#------------------------------------------------------------------------------
#$Date: 2021-12-07 05:50:23 +0200 (Tue, 07 Dec 2021) $
#$Revision: 271210 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/15/83/7158353.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_7158353
loop_
_publ_author_name
'McNaughton, Daniel A.'
'To, Tsz Ying Teresa'
'Hawkins, Bryson A.'
'Hibbs, David E.'
'Gale, Philip A.'
_publ_section_title
;
 Delivering anion transporters to lipid bilayers in water.
;
_journal_issue                   44
_journal_name_full               'Organic & biomolecular chemistry'
_journal_page_first              9624
_journal_page_last               9628
_journal_paper_doi               10.1039/d1ob02041b
_journal_volume                  19
_journal_year                    2021
_chemical_formula_moiety         'C18 H23 N3 O3, C16 H36 N, Cl'
_chemical_formula_sum            'C34 H59 Cl N4 O3'
_chemical_formula_weight         607.30
_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   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2021-09-11
_audit_creation_method
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6272)
;
_audit_update_record
;
2021-09-11 deposited with the CCDC.	2021-10-21 downloaded from the CCDC.
;
_cell_angle_alpha                108.557(3)
_cell_angle_beta                 100.746(2)
_cell_angle_gamma                95.887(2)
_cell_formula_units_Z            2
_cell_length_a                   8.1181(2)
_cell_length_b                   13.6649(4)
_cell_length_c                   17.6062(6)
_cell_measurement_reflns_used    11919
_cell_measurement_temperature    150.0(2)
_cell_measurement_theta_max      29.2290
_cell_measurement_theta_min      2.7680
_cell_volume                     1791.40(10)
_computing_cell_refinement       'CrysAlisPro 1.171.41.105a (Rigaku OD, 2021)'
_computing_data_collection       'CrysAlisPro 1.171.41.105a (Rigaku OD, 2021)'
_computing_data_reduction        'CrysAlisPro 1.171.41.105a (Rigaku OD, 2021)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2017/1 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT  (Sheldrick, 2015)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      150.0(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.4948
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     -3.00  82.00   1.00   15.00    --   11.41  57.00  90.00   85
  2  ω     -1.00  80.00   1.00   15.00    --   11.41  57.00 -30.00   81
  3  ω    -59.00  40.00   1.00   15.00    --   11.41 -57.00  60.00   99
  4  ω    -56.00  40.00   1.00   15.00    --   11.41 -57.00 -60.00   96
  5  ω    -58.00  40.00   1.00   15.00    --   11.41 -57.00-180.00   98
  6  ω      0.00  79.00   1.00   15.00    --   11.41  57.00-150.00   79
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0014266000
_diffrn_orient_matrix_UB_12      -0.0128311000
_diffrn_orient_matrix_UB_13      0.0358950000
_diffrn_orient_matrix_UB_21      0.0088609000
_diffrn_orient_matrix_UB_22      0.0539367000
_diffrn_orient_matrix_UB_23      0.0234300000
_diffrn_orient_matrix_UB_31      -0.0898597000
_diffrn_orient_matrix_UB_32      -0.0041905000
_diffrn_orient_matrix_UB_33      -0.0084610000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0292
_diffrn_reflns_av_unetI/netI     0.0291
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            25252
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.371
_diffrn_reflns_theta_min         2.509
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.143
_exptl_absorpt_correction_T_max  0.97867
_exptl_absorpt_correction_T_min  0.97867
_exptl_absorpt_correction_type   sphere
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.41.105a (Rigaku Oxford Diffraction, 2021)
Spherical absorption correction
using equivalent radius and absorption coefficient.
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_density_diffrn    1.126
_exptl_crystal_description       sphere
_exptl_crystal_F_000             664
_exptl_crystal_size_max          0.91
_exptl_crystal_size_mid          0.74
_exptl_crystal_size_min          0.53
_exptl_crystal_size_rad          0.328
_refine_diff_density_max         0.750
_refine_diff_density_min         -0.282
_refine_diff_density_rms         0.040
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.034
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     383
_refine_ls_number_reflns         7304
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.034
_refine_ls_R_factor_all          0.0562
_refine_ls_R_factor_gt           0.0422
_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)+(0.0499P)²+0.6651P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1050
_refine_ls_wR_factor_ref         0.1145
_reflns_Friedel_coverage         0.000
_reflns_number_gt                5820
_reflns_number_total             7304
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d1ob02041b2.cif
_cod_data_source_block           21bh013
_cod_depositor_comments
'Adding full bibliography for 7158352--7158354.cif.'
_cod_database_code               7158353
_shelx_shelxl_version_number     2017/1
_chemical_oxdiff_formula         'C19 N3 O2 Cl1'
_chemical_oxdiff_usercomment     cd029-tbacl
_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   0.928
_shelx_estimated_absorpt_t_min   0.881
_reflns_odcompleteness_completeness 99.93
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C13(H13), C14(H14), C16(H16)
2.b Secondary CH2 refined with riding coordinates:
 C1'(H1'A,H1'B), C2'(H2'A,H2'B), C4'(H4'A,H4'B), C6'(H6'A,H6'B), C7'(H7'A,
 H7'B), C8(H8A,H8B), C8'(H8'A,H8'B), C10'(H10A,H10B), C10(H10C,H10D), C11'(H11A,
 H11B), C11(H11C,H11D), C12'(H12A,H12B), C12(H12C,H12D), C14'(H14A,H14B),
 C15'(H15A,H15B), C15(H15C,H15D), C16'(H16A,H16B), C17(H17D,H17E), C18(H18A,
 H18B)
2.c Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C5(H5), C6(H6), N2(H2A), N3(H3A)
2.d Idealised Me refined as rotating group:
 C5'(H5'A,H5'B,H5'C), C9'(H9'A,H9'B,H9'C), C13'(H13A,H13B,H13C), C17'(H17A,
 H17B,H17C)
;
_smtbx_masks_void_probe_radius   1.2
_smtbx_masks_void_truncation_radius 1.2
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
- Detector area scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.731
_oxdiff_exptl_absorpt_empirical_full_min 0.511
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
C1 C 0.10930(19) 0.71604(12) 0.54719(9) 0.0284(3) Uani 1 1 d . . . . .
C1' C 0.43407(18) 0.51189(12) 0.25411(9) 0.0256(3) Uani 1 1 d . . . . .
H1'A H 0.404196 0.444800 0.207147 0.031 Uiso 1 1 calc R U . . .
H1'B H 0.334516 0.547953 0.251629 0.031 Uiso 1 1 calc R U . . .
C2' C 0.4638(2) 0.48740(13) 0.33344(10) 0.0315(4) Uani 1 1 d . . . . .
H2'A H 0.483851 0.553259 0.381163 0.038 Uiso 1 1 calc R U . . .
H2'B H 0.566324 0.454286 0.338407 0.038 Uiso 1 1 calc R U . . .
C2 C 0.11968(19) 0.64296(12) 0.47335(10) 0.0294(3) Uani 1 1 d . . . . .
H2 H 0.133651 0.573610 0.469884 0.035 Uiso 1 1 calc R U . . .
C3 C 0.10936(19) 0.67287(12) 0.40532(9) 0.0270(3) Uani 1 1 d . . . . .
H3 H 0.116359 0.623491 0.354462 0.032 Uiso 1 1 calc R U . . .
C4 C 0.08864(18) 0.77524(12) 0.40968(9) 0.0248(3) Uani 1 1 d . . . . .
C4' C 0.3100(2) 0.41372(13) 0.33410(10) 0.0308(4) Uani 1 1 d . . . . .
H4'A H 0.209563 0.449076 0.332618 0.037 Uiso 1 1 calc R U . . .
H4'B H 0.285326 0.350420 0.283962 0.037 Uiso 1 1 calc R U . . .
C5 C 0.0800(2) 0.84741(12) 0.48521(10) 0.0307(3) Uani 1 1 d . . . . .
H5 H 0.067734 0.917256 0.489555 0.037 Uiso 1 1 calc R U . . .
C5' C 0.3383(2) 0.38077(15) 0.40976(11) 0.0419(4) Uani 1 1 d . . . . .
H5'A H 0.442866 0.350832 0.413995 0.063 Uiso 1 1 calc R U . . .
H5'B H 0.241442 0.328195 0.404767 0.063 Uiso 1 1 calc R U . . .
H5'C H 0.348832 0.442075 0.459207 0.063 Uiso 1 1 calc R U . . .
C6 C 0.0892(2) 0.81723(13) 0.55321(10) 0.0321(4) Uani 1 1 d . . . . .
H6 H 0.081822 0.865977 0.604258 0.038 Uiso 1 1 calc R U . . .
C6' C 0.64105(19) 0.68179(12) 0.31511(9) 0.0280(3) Uani 1 1 d . . . . .
H6'A H 0.681707 0.665464 0.365579 0.034 Uiso 1 1 calc R U . . .
H6'B H 0.739394 0.721743 0.305718 0.034 Uiso 1 1 calc R U . . .
C7 C 0.0468(2) 0.88992(12) 0.32444(10) 0.0283(3) Uani 1 1 d . . . . .
C7' C 0.5081(2) 0.75167(13) 0.33054(10) 0.0364(4) Uani 1 1 d . . . . .
H7'A H 0.409407 0.713295 0.340924 0.044 Uiso 1 1 calc R U . . .
H7'B H 0.467661 0.770006 0.281015 0.044 Uiso 1 1 calc R U . . .
C8 C 0.0259(2) 0.97115(12) 0.21801(10) 0.0307(3) Uani 1 1 d . . . . .
H8A H 0.002617 1.030177 0.262301 0.037 Uiso 1 1 calc R U . . .
H8B H -0.068915 0.953921 0.168908 0.037 Uiso 1 1 calc R U . . .
C8' C 0.5823(3) 0.85236(15) 0.40480(11) 0.0486(5) Uani 1 1 d . . . . .
H8'A H 0.693698 0.882441 0.399141 0.058 Uiso 1 1 calc R U . . .
H8'B H 0.505489 0.904028 0.404173 0.058 Uiso 1 1 calc R U . . .
C9 C 0.1911(2) 1.00627(12) 0.19704(9) 0.0260(3) Uani 1 1 d . . . . .
C9' C 0.6062(3) 0.83604(19) 0.48593(12) 0.0618(6) Uani 1 1 d . . . . .
H9'A H 0.496459 0.806428 0.492215 0.093 Uiso 1 1 calc R U . . .
H9'B H 0.651148 0.903375 0.530506 0.093 Uiso 1 1 calc R U . . .
H9'C H 0.686502 0.787636 0.488246 0.093 Uiso 1 1 calc R U . . .
C10' C 0.73626(18) 0.52389(12) 0.23761(9) 0.0261(3) Uani 1 1 d . . . . .
H10A H 0.830591 0.572491 0.233469 0.031 Uiso 1 1 calc R U . . .
H10B H 0.772598 0.510808 0.289875 0.031 Uiso 1 1 calc R U . . .
C10 C 0.3433(2) 1.03342(14) 0.27032(10) 0.0368(4) Uani 1 1 d . . . . .
H10C H 0.356276 0.970883 0.286248 0.044 Uiso 1 1 calc R U . . .
H10D H 0.323288 1.089264 0.317917 0.044 Uiso 1 1 calc R U . . .
C11' C 0.7117(2) 0.42116(14) 0.16719(11) 0.0360(4) Uani 1 1 d . . . . .
H11A H 0.672539 0.431887 0.114166 0.043 Uiso 1 1 calc R U . . .
H11B H 0.623594 0.369448 0.172309 0.043 Uiso 1 1 calc R U . . .
C11 C 0.1737(2) 1.10496(13) 0.17428(10) 0.0332(4) Uani 1 1 d . . . . .
H11C H 0.075960 1.088889 0.126650 0.040 Uiso 1 1 calc R U . . .
H11D H 0.151515 1.160762 0.221254 0.040 Uiso 1 1 calc R U . . .
C12' C 0.8789(2) 0.37950(14) 0.16851(10) 0.0348(4) Uani 1 1 d . . . . .
H12A H 0.968337 0.433929 0.167686 0.042 Uiso 1 1 calc R U . . .
H12B H 0.913696 0.365295 0.220403 0.042 Uiso 1 1 calc R U . . .
C12 C 0.2247(2) 0.92080(13) 0.12312(10) 0.0352(4) Uani 1 1 d . . . . .
H12C H 0.236719 0.856632 0.136826 0.042 Uiso 1 1 calc R U . . .
H12D H 0.127028 0.903242 0.075234 0.042 Uiso 1 1 calc R U . . .
C13 C 0.3365(2) 1.14364(14) 0.15261(12) 0.0416(4) Uani 1 1 d . . . . .
H13 H 0.323324 1.207912 0.138103 0.050 Uiso 1 1 calc R U . . .
C13' C 0.8664(3) 0.28018(17) 0.09627(14) 0.0577(6) Uani 1 1 d . . . . .
H13A H 0.778744 0.225755 0.097015 0.087 Uiso 1 1 calc R U . . .
H13B H 0.976304 0.256181 0.100350 0.087 Uiso 1 1 calc R U . . .
H13C H 0.835912 0.294350 0.044722 0.087 Uiso 1 1 calc R U . . .
C14 C 0.5066(2) 1.07077(16) 0.24809(13) 0.0487(5) Uani 1 1 d . . . . .
H14 H 0.605441 1.087275 0.296194 0.058 Uiso 1 1 calc R U . . .
C14' C 0.51734(18) 0.59992(12) 0.16335(9) 0.0250(3) Uani 1 1 d . . . . .
H14A H 0.483233 0.531837 0.117476 0.030 Uiso 1 1 calc R U . . .
H14B H 0.413904 0.631835 0.168038 0.030 Uiso 1 1 calc R U . . .
C15' C 0.6413(2) 0.67010(13) 0.14109(9) 0.0309(4) Uani 1 1 d . . . . .
H15A H 0.747666 0.641060 0.138039 0.037 Uiso 1 1 calc R U . . .
H15B H 0.669822 0.740723 0.183960 0.037 Uiso 1 1 calc R U . . .
C15 C 0.4870(3) 1.16920(15) 0.22588(14) 0.0497(5) Uani 1 1 d . . . . .
H15C H 0.468087 1.225419 0.273559 0.060 Uiso 1 1 calc R U . . .
H15D H 0.592241 1.194394 0.211971 0.060 Uiso 1 1 calc R U . . .
C16' C 0.5618(2) 0.67786(15) 0.05819(10) 0.0406(4) Uani 1 1 d . . . . .
H16A H 0.525638 0.606369 0.016775 0.049 Uiso 1 1 calc R U . . .
H16B H 0.458912 0.710390 0.062831 0.049 Uiso 1 1 calc R U . . .
C16 C 0.3871(3) 0.95881(15) 0.10104(12) 0.0471(5) Uani 1 1 d . . . . .
H16 H 0.407931 0.902542 0.053074 0.056 Uiso 1 1 calc R U . . .
C17' C 0.6822(3) 0.74146(19) 0.02864(13) 0.0608(6) Uani 1 1 d . . . . .
H17A H 0.720511 0.811894 0.069918 0.091 Uiso 1 1 calc R U . . .
H17B H 0.623421 0.746603 -0.023508 0.091 Uiso 1 1 calc R U . . .
H17C H 0.780910 0.707094 0.020348 0.091 Uiso 1 1 calc R U . . .
C17 C 0.3670(3) 1.05724(15) 0.07862(13) 0.0511(5) Uani 1 1 d . . . . .
H17D H 0.269654 1.040843 0.030749 0.061 Uiso 1 1 calc R U . . .
H17E H 0.471120 1.081546 0.063403 0.061 Uiso 1 1 calc R U . . .
C18 C 0.5368(3) 0.98511(17) 0.17436(15) 0.0571(6) Uani 1 1 d . . . . .
H18A H 0.642224 1.009222 0.160016 0.069 Uiso 1 1 calc R U . . .
H18B H 0.551632 0.921613 0.188673 0.069 Uiso 1 1 calc R U . . .
N1 N 0.11567(17) 0.68492(12) 0.61909(9) 0.0350(3) Uani 1 1 d . . . . .
N1' N 0.58200(15) 0.57894(10) 0.24276(7) 0.0231(3) Uani 1 1 d . . . . .
N2 N 0.07595(16) 0.79707(10) 0.33745(8) 0.0275(3) Uani 1 1 d . . . . .
H2A H 0.087712 0.746020 0.294399 0.033 Uiso 1 1 calc R U . . .
N3 N 0.02932(18) 0.88086(10) 0.24451(8) 0.0320(3) Uani 1 1 d . . . . .
H3A H 0.019718 0.818361 0.207402 0.038 Uiso 1 1 calc R U . . .
O1 O 0.09361(18) 0.74809(11) 0.68232(8) 0.0466(3) Uani 1 1 d . . . . .
O2 O 0.14138(18) 0.59570(10) 0.61352(8) 0.0498(3) Uani 1 1 d . . . . .
O3 O 0.03640(17) 0.96890(9) 0.37894(7) 0.0413(3) Uani 1 1 d . . . . .
Cl1* Cl 0.09503(5) 0.64039(3) 0.16552(2) 0.03173(11) 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'
Cl Cl 0.1484 0.1585 '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'
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
0 -19 6 0.3397
-5 18 -6 0.2984
-5 15 -17 0.2592
0 -16 19 0.3052
-5 11 -19 0.2297
-5 7 -20 0.1982
-1 -7 25 0.2438
-5 2 -19 0.1801
-1 -1 24 0.2228
-5 -3 -17 0.1914
-1 4 21 0.2332
-4 -8 -13 0.2224
-1 10 15 0.2670
-2 18 1 0.3269
-4 -15 -1 0.2851
-2 19 -6 0.3417
-5 -16 12 0.3192
-2 16 -18 0.3443
-1 7 -24 0.3151
-7 0 21 0.2595
11 -2 -1 0.3395
1 -5 -21 0.3021
-7 5 19 0.2514
0 -14 -9 0.3260
-6 14 8 0.2917
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 C1 N1 119.38(14) . . ?
C6 C1 C2 121.31(14) . . ?
C6 C1 N1 119.30(14) . . ?
H1'A C1' H1'B 107.4 . . ?
C2' C1' H1'A 108.3 . . ?
C2' C1' H1'B 108.3 . . ?
N1' C1' H1'A 108.3 . . ?
N1' C1' H1'B 108.3 . . ?
N1' C1' C2' 115.97(12) . . ?
C1' C2' H2'A 109.6 . . ?
C1' C2' H2'B 109.6 . . ?
C1' C2' C4' 110.37(13) . . ?
H2'A C2' H2'B 108.1 . . ?
C4' C2' H2'A 109.6 . . ?
C4' C2' H2'B 109.6 . . ?
C1 C2 H2 120.6 . . ?
C3 C2 C1 118.71(14) . . ?
C3 C2 H2 120.6 . . ?
C2 C3 H3 119.4 . . ?
C2 C3 C4 121.16(14) . . ?
C4 C3 H3 119.4 . . ?
C5 C4 C3 118.78(14) . . ?
N2 C4 C3 116.80(13) . . ?
N2 C4 C5 124.42(14) . . ?
C2' C4' H4'A 109.1 . . ?
C2' C4' H4'B 109.1 . . ?
H4'A C4' H4'B 107.9 . . ?
C5' C4' C2' 112.43(13) . . ?
C5' C4' H4'A 109.1 . . ?
C5' C4' H4'B 109.1 . . ?
C4 C5 H5 120.0 . . ?
C6 C5 C4 120.04(14) . . ?
C6 C5 H5 120.0 . . ?
C4' C5' H5'A 109.5 . . ?
C4' C5' H5'B 109.5 . . ?
C4' C5' H5'C 109.5 . . ?
H5'A C5' H5'B 109.5 . . ?
H5'A C5' H5'C 109.5 . . ?
H5'B C5' H5'C 109.5 . . ?
C1 C6 H6 120.0 . . ?
C5 C6 C1 120.00(15) . . ?
C5 C6 H6 120.0 . . ?
H6'A C6' H6'B 107.4 . . ?
C7' C6' H6'A 108.4 . . ?
C7' C6' H6'B 108.4 . . ?
C7' C6' N1' 115.68(12) . . ?
N1' C6' H6'A 108.4 . . ?
N1' C6' H6'B 108.4 . . ?
N3 C7 N2 111.98(13) . . ?
O3 C7 N2 123.48(14) . . ?
O3 C7 N3 124.53(15) . . ?
C6' C7' H7'A 109.5 . . ?
C6' C7' H7'B 109.5 . . ?
C6' C7' C8' 110.83(15) . . ?
H7'A C7' H7'B 108.1 . . ?
C8' C7' H7'A 109.5 . . ?
C8' C7' H7'B 109.5 . . ?
H8A C8 H8B 107.7 . . ?
C9 C8 H8A 108.8 . . ?
C9 C8 H8B 108.8 . . ?
N3 C8 H8A 108.8 . . ?
N3 C8 H8B 108.8 . . ?
N3 C8 C9 113.64(13) . . ?
C7' C8' H8'A 108.8 . . ?
C7' C8' H8'B 108.8 . . ?
H8'A C8' H8'B 107.7 . . ?
C9' C8' C7' 113.72(17) . . ?
C9' C8' H8'A 108.8 . . ?
C9' C8' H8'B 108.8 . . ?
C8 C9 C10 111.51(13) . . ?
C8 C9 C11 108.30(12) . . ?
C8 C9 C12 110.94(13) . . ?
C10 C9 C11 108.29(13) . . ?
C10 C9 C12 109.16(13) . . ?
C11 C9 C12 108.55(12) . . ?
C8' C9' H9'A 109.5 . . ?
C8' C9' H9'B 109.5 . . ?
C8' C9' H9'C 109.5 . . ?
H9'A C9' H9'B 109.5 . . ?
H9'A C9' H9'C 109.5 . . ?
H9'B C9' H9'C 109.5 . . ?
H10A C10' H10B 107.3 . . ?
C11' C10' H10A 108.2 . . ?
C11' C10' H10B 108.2 . . ?
C11' C10' N1' 116.52(12) . . ?
N1' C10' H10A 108.2 . . ?
N1' C10' H10B 108.2 . . ?
C9 C10 H10C 109.6 . . ?
C9 C10 H10D 109.6 . . ?
C9 C10 C14 110.34(14) . . ?
H10C C10 H10D 108.1 . . ?
C14 C10 H10C 109.6 . . ?
C14 C10 H10D 109.6 . . ?
C10' C11' H11A 109.7 . . ?
C10' C11' H11B 109.7 . . ?
C10' C11' C12' 109.88(13) . . ?
H11A C11' H11B 108.2 . . ?
C12' C11' H11A 109.7 . . ?
C12' C11' H11B 109.7 . . ?
C9 C11 H11C 109.6 . . ?
C9 C11 H11D 109.6 . . ?
H11C C11 H11D 108.1 . . ?
C13 C11 C9 110.47(13) . . ?
C13 C11 H11C 109.6 . . ?
C13 C11 H11D 109.6 . . ?
C11' C12' H12A 109.1 . . ?
C11' C12' H12B 109.1 . . ?
H12A C12' H12B 107.8 . . ?
C13' C12' C11' 112.66(15) . . ?
C13' C12' H12A 109.1 . . ?
C13' C12' H12B 109.1 . . ?
C9 C12 H12C 109.6 . . ?
C9 C12 H12D 109.6 . . ?
H12C C12 H12D 108.1 . . ?
C16 C12 C9 110.22(14) . . ?
C16 C12 H12C 109.6 . . ?
C16 C12 H12D 109.6 . . ?
C11 C13 H13 109.5 . . ?
C11 C13 C17 108.90(15) . . ?
C15 C13 C11 109.75(15) . . ?
C15 C13 H13 109.5 . . ?
C15 C13 C17 109.66(17) . . ?
C17 C13 H13 109.5 . . ?
C12' C13' H13A 109.5 . . ?
C12' C13' H13B 109.5 . . ?
C12' C13' H13C 109.5 . . ?
H13A C13' H13B 109.5 . . ?
H13A C13' H13C 109.5 . . ?
H13B C13' H13C 109.5 . . ?
C10 C14 H14 109.6 . . ?
C15 C14 C10 109.14(15) . . ?
C15 C14 H14 109.6 . . ?
C18 C14 C10 109.64(16) . . ?
C18 C14 H14 109.6 . . ?
C18 C14 C15 109.25(18) . . ?
H14A C14' H14B 107.4 . . ?
C15' C14' H14A 108.3 . . ?
C15' C14' H14B 108.3 . . ?
C15' C14' N1' 115.87(12) . . ?
N1' C14' H14A 108.3 . . ?
N1' C14' H14B 108.3 . . ?
C14' C15' H15A 109.8 . . ?
C14' C15' H15B 109.8 . . ?
C14' C15' C16' 109.38(13) . . ?
H15A C15' H15B 108.2 . . ?
C16' C15' H15A 109.8 . . ?
C16' C15' H15B 109.8 . . ?
C13 C15 C14 109.39(16) . . ?
C13 C15 H15C 109.8 . . ?
C13 C15 H15D 109.8 . . ?
C14 C15 H15C 109.8 . . ?
C14 C15 H15D 109.8 . . ?
H15C C15 H15D 108.2 . . ?
C15' C16' H16A 109.0 . . ?
C15' C16' H16B 109.0 . . ?
H16A C16' H16B 107.8 . . ?
C17' C16' C15' 112.79(16) . . ?
C17' C16' H16A 109.0 . . ?
C17' C16' H16B 109.0 . . ?
C12 C16 H16 109.5 . . ?
C12 C16 C17 109.47(16) . . ?
C17 C16 H16 109.5 . . ?
C18 C16 C12 109.54(16) . . ?
C18 C16 H16 109.5 . . ?
C18 C16 C17 109.19(17) . . ?
C16' C17' H17A 109.5 . . ?
C16' C17' H17B 109.5 . . ?
C16' C17' H17C 109.5 . . ?
H17A C17' H17B 109.5 . . ?
H17A C17' H17C 109.5 . . ?
H17B C17' H17C 109.5 . . ?
C13 C17 H17D 109.8 . . ?
C13 C17 H17E 109.8 . . ?
C16 C17 C13 109.37(15) . . ?
C16 C17 H17D 109.8 . . ?
C16 C17 H17E 109.8 . . ?
H17D C17 H17E 108.2 . . ?
C14 C18 H18A 109.6 . . ?
C14 C18 H18B 109.6 . . ?
C16 C18 C14 110.12(15) . . ?
C16 C18 H18A 109.6 . . ?
C16 C18 H18B 109.6 . . ?
H18A C18 H18B 108.2 . . ?
O1 N1 C1 118.62(14) . . ?
O1 N1 O2 123.07(14) . . ?
O2 N1 C1 118.31(14) . . ?
C1' N1' C6' 111.33(11) . . ?
C1' N1' C10' 111.60(11) . . ?
C1' N1' C14' 106.19(10) . . ?
C6' N1' C10' 106.46(11) . . ?
C6' N1' C14' 110.39(11) . . ?
C14' N1' C10' 110.94(11) . . ?
C4 N2 C7 128.05(13) . . ?
C4 N2 H2A 116.0 . . ?
C7 N2 H2A 116.0 . . ?
C7 N3 C8 121.98(13) . . ?
C7 N3 H3A 119.0 . . ?
C8 N3 H3A 119.0 . . ?
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
C1 C2 1.388(2) . ?
C1 C6 1.382(2) . ?
C1 N1 1.452(2) . ?
C1' H1'A 0.9900 . ?
C1' H1'B 0.9900 . ?
C1' C2' 1.520(2) . ?
C1' N1' 1.5172(19) . ?
C2' H2'A 0.9900 . ?
C2' H2'B 0.9900 . ?
C2' C4' 1.526(2) . ?
C2 H2 0.9500 . ?
C2 C3 1.375(2) . ?
C3 H3 0.9500 . ?
C3 C4 1.406(2) . ?
C4 C5 1.400(2) . ?
C4 N2 1.3841(19) . ?
C4' H4'A 0.9900 . ?
C4' H4'B 0.9900 . ?
C4' C5' 1.523(2) . ?
C5 H5 0.9500 . ?
C5 C6 1.377(2) . ?
C5' H5'A 0.9800 . ?
C5' H5'B 0.9800 . ?
C5' H5'C 0.9800 . ?
C6 H6 0.9500 . ?
C6' H6'A 0.9900 . ?
C6' H6'B 0.9900 . ?
C6' C7' 1.518(2) . ?
C6' N1' 1.5239(19) . ?
C7 N2 1.3945(19) . ?
C7 N3 1.352(2) . ?
C7 O3 1.2177(19) . ?
C7' H7'A 0.9900 . ?
C7' H7'B 0.9900 . ?
C7' C8' 1.535(2) . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C8 C9 1.527(2) . ?
C8 N3 1.4523(19) . ?
C8' H8'A 0.9900 . ?
C8' H8'B 0.9900 . ?
C8' C9' 1.495(3) . ?
C9 C10 1.528(2) . ?
C9 C11 1.537(2) . ?
C9 C12 1.537(2) . ?
C9' H9'A 0.9800 . ?
C9' H9'B 0.9800 . ?
C9' H9'C 0.9800 . ?
C10' H10A 0.9900 . ?
C10' H10B 0.9900 . ?
C10' C11' 1.513(2) . ?
C10' N1' 1.5279(18) . ?
C10 H10C 0.9900 . ?
C10 H10D 0.9900 . ?
C10 C14 1.534(3) . ?
C11' H11A 0.9900 . ?
C11' H11B 0.9900 . ?
C11' C12' 1.524(2) . ?
C11 H11C 0.9900 . ?
C11 H11D 0.9900 . ?
C11 C13 1.532(2) . ?
C12' H12A 0.9900 . ?
C12' H12B 0.9900 . ?
C12' C13' 1.515(3) . ?
C12 H12C 0.9900 . ?
C12 H12D 0.9900 . ?
C12 C16 1.529(2) . ?
C13 H13 1.0000 . ?
C13 C15 1.522(3) . ?
C13 C17 1.534(3) . ?
C13' H13A 0.9800 . ?
C13' H13B 0.9800 . ?
C13' H13C 0.9800 . ?
C14 H14 1.0000 . ?
C14 C15 1.531(3) . ?
C14 C18 1.525(3) . ?
C14' H14A 0.9900 . ?
C14' H14B 0.9900 . ?
C14' C15' 1.508(2) . ?
C14' N1' 1.5246(18) . ?
C15' H15A 0.9900 . ?
C15' H15B 0.9900 . ?
C15' C16' 1.523(2) . ?
C15 H15C 0.9900 . ?
C15 H15D 0.9900 . ?
C16' H16A 0.9900 . ?
C16' H16B 0.9900 . ?
C16' C17' 1.512(3) . ?
C16 H16 1.0000 . ?
C16 C17 1.533(3) . ?
C16 C18 1.518(3) . ?
C17' H17A 0.9800 . ?
C17' H17B 0.9800 . ?
C17' H17C 0.9800 . ?
C17 H17D 0.9900 . ?
C17 H17E 0.9900 . ?
C18 H18A 0.9900 . ?
C18 H18B 0.9900 . ?
N1 O1 1.2292(18) . ?
N1 O2 1.2343(19) . ?
N2 H2A 0.8800 . ?
N3 H3A 0.8800 . ?
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
C1 C2 C3 C4 0.0(2) . . . . ?
C1' C2' C4' C5' 176.08(14) . . . . ?
C2' C1' N1' C6' -55.30(17) . . . . ?
C2' C1' N1' C10' 63.50(16) . . . . ?
C2' C1' N1' C14' -175.49(13) . . . . ?
C2 C1 C6 C5 -0.3(2) . . . . ?
C2 C1 N1 O1 -174.64(14) . . . . ?
C2 C1 N1 O2 4.7(2) . . . . ?
C2 C3 C4 C5 0.5(2) . . . . ?
C2 C3 C4 N2 -178.66(14) . . . . ?
C3 C4 C5 C6 -0.9(2) . . . . ?
C3 C4 N2 C7 176.61(14) . . . . ?
C4 C5 C6 C1 0.8(2) . . . . ?
C5 C4 N2 C7 -2.5(2) . . . . ?
C6 C1 C2 C3 -0.1(2) . . . . ?
C6 C1 N1 O1 3.9(2) . . . . ?
C6 C1 N1 O2 -176.77(15) . . . . ?
C6' C7' C8' C9' -73.9(2) . . . . ?
C7' C6' N1' C1' -59.75(16) . . . . ?
C7' C6' N1' C10' 178.41(13) . . . . ?
C7' C6' N1' C14' 57.93(16) . . . . ?
C8 C9 C10 C14 -178.71(14) . . . . ?
C8 C9 C11 C13 -179.99(13) . . . . ?
C8 C9 C12 C16 177.94(14) . . . . ?
C9 C8 N3 C7 104.36(17) . . . . ?
C9 C10 C14 C15 60.8(2) . . . . ?
C9 C10 C14 C18 -58.8(2) . . . . ?
C9 C11 C13 C15 -59.62(19) . . . . ?
C9 C11 C13 C17 60.42(19) . . . . ?
C9 C12 C16 C17 -60.1(2) . . . . ?
C9 C12 C16 C18 59.59(19) . . . . ?
C10' C11' C12' C13' -176.28(15) . . . . ?
C10 C9 C11 C13 58.94(17) . . . . ?
C10 C9 C12 C16 -58.78(18) . . . . ?
C10 C14 C15 C13 -60.0(2) . . . . ?
C10 C14 C18 C16 59.3(2) . . . . ?
C11' C10' N1' C1' 61.17(16) . . . . ?
C11' C10' N1' C6' -177.16(13) . . . . ?
C11' C10' N1' C14' -57.04(17) . . . . ?
C11 C9 C10 C14 -59.65(18) . . . . ?
C11 C9 C12 C16 59.06(18) . . . . ?
C11 C13 C15 C14 59.6(2) . . . . ?
C11 C13 C17 C16 -60.2(2) . . . . ?
C12 C9 C10 C14 58.36(18) . . . . ?
C12 C9 C11 C13 -59.46(18) . . . . ?
C12 C16 C17 C13 60.4(2) . . . . ?
C12 C16 C18 C14 -59.7(2) . . . . ?
C14' C15' C16' C17' -176.35(16) . . . . ?
C15' C14' N1' C1' 177.28(13) . . . . ?
C15' C14' N1' C6' 56.48(16) . . . . ?
C15' C14' N1' C10' -61.28(16) . . . . ?
C15 C13 C17 C16 59.9(2) . . . . ?
C15 C14 C18 C16 -60.3(2) . . . . ?
C17 C13 C15 C14 -60.0(2) . . . . ?
C17 C16 C18 C14 60.1(2) . . . . ?
C18 C14 C15 C13 59.8(2) . . . . ?
C18 C16 C17 C13 -59.6(2) . . . . ?
N1 C1 C2 C3 178.46(14) . . . . ?
N1 C1 C6 C5 -178.87(14) . . . . ?
N1' C1' C2' C4' -176.17(13) . . . . ?
N1' C6' C7' C8' 179.86(13) . . . . ?
N1' C10' C11' C12' 177.25(13) . . . . ?
N1' C14' C15' C16' 176.60(13) . . . . ?
N2 C4 C5 C6 178.18(15) . . . . ?
N2 C7 N3 C8 -169.76(13) . . . . ?
N3 C7 N2 C4 -175.33(14) . . . . ?
N3 C8 C9 C10 -58.16(18) . . . . ?
N3 C8 C9 C11 -177.22(13) . . . . ?
N3 C8 C9 C12 63.75(17) . . . . ?
O3 C7 N2 C4 3.8(3) . . . . ?
O3 C7 N3 C8 11.2(2) . . . . ?
loop_
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
-0.1561 -19.0637 6.4780 0.4774 -0.8778 0.0391
-5.2204 17.9531 -5.7136 -0.4280 0.7882 0.4422
-4.7822 14.8517 -16.5472 -0.7777 0.3710 0.5075
-0.4165 -16.2659 19.2790 0.9013 -0.4293 -0.0575
-4.6553 11.2693 -19.4764 -0.8371 0.1102 0.5359
-4.7518 6.8083 -20.2640 -0.8080 -0.1497 0.5699
-0.7579 -7.2028 24.6189 0.9772 0.1816 -0.1100
-4.7324 2.0050 -19.3993 -0.7153 -0.3883 0.5810
-0.7587 -1.4075 23.7457 0.8715 0.4737 -0.1268
-4.5354 -2.9445 -17.0653 -0.5683 -0.5988 0.5643
-0.5566 4.4811 20.5511 0.6810 0.7183 -0.1426
-4.4040 -7.7144 -13.0389 -0.3628 -0.7606 0.5384
-0.6605 10.0227 15.4602 0.4273 0.8970 -0.1135
-1.5782 17.9134 1.2540 -0.1826 0.9816 0.0561
-4.3463 -15.0041 -1.0304 0.1617 -0.8719 0.4622
-1.9034 19.2014 -6.3831 -0.4728 0.8692 0.1446
-5.0198 -16.1841 12.4149 0.6605 -0.6265 0.4139
-2.1426 16.0288 -18.4915 -0.8664 0.4123 0.2818
-1.4352 7.2494 -23.6064 -0.9383 -0.1748 0.2983
-7.1464 -0.2489 21.3306 0.7791 0.4230 0.4627
11.2790 -1.7136 -0.7866 -0.0223 -0.0109 -0.9997
0.9272 -4.5623 -20.6391 -0.6836 -0.7214 0.1104
-7.0793 5.0516 18.5730 0.6120 0.6449 0.4578
-0.3164 -14.3116 -8.6952 -0.1280 -0.9785 0.1620
-6.3749 14.0167 8.0105 0.1168 0.8872 0.4463
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 0.000 0.500 0.000 62.6 12.3 ?
