#------------------------------------------------------------------------------
#$Date: 2025-08-18 17:20:24 +0300 (Mon, 18 Aug 2025) $
#$Revision: 301776 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/51/74/1517432.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_1517432
loop_
_publ_author_name
'Tominaga, Masahide'
'Yoneta, Tetsuro'
'Ohara, Kazuaki'
'Yamaguchi, Kentaro'
'Itoh, Tsutomu'
'Minamoto, Chihiro'
'Azumaya, Isao'
_publ_section_title
;
 Self-Assembly of a Tetrapodal Adamantane with Carbazole Branches into
 Hollow Spherical Aggregates in Organic Media.
;
_journal_issue                   17
_journal_name_full               'Organic letters'
_journal_page_first              4622
_journal_paper_doi               10.1021/ol502116m
_journal_volume                  16
_journal_year                    2014
_chemical_formula_sum            'C43 H31 Cl6 N2'
_chemical_formula_weight         788.40
_space_group_IT_number           114
_symmetry_cell_setting           tetragonal
_symmetry_space_group_name_Hall  'P -4 2n'
_symmetry_space_group_name_H-M   'P -4 21 c'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   22.782(3)
_cell_length_b                   22.782(3)
_cell_length_c                   7.3730(15)
_cell_measurement_reflns_used    150
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      20
_cell_measurement_theta_min      5
_cell_volume                     3826.7(11)
_computing_cell_refinement       HKL2000
_computing_data_collection       'SPring-8 BL38B1 beamline program'
_computing_data_reduction        HKL2000
_computing_molecular_graphics    'Bruker XP'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.931
_diffrn_measured_fraction_theta_max 0.931
_diffrn_measurement_device_type  'ADSC Q315 CCD area detector'
_diffrn_measurement_method       omega_scan
_diffrn_radiation_monochromator  'Si 111'
_diffrn_radiation_source         'SPring-8 BL38B1 beamline'
_diffrn_radiation_type           Synchrotron
_diffrn_radiation_wavelength     0.80000
_diffrn_reflns_av_R_equivalents  0.0601
_diffrn_reflns_av_sigmaI/netI    0.0382
_diffrn_reflns_limit_h_max       25
_diffrn_reflns_limit_h_min       -25
_diffrn_reflns_limit_k_max       25
_diffrn_reflns_limit_k_min       -25
_diffrn_reflns_limit_l_max       7
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number            9390
_diffrn_reflns_theta_full        26.39
_diffrn_reflns_theta_max         26.39
_diffrn_reflns_theta_min         3.27
_diffrn_standards_decay_%        none
_exptl_absorpt_coefficient_mu    0.483
_exptl_absorpt_correction_T_max  0.9716
_exptl_absorpt_correction_T_min  0.9624
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.368
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       niddle
_exptl_crystal_F_000             1620
_exptl_crystal_size_max          0.08
_exptl_crystal_size_mid          0.06
_exptl_crystal_size_min          0.06
_refine_diff_density_max         0.194
_refine_diff_density_min         -0.379
_refine_diff_density_rms         0.055
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.70(18)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.059
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     234
_refine_ls_number_reflns         2582
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.059
_refine_ls_R_factor_all          0.0806
_refine_ls_R_factor_gt           0.0773
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.1166P)²+5.2892P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2107
_refine_ls_wR_factor_ref         0.2146
_reflns_number_gt                2458
_reflns_number_total             2582
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol502116m_si_002.cif
_cod_data_source_block           p-421c
_cod_depositor_comments
;Adding full bibliography for 1517432--1517433.cif.

The following automatic conversions were performed:

'_exptl_crystal_density_meas' value 'not measured' was changed to '?'
- the value is perceived as not measured.

Automatic conversion script
Id: cif_fix_values 3008 2015-01-20 13:52:24Z robertas 
;
_cod_original_sg_symbol_H-M      p-42(1)c
_cod_database_code               1517432
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, z'
'y, -x, -z'
'-y, x, -z'
'-x+1/2, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z+1/2'
'-y+1/2, -x+1/2, z+1/2'
'y+1/2, x+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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
C1 C 0.5735(4) 0.2136(3) 0.4053(19) 0.113(4) Uani 1 1 d .
H1A H 0.5466 0.1853 0.3433 0.136 Uiso 1 1 calc R
Cl1 Cl 0.53141(11) 0.26914(8) 0.4970(4) 0.0980(8) Uani 1 1 d .
Cl2 Cl 0.62255(12) 0.24339(13) 0.2375(5) 0.1272(13) Uani 1 1 d .
Cl3 Cl 0.61290(16) 0.17551(11) 0.5640(7) 0.175(2) Uani 1 1 d .
C1B C 0.9836(2) 0.0532(2) 0.8779(8) 0.0377(12) Uani 1 1 d .
C2B C 1.0000 0.0000 0.7571(10) 0.0410(15) Uani 1 2 d S
H2BA H 1.036(4) 0.009(5) 0.656(17) 0.049 Uiso 0.50 1 d P
C3B C 0.9310(2) 0.0361(2) 0.9983(8) 0.0397(11) Uani 1 1 d .
H3BA H 0.8972 0.0254 0.9206 0.048 Uiso 1 1 calc R
H3BB H 0.9194 0.0700 1.0740 0.048 Uiso 1 1 calc R
C1A C 0.9604(3) 0.3020(3) 0.4010(13) 0.073(2) Uani 1 1 d .
C2A C 1.0030(3) 0.3246(3) 0.5112(15) 0.085(2) Uani 1 1 d .
H2AA H 1.0186 0.3027 0.6098 0.102 Uiso 1 1 calc R
C3A C 1.0223(4) 0.3804(4) 0.473(2) 0.129(5) Uani 1 1 d .
H3AA H 1.0519 0.3980 0.5459 0.155 Uiso 1 1 calc R
C4A C 0.9972(7) 0.4123(4) 0.321(3) 0.148(7) Uani 1 1 d .
H4AA H 1.0109 0.4508 0.2946 0.177 Uiso 1 1 calc R
C5A C 0.9570(6) 0.3896(4) 0.223(2) 0.130(6) Uani 1 1 d .
H5AA H 0.9411 0.4124 0.1266 0.156 Uiso 1 1 calc R
C6A C 0.9354(4) 0.3333(3) 0.2501(13) 0.083(3) Uani 1 1 d .
C7A C 0.8896(3) 0.2437(3) 0.2723(9) 0.0578(16) Uani 1 1 d .
C8A C 0.8509(3) 0.2003(3) 0.2303(9) 0.0652(18) Uani 1 1 d .
H8AA H 0.8505 0.1645 0.2964 0.078 Uiso 1 1 calc R
C9A C 0.8121(4) 0.2097(5) 0.0882(12) 0.098(3) Uani 1 1 d .
H9AA H 0.7846 0.1797 0.0593 0.118 Uiso 1 1 calc R
C10A C 0.8115(6) 0.2603(6) -0.0122(14) 0.113(4) Uani 1 1 d .
H10A H 0.7841 0.2652 -0.1080 0.135 Uiso 1 1 calc R
C11A C 0.8507(6) 0.3033(6) 0.0271(13) 0.116(4) Uani 1 1 d .
H11A H 0.8507 0.3380 -0.0443 0.139 Uiso 1 1 calc R
C12A C 0.8925(4) 0.2982(3) 0.1732(11) 0.077(2) Uani 1 1 d .
N13A N 0.9320(2) 0.24716(19) 0.4071(8) 0.0520(12) Uani 1 1 d .
C14A C 0.9455(2) 0.2006(2) 0.5270(9) 0.0489(13) Uani 1 1 d .
C15A C 0.9976(2) 0.1704(2) 0.5101(8) 0.0472(12) Uani 1 1 d .
H15A H 1.0248 0.1810 0.4183 0.057 Uiso 1 1 calc R
C16A C 1.0101(2) 0.1245(2) 0.6273(8) 0.0463(13) Uani 1 1 d .
H16A H 1.0473 0.1057 0.6205 0.056 Uiso 1 1 calc R
C17A C 0.9688(2) 0.1051(2) 0.7562(8) 0.0386(11) Uani 1 1 d .
C18A C 0.9159(2) 0.1353(2) 0.7639(9) 0.0498(13) Uani 1 1 d .
H18A H 0.8866 0.1225 0.8468 0.060 Uiso 1 1 calc R
C19A C 0.9043(3) 0.1832(3) 0.6555(9) 0.0530(15) Uani 1 1 d .
H19A H 0.8685 0.2042 0.6684 0.064 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'
Cl Cl 0.1484 0.1585 '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
Cl3 C1 Cl1 113.3(8) . .
Cl3 C1 Cl2 109.6(6) . .
Cl1 C1 Cl2 109.7(5) . .
C17A C1B C3B 111.2(4) . .
C17A C1B C3B 109.7(4) . 3_667
C3B C1B C3B 108.7(4) . 3_667
C17A C1B C2B 108.8(5) . .
C3B C1B C2B 108.7(4) . .
C3B C1B C2B 109.7(4) 3_667 .
C1B C2B C1B 109.8(6) . 2_755
C1B C3B C1B 110.6(5) . 4_647
C2A C1A N13A 129.9(7) . .
C2A C1A C6A 123.6(7) . .
N13A C1A C6A 106.5(8) . .
C1A C2A C3A 117.1(11) . .
C4A C3A C2A 119.5(12) . .
C3A C4A C5A 121.2(9) . .
C4A C5A C6A 123.0(14) . .
C12A C6A C1A 108.0(6) . .
C12A C6A C5A 136.4(11) . .
C1A C6A C5A 115.5(11) . .
N13A C7A C8A 130.9(6) . .
N13A C7A C12A 106.3(6) . .
C8A C7A C12A 122.8(7) . .
C7A C8A C9A 118.1(8) . .
C8A C9A C10A 122.9(10) . .
C11A C10A C9A 119.1(9) . .
C12A C11A C10A 122.5(9) . .
C6A C12A C11A 136.6(9) . .
C6A C12A C7A 108.8(7) . .
C11A C12A C7A 114.6(10) . .
C7A N13A C1A 110.3(5) . .
C7A N13A C14A 123.8(5) . .
C1A N13A C14A 125.8(6) . .
C15A C14A C19A 120.1(5) . .
C15A C14A N13A 120.4(5) . .
C19A C14A N13A 119.4(5) . .
C16A C15A C14A 119.9(5) . .
C15A C16A C17A 121.3(5) . .
C18A C17A C16A 116.9(5) . .
C18A C17A C1B 123.6(5) . .
C16A C17A C1B 119.5(4) . .
C19A C18A C17A 122.3(5) . .
C18A C19A C14A 119.4(5) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
C1 Cl3 1.711(10) .
C1 Cl1 1.726(11) .
C1 Cl2 1.800(14) .
C1B C17A 1.524(7) .
C1B C3B 1.542(7) .
C1B C3B 1.546(7) 3_667
C1B C2B 1.549(7) .
C2B C1B 1.549(7) 2_755
C3B C1B 1.546(7) 4_647
C1A C2A 1.367(12) .
C1A N13A 1.407(8) .
C1A C6A 1.439(12) .
C2A C3A 1.375(12) .
C3A C4A 1.45(2) .
C4A C5A 1.28(2) .
C5A C6A 1.388(13) .
C6A C12A 1.385(13) .
C7A N13A 1.389(9) .
C7A C8A 1.360(10) .
C7A C12A 1.442(10) .
C8A C9A 1.388(10) .
C9A C10A 1.371(16) .
C10A C11A 1.356(16) .
C11A C12A 1.443(15) .
N13A C14A 1.415(7) .
C14A C15A 1.376(8) .
C14A C19A 1.392(8) .
C15A C16A 1.386(8) .
C16A C17A 1.409(8) .
C17A C18A 1.388(7) .
C18A C19A 1.379(8) .
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_4
C17A C1B C2B C1B 179.0(4) . 2_755
C3B C1B C2B C1B -59.7(3) . 2_755
C3B C1B C2B C1B 59.0(3) 3_667 2_755
C17A C1B C3B C1B -179.5(5) . 4_647
C3B C1B C3B C1B -58.6(4) 3_667 4_647
C2B C1B C3B C1B 60.7(5) . 4_647
N13A C1A C2A C3A -179.3(7) . .
C6A C1A C2A C3A 0.0(11) . .
C1A C2A C3A C4A 0.1(12) . .
C2A C3A C4A C5A 0.6(16) . .
C3A C4A C5A C6A -1.5(17) . .
C2A C1A C6A C12A -178.0(7) . .
N13A C1A C6A C12A 1.5(7) . .
C2A C1A C6A C5A -0.8(10) . .
N13A C1A C6A C5A 178.7(6) . .
C4A C5A C6A C12A 177.7(10) . .
C4A C5A C6A C1A 1.5(13) . .
N13A C7A C8A C9A 178.6(6) . .
C12A C7A C8A C9A -1.3(10) . .
C7A C8A C9A C10A 0.8(11) . .
C8A C9A C10A C11A 0.4(14) . .
C9A C10A C11A C12A -1.2(15) . .
C1A C6A C12A C11A 177.6(8) . .
C5A C6A C12A C11A 1.3(16) . .
C1A C6A C12A C7A -0.5(8) . .
C5A C6A C12A C7A -176.8(9) . .
C10A C11A C12A C6A -177.4(9) . .
C10A C11A C12A C7A 0.6(12) . .
N13A C7A C12A C6A -0.7(7) . .
C8A C7A C12A C6A 179.2(6) . .
N13A C7A C12A C11A -179.3(6) . .
C8A C7A C12A C11A 0.6(9) . .
C8A C7A N13A C1A -178.2(7) . .
C12A C7A N13A C1A 1.7(6) . .
C8A C7A N13A C14A 4.1(10) . .
C12A C7A N13A C14A -175.9(5) . .
C2A C1A N13A C7A 177.4(7) . .
C6A C1A N13A C7A -2.0(7) . .
C2A C1A N13A C14A -5.0(11) . .
C6A C1A N13A C14A 175.6(5) . .
C7A N13A C14A C15A 108.3(7) . .
C1A N13A C14A C15A -68.9(8) . .
C7A N13A C14A C19A -67.9(8) . .
C1A N13A C14A C19A 114.9(7) . .
C19A C14A C15A C16A -3.3(9) . .
N13A C14A C15A C16A -179.4(5) . .
C14A C15A C16A C17A 4.6(9) . .
C15A C16A C17A C18A -1.9(8) . .
C15A C16A C17A C1B 177.9(5) . .
C3B C1B C17A C18A 4.3(7) . .
C3B C1B C17A C18A -116.0(5) 3_667 .
C2B C1B C17A C18A 124.0(5) . .
C3B C1B C17A C16A -175.6(5) . .
C3B C1B C17A C16A 64.1(6) 3_667 .
C2B C1B C17A C16A -55.8(5) . .
C16A C17A C18A C19A -2.0(8) . .
C1B C17A C18A C19A 178.1(5) . .
C17A C18A C19A C14A 3.3(9) . .
C15A C14A C19A C18A -0.6(9) . .
N13A C14A C19A C18A 175.6(6) . .
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 139044067
