#------------------------------------------------------------------------------
#$Date: 2019-05-14 03:35:03 +0300 (Tue, 14 May 2019) $
#$Revision: 215119 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/12/34/7123431.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_7123431
loop_
_publ_author_name
'Wang, Fei'
'Sikma, Eric'
'Duan, Zhiming'
'Sarma, Tridib'
'Lei, Chuanhu'
'Zhang, Zhan'
'Humphrey, Simon M.'
'Sessler, Jonathan L.'
_publ_section_title
;
 Shape-persistent pyrrole-based covalent organic cages: synthesis,
 structure and selective gas adsorption properties
;
_journal_name_full               'Chemical Communications'
_journal_paper_doi               10.1039/C9CC02490E
_journal_year                    2019
_chemical_formula_sum            'C84 H84 N12'
_chemical_formula_weight         1261.63
_space_group_crystal_system      trigonal
_space_group_IT_number           155
_space_group_name_Hall           'R 3 2"'
_space_group_name_H-M_alt        'R 3 2 :H'
_symmetry_space_group_name_Hall  'R 3 2"'
_symmetry_space_group_name_H-M   'R 3 2 :H'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2014/7
_audit_update_record
;
2019-03-20 deposited with the CCDC.    2019-04-09 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                120
_cell_formula_units_Z            6
_cell_length_a                   16.3765(4)
_cell_length_b                   16.3765(4)
_cell_length_c                   61.2246(15)
_cell_measurement_reflns_used    11229
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      64.5300
_cell_measurement_theta_min      4.2440
_cell_volume                     14220.0(6)
_computing_cell_refinement       'CrysAlisPro 1.171.39.32a (Rigaku OD, 2017)'
_computing_data_collection       'CrysAlisPro 1.171.39.32a (Rigaku OD, 2017)'
_computing_data_reduction        'CrysAlisPro 1.171.39.32a (Rigaku OD, 2017)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      173(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.974
_diffrn_measurement_device_type  'XtaLAB AFC12 (RINC): Kappa dual home/near'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0603
_diffrn_reflns_av_unetI/netI     0.0289
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.974
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       76
_diffrn_reflns_limit_l_min       -71
_diffrn_reflns_number            47303
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.973
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         76.320
_diffrn_reflns_theta_min         3.435
_diffrn_source                   'fine-focus sealed X-ray tube'
_exptl_absorpt_coefficient_mu    0.409
_exptl_absorpt_correction_T_max  0.898
_exptl_absorpt_correction_T_min  0.874
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.39.32a (Rigaku Oxford Diffraction, 2017)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    0.884
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             4032
_exptl_crystal_size_max          0.340
_exptl_crystal_size_mid          0.290
_exptl_crystal_size_min          0.270
_refine_diff_density_max         0.301
_refine_diff_density_min         -0.219
_refine_diff_density_rms         0.051
_refine_ls_abs_structure_details
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   0.0(11)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.991
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     294
_refine_ls_number_reflns         6410
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      0.992
_refine_ls_R_factor_all          0.1035
_refine_ls_R_factor_gt           0.0806
_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)+(0.1000P)²+15.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2201
_refine_ls_wR_factor_ref         0.2339
_reflns_Friedel_coverage         0.804
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     0.973
_reflns_number_gt                4133
_reflns_number_total             6410
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            c9cc02490e2.cif
_cod_data_source_block           exp_268_sq
_cod_original_cell_volume        14220.0(8)
_cod_database_code               7123431
_shelx_shelxl_version_number     2014/7
_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_min   0.874
_shelx_estimated_absorpt_t_max   0.898
_exptl_absorpt_special_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-y, x-y, z'
'-x+y, -x, z'
'y, x, -z'
'x-y, -y, -z'
'-x, -x+y, -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'
'y+2/3, x+1/3, -z+1/3'
'x-y+2/3, -y+1/3, -z+1/3'
'-x+2/3, -x+y+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'
'y+1/3, x+2/3, -z+2/3'
'x-y+1/3, -y+2/3, -z+2/3'
'-x+1/3, -x+y+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
N1 N -0.0172(3) 0.2774(3) 0.22634(6) 0.0822(10) Uani 1 1 d . .
H1 H -0.0608 0.2174 0.2261 0.099 Uiso 1 1 calc R U
N2 N -0.0229(3) 0.2794(3) 0.28206(6) 0.0834(10) Uani 1 1 d . .
H2 H 0.0296 0.2771 0.2831 0.100 Uiso 1 1 calc R U
N3 N -0.0236(3) 0.1972(3) 0.18329(6) 0.0861(11) Uani 1 1 d . .
N4 N -0.0119(3) 0.2048(3) 0.32366(7) 0.0914(12) Uani 1 1 d . .
C1 C 0.0345(4) 0.2818(4) 0.18760(8) 0.0885(14) Uani 1 1 d . .
C2 C 0.0404(4) 0.3265(4) 0.20915(8) 0.0852(13) Uani 1 1 d . .
C3 C 0.0961(5) 0.4155(5) 0.21564(10) 0.115(2) Uani 1 1 d . .
C4 C 0.0726(5) 0.4229(4) 0.23786(9) 0.112(2) Uani 1 1 d . .
C5 C 0.0034(4) 0.3357(4) 0.24384(7) 0.0831(13) Uani 1 1 d . .
C6 C -0.0520(4) 0.3061(4) 0.26385(7) 0.0845(13) Uani 1 1 d . .
C7 C -0.1342(4) 0.3036(4) 0.26865(9) 0.0942(15) Uani 1 1 d . .
C8 C -0.1594(4) 0.2706(4) 0.29079(8) 0.0862(14) Uani 1 1 d . .
C9 C -0.0882(4) 0.2564(3) 0.29857(7) 0.0776(12) Uani 1 1 d . .
C10 C -0.0785(4) 0.2231(4) 0.31970(8) 0.0867(14) Uani 1 1 d . .
C11 C -0.0203(4) 0.1669(4) 0.16094(8) 0.0884(14) Uani 1 1 d . .
H11A H 0.0329 0.2189 0.1530 0.106 Uiso 1 1 calc R U
H11B H -0.0794 0.1515 0.1532 0.106 Uiso 1 1 calc R U
C12 C -0.0079(4) 0.0812(4) 0.16124(6) 0.0761(13) Uani 1 1 d . .
C13 C 0.0816(4) 0.0910(4) 0.16146(7) 0.0801(13) Uani 1 1 d . .
C14 C -0.0101(4) 0.1725(4) 0.34593(8) 0.0908(15) Uani 1 1 d . .
H14A H -0.0680 0.1605 0.3538 0.109 Uiso 1 1 calc R U
H14B H 0.0448 0.2224 0.3539 0.109 Uiso 1 1 calc R U
C15 C -0.0040(4) 0.0828(4) 0.34565(7) 0.0863(15) Uani 1 1 d . .
C16 C -0.0882(4) -0.0053(4) 0.34553(8) 0.0828(14) Uani 1 1 d . .
C17 C 0.1635(9) 0.4926(6) 0.20180(15) 0.185(5) Uani 1 1 d . .
H17A H 0.1326 0.4895 0.1877 0.222 Uiso 1 1 calc R U
H17B H 0.1788 0.5531 0.2088 0.222 Uiso 1 1 calc R U
C18 C 0.2443(16) 0.4933(16) 0.1978(2) 0.45(2) Uani 1 1 d . .
H18A H 0.2878 0.5514 0.1900 0.678 Uiso 1 1 calc R U
H18B H 0.2313 0.4387 0.1888 0.678 Uiso 1 1 calc R U
H18C H 0.2728 0.4904 0.2116 0.678 Uiso 1 1 calc R U
C19 C 0.1140(8) 0.5129(7) 0.25215(14) 0.183(5) Uani 1 1 d D .
H19A H 0.1198 0.5663 0.2434 0.219 Uiso 1 1 calc R U
H19B H 0.0711 0.5027 0.2645 0.219 Uiso 1 1 calc R U
C20 C 0.2076(18) 0.536(2) 0.2605(3) 0.381(15) Uani 1 1 d D .
C21 C -0.1913(6) 0.3272(7) 0.25366(13) 0.150(3) Uani 1 1 d . .
H21A H -0.2468 0.3189 0.2620 0.181 Uiso 1 1 calc R U
H21B H -0.1529 0.3952 0.2501 0.181 Uiso 1 1 calc R U
C22 C -0.2228(10) 0.2812(14) 0.23491(15) 0.279(10) Uani 1 1 d . .
H22A H -0.2331 0.2172 0.2365 0.418 Uiso 1 1 calc R U
H22B H -0.1763 0.3145 0.2234 0.418 Uiso 1 1 calc R U
H22C H -0.2824 0.2781 0.2310 0.418 Uiso 1 1 calc R U
C23 C -0.2463(5) 0.2501(5) 0.30263(9) 0.1056(17) Uani 1 1 d . .
H23A H -0.2677 0.2935 0.2974 0.127 Uiso 1 1 calc R U
H23B H -0.2315 0.2627 0.3184 0.127 Uiso 1 1 calc R U
C24 C -0.3261(5) 0.1497(6) 0.29993(13) 0.142(3) Uani 1 1 d . .
H24A H -0.3404 0.1360 0.2844 0.213 Uiso 1 1 calc R U
H24B H -0.3821 0.1419 0.3076 0.213 Uiso 1 1 calc R U
H24C H -0.3073 0.1063 0.3061 0.213 Uiso 1 1 calc R U
C25 C 0.1680(5) 0.1868(4) 0.16307(10) 0.1028(17) Uani 1 1 d . .
C26 C 0.2106(6) 0.2345(6) 0.14054(13) 0.149(3) Uani 1 1 d . .
C27 C -0.1840(5) -0.0121(5) 0.34434(11) 0.118(2) Uani 1 1 d . .
H27A H -0.1764 0.0456 0.3372 0.142 Uiso 1 1 calc R U
H27B H -0.2258 -0.0663 0.3349 0.142 Uiso 1 1 calc R U
C28 C -0.2311(8) -0.0237(9) 0.36594(16) 0.196(4) Uani 1 1 d . .
H28A H -0.2213 -0.0673 0.3750 0.293 Uiso 1 1 calc R U
H28B H -0.2988 -0.0490 0.3637 0.293 Uiso 1 1 calc R U
H28C H -0.2040 0.0377 0.3732 0.293 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 0.0181 0.0091 '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 0.0311 0.0180 '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
C5 N1 C2 109.6(4) . .
C5 N1 H1 125.2 . .
C2 N1 H1 125.2 . .
C6 N2 C9 109.7(4) . .
C6 N2 H2 125.1 . .
C9 N2 H2 125.1 . .
C1 N3 C11 115.7(4) . .
C10 N4 C14 115.4(5) . .
N3 C1 C2 123.8(5) . .
C3 C2 N1 107.7(5) . .
C3 C2 C1 130.0(5) . .
N1 C2 C1 122.3(5) . .
C2 C3 C4 108.0(5) . .
C2 C3 C17 125.3(6) . .
C4 C3 C17 126.5(7) . .
C5 C4 C3 106.5(5) . .
C5 C4 C19 126.0(6) . .
C3 C4 C19 127.4(6) . .
C4 C5 N1 108.1(4) . .
C4 C5 C6 129.2(5) . .
N1 C5 C6 122.3(5) . .
C7 C6 N2 108.2(4) . .
C7 C6 C5 129.4(5) . .
N2 C6 C5 122.3(5) . .
C6 C7 C8 108.0(4) . .
C6 C7 C21 126.8(5) . .
C8 C7 C21 125.2(5) . .
C9 C8 C7 106.2(4) . .
C9 C8 C23 126.1(5) . .
C7 C8 C23 127.6(5) . .
N2 C9 C8 107.8(4) . .
N2 C9 C10 122.9(5) . .
C8 C9 C10 129.3(5) . .
N4 C10 C9 121.4(5) . .
N3 C11 C12 110.3(4) . .
N3 C11 H11A 109.6 . .
C12 C11 H11A 109.6 . .
N3 C11 H11B 109.6 . .
C12 C11 H11B 109.6 . .
H11A C11 H11B 108.1 . .
C13 C12 C13 121.4(6) . 2
C13 C12 C11 120.9(5) . .
C13 C12 C11 117.7(5) 2 .
C12 C13 C12 118.6(6) . 3
C12 C13 C25 120.6(5) . .
C12 C13 C25 120.8(5) 3 .
N4 C14 C15 111.2(4) . .
N4 C14 H14A 109.4 . .
C15 C14 H14A 109.4 . .
N4 C14 H14B 109.4 . .
C15 C14 H14B 109.4 . .
H14A C14 H14B 108.0 . .
C16 C15 C16 120.9(6) 3 .
C16 C15 C14 120.1(6) 3 .
C16 C15 C14 119.0(5) . .
C15 C16 C15 119.1(6) 2 .
C15 C16 C27 119.5(6) 2 .
C15 C16 C27 121.3(6) . .
C18 C17 C3 115.4(15) . .
C18 C17 H17A 108.4 . .
C3 C17 H17A 108.4 . .
C18 C17 H17B 108.4 . .
C3 C17 H17B 108.4 . .
H17A C17 H17B 107.5 . .
C17 C18 H18A 109.5 . .
C17 C18 H18B 109.5 . .
H18A C18 H18B 109.5 . .
C17 C18 H18C 109.5 . .
H18A C18 H18C 109.5 . .
H18B C18 H18C 109.5 . .
C20 C19 C4 110.0(13) . .
C20 C19 H19A 109.7 . .
C4 C19 H19A 109.7 . .
C20 C19 H19B 109.7 . .
C4 C19 H19B 109.7 . .
H19A C19 H19B 108.2 . .
C22 C21 C7 120.1(9) . .
C22 C21 H21A 107.3 . .
C7 C21 H21A 107.3 . .
C22 C21 H21B 107.3 . .
C7 C21 H21B 107.3 . .
H21A C21 H21B 106.9 . .
C21 C22 H22A 109.5 . .
C21 C22 H22B 109.5 . .
H22A C22 H22B 109.5 . .
C21 C22 H22C 109.5 . .
H22A C22 H22C 109.5 . .
H22B C22 H22C 109.5 . .
C8 C23 C24 113.8(5) . .
C8 C23 H23A 108.8 . .
C24 C23 H23A 108.8 . .
C8 C23 H23B 108.8 . .
C24 C23 H23B 108.8 . .
H23A C23 H23B 107.7 . .
C23 C24 H24A 109.5 . .
C23 C24 H24B 109.5 . .
H24A C24 H24B 109.5 . .
C23 C24 H24C 109.5 . .
H24A C24 H24C 109.5 . .
H24B C24 H24C 109.5 . .
C13 C25 C26 114.6(5) . .
C28 C27 C16 114.6(7) . .
C28 C27 H27A 108.6 . .
C16 C27 H27A 108.6 . .
C28 C27 H27B 108.6 . .
C16 C27 H27B 108.6 . .
H27A C27 H27B 107.6 . .
C27 C28 H28A 109.5 . .
C27 C28 H28B 109.5 . .
H28A C28 H28B 109.5 . .
C27 C28 H28C 109.5 . .
H28A C28 H28C 109.5 . .
H28B C28 H28C 109.5 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
N1 C5 1.360(6) .
N1 C2 1.374(6) .
N1 H1 0.8800 .
N2 C6 1.368(6) .
N2 C9 1.380(6) .
N2 H2 0.8800 .
N3 C1 1.255(7) .
N3 C11 1.466(6) .
N4 C10 1.291(7) .
N4 C14 1.468(6) .
C1 C2 1.489(7) .
C2 C3 1.335(8) .
C3 C4 1.435(8) .
C3 C17 1.462(10) .
C4 C5 1.356(8) .
C4 C19 1.549(10) .
C5 C6 1.456(7) .
C6 C7 1.359(7) .
C7 C8 1.441(7) .
C7 C21 1.492(8) .
C8 C9 1.384(7) .
C8 C23 1.478(7) .
C9 C10 1.444(7) .
C11 C12 1.515(7) .
C11 H11A 0.9900 .
C11 H11B 0.9900 .
C12 C13 1.393(7) .
C12 C13 1.426(7) 2
C13 C12 1.426(7) 3
C13 C25 1.502(8) .
C14 C15 1.520(8) .
C14 H14A 0.9900 .
C14 H14B 0.9900 .
C15 C16 1.382(7) 3
C15 C16 1.412(7) .
C16 C15 1.382(7) 2
C16 C27 1.518(9) .
C17 C18 1.34(3) .
C17 H17A 0.9900 .
C17 H17B 0.9900 .
C18 H18A 0.9800 .
C18 H18B 0.9800 .
C18 H18C 0.9800 .
C19 C20 1.476(18) .
C19 H19A 0.9900 .
C19 H19B 0.9900 .
C21 C22 1.328(13) .
C21 H21A 0.9900 .
C21 H21B 0.9900 .
C22 H22A 0.9800 .
C22 H22B 0.9800 .
C22 H22C 0.9800 .
C23 C24 1.512(10) .
C23 H23A 0.9900 .
C23 H23B 0.9900 .
C24 H24A 0.9800 .
C24 H24B 0.9800 .
C24 H24C 0.9800 .
C25 C26 1.566(9) .
C27 C28 1.495(11) .
C27 H27A 0.9900 .
C27 H27B 0.9900 .
C28 H28A 0.9800 .
C28 H28B 0.9800 .
C28 H28C 0.9800 .
