#------------------------------------------------------------------------------
#$Date: 2021-01-07 09:07:05 +0200 (Thu, 07 Jan 2021) $
#$Revision: 260816 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/15/77/7157745.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_7157745
loop_
_publ_author_name
'Yao, Chao'
'Wu, Piao'
'Huang, Yue'
'Chen, Yaoqi'
'Li, Lin'
'Li, Yue-Ming'
_publ_section_title
;
 Binaphthyl-based chiral ligands: design, synthesis and evaluation of
 their performance in enantioselective addition of diethylzinc to aromatic
 aldehydes.
;
_journal_issue                   47
_journal_name_full               'Organic & biomolecular chemistry'
_journal_page_first              9712
_journal_page_last               9725
_journal_paper_doi               10.1039/d0ob02127j
_journal_volume                  18
_journal_year                    2020
_chemical_absolute_configuration syn
_chemical_formula_moiety         'C36 H32 N2 O2'
_chemical_formula_sum            'C36 H32 N2 O2'
_chemical_formula_weight         524.63
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_audit_creation_date             2020-01-09
_audit_creation_method
;
Olex2 1.2
(compiled 2017.01.04 svn.r3372 for OlexSys, GUI svn.r5292)
;
_audit_update_record
;
2020-10-17 deposited with the CCDC.	2020-11-17 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   9.3208(3)
_cell_length_b                   15.9714(5)
_cell_length_c                   19.0521(6)
_cell_measurement_reflns_used    20002
_cell_measurement_temperature    133.15
_cell_measurement_theta_max      32.6990
_cell_measurement_theta_min      2.4180
_cell_volume                     2836.21(16)
_computing_cell_refinement       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_collection       'CrystalClear(Rigaku, 2008)'
_computing_data_reduction        'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      133.15
_diffrn_detector                 'CCD plate'
_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   -115.00  65.00   1.00    2.00    --  -25.00  45.00   0.00  180
  2  ω   -115.00  65.00   1.00    2.00    --  -25.00  45.00  90.00  180
  3  ω   -115.00  65.00   1.00    2.00    --  -25.00  45.00 180.00  180
;
_diffrn_measurement_device       'abstract diffractometer'
_diffrn_measurement_device_type  'Rigaku Saturn 70'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0108446000
_diffrn_orient_matrix_UB_12      -0.0239886000
_diffrn_orient_matrix_UB_13      0.0308794000
_diffrn_orient_matrix_UB_21      -0.0727992000
_diffrn_orient_matrix_UB_22      0.0062017000
_diffrn_orient_matrix_UB_23      0.0095124000
_diffrn_orient_matrix_UB_31      -0.0192958000
_diffrn_orient_matrix_UB_32      -0.0368552000
_diffrn_orient_matrix_UB_33      -0.0185083000
_diffrn_radiation_monochromator  confocal
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0416
_diffrn_reflns_av_unetI/netI     0.0304
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_number            38259
_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         29.573
_diffrn_reflns_theta_min         2.433
_diffrn_source                   'rotating anode'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.076
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.78355
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.39.46 (Rigaku Oxford Diffraction, 2018)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.229
_exptl_crystal_description       plate
_exptl_crystal_F_000             1112
_exptl_crystal_size_max          0.24
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.14
_refine_diff_density_max         0.156
_refine_diff_density_min         -0.180
_refine_diff_density_rms         0.034
_refine_ls_abs_structure_details
;
 Flack x determined using 2506 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.1(5)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.042
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     420
_refine_ls_number_reflns         7943
_refine_ls_number_restraints     26
_refine_ls_restrained_S_all      1.052
_refine_ls_R_factor_all          0.0537
_refine_ls_R_factor_gt           0.0426
_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)+(0.0446P)²+0.2840P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0930
_refine_ls_wR_factor_ref         0.0993
_reflns_Friedel_coverage         0.793
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     1.000
_reflns_number_gt                6741
_reflns_number_total             7943
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d0ob02127j2.cif
_cod_data_source_block           r20200109b
_cod_depositor_comments
'Adding full bibliography for 7157743--7157745.cif.'
_cod_database_code               7157745
_shelx_shelxl_version_number     2016/6
_chemical_oxdiff_formula         C36H32N2O2
_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.
;
_reflns_odcompleteness_completeness 99.91
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     29.51
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2. Restrained distances
 N2-C31 = N2-C31A
 1.48 with sigma of 0.01
 C31-C32 = C32-C33 = C33-C34 = C34-C35 = C35-C36 = C36-C31
 1.54 with sigma of 0.01
 C31A-C32A = C32A-C33A = C33A-C34A = C34A-C35A = C35A-C36A = C36A-C31A
 1.54 with sigma of 0.01
 C31-C33 = C33-C35 = C35-C31 = C32-C34 = C34-C36 = C36-C32
 2.52 with sigma of 0.01
 C31A-C33A = C33A-C35A = C35A-C31A = C32A-C34A = C34A-C36A = C36A-C32A
 2.52 with sigma of 0.01
3. Others
 Sof(C31A)=Sof(H31A)=Sof(C32A)=Sof(H32C)=Sof(H32D)=Sof(C33A)=Sof(H33C)=
 Sof(H33D)=Sof(C34A)=Sof(H34C)=Sof(H34D)=Sof(C35A)=Sof(H35C)=Sof(H35D)=
 Sof(C36A)=Sof(H36C)=Sof(H36D)=1-FVAR(1)
 Sof(C31)=Sof(H31)=Sof(C32)=Sof(H32A)=Sof(H32B)=Sof(C33)=Sof(H33A)=Sof(H33B)=
 Sof(C34)=Sof(H34A)=Sof(H34B)=Sof(C35)=Sof(H35A)=Sof(H35B)=Sof(C36)=Sof(H36A)=
 Sof(H36B)=FVAR(1)
4.a Ternary CH refined with riding coordinates:
 C22(H22), C31(H31), C31A(H31A)
4.b Secondary CH2 refined with riding coordinates:
 C23(H23A,H23B), C32(H32A,H32B), C33(H33A,H33B), C34(H34A,H34B), C35(H35A,
 H35B), C36(H36A,H36B), C32A(H32C,H32D), C33A(H33C,H33D), C34A(H34C,H34D),
 C35A(H35C,H35D), C36A(H36C,H36D)
4.c Aromatic/amide H refined with riding coordinates:
 C3(H3), C4(H4), C7(H7), C8(H8), C9(H9), C10(H10), C13(H13), C14(H14),
 C17(H17), C18(H18), C19(H19), C20(H20), C25(H25), C26(H26), C27(H27), C28(H28),
  C29(H29)
;
_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 1.441
_oxdiff_exptl_absorpt_empirical_full_min 0.620
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -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
O2 O 0.57940(15) 0.39962(10) 0.17094(8) 0.0442(3) Uani 1 1 d . . . . .
O1 O -0.07009(15) 0.35643(10) 0.29689(7) 0.0426(3) Uani 1 1 d . . . . .
N2 N 0.34748(19) 0.44001(11) 0.15873(9) 0.0368(4) Uani 1 1 d D . . . .
N1 N 0.04337(17) 0.39316(10) 0.19682(8) 0.0344(3) Uani 1 1 d . . . . .
C1 C 0.2864(2) 0.39465(11) 0.31387(9) 0.0292(4) Uani 1 1 d . . . . .
C2 C 0.1528(2) 0.43202(11) 0.30810(10) 0.0345(4) Uani 1 1 d . . . . .
C3 C 0.1227(3) 0.50934(13) 0.34192(12) 0.0461(5) Uani 1 1 d . . . . .
H3 H 0.031229 0.534787 0.336507 0.055 Uiso 1 1 calc R . . . .
C4 C 0.2247(3) 0.54690(13) 0.38202(13) 0.0507(6) Uani 1 1 d . . . . .
H4 H 0.204118 0.599111 0.403695 0.061 Uiso 1 1 calc R . . . .
C5 C 0.3608(3) 0.50976(12) 0.39209(10) 0.0406(5) Uani 1 1 d . . . . .
C6 C 0.3934(2) 0.43268(11) 0.35713(9) 0.0333(4) Uani 1 1 d . . . . .
C7 C 0.5303(2) 0.39657(12) 0.36786(10) 0.0385(4) Uani 1 1 d . . . . .
H7 H 0.554186 0.346059 0.344267 0.046 Uiso 1 1 calc R . . . .
C8 C 0.6293(3) 0.43292(14) 0.41160(11) 0.0481(5) Uani 1 1 d . . . . .
H8 H 0.720722 0.407758 0.417940 0.058 Uiso 1 1 calc R . . . .
C9 C 0.5948(3) 0.50792(15) 0.44721(11) 0.0523(6) Uani 1 1 d . . . . .
H9 H 0.662457 0.532240 0.478446 0.063 Uiso 1 1 calc R . . . .
C10 C 0.4657(3) 0.54548(14) 0.43710(12) 0.0518(6) Uani 1 1 d . . . . .
H10 H 0.445218 0.596584 0.460561 0.062 Uiso 1 1 calc R . . . .
C11 C 0.31694(19) 0.31277(10) 0.27775(9) 0.0273(3) Uani 1 1 d . . . . .
C12 C 0.39798(19) 0.30972(11) 0.21710(9) 0.0284(3) Uani 1 1 d . . . . .
C13 C 0.4359(2) 0.23135(12) 0.18676(9) 0.0341(4) Uani 1 1 d . . . . .
H13 H 0.497031 0.229871 0.146869 0.041 Uiso 1 1 calc R . . . .
C14 C 0.3853(2) 0.15835(12) 0.21446(10) 0.0363(4) Uani 1 1 d . . . . .
H14 H 0.409573 0.106627 0.192878 0.044 Uiso 1 1 calc R . . . .
C15 C 0.29699(19) 0.15865(11) 0.27505(10) 0.0316(4) Uani 1 1 d . . . . .
C16 C 0.26510(19) 0.23641(11) 0.30849(9) 0.0284(3) Uani 1 1 d . . . . .
C17 C 0.1827(2) 0.23477(12) 0.37101(10) 0.0348(4) Uani 1 1 d . . . . .
H17 H 0.162717 0.285690 0.394869 0.042 Uiso 1 1 calc R . . . .
C18 C 0.1313(2) 0.16094(13) 0.39754(11) 0.0437(5) Uani 1 1 d . . . . .
H18 H 0.075461 0.161211 0.439244 0.052 Uiso 1 1 calc R . . . .
C19 C 0.1607(3) 0.08487(13) 0.36359(12) 0.0475(5) Uani 1 1 d . . . . .
H19 H 0.123874 0.034051 0.382215 0.057 Uiso 1 1 calc R . . . .
C20 C 0.2416(2) 0.08348(12) 0.30414(12) 0.0413(5) Uani 1 1 d . . . . .
H20 H 0.261266 0.031538 0.281823 0.050 Uiso 1 1 calc R . . . .
C21 C 0.04135(19) 0.39361(11) 0.26319(10) 0.0329(4) Uani 1 1 d . . . . .
C22 C -0.0890(2) 0.34913(12) 0.17345(10) 0.0343(4) Uani 1 1 d . . . . .
H22 H -0.158417 0.391194 0.154519 0.041 Uiso 1 1 calc R . . . .
C23 C -0.1488(2) 0.31262(14) 0.24204(11) 0.0402(4) Uani 1 1 d . . . . .
H23A H -0.253150 0.323286 0.246048 0.048 Uiso 1 1 calc R . . . .
H23B H -0.131661 0.251530 0.244577 0.048 Uiso 1 1 calc R . . . .
C24 C -0.05678(19) 0.28557(12) 0.11742(10) 0.0337(4) Uani 1 1 d . . . . .
C25 C 0.0567(2) 0.22989(13) 0.12478(11) 0.0396(4) Uani 1 1 d . . . . .
H25 H 0.113130 0.230593 0.166289 0.047 Uiso 1 1 calc R . . . .
C26 C 0.0877(2) 0.17342(15) 0.07189(13) 0.0505(5) Uani 1 1 d . . . . .
H26 H 0.165940 0.135790 0.077083 0.061 Uiso 1 1 calc R . . . .
C27 C 0.0054(3) 0.17145(17) 0.01136(12) 0.0548(6) Uani 1 1 d . . . . .
H27 H 0.028154 0.133292 -0.025234 0.066 Uiso 1 1 calc R . . . .
C28 C -0.1096(3) 0.22499(16) 0.00442(12) 0.0519(6) Uani 1 1 d . . . . .
H28 H -0.167714 0.222940 -0.036519 0.062 Uiso 1 1 calc R . . . .
C29 C -0.1403(2) 0.28149(14) 0.05693(11) 0.0427(5) Uani 1 1 d . . . . .
H29 H -0.219706 0.318266 0.051797 0.051 Uiso 1 1 calc R . . . .
C30 C 0.45020(19) 0.38780(12) 0.18063(9) 0.0311(4) Uani 1 1 d . . . . .
C31 C 0.3810(8) 0.5299(3) 0.1366(2) 0.0287(11) Uani 0.613(4) 1 d D . P A 1
H31 H 0.463278 0.550491 0.165555 0.034 Uiso 0.613(4) 1 calc R . P A 1
C32 C 0.4258(5) 0.5322(2) 0.05897(18) 0.0491(10) Uani 0.613(4) 1 d D . P A 1
H32A H 0.349109 0.506693 0.030048 0.059 Uiso 0.613(4) 1 calc R . P A 1
H32B H 0.513960 0.498441 0.052644 0.059 Uiso 0.613(4) 1 calc R . P A 1
C33 C 0.4536(5) 0.6221(2) 0.0335(2) 0.0591(12) Uani 0.613(4) 1 d D . P A 1
H33A H 0.537637 0.645502 0.058489 0.071 Uiso 0.613(4) 1 calc R . P A 1
H33B H 0.475689 0.621444 -0.017343 0.071 Uiso 0.613(4) 1 calc R . P A 1
C34 C 0.3224(6) 0.6776(3) 0.0468(2) 0.0484(12) Uani 0.613(4) 1 d D . P A 1
H34A H 0.343912 0.735766 0.032305 0.058 Uiso 0.613(4) 1 calc R . P A 1
H34B H 0.240571 0.657269 0.018351 0.058 Uiso 0.613(4) 1 calc R . P A 1
C35 C 0.2826(6) 0.6759(2) 0.1237(2) 0.0490(11) Uani 0.613(4) 1 d D . P A 1
H35A H 0.195523 0.710267 0.131162 0.059 Uiso 0.613(4) 1 calc R . P A 1
H35B H 0.361436 0.700923 0.151551 0.059 Uiso 0.613(4) 1 calc R . P A 1
C36 C 0.2546(4) 0.5864(2) 0.1494(2) 0.0445(9) Uani 0.613(4) 1 d D . P A 1
H36A H 0.233132 0.587674 0.200318 0.053 Uiso 0.613(4) 1 calc R . P A 1
H36B H 0.169576 0.563592 0.124910 0.053 Uiso 0.613(4) 1 calc R . P A 1
C31A C 0.3716(12) 0.5130(4) 0.1197(4) 0.031(2) Uani 0.387(4) 1 d D . P A 2
H31A H 0.471015 0.513462 0.100002 0.037 Uiso 0.387(4) 1 calc R . P A 2
C32A C 0.2612(7) 0.5243(3) 0.0619(3) 0.0461(16) Uani 0.387(4) 1 d D . P A 2
H32C H 0.163274 0.521672 0.081878 0.055 Uiso 0.387(4) 1 calc R . P A 2
H32D H 0.271105 0.479005 0.026776 0.055 Uiso 0.387(4) 1 calc R . P A 2
C33A C 0.2855(9) 0.6099(3) 0.0267(3) 0.059(2) Uani 0.387(4) 1 d D . P A 2
H33C H 0.380092 0.610021 0.003053 0.071 Uiso 0.387(4) 1 calc R . P A 2
H33D H 0.210855 0.619127 -0.009387 0.071 Uiso 0.387(4) 1 calc R . P A 2
C34A C 0.2803(8) 0.6806(3) 0.0801(5) 0.0469(17) Uani 0.387(4) 1 d D . P A 2
H34C H 0.304856 0.733975 0.056488 0.056 Uiso 0.387(4) 1 calc R . P A 2
H34D H 0.181507 0.685653 0.098638 0.056 Uiso 0.387(4) 1 calc R . P A 2
C35A C 0.3826(8) 0.6665(3) 0.1403(3) 0.0458(15) Uani 0.387(4) 1 d D . P A 2
H35C H 0.370756 0.711613 0.175394 0.055 Uiso 0.387(4) 1 calc R . P A 2
H35D H 0.482550 0.668329 0.122778 0.055 Uiso 0.387(4) 1 calc R . P A 2
C36A C 0.3542(7) 0.5812(3) 0.1751(3) 0.0403(13) Uani 0.387(4) 1 d D . P A 2
H36C H 0.423000 0.572021 0.213954 0.048 Uiso 0.387(4) 1 calc R . P A 2
H36D H 0.255824 0.579766 0.194673 0.048 Uiso 0.387(4) 1 calc R . P A 2
H2 H 0.256(3) 0.4266(14) 0.1665(12) 0.043(6) Uiso 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'
O O 0.0106 0.0060 '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
C21 O1 C23 104.86(14) . . ?
C30 N2 C31 121.7(3) . . ?
C30 N2 C31A 124.7(5) . . ?
C30 N2 H2 118.8(15) . . ?
C31 N2 H2 117.9(15) . . ?
C31A N2 H2 116.3(15) . . ?
C21 N1 C22 106.83(16) . . ?
C2 C1 C6 119.33(16) . . ?
C2 C1 C11 120.54(16) . . ?
C6 C1 C11 120.07(16) . . ?
C1 C2 C3 121.06(18) . . ?
C1 C2 C21 119.90(15) . . ?
C3 C2 C21 118.96(18) . . ?
C2 C3 H3 120.0 . . ?
C4 C3 C2 120.0(2) . . ?
C4 C3 H3 120.0 . . ?
C3 C4 H4 119.4 . . ?
C3 C4 C5 121.24(18) . . ?
C5 C4 H4 119.4 . . ?
C4 C5 C6 119.22(19) . . ?
C4 C5 C10 122.09(19) . . ?
C10 C5 C6 118.7(2) . . ?
C1 C6 C5 119.03(18) . . ?
C7 C6 C1 122.64(16) . . ?
C7 C6 C5 118.32(18) . . ?
C6 C7 H7 119.3 . . ?
C8 C7 C6 121.44(19) . . ?
C8 C7 H7 119.3 . . ?
C7 C8 H8 120.1 . . ?
C7 C8 C9 119.8(2) . . ?
C9 C8 H8 120.1 . . ?
C8 C9 H9 119.8 . . ?
C10 C9 C8 120.5(2) . . ?
C10 C9 H9 119.8 . . ?
C5 C10 H10 119.4 . . ?
C9 C10 C5 121.2(2) . . ?
C9 C10 H10 119.4 . . ?
C12 C11 C1 121.11(15) . . ?
C12 C11 C16 119.67(15) . . ?
C16 C11 C1 119.18(14) . . ?
C11 C12 C13 120.43(16) . . ?
C11 C12 C30 122.19(15) . . ?
C13 C12 C30 117.38(15) . . ?
C12 C13 H13 119.7 . . ?
C14 C13 C12 120.57(16) . . ?
C14 C13 H13 119.7 . . ?
C13 C14 H14 119.6 . . ?
C13 C14 C15 120.86(16) . . ?
C15 C14 H14 119.6 . . ?
C14 C15 C16 119.17(16) . . ?
C14 C15 C20 121.75(16) . . ?
C20 C15 C16 119.08(17) . . ?
C15 C16 C11 119.12(15) . . ?
C17 C16 C11 122.72(15) . . ?
C17 C16 C15 118.16(16) . . ?
C16 C17 H17 119.5 . . ?
C18 C17 C16 121.02(17) . . ?
C18 C17 H17 119.5 . . ?
C17 C18 H18 119.8 . . ?
C17 C18 C19 120.49(19) . . ?
C19 C18 H18 119.8 . . ?
C18 C19 H19 119.8 . . ?
C20 C19 C18 120.39(19) . . ?
C20 C19 H19 119.8 . . ?
C15 C20 H20 119.6 . . ?
C19 C20 C15 120.84(18) . . ?
C19 C20 H20 119.6 . . ?
O1 C21 C2 116.43(16) . . ?
N1 C21 O1 118.80(18) . . ?
N1 C21 C2 124.78(17) . . ?
N1 C22 H22 109.1 . . ?
N1 C22 C23 103.05(15) . . ?
N1 C22 C24 111.46(15) . . ?
C23 C22 H22 109.1 . . ?
C24 C22 H22 109.1 . . ?
C24 C22 C23 114.86(16) . . ?
O1 C23 C22 104.19(15) . . ?
O1 C23 H23A 110.9 . . ?
O1 C23 H23B 110.9 . . ?
C22 C23 H23A 110.9 . . ?
C22 C23 H23B 110.9 . . ?
H23A C23 H23B 108.9 . . ?
C25 C24 C22 120.86(17) . . ?
C25 C24 C29 118.64(19) . . ?
C29 C24 C22 120.51(17) . . ?
C24 C25 H25 119.9 . . ?
C26 C25 C24 120.2(2) . . ?
C26 C25 H25 119.9 . . ?
C25 C26 H26 119.8 . . ?
C25 C26 C27 120.4(2) . . ?
C27 C26 H26 119.8 . . ?
C26 C27 H27 120.1 . . ?
C28 C27 C26 119.8(2) . . ?
C28 C27 H27 120.1 . . ?
C27 C28 H28 120.1 . . ?
C29 C28 C27 119.9(2) . . ?
C29 C28 H28 120.1 . . ?
C24 C29 H29 119.5 . . ?
C28 C29 C24 121.1(2) . . ?
C28 C29 H29 119.5 . . ?
O2 C30 N2 123.87(18) . . ?
O2 C30 C12 120.72(16) . . ?
N2 C30 C12 115.38(16) . . ?
N2 C31 H31 108.3 . . ?
N2 C31 C32 110.0(3) . . ?
C32 C31 H31 108.3 . . ?
C36 C31 N2 111.1(4) . . ?
C36 C31 H31 108.3 . . ?
C36 C31 C32 110.8(4) . . ?
C31 C32 H32A 109.3 . . ?
C31 C32 H32B 109.3 . . ?
C31 C32 C33 111.8(3) . . ?
H32A C32 H32B 107.9 . . ?
C33 C32 H32A 109.3 . . ?
C33 C32 H32B 109.3 . . ?
C32 C33 H33A 109.5 . . ?
C32 C33 H33B 109.5 . . ?
H33A C33 H33B 108.1 . . ?
C34 C33 C32 110.7(3) . . ?
C34 C33 H33A 109.5 . . ?
C34 C33 H33B 109.5 . . ?
C33 C34 H34A 109.6 . . ?
C33 C34 H34B 109.6 . . ?
H34A C34 H34B 108.1 . . ?
C35 C34 C33 110.2(3) . . ?
C35 C34 H34A 109.6 . . ?
C35 C34 H34B 109.6 . . ?
C34 C35 H35A 109.3 . . ?
C34 C35 H35B 109.3 . . ?
C34 C35 C36 111.6(3) . . ?
H35A C35 H35B 108.0 . . ?
C36 C35 H35A 109.3 . . ?
C36 C35 H35B 109.3 . . ?
C31 C36 C35 112.0(3) . . ?
C31 C36 H36A 109.2 . . ?
C31 C36 H36B 109.2 . . ?
C35 C36 H36A 109.2 . . ?
C35 C36 H36B 109.2 . . ?
H36A C36 H36B 107.9 . . ?
N2 C31A H31A 110.7 . . ?
N2 C31A C32A 112.0(6) . . ?
N2 C31A C36A 102.2(5) . . ?
C32A C31A H31A 110.7 . . ?
C32A C31A C36A 110.2(6) . . ?
C36A C31A H31A 110.7 . . ?
C31A C32A H32C 109.9 . . ?
C31A C32A H32D 109.9 . . ?
C31A C32A C33A 108.8(5) . . ?
H32C C32A H32D 108.3 . . ?
C33A C32A H32C 109.9 . . ?
C33A C32A H32D 109.9 . . ?
C32A C33A H33C 109.4 . . ?
C32A C33A H33D 109.4 . . ?
H33C C33A H33D 108.0 . . ?
C34A C33A C32A 111.4(5) . . ?
C34A C33A H33C 109.4 . . ?
C34A C33A H33D 109.4 . . ?
C33A C34A H34C 109.2 . . ?
C33A C34A H34D 109.2 . . ?
H34C C34A H34D 107.9 . . ?
C35A C34A C33A 112.1(5) . . ?
C35A C34A H34C 109.2 . . ?
C35A C34A H34D 109.2 . . ?
C34A C35A H35C 109.5 . . ?
C34A C35A H35D 109.5 . . ?
C34A C35A C36A 110.6(5) . . ?
H35C C35A H35D 108.1 . . ?
C36A C35A H35C 109.5 . . ?
C36A C35A H35D 109.5 . . ?
C31A C36A C35A 108.4(5) . . ?
C31A C36A H36C 110.0 . . ?
C31A C36A H36D 110.0 . . ?
C35A C36A H36C 110.0 . . ?
C35A C36A H36D 110.0 . . ?
H36C C36A H36D 108.4 . . ?
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
O2 C30 1.233(2) . ?
O1 C21 1.358(2) . ?
O1 C23 1.456(3) . ?
N2 C30 1.337(2) . ?
N2 C31 1.528(5) . ?
N2 C31A 1.401(8) . ?
N2 H2 0.89(2) . ?
N1 C21 1.265(2) . ?
N1 C22 1.488(2) . ?
C1 C2 1.385(3) . ?
C1 C6 1.429(3) . ?
C1 C11 1.505(2) . ?
C2 C3 1.421(3) . ?
C2 C21 1.479(3) . ?
C3 H3 0.9500 . ?
C3 C4 1.359(3) . ?
C4 H4 0.9500 . ?
C4 C5 1.413(3) . ?
C5 C6 1.432(3) . ?
C5 C10 1.420(3) . ?
C6 C7 1.415(3) . ?
C7 H7 0.9500 . ?
C7 C8 1.372(3) . ?
C8 H8 0.9500 . ?
C8 C9 1.414(3) . ?
C9 H9 0.9500 . ?
C9 C10 1.358(4) . ?
C10 H10 0.9500 . ?
C11 C12 1.381(2) . ?
C11 C16 1.437(2) . ?
C12 C13 1.423(2) . ?
C12 C30 1.508(3) . ?
C13 H13 0.9500 . ?
C13 C14 1.364(3) . ?
C14 H14 0.9500 . ?
C14 C15 1.418(3) . ?
C15 C16 1.427(2) . ?
C15 C20 1.419(3) . ?
C16 C17 1.418(3) . ?
C17 H17 0.9500 . ?
C17 C18 1.369(3) . ?
C18 H18 0.9500 . ?
C18 C19 1.403(3) . ?
C19 H19 0.9500 . ?
C19 C20 1.361(3) . ?
C20 H20 0.9500 . ?
C22 H22 1.0000 . ?
C22 C23 1.536(3) . ?
C22 C24 1.503(3) . ?
C23 H23A 0.9900 . ?
C23 H23B 0.9900 . ?
C24 C25 1.389(3) . ?
C24 C29 1.392(3) . ?
C25 H25 0.9500 . ?
C25 C26 1.383(3) . ?
C26 H26 0.9500 . ?
C26 C27 1.386(3) . ?
C27 H27 0.9500 . ?
C27 C28 1.378(4) . ?
C28 H28 0.9500 . ?
C28 C29 1.377(3) . ?
C29 H29 0.9500 . ?
C31 H31 1.0000 . ?
C31 C32 1.538(6) . ?
C31 C36 1.504(7) . ?
C32 H32A 0.9900 . ?
C32 H32B 0.9900 . ?
C32 C33 1.538(5) . ?
C33 H33A 0.9900 . ?
C33 H33B 0.9900 . ?
C33 C34 1.531(6) . ?
C34 H34A 0.9900 . ?
C34 H34B 0.9900 . ?
C34 C35 1.512(5) . ?
C35 H35A 0.9900 . ?
C35 H35B 0.9900 . ?
C35 C36 1.533(5) . ?
C36 H36A 0.9900 . ?
C36 H36B 0.9900 . ?
C31A H31A 1.0000 . ?
C31A C32A 1.518(8) . ?
C31A C36A 1.525(7) . ?
C32A H32C 0.9900 . ?
C32A H32D 0.9900 . ?
C32A C33A 1.539(6) . ?
C33A H33C 0.9900 . ?
C33A H33D 0.9900 . ?
C33A C34A 1.521(8) . ?
C34A H34C 0.9900 . ?
C34A H34D 0.9900 . ?
C34A C35A 1.508(7) . ?
C35A H35C 0.9900 . ?
C35A H35D 0.9900 . ?
C35A C36A 1.538(6) . ?
C36A H36C 0.9900 . ?
C36A H36D 0.9900 . ?
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
N2 C31 C32 C33 177.3(4) . . . . ?
N2 C31 C36 C35 -176.7(4) . . . . ?
N2 C31A C32A C33A 174.2(6) . . . . ?
N2 C31A C36A C35A 178.3(6) . . . . ?
N1 C22 C23 O1 14.34(18) . . . . ?
N1 C22 C24 C25 46.8(2) . . . . ?
N1 C22 C24 C29 -133.08(17) . . . . ?
C1 C2 C3 C4 -1.5(3) . . . . ?
C1 C2 C21 O1 108.00(19) . . . . ?
C1 C2 C21 N1 -71.9(3) . . . . ?
C1 C6 C7 C8 -177.70(19) . . . . ?
C1 C11 C12 C13 174.79(17) . . . . ?
C1 C11 C12 C30 -4.9(3) . . . . ?
C1 C11 C16 C15 -178.56(16) . . . . ?
C1 C11 C16 C17 1.6(3) . . . . ?
C2 C1 C6 C5 -1.6(3) . . . . ?
C2 C1 C6 C7 177.43(17) . . . . ?
C2 C1 C11 C12 104.0(2) . . . . ?
C2 C1 C11 C16 -78.3(2) . . . . ?
C2 C3 C4 C5 -1.2(3) . . . . ?
C3 C2 C21 O1 -75.1(2) . . . . ?
C3 C2 C21 N1 104.9(2) . . . . ?
C3 C4 C5 C6 2.4(3) . . . . ?
C3 C4 C5 C10 -176.2(2) . . . . ?
C4 C5 C6 C1 -1.0(3) . . . . ?
C4 C5 C6 C7 179.95(19) . . . . ?
C4 C5 C10 C9 178.6(2) . . . . ?
C5 C6 C7 C8 1.3(3) . . . . ?
C6 C1 C2 C3 2.8(3) . . . . ?
C6 C1 C2 C21 179.64(17) . . . . ?
C6 C1 C11 C12 -78.9(2) . . . . ?
C6 C1 C11 C16 98.8(2) . . . . ?
C6 C5 C10 C9 0.0(3) . . . . ?
C6 C7 C8 C9 0.2(3) . . . . ?
C7 C8 C9 C10 -1.7(3) . . . . ?
C8 C9 C10 C5 1.5(3) . . . . ?
C10 C5 C6 C1 177.62(19) . . . . ?
C10 C5 C6 C7 -1.4(3) . . . . ?
C11 C1 C2 C3 -179.96(17) . . . . ?
C11 C1 C2 C21 -3.2(3) . . . . ?
C11 C1 C6 C5 -178.76(16) . . . . ?
C11 C1 C6 C7 0.2(3) . . . . ?
C11 C12 C13 C14 4.2(3) . . . . ?
C11 C12 C30 O2 121.7(2) . . . . ?
C11 C12 C30 N2 -60.1(2) . . . . ?
C11 C16 C17 C18 177.94(19) . . . . ?
C12 C11 C16 C15 -0.8(2) . . . . ?
C12 C11 C16 C17 179.34(17) . . . . ?
C12 C13 C14 C15 -1.6(3) . . . . ?
C13 C12 C30 O2 -58.1(2) . . . . ?
C13 C12 C30 N2 120.14(19) . . . . ?
C13 C14 C15 C16 -2.1(3) . . . . ?
C13 C14 C15 C20 179.12(18) . . . . ?
C14 C15 C16 C11 3.3(2) . . . . ?
C14 C15 C16 C17 -176.84(17) . . . . ?
C14 C15 C20 C19 177.9(2) . . . . ?
C15 C16 C17 C18 -1.9(3) . . . . ?
C16 C11 C12 C13 -2.9(3) . . . . ?
C16 C11 C12 C30 177.37(16) . . . . ?
C16 C15 C20 C19 -0.9(3) . . . . ?
C16 C17 C18 C19 0.7(3) . . . . ?
C17 C18 C19 C20 0.5(3) . . . . ?
C18 C19 C20 C15 -0.4(3) . . . . ?
C20 C15 C16 C11 -177.87(17) . . . . ?
C20 C15 C16 C17 2.0(2) . . . . ?
C21 O1 C23 C22 -14.06(18) . . . . ?
C21 N1 C22 C23 -9.6(2) . . . . ?
C21 N1 C22 C24 -133.29(16) . . . . ?
C21 C2 C3 C4 -178.3(2) . . . . ?
C22 N1 C21 O1 0.7(2) . . . . ?
C22 N1 C21 C2 -179.40(16) . . . . ?
C22 C24 C25 C26 -178.06(19) . . . . ?
C22 C24 C29 C28 178.32(19) . . . . ?
C23 O1 C21 N1 9.1(2) . . . . ?
C23 O1 C21 C2 -170.79(16) . . . . ?
C23 C22 C24 C25 -69.9(2) . . . . ?
C23 C22 C24 C29 110.2(2) . . . . ?
C24 C22 C23 O1 135.76(16) . . . . ?
C24 C25 C26 C27 -0.5(3) . . . . ?
C25 C24 C29 C28 -1.6(3) . . . . ?
C25 C26 C27 C28 -1.2(3) . . . . ?
C26 C27 C28 C29 1.5(3) . . . . ?
C27 C28 C29 C24 -0.1(3) . . . . ?
C29 C24 C25 C26 1.9(3) . . . . ?
C30 N2 C31 C32 85.7(5) . . . . ?
C30 N2 C31 C36 -151.3(3) . . . . ?
C30 N2 C31A C32A 138.7(5) . . . . ?
C30 N2 C31A C36A -103.4(6) . . . . ?
C30 C12 C13 C14 -176.05(17) . . . . ?
C31 N2 C30 O2 -16.3(3) . . . . ?
C31 N2 C30 C12 165.5(3) . . . . ?
C31 C32 C33 C34 -55.4(6) . . . . ?
C32 C31 C36 C35 -54.1(6) . . . . ?
C32 C33 C34 C35 56.4(5) . . . . ?
C33 C34 C35 C36 -56.8(6) . . . . ?
C34 C35 C36 C31 56.5(6) . . . . ?
C36 C31 C32 C33 54.1(6) . . . . ?
C31A N2 C30 O2 2.6(5) . . . . ?
C31A N2 C30 C12 -175.6(4) . . . . ?
C31A C32A C33A C34A -56.1(8) . . . . ?
C32A C31A C36A C35A -62.5(8) . . . . ?
C32A C33A C34A C35A 53.9(9) . . . . ?
C33A C34A C35A C36A -55.1(9) . . . . ?
C34A C35A C36A C31A 58.6(8) . . . . ?
C36A C31A C32A C33A 61.2(8) . . . . ?
