 1 d . . . . .
C5 C 0.3217(3) 0.8004(7) 0.3267(3) 0.0480(13) Uani 1 1 d . . . . .
C2 C 0.1622(3) 0.8081(7) 0.3292(3) 0.0504(13) Uani 1 1 d . . . . .
C12 C 0.6815(3) 0.7814(6) 0.4701(3) 0.0479(13) Uani 1 1 d . . . . .
C6 C 0.2942(3) 0.9036(7) 0.3753(3) 0.0531(14) Uani 1 1 d . . . . .
H6 H 0.329003 0.971216 0.407636 0.064 Uiso 1 1 calc R U . . .
N1 N 0.0535(3) 0.7247(8) 0.3890(3) 0.095(2) Uani 1 1 d . . . . .
H1A H 0.001293 0.716924 0.380512 0.114 Uiso 1 1 calc R U . . .
H1B H 0.071293 0.776417 0.432696 0.114 Uiso 1 1 calc R U . . .
H1C H 0.074453 0.625967 0.391653 0.114 Uiso 1 1 calc R U . . .
C4 C 0.2703(4) 0.7001(7) 0.2801(3) 0.0593(15) Uani 1 1 d . . . . .
H4 H 0.288437 0.629109 0.247625 0.071 Uiso 1 1 calc R U . . .
C16 C 0.7400(3) 0.8382(7) 0.4244(3) 0.0567(15) Uani 1 1 d . . . . .
H16A H 0.722204 0.940520 0.400310 0.068 Uiso 1 1 calc R U . . .
H16B H 0.790590 0.856355 0.458523 0.068 Uiso 1 1 calc R U . . .
C11 C 0.6031(3) 0.8238(7) 0.4482(3) 0.0586(15) Uani 1 1 d . . . . .
H11 H 0.585981 0.883691 0.404045 0.070 Uiso 1 1 calc R U . . .
C13 C 0.7051(3) 0.6934(7) 0.5357(3) 0.0536(14) Uani 1 1 d . . . . .
H13 H 0.757749 0.664195 0.551489 0.064 Uiso 1 1 calc R U . . .
C7 C 0.2149(3) 0.9066(7) 0.3760(3) 0.0558(14) Uani 1 1 d . . . . .
H7 H 0.196907 0.976835 0.408836 0.067 Uiso 1 1 calc R U . . .
C3 C 0.1907(4) 0.7047(7) 0.2816(3) 0.0612(16) Uani 1 1 d . . . . .
H3 H 0.155912 0.636500 0.249596 0.073 Uiso 1 1 calc R U . . .
C10 C 0.5495(3) 0.7780(7) 0.4914(4) 0.0623(16) Uani 1 1 d . . . . .
H10 H 0.496673 0.806109 0.475812 0.075 Uiso 1 1 calc R U . . .
C15 C 0.5744(4) 0.6920(8) 0.5567(3) 0.0597(15) Uani 1 1 d . . . . .
C14 C 0.6526(4) 0.6481(8) 0.5781(3) 0.0630(16) Uani 1 1 d . . . . .
H14 H 0.669633 0.587068 0.621981 0.076 Uiso 1 1 calc R U . . .
C1 C 0.0757(4) 0.8142(9) 0.3272(5) 0.082(2) Uani 1 1 d . . . . .
H1D H 0.059897 0.926266 0.329725 0.098 Uiso 1 1 calc R U . . .
H1E H 0.047305 0.770178 0.279136 0.098 Uiso 1 1 calc R U . . .
C8 C 0.4329(4) 0.7052(9) 0.2814(5) 0.087(2) Uani 1 1 d . . . . .
H8A H 0.408548 0.727245 0.229293 0.130 Uiso 1 1 calc R U . . .
H8B H 0.423199 0.594716 0.293077 0.130 Uiso 1 1 calc R U . . .
H8C H 0.488629 0.723136 0.289285 0.130 Uiso 1 1 calc R U . . .
C9 C 0.4456(4) 0.6784(10) 0.5835(5) 0.099(3) Uani 1 1 d . . . . .
H9A H 0.423002 0.627418 0.535896 0.149 Uiso 1 1 calc R U . . .
H9B H 0.438528 0.793442 0.578639 0.149 Uiso 1 1 calc R U . . .
H9C H 0.420027 0.638802 0.622108 0.149 Uiso 1 1 calc R U . . .
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0035 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'
I I -0.4119 1.8326 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0065 0.0032 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0116 0.0061 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Zn Zn 0.3121 1.4667 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
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
I1 Zn1 I3 108.58(3) . . ?
I1 Zn1 I4 108.93(3) . . ?
I3 Zn1 I4 109.06(3) . . ?
I2 Zn1 I1 109.38(2) . . ?
I2 Zn1 I3 108.23(2) . . ?
I2 Zn1 I4 112.58(3) . . ?
C5 O1 C8 117.8(5) . . ?
H2A N2 H2B 109.5 . . ?
H2A N2 H2C 109.5 . . ?
H2B N2 H2C 109.5 . . ?
C16 N2 H2A 109.5 . . ?
C16 N2 H2B 109.5 . . ?
C16 N2 H2C 109.5 . . ?
C15 O2 C9 118.3(5) . . ?
O1 C5 C6 115.0(5) . . ?
O1 C5 C4 125.3(5) . . ?
C4 C5 C6 119.6(5) . . ?
C7 C2 C3 117.9(5) . . ?
C7 C2 C1 122.0(6) . . ?
C3 C2 C1 120.0(6) . . ?
C11 C12 C16 120.3(5) . . ?
C13 C12 C16 121.5(5) . . ?
C13 C12 C11 118.2(5) . . ?
C5 C6 H6 120.0 . . ?
C5 C6 C7 120.0(5) . . ?
C7 C6 H6 120.0 . . ?
H1A N1 H1B 109.5 . . ?
H1A N1 H1C 109.5 . . ?
H1B N1 H1C 109.5 . . ?
C1 N1 H1A 109.5 . . ?
C1 N1 H1B 109.5 . . ?
C1 N1 H1C 109.5 . . ?
C5 C4 H4 120.2 . . ?
C5 C4 C3 119.6(5) . . ?
C3 C4 H4 120.2 . . ?
N2 C16 C12 112.5(4) . . ?
N2 C16 H16A 109.1 . . ?
N2 C16 H16B 109.1 . . ?
C12 C16 H16A 109.1 . . ?
C12 C16 H16B 109.1 . . ?
H16A C16 H16B 107.8 . . ?
C12 C11 H11 119.6 . . ?
C12 C11 C10 120.8(5) . . ?
C10 C11 H11 119.6 . . ?
C12 C13 H13 119.4 . . ?
C14 C13 C12 121.1(5) . . ?
C14 C13 H13 119.4 . . ?
C2 C7 C6 121.4(5) . . ?
C2 C7 H7 119.3 . . ?
C6 C7 H7 119.3 . . ?
C2 C3 C4 121.5(5) . . ?
C2 C3 H3 119.2 . . ?
C4 C3 H3 119.2 . . ?
C11 C10 H10 120.1 . . ?
C15 C10 C11 119.9(5) . . ?
C15 C10 H10 120.1 . . ?
O2 C15 C14 115.6(6) . . ?
C10 C15 O2 125.0(6) . . ?
C10 C15 C14 119.4(6) . . ?
C13 C14 C15 120.6(6) . . ?
C13 C14 H14 119.7 . . ?
C15 C14 H14 119.7 . . ?
C2 C1 H1D 108.9 . . ?
C2 C1 H1E 108.9 . . ?
N1 C1 C2 113.2(6) . . ?
N1 C1 H1D 108.9 . . ?
N1 C1 H1E 108.9 . . ?
H1D C1 H1E 107.7 . . ?
O1 C8 H8A 109.5 . . ?
O1 C8 H8B 109.5 . . ?
O1 C8 H8C 109.5 . . ?
H8A C8 H8B 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
O2 C9 H9A 109.5 . . ?
O2 C9 H9B 109.5 . . ?
O2 C9 H9C 109.5 . . ?
H9A C9 H9B 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
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
I1 Zn1 2.6081(7) . ?
I3 Zn1 2.6120(7) . ?
I2 Zn1 2.6078(7) . ?
I4 Zn1 2.6233(7) . ?
O1 C5 1.365(6) . ?
O1 C8 1.423(7) . ?
N2 H2A 0.8900 . ?
N2 H2B 0.8900 . ?
N2 H2C 0.8900 . ?
N2 C16 1.473(7) . ?
O2 C15 1.366(7) . ?
O2 C9 1.421(8) . ?
C5 C6 1.381(7) . ?
C5 C4 1.366(7) . ?
C2 C7 1.371(8) . ?
C2 C3 1.377(8) . ?
C2 C1 1.496(8) . ?
C12 C16 1.513(8) . ?
C12 C11 1.380(8) . ?
C12 C13 1.373(7) . ?
C6 H6 0.9300 . ?
C6 C7 1.381(7) . ?
N1 H1A 0.8900 . ?
N1 H1B 0.8900 . ?
N1 H1C 0.8900 . ?
N1 C1 1.456(8) . ?
C4 H4 0.9300 . ?
C4 C3 1.390(8) . ?
C16 H16A 0.9700 . ?
C16 H16B 0.9700 . ?
C11 H11 0.9300 . ?
C11 C10 1.390(8) . ?
C13 H13 0.9300 . ?
C13 C14 1.363(8) . ?
C7 H7 0.9300 . ?
C3 H3 0.9300 . ?
C10 H10 0.9300 . ?
C10 C15 1.362(8) . ?
C15 C14 1.378(8) . ?
C14 H14 0.9300 . ?
C1 H1D 0.9700 . ?
C1 H1E 0.9700 . ?
C8 H8A 0.9600 . ?
C8 H8B 0.9600 . ?
C8 H8C 0.9600 . ?
C9 H9A 0.9600 . ?
C9 H9B 0.9600 . ?
C9 H9C 0.9600 . ?
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
O1 C5 C6 C7 178.7(5) . . . . ?
O1 C5 C4 C3 -178.6(6) . . . . ?
O2 C15 C14 C13 -179.0(6) . . . . ?
C5 C6 C7 C2 0.2(9) . . . . ?
C5 C4 C3 C2 -0.2(10) . . . . ?
C12 C11 C10 C15 0.8(9) . . . . ?
C12 C13 C14 C15 -1.0(10) . . . . ?
C6 C5 C4 C3 0.8(9) . . . . ?
C4 C5 C6 C7 -0.8(9) . . . . ?
C16 C12 C11 C10 -177.3(5) . . . . ?
C16 C12 C13 C14 177.4(5) . . . . ?
C11 C12 C16 N2 -92.2(7) . . . . ?
C11 C12 C13 C14 0.4(9) . . . . ?
C11 C10 C15 O2 179.2(6) . . . . ?
C11 C10 C15 C14 -1.5(10) . . . . ?
C13 C12 C16 N2 90.9(6) . . . . ?
C13 C12 C11 C10 -0.2(9) . . . . ?
C7 C2 C3 C4 -0.4(9) . . . . ?
C7 C2 C1 N1 -80.8(8) . . . . ?
C3 C2 C7 C6 0.4(9) . . . . ?
C3 C2 C1 N1 101.2(8) . . . . ?
C10 C15 C14 C13 1.6(10) . . . . ?
C1 C2 C7 C6 -177.7(6) . . . . ?
C1 C2 C3 C4 177.7(6) . . . . ?
C8 O1 C5 C6 179.4(6) . . . . ?
C8 O1 C5 C4 -1.2(9) . . . . ?
C9 O2 C15 C10 1.7(10) . . . . ?
C9 O2 C15 C14 -177.7(6) . . . . ?
