#------------------------------------------------------------------------------
#$Date: 2023-05-05 05:17:08 +0300 (Fri, 05 May 2023) $
#$Revision: 283300 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/71/20/7712066.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_7712066
loop_
_publ_author_name
'Zhang, Haina'
'You, Xiuli'
'Zhang, Mengxia'
'Guo, Wenjing'
'Wei, Zhenhong'
'Cai, Hu'
_publ_section_title
;
 Two metal-free perovskite molecules with different 3D frameworks show
 reversible phase transition, dielectric anomaly and SHG effect.
;
_journal_issue                   6
_journal_name_full
'Dalton transactions (Cambridge, England : 2003)'
_journal_page_first              1753
_journal_page_last               1760
_journal_paper_doi               10.1039/d2dt03889g
_journal_volume                  52
_journal_year                    2023
_chemical_formula_moiety         '2(C7 H16 N2), 6(I), H2 O, 2(N)'
_chemical_formula_sum            'C14 H34 I6 N6 O'
_chemical_formula_weight         1063.87
_space_group_crystal_system      orthorhombic
_space_group_IT_number           40
_space_group_name_Hall           'A 2 -2a'
_space_group_name_H-M_alt        'A m a 2'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_audit_creation_date             2022-04-05
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2022-11-16 deposited with the CCDC.	2023-01-06 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   30.562(6)
_cell_length_b                   10.349(2)
_cell_length_c                   9.908(2)
_cell_measurement_reflns_used    3446
_cell_measurement_temperature    273(2)
_cell_measurement_theta_max      26.22
_cell_measurement_theta_min      2.67
_cell_volume                     3133.8(11)
_computing_cell_refinement       'SAINT v8.34A (Bruker, 2013)'
_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)'
_diffrn_ambient_temperature      273.15
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.994
_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_reflns_av_R_equivalents  0.0453
_diffrn_reflns_av_unetI/netI     0.0442
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_limit_h_max       37
_diffrn_reflns_limit_h_min       -39
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            9204
_diffrn_reflns_point_group_measured_fraction_full 0.808
_diffrn_reflns_point_group_measured_fraction_max 0.769
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.600
_diffrn_reflns_theta_min         1.333
_exptl_absorpt_coefficient_mu    5.962
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.4237
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details
;
SADABS-2014/5 (Bruker,2014/5) was used for absorption correction.
wR2(int) was 0.1022 before and 0.0469 after correction.
The Ratio of minimum to maximum transmission is 0.5683.
The λ/2 correction factor is 0.00150.
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    2.255
_exptl_crystal_description       block
_exptl_crystal_F_000             1944
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.2
_refine_diff_density_max         0.647
_refine_diff_density_min         -0.825
_refine_diff_density_rms         0.114
_refine_ls_abs_structure_details
;
 Flack x determined using 803 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.06(5)
_refine_ls_extinction_coef       0.00118(6)
_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   0.967
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     132
_refine_ls_number_reflns         2852
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      0.967
_refine_ls_R_factor_all          0.0323
_refine_ls_R_factor_gt           0.0293
_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)+(0.0297P)²+2.0684P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0613
_refine_ls_wR_factor_ref         0.0629
_reflns_Friedel_coverage         0.463
_reflns_Friedel_fraction_full    0.592
_reflns_Friedel_fraction_max     0.516
_reflns_number_gt                2678
_reflns_number_total             3709
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d2dt03889g2.cif
_cod_data_source_block           t_CCDC1
_cod_depositor_comments
'Adding full bibliography for 7712063--7712066.cif.'
_cod_original_cell_volume        3133.9(11)
_cod_database_code               7712066
_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) groups, All N(H,H) groups
 At 1.5 times of:
  All O(H,H) groups
2. Others
 Fixed Sof: H1C(0.5) H1D(0.5)
3.a Free rotating group:
 O1(H1C,H1D)
3.b Ternary CH refined with riding coordinates:
 N1(H1), C5(H5)
3.c Secondary CH2 refined with riding coordinates:
 N2(H2A,H2B), C1(H1A,H1B), C2(H2C,H2D), C3(H3A,H3B), C4(H4A,H4B), C6(H6A,H6B),
 C7(H7A,H7B)
;
_olex2_submission_special_instructions 'No special instructions were received'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, z'
'x+1/2, -y, z'
'-x+1/2, y, z'
'x, y+1/2, z+1/2'
'-x, -y+1/2, z+1/2'
'x+1/2, -y+1/2, z+1/2'
'-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 0.37857(2) 0.47220(6) 0.96843(8) 0.04448(17) Uani 1 1 d . . . . .
I2 I 0.250000 0.24756(7) 0.30171(7) 0.03113(19) Uani 1 2 d S T P . .
I3 I 0.250000 0.21950(7) 0.75196(8) 0.0374(2) Uani 1 2 d S T P . .
I4 I 0.48460(2) 0.24657(5) 0.27021(5) 0.04015(16) Uani 1 1 d . . . . .
N1 N 0.3321(2) 0.4010(6) 0.4937(6) 0.0369(16) Uani 1 1 d . . . . .
H1 H 0.307419 0.346469 0.466940 0.044 Uiso 1 1 calc R . . . .
N2 N 0.41685(19) 0.4888(6) 0.6202(6) 0.0325(14) Uani 1 1 d . . . . .
H2A H 0.445390 0.499510 0.606337 0.039 Uiso 1 1 calc R . . . .
H2B H 0.411664 0.506345 0.706635 0.039 Uiso 1 1 calc R . . . .
O1 O 0.500000 0.500000 0.4954(7) 0.037(2) Uani 1 2 d S T P . .
H1C H 0.505036 0.551853 0.430733 0.055 Uiso 0.5 1 d G . . . .
H1D H 0.512862 0.430505 0.472679 0.055 Uiso 0.5 1 d G . . . .
N4 N 0.250000 -0.0425(11) 0.5102(12) 0.065(4) Uani 1 2 d S T P . .
N5 N 0.500000 0.500000 0.0220(12) 0.050(3) Uani 1 2 d S T P . .
C1 C 0.3573(3) 0.4286(11) 0.3662(9) 0.056(3) Uani 1 1 d . . . . .
H1A H 0.337063 0.449563 0.293919 0.067 Uiso 1 1 calc R . . . .
H1B H 0.373758 0.352640 0.339777 0.067 Uiso 1 1 calc R . . . .
C2 C 0.3891(3) 0.5443(10) 0.3903(10) 0.043(2) Uani 1 1 d . . . . .
H2C H 0.418030 0.519739 0.359073 0.052 Uiso 1 1 calc R . . . .
H2D H 0.379480 0.616795 0.335881 0.052 Uiso 1 1 calc R . . . .
C3 C 0.3126(2) 0.5213(8) 0.5505(9) 0.043(2) Uani 1 1 d . . . . .
H3A H 0.294352 0.499657 0.627209 0.051 Uiso 1 1 calc R . . . .
H3B H 0.294338 0.562080 0.482786 0.051 Uiso 1 1 calc R . . . .
C4 C 0.3481(3) 0.6147(7) 0.5945(9) 0.041(2) Uani 1 1 d . . . . .
H4A H 0.339320 0.701573 0.569353 0.049 Uiso 1 1 calc R . . . .
H4B H 0.350360 0.612062 0.692096 0.049 Uiso 1 1 calc R . . . .
C5 C 0.3925(3) 0.5876(7) 0.5349(9) 0.0321(17) Uani 1 1 d . . . . .
H5 H 0.409293 0.668284 0.536647 0.039 Uiso 1 1 calc R . . . .
C6 C 0.3576(3) 0.3238(7) 0.5972(9) 0.0374(19) Uani 1 1 d . . . . .
H6A H 0.346110 0.343087 0.686272 0.045 Uiso 1 1 calc R . . . .
H6B H 0.352868 0.232471 0.580416 0.045 Uiso 1 1 calc R . . . .
C7 C 0.4062(2) 0.3505(7) 0.5963(9) 0.0377(19) Uani 1 1 d . . . . .
H7A H 0.420084 0.298493 0.665509 0.045 Uiso 1 1 calc R . . . .
H7B H 0.418135 0.324448 0.509791 0.045 Uiso 1 1 calc R . . . .
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'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
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'
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
C1 N1 H1 106.0 . . ?
C1 N1 C6 114.0(7) . . ?
C3 N1 H1 106.0 . . ?
C3 N1 C1 111.2(7) . . ?
C3 N1 C6 113.0(6) . . ?
C6 N1 H1 106.0 . . ?
H2A N2 H2B 107.3 . . ?
C5 N2 H2A 108.1 . . ?
C5 N2 H2B 108.1 . . ?
C7 N2 H2A 108.1 . . ?
C7 N2 H2B 108.1 . . ?
C7 N2 C5 116.8(6) . . ?
H1C O1 H1C 82.1 . 2_665 ?
H1C O1 H1D 49.4 . 2_665 ?
H1C O1 H1D 104.5 2_665 2_665 ?
H1C O1 H1D 104.5 . . ?
H1D O1 H1C 49.4 . 2_665 ?
H1D O1 H1D 149.2 . 2_665 ?
N1 C1 H1A 109.8 . . ?
N1 C1 H1B 109.8 . . ?
N1 C1 C2 109.6(7) . . ?
H1A C1 H1B 108.2 . . ?
C2 C1 H1A 109.8 . . ?
C2 C1 H1B 109.8 . . ?
C1 C2 H2C 108.6 . . ?
C1 C2 H2D 108.6 . . ?
H2C C2 H2D 107.6 . . ?
C5 C2 C1 114.6(7) . . ?
C5 C2 H2C 108.6 . . ?
C5 C2 H2D 108.6 . . ?
N1 C3 H3A 109.5 . . ?
N1 C3 H3B 109.5 . . ?
N1 C3 C4 110.8(6) . . ?
H3A C3 H3B 108.1 . . ?
C4 C3 H3A 109.5 . . ?
C4 C3 H3B 109.5 . . ?
C3 C4 H4A 108.7 . . ?
C3 C4 H4B 108.7 . . ?
H4A C4 H4B 107.6 . . ?
C5 C4 C3 114.3(7) . . ?
C5 C4 H4A 108.7 . . ?
C5 C4 H4B 108.7 . . ?
N2 C5 H5 107.9 . . ?
C2 C5 N2 111.2(7) . . ?
C2 C5 C4 111.5(7) . . ?
C2 C5 H5 107.9 . . ?
C4 C5 N2 110.4(7) . . ?
C4 C5 H5 107.9 . . ?
N1 C6 H6A 108.8 . . ?
N1 C6 H6B 108.8 . . ?
H6A C6 H6B 107.7 . . ?
C7 C6 N1 113.8(6) . . ?
C7 C6 H6A 108.8 . . ?
C7 C6 H6B 108.8 . . ?
N2 C7 C6 113.0(6) . . ?
N2 C7 H7A 109.0 . . ?
N2 C7 H7B 109.0 . . ?
C6 C7 H7A 109.0 . . ?
C6 C7 H7B 109.0 . . ?
H7A C7 H7B 107.8 . . ?
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 H1 0.9800 . ?
N1 C1 1.506(11) . ?
N1 C3 1.490(10) . ?
N1 C6 1.514(10) . ?
N2 H2A 0.8900 . ?
N2 H2B 0.8900 . ?
N2 C5 1.521(10) . ?
N2 C7 1.487(9) . ?
O1 H1C 0.85(17) 2_665 ?
O1 H1C 0.8501 . ?
O1 H1D 0.8501 . ?
O1 H1D 0.85(7) 2_665 ?
C1 H1A 0.9700 . ?
C1 H1B 0.9700 . ?
C1 C2 1.561(14) . ?
C2 H2C 0.9700 . ?
C2 H2D 0.9700 . ?
C2 C5 1.505(12) . ?
C3 H3A 0.9700 . ?
C3 H3B 0.9700 . ?
C3 C4 1.516(11) . ?
C4 H4A 0.9700 . ?
C4 H4B 0.9700 . ?
C4 C5 1.507(11) . ?
C5 H5 0.9800 . ?
C6 H6A 0.9700 . ?
C6 H6B 0.9700 . ?
C6 C7 1.511(11) . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
