#------------------------------------------------------------------------------
#$Date: 2025-10-06 10:29:43 +0200 (Mon 06 de Oct de 2025) $
#$Revision: 302580 $
#$URL: svn://www.crystallography.net/cod/cif/7/25/07/7250772.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_7250772
loop_
_publ_author_name
'Geng, Shuai'
'He, Yu-Ou'
'Han, Wang-Kang'
'Gu, Zhi-Guo'
_publ_section_title
;
 π-Stacked organic frameworks with captured ammonia for benzamide
 synthesis
;
_journal_issue                   36
_journal_name_full               CrystEngComm
_journal_page_first              6074
_journal_page_last               6078
_journal_paper_doi               10.1039/D5CE00604J
_journal_volume                  27
_journal_year                    2025
_chemical_formula_moiety         '3(C12 H12 N2), 8(H3 N)'
_chemical_formula_sum            'C36 H60 N14'
_chemical_formula_weight         688.98
_space_group_crystal_system      trigonal
_space_group_IT_number           148
_space_group_name_Hall           '-R 3'
_space_group_name_H-M_alt        'R -3 :H'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_audit_creation_date             2024-02-23
_audit_creation_method
;
Olex2 1.5
(compiled 2023.08.24 svn.re1ec1418 for OlexSys, GUI svn.r6817)
;
_audit_update_record
;
2025-05-27 deposited with the CCDC.	2025-08-04 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                120
_cell_formula_units_Z            3
_cell_length_a                   20.5422(7)
_cell_length_b                   20.5422(7)
_cell_length_c                   7.9574(5)
_cell_measurement_reflns_used    3101
_cell_measurement_temperature    298.00
_cell_measurement_theta_max      51.086
_cell_measurement_theta_min      3.744
_cell_volume                     2908.0(2)
_computing_cell_refinement       'SAINT V8.40B (?, 2016)'
_computing_data_reduction        'SAINT V8.40B (?, 2016)'
_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 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_temperature      298.00
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_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  0.0727
_diffrn_reflns_av_unetI/netI     0.0312
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       23
_diffrn_reflns_limit_h_min       -23
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            8389
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        24.349
_diffrn_reflns_theta_max         24.349
_diffrn_reflns_theta_min         1.983
_diffrn_source_current           1.4
_diffrn_source_power             0.07
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.075
_exptl_absorpt_correction_T_max  0.7501
_exptl_absorpt_correction_T_min  0.4533
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1276 before and 0.0599 after correction.
The Ratio of minimum to maximum transmission is 0.6043.
The λ/2 correction factor is Not present.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.180
_exptl_crystal_description       block
_exptl_crystal_F_000             1122
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.263
_refine_diff_density_min         -0.311
_refine_diff_density_rms         0.058
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.117
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     76
_refine_ls_number_reflns         1066
_refine_ls_number_restraints     18
_refine_ls_restrained_S_all      1.163
_refine_ls_R_factor_all          0.0900
_refine_ls_R_factor_gt           0.0684
_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)+(0.1164P)²+1.9318P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1910
_refine_ls_wR_factor_ref         0.2148
_reflns_Friedel_coverage         0.000
_reflns_number_gt                770
_reflns_number_total             1066
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d5ce00604j2.cif
_cod_data_source_block           11
_cod_depositor_comments
'Adding full bibliography for 7250772--7250775.cif.'
_cod_original_cell_volume        2908.0(3)
_cod_original_sg_symbol_H-M      'R -3'
_cod_database_code               7250772
_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.
;
_shelx_estimated_absorpt_t_max   0.991
_shelx_estimated_absorpt_t_min   0.985
_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 N(H,H,H) groups
2. Restrained distances
 H3A-N3 = N3-H3B
 0.9 with sigma of 0.02
 H2C-N2 = N2-H2A
 0.9 with sigma of 0.02
 H3A-N3 = N3-H3C
 0.9 with sigma of 0.02
 H3B-N3 = N3-H3C
 0.9 with sigma of 0.02
 H2C-N2 = N2-H2B
 0.9 with sigma of 0.02
 H2A-N2 = N2-H2B
 0.9 with sigma of 0.02
 H3A-H3C
 1.465 with sigma of 0.04
 H3A-H3B
 1.465 with sigma of 0.04
 H2C-H2A
 1.465 with sigma of 0.04
 H3B-H3C
 1.465 with sigma of 0.04
 H2C-H2B
 1.465 with sigma of 0.04
 H2A-H2B
 1.465 with sigma of 0.04
3. Others
 Fixed Sof: H3B(0.333333) H3C(0.333333)
4.a Everything fixed:
 H2A, H2B, H2C, H3A, H3B, H3C
4.b Secondary CH2 refined with riding coordinates:
 C6(H6A,H6B)
4.c Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C3(H3), C5(H5)
;
_shelx_res_file
;
TITL 11_a.res in R-3
    11.res
    created by SHELXL-2018/3 at 11:16:28 on 23-Feb-2024
REM Old TITL 11 in R-3
REM SHELXT solution in R-3
REM R1 0.169, Rweak 0.012, Alpha 0.024, Orientation as input
REM Formula found by SHELXT: C18 N7
CELL 0.71073 20.5422 20.5422 7.9574 90 90 120
ZERR 3 0.0007 0.0007 0.0005 0 0 0
LATT 3
SYMM -Y,+X-Y,+Z
SYMM +Y-X,-X,+Z
SFAC C H N
UNIT 108 180 42
DFIX 0.9 H3a N3 N3 H3b
DANG 1.465 H3a H3c
DFIX 0.9 H2c N2 N2 H2a
DANG 1.465 H3a H3b
DANG 1.465 H2c H2a
DFIX 0.9 H3a N3 N3 H3c
DANG 1.465 H3b H3c
DFIX 0.9 H3b N3 N3 H3c
DFIX 0.9 H2c N2 N2 H2b
DANG 1.465 H2c H2b
DANG 1.465 H2a H2b
DFIX 0.9 H2a N2 N2 H2b

L.S. 4 0 0
PLAN  1
SIZE 0.12 0.18 0.2
TEMP 24.85
CONF
list 4
MORE -1
BOND $H
fmap 2 53
acta
REM <olex2.extras>
REM <HklSrc "%.\\11.hkl">
REM </olex2.extras>

WGHT    0.116400    1.931800
FVAR       0.45601
N1    3    0.480619    0.099350    0.507980    11.00000    0.07188    0.08727 =
         0.06625   -0.01267   -0.00088    0.04675
C1    1    0.434207    0.026705    0.476215    11.00000    0.06553    0.08464 =
         0.06822   -0.00066    0.00429    0.03737
AFIX  43
H1    2    0.405131   -0.003751    0.564220    11.00000   -1.20000
AFIX   0
C2    1    0.520612    0.140487    0.377652    11.00000    0.07724    0.06933 =
         0.08220   -0.01623   -0.00178    0.03526
AFIX  43
H2    2    0.553818    0.191331    0.395940    11.00000   -1.20000
AFIX   0
C3    1    0.516327    0.113158    0.217866    11.00000    0.07639    0.06984 =
         0.06696   -0.00510    0.00730    0.03393
AFIX  43
H3    2    0.544871    0.145296    0.131497    11.00000   -1.20000
AFIX   0
C4    1    0.469146    0.037386    0.186750    11.00000    0.05370    0.07132 =
         0.06431   -0.01215   -0.00760    0.03544
C5    1    0.426715   -0.005912    0.321353    11.00000    0.05764    0.06899 =
         0.07337   -0.00537   -0.00296    0.02965
AFIX  43
H5    2    0.393229   -0.056962    0.306832    11.00000   -1.20000
AFIX   0
C6    1    0.466184    0.004705    0.015874    11.00000    0.06349    0.08039 =
         0.06568   -0.01892   -0.01024    0.03748
AFIX  23
H6A   2    0.464239    0.037430   -0.069407    11.00000   -1.20000
H6B   2    0.420695   -0.043834    0.006758    11.00000   -1.20000
AFIX   0

N2    3    0.544242    0.192026    0.797797    11.00000    0.10146    0.10281 =
         0.08716   -0.04239   -0.02530    0.06034
AFIX   1
H2A   2    0.571170    0.221860    0.734180    11.00000   -1.50000
AFIX   1
H2B   2    0.520020    0.153540    0.728930    11.00000   -1.50000
AFIX   1
H2C   2    0.513630    0.202200    0.862560    11.00000   -1.50000
AFIX   0

N3    3    0.666667    0.333333    0.133721    10.33333    0.17690    0.17690 =
         0.14250    0.00000    0.00000    0.08845
PART -1
AFIX   1
H3A   2    0.666670    0.333330    0.246130    10.33333   -1.50000
AFIX   1
H3B   2    0.650100    0.286990    0.092160    10.33333   -1.50000
AFIX   1
H3C   2    0.712000    0.364930    0.089450    10.33333   -1.50000
AFIX   0
HKLF 4




REM  11_a.res in R-3
REM wR2 = 0.2148, GooF = S = 1.117, Restrained GooF = 1.163 for all data
REM R1 = 0.0684 for 770 Fo > 4sig(Fo) and 0.0900 for all 1066 data
REM 76 parameters refined using 18 restraints

END

WGHT      0.1164      1.9400

REM Highest difference peak  0.263,  deepest hole -0.311,  1-sigma level  0.058
Q1    1   0.5753  0.1867  0.8354  11.00000  0.05    0.26
;
_shelx_res_checksum              82199
_olex2_submission_special_instructions 'No special instructions were received'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-y, x-y, z'
'-x+y, -x, z'
'x+2/3, y+1/3, z+1/3'
'-y+2/3, x-y+1/3, z+1/3'
'-x+y+2/3, -x+1/3, z+1/3'
'x+1/3, y+2/3, z+2/3'
'-y+1/3, x-y+2/3, z+2/3'
'-x+y+1/3, -x+2/3, z+2/3'
'-x, -y, -z'
'y, -x+y, -z'
'x-y, x, -z'
'-x+2/3, -y+1/3, -z+1/3'
'y+2/3, -x+y+1/3, -z+1/3'
'x-y+2/3, x+1/3, -z+1/3'
'-x+1/3, -y+2/3, -z+2/3'
'y+1/3, -x+y+2/3, -z+2/3'
'x-y+1/3, x+2/3, -z+2/3'
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 0.48062(14) 0.09935(15) 0.5080(3) 0.0720(8) Uani 1 1 d . . . . .
C1 C 0.43421(17) 0.02671(19) 0.4762(4) 0.0729(8) Uani 1 1 d . . . . .
H1 H 0.405131 -0.003751 0.564220 0.087 Uiso 1 1 calc R U . . .
C2 C 0.52061(18) 0.14049(18) 0.3777(4) 0.0769(9) Uani 1 1 d . . . . .
H2 H 0.553818 0.191331 0.395940 0.092 Uiso 1 1 calc R U . . .
C3 C 0.51633(17) 0.11316(17) 0.2179(4) 0.0722(8) Uani 1 1 d . . . . .
H3 H 0.544871 0.145296 0.131497 0.087 Uiso 1 1 calc R U . . .
C4 C 0.46915(14) 0.03739(16) 0.1867(3) 0.0613(8) Uani 1 1 d . . . . .
C5 C 0.42671(15) -0.00591(17) 0.3214(4) 0.0676(8) Uani 1 1 d . . . . .
H5 H 0.393229 -0.056962 0.306832 0.081 Uiso 1 1 calc R U . . .
C6 C 0.46618(16) 0.00470(18) 0.0159(4) 0.0692(8) Uani 1 1 d . . . . .
H6A H 0.464239 0.037430 -0.069407 0.083 Uiso 1 1 calc R U . . .
H6B H 0.420695 -0.043834 0.006758 0.083 Uiso 1 1 calc R U . . .
N2 N 0.54424(17) 0.19203(17) 0.7978(4) 0.0930(10) Uani 1 1 d D . . . .
H2A H 0.571170 0.221860 0.734180 0.140 Uiso 1 1 d D U . . .
H2B H 0.520020 0.153540 0.728930 0.140 Uiso 1 1 d D U . . .
H2C H 0.513630 0.202200 0.862560 0.140 Uiso 1 1 d D U . . .
N3 N 0.666667 0.333333 0.1337(9) 0.165(3) Uani 1 3 d DS T P . .
H3A H 0.666670 0.333330 0.246130 0.248 Uiso 0.3333 1 d D U P A -1
H3B H 0.650100 0.286990 0.092160 0.248 Uiso 0.3333 1 d D U P B -1
H3C H 0.712000 0.364930 0.089450 0.248 Uiso 0.3333 1 d D U 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 0.0719(16) 0.0873(18) 0.0663(14) -0.0127(12) -0.0009(11) 0.0468(15)
C1 0.0655(17) 0.085(2) 0.0682(17) -0.0007(14) 0.0043(13) 0.0374(16)
C2 0.0772(19) 0.0693(18) 0.082(2) -0.0162(15) -0.0018(16) 0.0353(16)
C3 0.0764(19) 0.0698(18) 0.0670(17) -0.0051(13) 0.0073(13) 0.0339(15)
C4 0.0537(15) 0.0713(17) 0.0643(16) -0.0121(12) -0.0076(11) 0.0354(13)
C5 0.0576(15) 0.0690(17) 0.0734(17) -0.0054(13) -0.0030(13) 0.0296(14)
C6 0.0635(16) 0.0804(18) 0.0657(17) -0.0189(13) -0.0102(12) 0.0375(14)
N2 0.101(2) 0.103(2) 0.0872(19) -0.0424(16) -0.0253(15) 0.0603(18)
N3 0.177(5) 0.177(5) 0.143(7) 0.000 0.000 0.088(3)
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'
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
C2 N1 C1 115.6(2) . . ?
N1 C1 H1 118.0 . . ?
N1 C1 C5 124.0(3) . . ?
C5 C1 H1 118.0 . . ?
N1 C2 H2 117.7 . . ?
N1 C2 C3 124.6(3) . . ?
C3 C2 H2 117.7 . . ?
C2 C3 H3 120.3 . . ?
C2 C3 C4 119.4(3) . . ?
C4 C3 H3 120.3 . . ?
C3 C4 C5 116.4(2) . . ?
C3 C4 C6 120.9(3) . . ?
C5 C4 C6 122.7(3) . . ?
C1 C5 C4 119.9(3) . . ?
C1 C5 H5 120.0 . . ?
C4 C5 H5 120.0 . . ?
C4 C6 C6 111.9(3) . 10_655 ?
C4 C6 H6A 109.2 . . ?
C4 C6 H6B 109.2 . . ?
C6 C6 H6A 109.2 10_655 . ?
C6 C6 H6B 109.2 10_655 . ?
H6A C6 H6B 107.9 . . ?
H2A N2 H2B 99.4 . . ?
H2A N2 H2C 119.3 . . ?
H2B N2 H2C 114.2 . . ?
H3A N3 H3B 111.6 . . ?
H3A N3 H3C 113.1 . . ?
H3B N3 H3C 109.1 . . ?
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 C1 1.333(4) . ?
N1 C2 1.331(4) . ?
C1 H1 0.9300 . ?
C1 C5 1.374(4) . ?
C2 H2 0.9300 . ?
C2 C3 1.375(4) . ?
C3 H3 0.9300 . ?
C3 C4 1.384(4) . ?
C4 C5 1.387(4) . ?
C4 C6 1.504(4) . ?
C5 H5 0.9300 . ?
C6 C6 1.517(6) 10_655 ?
C6 H6A 0.9700 . ?
C6 H6B 0.9700 . ?
N2 H2A 0.7738 . ?
N2 H2B 0.8829 . ?
N2 H2C 0.9144 . ?
N3 H3A 0.8945 . ?
N3 H3B 0.8986 . ?
N3 H3C 0.8990 . ?
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
N1 C1 C5 C4 0.2(4) . . . . ?
N1 C2 C3 C4 -1.8(5) . . . . ?
C1 N1 C2 C3 0.5(5) . . . . ?
C2 N1 C1 C5 0.3(4) . . . . ?
C2 C3 C4 C5 2.2(4) . . . . ?
C2 C3 C4 C6 -176.6(3) . . . . ?
C3 C4 C5 C1 -1.5(4) . . . . ?
C3 C4 C6 C6 76.3(4) . . . 10_655 ?
C5 C4 C6 C6 -102.4(4) . . . 10_655 ?
C6 C4 C5 C1 177.3(2) . . . . ?
