#------------------------------------------------------------------------------
#$Date: 2021-10-06 16:48:56 +0300 (Wed, 06 Oct 2021) $
#$Revision: 269622 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/12/89/7128906.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_7128906
loop_
_publ_author_name
'Thiele, Maike'
'Octa-Smolin, Frescilia'
'Thölke, Simon'
'Wölper, Christoph'
'Linders, Jürgen'
'Mayer, Christian'
'Haberhauer, Gebhard'
'Niemeyer, Jochen'
_publ_section_title
;
 A supramolecular double-helix based on complementary
 phosphate-guanidinium pairing.
;
_journal_issue                   77
_journal_name_full
'Chemical communications (Cambridge, England)'
_journal_page_first              9842
_journal_page_last               9845
_journal_paper_doi               10.1039/d1cc04644f
_journal_volume                  57
_journal_year                    2021
_chemical_formula_sum            'C23 H20 Br N3'
_chemical_formula_weight         418.33
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   mixed
_audit_creation_method           SHELXL-2014/7
_audit_update_record
;
2021-04-16 deposited with the CCDC.	2021-08-27 downloaded from the CCDC.
;
_cell_angle_alpha                91.7000(10)
_cell_angle_beta                 93.9750(10)
_cell_angle_gamma                108.2000(10)
_cell_formula_units_Z            2
_cell_length_a                   8.8577(2)
_cell_length_b                   8.9307(2)
_cell_length_c                   18.7699(4)
_cell_measurement_reflns_used    9984
_cell_measurement_temperature    100(1)
_cell_measurement_theta_max      16.7
_cell_measurement_theta_min      2.43
_cell_volume                     1405.06(5)
_computing_cell_refinement       'BRUKER D8 KAPPA APEX 2 (3.0-2009)'
_computing_data_collection       'BRUKER D8 KAPPA APEX 2 (3.0-2009)'
_computing_data_reduction        'BRUKER D8 KAPPA APEX 2 (3.0-2009)'
_computing_molecular_graphics    'BRUKER AXS SHELXTL (c) 2008 / Vers. 2008/4'
_computing_publication_material  'BRUKER AXS SHELXTL (c) 2008 / Vers. 2008/4'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_solution    'BRUKER D8 KAPPA APEX 2 (3.0-2009)'
_diffrn_ambient_temperature      100(1)
_diffrn_detector_area_resol_mean 512
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.964
_diffrn_measurement_device_type
; 
 Bruker D8 KAPPA series II with APEX II area detector system
;
_diffrn_measurement_method
;
 Data collection strategy APEX 2/COSMO
;
_diffrn_radiation_monochromator  'Triumph Goebel mirror'
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0330
_diffrn_reflns_av_unetI/netI     0.0487
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.964
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_number            38397
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.964
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         32.575
_diffrn_reflns_theta_min         2.404
_exptl_absorpt_coefficient_mu    1.471
_exptl_absorpt_correction_T_max  0.75
_exptl_absorpt_correction_T_min  0.61
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
; 
 BRUKER AXS SMART APEX 2 Vers. 3.0-2009
 R.H. Blessing, Acta Cryst. (1995) A51 33-38 
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    0.989
_exptl_crystal_description       tablet
_exptl_crystal_F_000             428
_exptl_crystal_size_max          0.173
_exptl_crystal_size_mid          0.125
_exptl_crystal_size_min          0.095
_platon_squeeze_details
;
;
_refine_diff_density_max         0.851
_refine_diff_density_min         -0.381
_refine_diff_density_rms         0.101
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.052
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     260
_refine_ls_number_reflns         9887
_refine_ls_number_restraints     4
_refine_ls_restrained_S_all      1.053
_refine_ls_R_factor_all          0.0594
_refine_ls_R_factor_gt           0.0464
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0678P)²+0.3442P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1161
_refine_ls_wR_factor_ref         0.1212
_reflns_Friedel_coverage         0.000
_reflns_number_gt                7853
_reflns_number_total             9887
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d1cc04644f2.cif
_cod_data_source_block           st010_4m
_cod_depositor_comments
'Adding full bibliography for 7128905--7128910.cif.'
_cod_database_code               7128906
_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   0.785
_shelx_estimated_absorpt_t_max   0.873
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'
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
Br1 Br 0.77511(2) 0.59338(2) 0.41095(2) 0.01943(6) Uani 1 1 d . . . . .
N1 N 0.31117(18) 0.7072(2) 0.35722(9) 0.0190(3) Uani 1 1 d . . . . .
N2 N 0.4281(2) 0.6444(3) 0.46192(10) 0.0331(5) Uani 1 1 d D . . . .
H2A H 0.407(4) 0.611(3) 0.5025(11) 0.040 Uiso 1 1 d D U . . .
H2B H 0.509(3) 0.636(3) 0.4410(15) 0.040 Uiso 1 1 d D U . . .
N3 N 0.1753(3) 0.6569(3) 0.45993(11) 0.0369(5) Uani 1 1 d D . . . .
H3A H 0.093(3) 0.664(4) 0.4395(15) 0.044 Uiso 1 1 d D U . . .
H3B H 0.173(4) 0.611(3) 0.4953(12) 0.044 Uiso 1 1 d D U . . .
C1 C 0.3990(2) 0.9319(2) 0.23179(9) 0.0152(3) Uani 1 1 d . . . . .
C2 C 0.4881(2) 0.9176(2) 0.29354(10) 0.0180(3) Uani 1 1 d . . . . .
C3 C 0.5978(2) 1.0518(2) 0.33071(11) 0.0225(4) Uani 1 1 d . . . . .
H3 H 0.6585 1.0399 0.3726 0.027 Uiso 1 1 calc R U . . .
C4 C 0.6167(2) 1.1993(2) 0.30636(12) 0.0249(4) Uani 1 1 d . . . . .
H4 H 0.6935 1.2887 0.3305 0.030 Uiso 1 1 calc R U . . .
C5 C 0.5232(2) 1.2195(2) 0.24579(11) 0.0203(4) Uani 1 1 d . . . . .
C6 C 0.5349(3) 1.3734(2) 0.22265(12) 0.0265(4) Uani 1 1 d . . . . .
H6 H 0.6103 1.4633 0.2472 0.032 Uiso 1 1 calc R U . . .
C7 C 0.4407(3) 1.3929(2) 0.16654(13) 0.0282(4) Uani 1 1 d . . . . .
H7 H 0.4498 1.4963 0.1522 0.034 Uiso 1 1 calc R U . . .
C8 C 0.3281(3) 1.2606(2) 0.12877(12) 0.0250(4) Uani 1 1 d . . . . .
H8 H 0.2614 1.2755 0.0895 0.030 Uiso 1 1 calc R U . . .
C9 C 0.3155(2) 1.1112(2) 0.14894(10) 0.0192(3) Uani 1 1 d . . . . .
H9 H 0.2403 1.0232 0.1231 0.023 Uiso 1 1 calc R U . . .
C10 C 0.4127(2) 1.0857(2) 0.20769(10) 0.0164(3) Uani 1 1 d . . . . .
C11 C 0.2857(2) 0.7849(2) 0.19625(10) 0.0158(3) Uani 1 1 d . . . . .
C12 C 0.1749(2) 0.6848(2) 0.23638(10) 0.0176(3) Uani 1 1 d . . . . .
C13 C 0.0673(2) 0.5422(2) 0.20534(11) 0.0225(4) Uani 1 1 d . . . . .
H13 H -0.0090 0.4759 0.2334 0.027 Uiso 1 1 calc R U . . .
C14 C 0.0717(2) 0.4984(2) 0.13529(11) 0.0236(4) Uani 1 1 d . . . . .
H14 H -0.0032 0.4033 0.1149 0.028 Uiso 1 1 calc R U . . .
C15 C 0.1866(2) 0.5932(2) 0.09276(11) 0.0208(4) Uani 1 1 d . . . . .
C16 C 0.2009(3) 0.5436(3) 0.02213(11) 0.0260(4) Uani 1 1 d . . . . .
H16 H 0.1275 0.4478 0.0015 0.031 Uiso 1 1 calc R U . . .
C17 C 0.3187(3) 0.6312(3) -0.01736(12) 0.0305(5) Uani 1 1 d . . . . .
H17 H 0.3267 0.5962 -0.0648 0.037 Uiso 1 1 calc R U . . .
C18 C 0.4280(3) 0.7738(3) 0.01303(11) 0.0291(4) Uani 1 1 d . . . . .
H18 H 0.5096 0.8346 -0.0143 0.035 Uiso 1 1 calc R U . . .
C19 C 0.4179(2) 0.8255(2) 0.08157(11) 0.0226(4) Uani 1 1 d . . . . .
H19 H 0.4932 0.9211 0.1013 0.027 Uiso 1 1 calc R U . . .
C20 C 0.2961(2) 0.7380(2) 0.12339(10) 0.0174(3) Uani 1 1 d . . . . .
C21 C 0.4638(2) 0.7573(2) 0.32342(10) 0.0196(4) Uani 1 1 d . . . . .
H21A H 0.4624 0.6795 0.2845 0.024 Uiso 1 1 calc R U . . .
H21B H 0.5530 0.7624 0.3593 0.024 Uiso 1 1 calc R U . . .
C22 C 0.1715(2) 0.7261(2) 0.31508(10) 0.0193(3) Uani 1 1 d . . . . .
H22A H 0.1716 0.8366 0.3213 0.023 Uiso 1 1 calc R U . . .
H22B H 0.0724 0.6566 0.3329 0.023 Uiso 1 1 calc R U . . .
C23 C 0.3043(2) 0.6688(3) 0.42506(11) 0.0234(4) Uani 1 1 d . . . . .
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'
Br Br -0.2901 2.4595 '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
C23 N1 C22 121.53(15) . . ?
C23 N1 C21 121.78(16) . . ?
C22 N1 C21 116.04(14) . . ?
C2 C1 C10 119.27(17) . . ?
C2 C1 C11 117.57(16) . . ?
C10 C1 C11 123.05(16) . . ?
C1 C2 C3 121.03(17) . . ?
C1 C2 C21 119.88(17) . . ?
C3 C2 C21 119.05(17) . . ?
C4 C3 C2 120.11(18) . . ?
C3 C4 C5 120.59(19) . . ?
C4 C5 C10 119.95(17) . . ?
C4 C5 C6 121.01(19) . . ?
C10 C5 C6 119.03(18) . . ?
C7 C6 C5 121.0(2) . . ?
C6 C7 C8 120.61(19) . . ?
C9 C8 C7 119.9(2) . . ?
C8 C9 C10 121.24(19) . . ?
C9 C10 C5 118.26(16) . . ?
C9 C10 C1 122.77(17) . . ?
C5 C10 C1 118.92(17) . . ?
C12 C11 C20 119.28(17) . . ?
C12 C11 C1 118.76(16) . . ?
C20 C11 C1 121.77(15) . . ?
C11 C12 C13 120.78(17) . . ?
C11 C12 C22 119.95(17) . . ?
C13 C12 C22 119.25(16) . . ?
C14 C13 C12 120.66(18) . . ?
C13 C14 C15 120.82(18) . . ?
C16 C15 C14 121.47(19) . . ?
C16 C15 C20 119.31(18) . . ?
C14 C15 C20 119.14(18) . . ?
C17 C16 C15 121.3(2) . . ?
C16 C17 C18 119.5(2) . . ?
C19 C18 C17 120.8(2) . . ?
C18 C19 C20 120.84(19) . . ?
C19 C20 C15 118.24(17) . . ?
C19 C20 C11 122.43(17) . . ?
C15 C20 C11 119.22(16) . . ?
N1 C21 C2 109.54(15) . . ?
N1 C22 C12 110.86(15) . . ?
N1 C23 N3 121.64(18) . . ?
N1 C23 N2 121.38(18) . . ?
N3 C23 N2 116.96(18) . . ?
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 C23 1.329(2) . ?
N1 C22 1.479(2) . ?
N1 C21 1.480(2) . ?
N2 C23 1.335(3) . ?
N3 C23 1.333(3) . ?
C1 C2 1.388(2) . ?
C1 C10 1.430(2) . ?
C1 C11 1.486(3) . ?
C2 C3 1.413(3) . ?
C2 C21 1.511(3) . ?
C3 C4 1.371(3) . ?
C4 C5 1.409(3) . ?
C5 C10 1.421(3) . ?
C5 C6 1.429(3) . ?
C6 C7 1.348(3) . ?
C7 C8 1.418(3) . ?
C8 C9 1.371(3) . ?
C9 C10 1.420(3) . ?
C11 C12 1.387(2) . ?
C11 C20 1.436(3) . ?
C12 C13 1.411(3) . ?
C12 C22 1.517(3) . ?
C13 C14 1.367(3) . ?
C14 C15 1.416(3) . ?
C15 C16 1.412(3) . ?
C15 C20 1.428(3) . ?
C16 C17 1.372(3) . ?
C17 C18 1.412(3) . ?
C18 C19 1.372(3) . ?
C19 C20 1.420(3) . ?
loop_
_platon_squeeze_void_nr
_platon_squeeze_void_average_x
_platon_squeeze_void_average_y
_platon_squeeze_void_average_z
_platon_squeeze_void_volume
_platon_squeeze_void_count_electrons
_platon_squeeze_void_content
1 0.002 0.000 0.012 561 281 ' '
