#------------------------------------------------------------------------------
#$Date: 2021-01-07 06:41:23 +0200 (Thu, 07 Jan 2021) $
#$Revision: 260643 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/12/71/7127138.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_7127138
loop_
_publ_author_name
'Jaoul, Arnaud'
'Yang, Yan'
'Casaretto, Nicolas'
'Clavaguéra, Carine'
'Maron, Laurent'
'Nocton, Grégory'
_publ_section_title
;
 Atom economical coupling of benzophenone and N-heterocyclic aromatics
 with SmI₂.
;
_journal_issue                   79
_journal_name_full
'Chemical communications (Cambridge, England)'
_journal_page_first              11875
_journal_page_last               11878
_journal_paper_doi               10.1039/d0cc05164k
_journal_volume                  56
_journal_year                    2020
_chemical_formula_moiety         'C33 H29 I2 N4 O Sm'
_chemical_formula_sum            'C33 H29 I2 N4 O Sm'
_chemical_formula_weight         901.76
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_date             2020-02-21
_audit_creation_method
;
Olex2 1.3
(compiled Nov 21 2019 18:26:39 for OlexSys, GUI svn.r6003)
;
_cell_angle_alpha                90
_cell_angle_beta                 100.528(4)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   9.2854(10)
_cell_length_b                   15.4014(14)
_cell_length_c                   24.686(3)
_cell_measurement_reflns_used    8765
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      24.521
_cell_measurement_theta_min      2.231
_cell_volume                     3470.9(6)
_computing_cell_refinement       'SAINT V8.38A (Bruker, 2018)'
_computing_data_reduction        'SAINT V8.38A (Bruker, 2018)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_temperature      149.99
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.996
_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  0.0738
_diffrn_reflns_av_unetI/netI     0.0517
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       32
_diffrn_reflns_limit_l_min       -32
_diffrn_reflns_number            56938
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.342
_diffrn_reflns_theta_min         2.594
_diffrn_source_current           31.0
_diffrn_source_power             1.705
_diffrn_source_voltage           55.0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    3.500
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_correction_T_min  0.6000
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1041 before and 0.0630 after correction.
The Ratio of minimum to maximum transmission is 0.8046.
The λ/2 correction factor is Not present.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.726
_exptl_crystal_description       plate
_exptl_crystal_F_000             1724
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.06
_exptl_crystal_size_min          0.04
_refine_diff_density_max         2.825
_refine_diff_density_min         -1.383
_refine_diff_density_rms         0.150
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.052
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     370
_refine_ls_number_reflns         8630
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.052
_refine_ls_R_factor_all          0.0594
_refine_ls_R_factor_gt           0.0420
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0224P)²+14.7387P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0828
_refine_ls_wR_factor_ref         0.0882
_reflns_Friedel_coverage         0.000
_reflns_number_gt                6751
_reflns_number_total             8630
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d0cc05164k2.cif
_cod_data_source_block           4
_cod_depositor_comments
'Adding full bibliography for 7127135--7127141.cif.'
_cod_original_cell_volume        3470.8(6)
_cod_database_code               7127138
_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   0.873
_shelx_estimated_absorpt_t_min   0.541
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C3(H3), C4(H4), C5(H5), C6(H6), C7(H7), C8(H8), C9(H9),
 C10(H10), C13(H13), C14(H14), C15(H15), C16(H16), C17(H17), C19(H19), C20(H20),
  C21(H21), C22(H22), C24(H24), C25(H25), C26(H26), C27(H27), C28(H28),
 C29(H29), C30(H30), C31(H31), C32(H32), C33(H33)
;
_smtbx_masks_void_probe_radius   1.2
_smtbx_masks_void_truncation_radius 1.2
_olex2_submission_special_instructions 'No special instructions were received'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -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
Sm1 Sm 0.52464(3) 0.29382(2) 0.61384(2) 0.02022(7) Uani 1 1 d . . . . .
I1 I 0.40579(4) 0.10296(2) 0.60399(2) 0.03203(10) Uani 1 1 d . . . . .
I2 I 0.66841(4) 0.47092(2) 0.59559(2) 0.03036(9) Uani 1 1 d . . . . .
O0AA O 0.3818(3) 0.3258(2) 0.66913(13) 0.0208(7) Uani 1 1 d . . . . .
N1AA N 0.7705(5) 0.2128(3) 0.63031(18) 0.0264(9) Uani 1 1 d . . . . .
N1 N 0.2850(5) 0.3352(3) 0.54561(18) 0.0288(10) Uani 1 1 d . . . . .
N2 N 0.5748(5) 0.2662(3) 0.51173(18) 0.0276(10) Uani 1 1 d . . . . .
N3 N 0.6543(4) 0.3390(3) 0.71374(18) 0.0251(9) Uani 1 1 d . . . . .
C1 C 0.2219(6) 0.2860(4) 0.5028(2) 0.0353(13) Uani 1 1 d . . . . .
H1 H 0.277460 0.240889 0.490272 0.042 Uiso 1 1 calc R U . . .
C2 C 0.0790(7) 0.2988(4) 0.4763(3) 0.0423(15) Uani 1 1 d . . . . .
H2 H 0.037593 0.263882 0.445671 0.051 Uiso 1 1 calc R U . . .
C3 C -0.0027(7) 0.3637(4) 0.4953(3) 0.0431(16) Uani 1 1 d . . . . .
H3 H -0.101932 0.372911 0.478317 0.052 Uiso 1 1 calc R U . . .
C4 C 0.0608(6) 0.4144(4) 0.5385(3) 0.0384(14) Uani 1 1 d . . . . .
H4 H 0.006751 0.458982 0.552350 0.046 Uiso 1 1 calc R U . . .
C5 C 0.2062(6) 0.3990(4) 0.5618(2) 0.0326(13) Uani 1 1 d . . . . .
H5 H 0.251658 0.435854 0.590778 0.039 Uiso 1 1 calc R U . . .
C6 C 0.5604(6) 0.3307(4) 0.4747(2) 0.0287(12) Uani 1 1 d . . . . .
H6 H 0.534667 0.386704 0.485889 0.034 Uiso 1 1 calc R U . . .
C7 C 0.5809(6) 0.3201(4) 0.4217(2) 0.0314(12) Uani 1 1 d . . . . .
H7 H 0.571420 0.367812 0.396968 0.038 Uiso 1 1 calc R U . . .
C8 C 0.6155(7) 0.2385(4) 0.4049(2) 0.0427(16) Uani 1 1 d . . . . .
H8 H 0.630353 0.228996 0.368305 0.051 Uiso 1 1 calc R U . . .
C9 C 0.6281(7) 0.1714(4) 0.4418(2) 0.0416(15) Uani 1 1 d . . . . .
H9 H 0.649944 0.114507 0.430895 0.050 Uiso 1 1 calc R U . . .
C10 C 0.6091(7) 0.1871(3) 0.4942(2) 0.0347(13) Uani 1 1 d . . . . .
H10 H 0.620574 0.140267 0.519722 0.042 Uiso 1 1 calc R U . . .
C11 C 0.3988(5) 0.3666(3) 0.7204(2) 0.0214(10) Uani 1 1 d . . . . .
C12 C 0.3202(5) 0.4553(3) 0.71207(19) 0.0223(10) Uani 1 1 d . . . . .
C13 C 0.3906(6) 0.5349(3) 0.7167(2) 0.0264(11) Uani 1 1 d . . . . .
H13 H 0.493771 0.537488 0.728439 0.032 Uiso 1 1 calc R U . . .
C14 C 0.3108(6) 0.6116(4) 0.7041(2) 0.0307(12) Uani 1 1 d . . . . .
H14 H 0.359660 0.666027 0.707637 0.037 Uiso 1 1 calc R U . . .
C15 C 0.1608(6) 0.6080(4) 0.6864(2) 0.0342(13) Uani 1 1 d . . . . .
H15 H 0.106544 0.660107 0.678053 0.041 Uiso 1 1 calc R U . . .
C16 C 0.0899(6) 0.5291(4) 0.6810(2) 0.0332(13) Uani 1 1 d . . . . .
H16 H -0.012934 0.526533 0.668362 0.040 Uiso 1 1 calc R U . . .
C17 C 0.1693(6) 0.4540(3) 0.6941(2) 0.0272(11) Uani 1 1 d . . . . .
H17 H 0.119482 0.399806 0.690823 0.033 Uiso 1 1 calc R U . . .
C18 C 0.5640(5) 0.3752(3) 0.7440(2) 0.0202(10) Uani 1 1 d . . . . .
C19 C 0.6195(6) 0.4154(3) 0.7940(2) 0.0263(11) Uani 1 1 d . . . . .
H19 H 0.554295 0.440823 0.814966 0.032 Uiso 1 1 calc R U . . .
C20 C 0.7663(6) 0.4184(4) 0.8130(2) 0.0314(12) Uani 1 1 d . . . . .
H20 H 0.803982 0.445828 0.847064 0.038 Uiso 1 1 calc R U . . .
C21 C 0.8598(6) 0.3813(4) 0.7823(2) 0.0345(13) Uani 1 1 d . . . . .
H21 H 0.962875 0.382155 0.794750 0.041 Uiso 1 1 calc R U . . .
C22 C 0.7995(6) 0.3431(4) 0.7332(2) 0.0336(13) Uani 1 1 d . . . . .
H22 H 0.863712 0.317954 0.711762 0.040 Uiso 1 1 calc R U . . .
C23 C 0.3336(5) 0.3109(3) 0.7622(2) 0.0231(11) Uani 1 1 d . . . . .
C24 C 0.2883(6) 0.3467(3) 0.8075(2) 0.0271(11) Uani 1 1 d . . . . .
H24 H 0.293329 0.407796 0.812881 0.032 Uiso 1 1 calc R U . . .
C25 C 0.2352(6) 0.2941(4) 0.8452(2) 0.0374(14) Uani 1 1 d . . . . .
H25 H 0.202561 0.319576 0.875874 0.045 Uiso 1 1 calc R U . . .
C26 C 0.2296(6) 0.2051(4) 0.8384(2) 0.0358(13) Uani 1 1 d . . . . .
H26 H 0.194847 0.169204 0.864482 0.043 Uiso 1 1 calc R U . . .
C27 C 0.2751(6) 0.1689(4) 0.7932(3) 0.0341(13) Uani 1 1 d . . . . .
H27 H 0.270761 0.107741 0.788149 0.041 Uiso 1 1 calc R U . . .
C28 C 0.3267(6) 0.2205(3) 0.7553(2) 0.0295(12) Uani 1 1 d . . . . .
H28 H 0.357647 0.194789 0.724351 0.035 Uiso 1 1 calc R U . . .
C29 C 0.7961(6) 0.1455(4) 0.6647(2) 0.0324(13) Uani 1 1 d . . . . .
H29 H 0.716582 0.122680 0.679582 0.039 Uiso 1 1 calc R U . . .
C30 C 0.9319(6) 0.1073(4) 0.6799(2) 0.0376(14) Uani 1 1 d . . . . .
H30 H 0.944799 0.059080 0.704300 0.045 Uiso 1 1 calc R U . . .
C31 C 1.0486(6) 0.1403(4) 0.6591(3) 0.0380(14) Uani 1 1 d . . . . .
H31 H 1.143411 0.115554 0.669043 0.046 Uiso 1 1 calc R U . . .
C32 C 1.0249(7) 0.2098(4) 0.6237(3) 0.0451(16) Uani 1 1 d . . . . .
H32 H 1.103319 0.233812 0.608707 0.054 Uiso 1 1 calc R U . . .
C33 C 0.8839(6) 0.2447(4) 0.6101(3) 0.0339(13) Uani 1 1 d . . . . .
H33 H 0.867992 0.292727 0.585571 0.041 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 0.0033 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'
I I -0.4742 1.8119 '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'
Sm Sm -0.1638 3.4418 '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
I2 Sm1 I1 165.289(13) . . ?
O0AA Sm1 I1 90.84(9) . . ?
O0AA Sm1 I2 103.00(9) . . ?
O0AA Sm1 N1AA 130.64(13) . . ?
O0AA Sm1 N1 78.46(13) . . ?
O0AA Sm1 N2 151.17(13) . . ?
O0AA Sm1 N3 64.54(13) . . ?
N1AA Sm1 I1 81.19(10) . . ?
N1AA Sm1 I2 93.23(10) . . ?
N1AA Sm1 N1 148.03(14) . . ?
N1AA Sm1 N2 76.68(13) . . ?
N1AA Sm1 N3 74.87(13) . . ?
N1 Sm1 I1 86.12(10) . . ?
N1 Sm1 I2 91.74(10) . . ?
N1 Sm1 N2 72.90(13) . . ?
N1 Sm1 N3 136.85(13) . . ?
N2 Sm1 I1 84.10(9) . . ?
N2 Sm1 I2 81.36(10) . . ?
N3 Sm1 I1 114.53(9) . . ?
N3 Sm1 I2 76.61(9) . . ?
N3 Sm1 N2 142.63(13) . . ?
C11 O0AA Sm1 134.8(3) . . ?
C29 N1AA Sm1 121.9(3) . . ?
C29 N1AA C33 117.5(5) . . ?
C33 N1AA Sm1 120.0(3) . . ?
C1 N1 Sm1 124.6(4) . . ?
C5 N1 Sm1 115.9(4) . . ?
C5 N1 C1 117.9(5) . . ?
C6 N2 Sm1 120.8(3) . . ?
C6 N2 C10 116.8(5) . . ?
C10 N2 Sm1 122.4(3) . . ?
C18 N3 Sm1 113.9(3) . . ?
C18 N3 C22 117.9(4) . . ?
C22 N3 Sm1 127.1(3) . . ?
N1 C1 H1 118.8 . . ?
N1 C1 C2 122.3(6) . . ?
C2 C1 H1 118.8 . . ?
C1 C2 H2 120.6 . . ?
C1 C2 C3 118.7(6) . . ?
C3 C2 H2 120.6 . . ?
C2 C3 H3 120.3 . . ?
C4 C3 C2 119.4(6) . . ?
C4 C3 H3 120.3 . . ?
C3 C4 H4 120.8 . . ?
C3 C4 C5 118.3(6) . . ?
C5 C4 H4 120.8 . . ?
N1 C5 C4 123.3(6) . . ?
N1 C5 H5 118.3 . . ?
C4 C5 H5 118.3 . . ?
N2 C6 H6 118.3 . . ?
N2 C6 C7 123.4(5) . . ?
C7 C6 H6 118.3 . . ?
C6 C7 H7 120.7 . . ?
C6 C7 C8 118.6(5) . . ?
C8 C7 H7 120.7 . . ?
C7 C8 H8 120.5 . . ?
C9 C8 C7 118.9(5) . . ?
C9 C8 H8 120.5 . . ?
C8 C9 H9 120.3 . . ?
C10 C9 C8 119.4(5) . . ?
C10 C9 H9 120.3 . . ?
N2 C10 C9 122.9(5) . . ?
N2 C10 H10 118.5 . . ?
C9 C10 H10 118.5 . . ?
O0AA C11 C12 107.8(4) . . ?
O0AA C11 C18 108.7(4) . . ?
O0AA C11 C23 111.2(4) . . ?
C12 C11 C23 110.2(4) . . ?
C18 C11 C12 112.7(4) . . ?
C18 C11 C23 106.2(4) . . ?
C13 C12 C11 124.6(4) . . ?
C13 C12 C17 118.2(5) . . ?
C17 C12 C11 117.0(4) . . ?
C12 C13 H13 119.8 . . ?
C12 C13 C14 120.4(5) . . ?
C14 C13 H13 119.8 . . ?
C13 C14 H14 120.0 . . ?
C15 C14 C13 119.9(5) . . ?
C15 C14 H14 120.0 . . ?
C14 C15 H15 119.9 . . ?
C16 C15 C14 120.1(5) . . ?
C16 C15 H15 119.9 . . ?
C15 C16 H16 120.2 . . ?
C15 C16 C17 119.5(5) . . ?
C17 C16 H16 120.2 . . ?
C12 C17 H17 119.1 . . ?
C16 C17 C12 121.8(5) . . ?
C16 C17 H17 119.1 . . ?
N3 C18 C11 115.7(4) . . ?
N3 C18 C19 120.7(4) . . ?
C19 C18 C11 123.6(4) . . ?
C18 C19 H19 119.8 . . ?
C20 C19 C18 120.4(5) . . ?
C20 C19 H19 119.8 . . ?
C19 C20 H20 120.3 . . ?
C19 C20 C21 119.4(5) . . ?
C21 C20 H20 120.3 . . ?
C20 C21 H21 121.1 . . ?
C22 C21 C20 117.8(5) . . ?
C22 C21 H21 121.1 . . ?
N3 C22 C21 123.8(5) . . ?
N3 C22 H22 118.1 . . ?
C21 C22 H22 118.1 . . ?
C24 C23 C11 122.2(5) . . ?
C24 C23 C28 118.9(5) . . ?
C28 C23 C11 118.9(4) . . ?
C23 C24 H24 119.8 . . ?
C23 C24 C25 120.5(5) . . ?
C25 C24 H24 119.8 . . ?
C24 C25 H25 119.8 . . ?
C26 C25 C24 120.4(5) . . ?
C26 C25 H25 119.8 . . ?
C25 C26 H26 120.3 . . ?
C27 C26 C25 119.3(5) . . ?
C27 C26 H26 120.3 . . ?
C26 C27 H27 119.6 . . ?
C28 C27 C26 120.7(5) . . ?
C28 C27 H27 119.6 . . ?
C23 C28 H28 119.9 . . ?
C27 C28 C23 120.2(5) . . ?
C27 C28 H28 119.9 . . ?
N1AA C29 H29 118.3 . . ?
N1AA C29 C30 123.5(5) . . ?
C30 C29 H29 118.3 . . ?
C29 C30 H30 120.6 . . ?
C31 C30 C29 118.9(5) . . ?
C31 C30 H30 120.6 . . ?
C30 C31 H31 120.7 . . ?
C32 C31 C30 118.7(5) . . ?
C32 C31 H31 120.7 . . ?
C31 C32 H32 120.5 . . ?
C31 C32 C33 119.1(5) . . ?
C33 C32 H32 120.5 . . ?
N1AA C33 C32 122.3(5) . . ?
N1AA C33 H33 118.8 . . ?
C32 C33 H33 118.8 . . ?
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
Sm1 I1 3.1337(5) . ?
Sm1 I2 3.1057(5) . ?
Sm1 O0AA 2.128(3) . ?
Sm1 N1AA 2.568(4) . ?
Sm1 N1 2.612(4) . ?
Sm1 N2 2.680(4) . ?
Sm1 N3 2.633(4) . ?
O0AA C11 1.395(6) . ?
N1AA C29 1.333(7) . ?
N1AA C33 1.338(7) . ?
N1 C1 1.345(7) . ?
N1 C5 1.330(7) . ?
N2 C6 1.340(7) . ?
N2 C10 1.350(7) . ?
N3 C18 1.341(6) . ?
N3 C22 1.347(7) . ?
C1 H1 0.9500 . ?
C1 C2 1.382(8) . ?
C2 H2 0.9500 . ?
C2 C3 1.388(9) . ?
C3 H3 0.9500 . ?
C3 C4 1.366(9) . ?
C4 H4 0.9500 . ?
C4 C5 1.388(8) . ?
C5 H5 0.9500 . ?
C6 H6 0.9500 . ?
C6 C7 1.365(7) . ?
C7 H7 0.9500 . ?
C7 C8 1.380(8) . ?
C8 H8 0.9500 . ?
C8 C9 1.367(8) . ?
C9 H9 0.9500 . ?
C9 C10 1.360(8) . ?
C10 H10 0.9500 . ?
C11 C12 1.545(7) . ?
C11 C18 1.544(7) . ?
C11 C23 1.548(7) . ?
C12 C13 1.385(7) . ?
C12 C17 1.390(7) . ?
C13 H13 0.9500 . ?
C13 C14 1.398(7) . ?
C14 H14 0.9500 . ?
C14 C15 1.382(8) . ?
C15 H15 0.9500 . ?
C15 C16 1.376(8) . ?
C16 H16 0.9500 . ?
C16 C17 1.379(7) . ?
C17 H17 0.9500 . ?
C18 C19 1.393(7) . ?
C19 H19 0.9500 . ?
C19 C20 1.359(7) . ?
C20 H20 0.9500 . ?
C20 C21 1.376(8) . ?
C21 H21 0.9500 . ?
C21 C22 1.371(8) . ?
C22 H22 0.9500 . ?
C23 C24 1.379(7) . ?
C23 C28 1.402(7) . ?
C24 H24 0.9500 . ?
C24 C25 1.391(7) . ?
C25 H25 0.9500 . ?
C25 C26 1.381(8) . ?
C26 H26 0.9500 . ?
C26 C27 1.380(8) . ?
C27 H27 0.9500 . ?
C27 C28 1.379(8) . ?
C28 H28 0.9500 . ?
C29 H29 0.9500 . ?
C29 C30 1.380(8) . ?
C30 H30 0.9500 . ?
C30 C31 1.378(8) . ?
C31 H31 0.9500 . ?
C31 C32 1.373(9) . ?
C32 H32 0.9500 . ?
C32 C33 1.399(8) . ?
C33 H33 0.9500 . ?
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
Sm1 O0AA C11 C12 110.7(4) . . . . ?
Sm1 O0AA C11 C18 -11.7(6) . . . . ?
Sm1 O0AA C11 C23 -128.3(4) . . . . ?
Sm1 N1AA C29 C30 -171.6(4) . . . . ?
Sm1 N1AA C33 C32 171.5(5) . . . . ?
Sm1 N1 C1 C2 163.6(4) . . . . ?
Sm1 N1 C5 C4 -162.8(4) . . . . ?
Sm1 N2 C6 C7 -178.3(4) . . . . ?
Sm1 N2 C10 C9 176.8(5) . . . . ?
Sm1 N3 C18 C11 12.4(5) . . . . ?
Sm1 N3 C18 C19 -169.4(4) . . . . ?
Sm1 N3 C22 C21 168.2(4) . . . . ?
O0AA C11 C12 C13 -110.4(5) . . . . ?
O0AA C11 C12 C17 63.8(5) . . . . ?
O0AA C11 C18 N3 -3.7(6) . . . . ?
O0AA C11 C18 C19 178.1(4) . . . . ?
O0AA C11 C23 C24 -156.0(5) . . . . ?
O0AA C11 C23 C28 26.9(6) . . . . ?
N1AA C29 C30 C31 0.6(9) . . . . ?
N1 C1 C2 C3 -1.2(9) . . . . ?
N2 C6 C7 C8 1.2(9) . . . . ?
N3 C18 C19 C20 -0.1(8) . . . . ?
C1 N1 C5 C4 3.2(8) . . . . ?
C1 C2 C3 C4 1.5(9) . . . . ?
C2 C3 C4 C5 0.3(9) . . . . ?
C3 C4 C5 N1 -2.9(9) . . . . ?
C5 N1 C1 C2 -1.2(8) . . . . ?
C6 N2 C10 C9 -0.4(9) . . . . ?
C6 C7 C8 C9 0.0(10) . . . . ?
C7 C8 C9 C10 -1.3(10) . . . . ?
C8 C9 C10 N2 1.5(10) . . . . ?
C10 N2 C6 C7 -1.0(8) . . . . ?
C11 C12 C13 C14 174.8(5) . . . . ?
C11 C12 C17 C16 -174.6(5) . . . . ?
C11 C18 C19 C20 178.0(5) . . . . ?
C11 C23 C24 C25 -177.7(5) . . . . ?
C11 C23 C28 C27 177.2(5) . . . . ?
C12 C11 C18 N3 -123.2(5) . . . . ?
C12 C11 C18 C19 58.7(6) . . . . ?
C12 C11 C23 C24 -36.6(6) . . . . ?
C12 C11 C23 C28 146.4(5) . . . . ?
C12 C13 C14 C15 -0.6(8) . . . . ?
C13 C12 C17 C16 0.1(8) . . . . ?
C13 C14 C15 C16 -0.3(8) . . . . ?
C14 C15 C16 C17 1.0(9) . . . . ?
C15 C16 C17 C12 -0.9(8) . . . . ?
C17 C12 C13 C14 0.7(7) . . . . ?
C18 N3 C22 C21 0.6(8) . . . . ?
C18 C11 C12 C13 9.6(7) . . . . ?
C18 C11 C12 C17 -176.2(4) . . . . ?
C18 C11 C23 C24 85.8(6) . . . . ?
C18 C11 C23 C28 -91.2(5) . . . . ?
C18 C19 C20 C21 -0.1(8) . . . . ?
C19 C20 C21 C22 0.4(8) . . . . ?
C20 C21 C22 N3 -0.7(9) . . . . ?
C22 N3 C18 C11 -178.4(5) . . . . ?
C22 N3 C18 C19 -0.2(7) . . . . ?
C23 C11 C12 C13 128.0(5) . . . . ?
C23 C11 C12 C17 -57.7(6) . . . . ?
C23 C11 C18 N3 116.1(5) . . . . ?
C23 C11 C18 C19 -62.1(6) . . . . ?
C23 C24 C25 C26 1.1(9) . . . . ?
C24 C23 C28 C27 0.1(8) . . . . ?
C24 C25 C26 C27 -1.0(9) . . . . ?
C25 C26 C27 C28 0.5(9) . . . . ?
C26 C27 C28 C23 0.0(9) . . . . ?
C28 C23 C24 C25 -0.7(8) . . . . ?
C29 N1AA C33 C32 0.2(9) . . . . ?
C29 C30 C31 C32 -0.4(9) . . . . ?
C30 C31 C32 C33 0.1(10) . . . . ?
C31 C32 C33 N1AA 0.0(10) . . . . ?
C33 N1AA C29 C30 -0.5(9) . . . . ?
loop_
_smtbx_masks_void_nr
_smtbx_masks_void_average_x
_smtbx_masks_void_average_y
_smtbx_masks_void_average_z
_smtbx_masks_void_volume
_smtbx_masks_void_count_electrons
_smtbx_masks_void_content
1 -0.670 0.000 0.500 199.4 68.7 '1.6 C5H5N'
2 -0.046 0.500 0.000 199.4 68.7 '1.6 C5H5N'
