#------------------------------------------------------------------------------
#$Date: 2022-03-05 00:23:04 +0200 (Sat, 05 Mar 2022) $
#$Revision: 273413 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/15/85/7158507.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_7158507
loop_
_publ_author_name
'Hirao, Yasukazu'
'Eto, Hajime'
'Teraoka, Mitsuru'
'Kubo, Takashi'
_publ_section_title
;
 A strong hydride donating, acid stable and reusable 1,4-dihydropyridine
 for selective aldimine and aldehyde reductions.
;
_journal_issue                   8
_journal_name_full               'Organic & biomolecular chemistry'
_journal_page_first              1671
_journal_page_last               1679
_journal_paper_doi               10.1039/d1ob02358f
_journal_volume                  20
_journal_year                    2022
_chemical_formula_moiety         'C30 H33 N'
_chemical_formula_sum            'C30 H33 N'
_chemical_formula_weight         407.57
_chemical_name_systematic
;
2,6-dimesityl-1-methyl-4-phenyl-1,4-dihydropyridine 
;
_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     direct
_atom_sites_solution_secondary   difmap
_audit_creation_date             2021-11-02
_audit_creation_method
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6408)
;
_audit_update_record
;
2021-11-19 deposited with the CCDC.	2022-02-01 downloaded from the CCDC.
;
_cell_angle_alpha                107.498(8)
_cell_angle_beta                 103.650(7)
_cell_angle_gamma                107.038(8)
_cell_formula_units_Z            4
_cell_length_a                   12.0239(10)
_cell_length_b                   14.1732(12)
_cell_length_c                   17.0536(15)
_cell_measurement_reflns_used    13400
_cell_measurement_temperature    200(2)
_cell_measurement_theta_max      27.45
_cell_measurement_theta_min      3.01
_cell_volume                     2477.1(5)
_computing_cell_refinement       'RAPID AUTO'
_computing_data_collection       'RAPID AUTO'
_computing_data_reduction        'RAPID AUTO'
_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    'SIR2004  (Burla et al.,  2005)'
_diffrn_ambient_temperature      200.15
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type
;
Rigaku MicroMax-007HF,VariMax-Mo and RAPID II
;
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71075
_diffrn_reflns_av_R_equivalents  0.0418
_diffrn_reflns_av_unetI/netI     0.0639
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            24279
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.477
_diffrn_reflns_theta_min         3.007
_diffrn_source                   'micro-focus rotating anode'
_exptl_absorpt_coefficient_mu    0.062
_exptl_absorpt_correction_T_max  0.9938
_exptl_absorpt_correction_T_min  0.9816
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
Empirical Absorption Correction   March 2001 T. Higashi
    Rigaku Corporation, Tokyo, Japan
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.093
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       platelet
_exptl_crystal_F_000             880
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.248
_refine_diff_density_min         -0.187
_refine_diff_density_rms         0.035
_refine_ls_extinction_coef       0.0009(9)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.019
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     574
_refine_ls_number_reflns         11299
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.019
_refine_ls_R_factor_all          0.1359
_refine_ls_R_factor_gt           0.0688
_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)+(0.0735P)²+0.6595P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1544
_refine_ls_wR_factor_ref         0.1831
_reflns_Friedel_coverage         0.000
_reflns_number_gt                6206
_reflns_number_total             11299
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d1ob02358f2.cif
_cod_data_source_block           Mes2PyH
_cod_depositor_comments          'Adding full bibliography for 7158507.cif.'
_cod_original_cell_volume        2477.1(4)
_cod_database_code               7158507
_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   0.994
_shelx_estimated_absorpt_t_min   0.982
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C3(H3), C33(H33)
2.b Aromatic/amide H refined with riding coordinates:
 C2(H2), C4(H4), C9(H9), C11(H11), C17(H17), C18(H18), C19(H19), C20(H20),
 C21(H21), C24(H24), C26(H26), C32(H32), C34(H34), C39(H39), C41(H41), C47(H47),
  C48(H48), C49(H49), C50(H50), C51(H51), C54(H54), C56(H56)
2.c Idealised Me refined as rotating group:
 C6(H6A,H6B,H6C), C13(H13A,H13B,H13C), C14(H14A,H14B,H14C), C15(H15A,H15B,
 H15C), C28(H28A,H28B,H28C), C29(H29A,H29B,H29C), C30(H30A,H30B,H30C), C36(H36A,
 H36B,H36C), C43(H43A,H43B,H43C), C44(H44A,H44B,H44C), C45(H45A,H45B,H45C),
 C58(H58A,H58B,H58C), C59(H59A,H59B,H59C), C60(H60A,H60B,H60C)
;
_olex2_submission_special_instructions 'No special instructions were received'
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
N1 N 0.81749(18) 0.05697(15) 0.18448(12) 0.0458(5) Uani 1 1 d . . . . .
C1 C 0.8404(2) 0.06121(17) 0.10829(14) 0.0421(5) Uani 1 1 d . . . . .
C2 C 0.9053(2) 0.00897(18) 0.07410(15) 0.0462(6) Uani 1 1 d . . . . .
H2 H 0.926860 0.020936 0.026784 0.055 Uiso 1 1 calc R U . . .
C3 C 0.9460(2) -0.06752(18) 0.10627(15) 0.0458(5) Uani 1 1 d . . . . .
H3 H 1.033736 -0.053504 0.109254 0.055 Uiso 1 1 calc R U . . .
C4 C 0.9432(2) -0.04402(19) 0.19767(15) 0.0486(6) Uani 1 1 d . . . . .
H4 H 0.989612 -0.068951 0.233908 0.058 Uiso 1 1 calc R U . . .
C5 C 0.8793(2) 0.00973(18) 0.23092(14) 0.0438(5) Uani 1 1 d . . . . .
C6 C 0.7302(3) 0.0976(2) 0.21318(17) 0.0583(7) Uani 1 1 d . . . . .
H6A H 0.675715 0.045101 0.228410 0.087 Uiso 1 1 calc R U . . .
H6B H 0.679840 0.109349 0.165666 0.087 Uiso 1 1 calc R U . . .
H6C H 0.776013 0.165687 0.264894 0.087 Uiso 1 1 calc R U . . .
C7 C 0.7933(2) 0.12913(18) 0.06854(14) 0.0436(5) Uani 1 1 d . . . . .
C8 C 0.8565(2) 0.24123(18) 0.10727(15) 0.0468(6) Uani 1 1 d . . . . .
C9 C 0.8135(2) 0.3028(2) 0.06781(17) 0.0539(6) Uani 1 1 d . . . . .
H9 H 0.857103 0.378753 0.093550 0.065 Uiso 1 1 calc R U . . .
C10 C 0.7089(3) 0.2567(2) -0.00793(18) 0.0566(7) Uani 1 1 d . . . . .
C11 C 0.6477(3) 0.1455(2) -0.04468(17) 0.0574(7) Uani 1 1 d . . . . .
H11 H 0.575936 0.112604 -0.096680 0.069 Uiso 1 1 calc R U . . .
C12 C 0.6877(2) 0.08046(19) -0.00800(15) 0.0488(6) Uani 1 1 d . . . . .
C13 C 0.9695(3) 0.2950(2) 0.18966(17) 0.0632(7) Uani 1 1 d . . . . .
H13A H 1.011840 0.370333 0.199473 0.095 Uiso 1 1 calc R U . . .
H13B H 1.026222 0.258028 0.183605 0.095 Uiso 1 1 calc R U . . .
H13C H 0.944356 0.291857 0.239754 0.095 Uiso 1 1 calc R U . . .
C14 C 0.6627(3) 0.3248(2) -0.0498(2) 0.0771(9) Uani 1 1 d . . . . .
H14A H 0.648804 0.295596 -0.112740 0.116 Uiso 1 1 calc R U . . .
H14B H 0.724962 0.398848 -0.021927 0.116 Uiso 1 1 calc R U . . .
H14C H 0.584435 0.323917 -0.041676 0.116 Uiso 1 1 calc R U . . .
C15 C 0.6151(3) -0.0399(2) -0.04980(17) 0.0624(7) Uani 1 1 d . . . . .
H15A H 0.670324 -0.075948 -0.064036 0.094 Uiso 1 1 calc R U . . .
H15B H 0.546767 -0.058795 -0.103777 0.094 Uiso 1 1 calc R U . . .
H15C H 0.581190 -0.063065 -0.008696 0.094 Uiso 1 1 calc R U . . .
C16 C 0.8642(2) -0.18453(18) 0.04373(14) 0.0442(5) Uani 1 1 d . . . . .
C17 C 0.9114(3) -0.2512(2) -0.00283(16) 0.0534(6) Uani 1 1 d . . . . .
H17 H 0.996572 -0.224183 0.003149 0.064 Uiso 1 1 calc R U . . .
C18 C 0.8338(3) -0.3584(2) -0.05873(17) 0.0649(8) Uani 1 1 d . . . . .
H18 H 0.866907 -0.404007 -0.089893 0.078 Uiso 1 1 calc R U . . .
C19 C 0.7111(3) -0.3975(2) -0.06859(17) 0.0632(7) Uani 1 1 d . . . . .
H19 H 0.658857 -0.470221 -0.106567 0.076 Uiso 1 1 calc R U . . .
C20 C 0.6628(3) -0.3315(2) -0.02335(16) 0.0608(7) Uani 1 1 d . . . . .
H20 H 0.577376 -0.358494 -0.030150 0.073 Uiso 1 1 calc R U . . .
C21 C 0.7392(2) -0.2258(2) 0.03187(16) 0.0534(6) Uani 1 1 d . . . . .
H21 H 0.705063 -0.180620 0.062312 0.064 Uiso 1 1 calc R U . . .
C22 C 0.8750(2) 0.02751(19) 0.32131(15) 0.0493(6) Uani 1 1 d . . . . .
C23 C 0.7842(3) -0.0481(2) 0.33397(17) 0.0606(7) Uani 1 1 d . . . . .
C24 C 0.7845(3) -0.0298(2) 0.41919(19) 0.0695(8) Uani 1 1 d . . . . .
H24 H 0.723503 -0.081692 0.427920 0.083 Uiso 1 1 calc R U . . .
C25 C 0.8706(3) 0.0612(3) 0.49128(17) 0.0663(8) Uani 1 1 d . . . . .
C26 C 0.9577(3) 0.1351(2) 0.47690(16) 0.0678(8) Uani 1 1 d . . . . .
H26 H 1.016840 0.198555 0.525707 0.081 Uiso 1 1 calc R U . . .
C27 C 0.9626(2) 0.1206(2) 0.39328(15) 0.0589(7) Uani 1 1 d . . . . .
C28 C 0.6873(4) -0.1483(2) 0.2573(2) 0.0985(12) Uani 1 1 d . . . . .
H28A H 0.640056 -0.128037 0.214671 0.148 Uiso 1 1 calc R U . . .
H28B H 0.630640 -0.190677 0.278389 0.148 Uiso 1 1 calc R U . . .
H28C H 0.728427 -0.191323 0.228999 0.148 Uiso 1 1 calc R U . . .
C29 C 0.8703(4) 0.0792(3) 0.58326(19) 0.0984(12) Uani 1 1 d . . . . .
H29A H 0.956125 0.116252 0.625266 0.148 Uiso 1 1 calc R U . . .
H29B H 0.831804 0.009695 0.586173 0.148 Uiso 1 1 calc R U . . .
H29C H 0.822950 0.123316 0.597944 0.148 Uiso 1 1 calc R U . . .
C30 C 1.0614(3) 0.2028(3) 0.38200(19) 0.0919(11) Uani 1 1 d . . . . .
H30A H 1.027211 0.208967 0.326504 0.138 Uiso 1 1 calc R U . . .
H30B H 1.131245 0.180651 0.381070 0.138 Uiso 1 1 calc R U . . .
H30C H 1.090606 0.272475 0.431043 0.138 Uiso 1 1 calc R U . . .
N2 N 0.64426(18) 0.41557(13) 0.29497(12) 0.0442(5) Uani 1 1 d . . . . .
C31 C 0.5720(2) 0.38735(17) 0.34410(14) 0.0409(5) Uani 1 1 d . . . . .
C32 C 0.5619(2) 0.46160(18) 0.40862(15) 0.0464(6) Uani 1 1 d . . . . .
H32 H 0.514604 0.437634 0.441385 0.056 Uiso 1 1 calc R U . . .
C33 C 0.6205(2) 0.58116(18) 0.43323(15) 0.0465(6) Uani 1 1 d . . . . .
H33 H 0.665874 0.617613 0.498290 0.056 Uiso 1 1 calc R U . . .
C34 C 0.7133(2) 0.60091(18) 0.38838(14) 0.0460(6) Uani 1 1 d . . . . .
H34 H 0.771630 0.672542 0.408014 0.055 Uiso 1 1 calc R U . . .
C35 C 0.7192(2) 0.52484(17) 0.32302(14) 0.0407(5) Uani 1 1 d . . . . .
C36 C 0.6382(3) 0.33492(18) 0.21570(15) 0.0543(6) Uani 1 1 d . . . . .
H36A H 0.601628 0.348334 0.164459 0.081 Uiso 1 1 calc R U . . .
H36B H 0.586509 0.263253 0.209236 0.081 Uiso 1 1 calc R U . . .
H36C H 0.722246 0.338833 0.219984 0.081 Uiso 1 1 calc R U . . .
C37 C 0.5121(2) 0.27026(17) 0.32461(14) 0.0439(5) Uani 1 1 d . . . . .
C38 C 0.5836(2) 0.2205(2) 0.35918(16) 0.0521(6) Uani 1 1 d . . . . .
C39 C 0.5275(3) 0.1112(2) 0.34086(19) 0.0659(8) Uani 1 1 d . . . . .
H39 H 0.576559 0.076754 0.363054 0.079 Uiso 1 1 calc R U . . .
C40 C 0.4029(3) 0.0518(2) 0.2914(2) 0.0703(9) Uani 1 1 d . . . . .
C41 C 0.3340(3) 0.1029(2) 0.25963(19) 0.0697(8) Uani 1 1 d . . . . .
H41 H 0.247787 0.062897 0.226348 0.084 Uiso 1 1 calc R U . . .
C42 C 0.3854(2) 0.2109(2) 0.27425(16) 0.0533(6) Uani 1 1 d . . . . .
C43 C 0.7175(3) 0.2830(2) 0.41768(19) 0.0680(8) Uani 1 1 d . . . . .
H43A H 0.764174 0.315801 0.386150 0.102 Uiso 1 1 calc R U . . .
H43B H 0.752299 0.234446 0.434511 0.102 Uiso 1 1 calc R U . . .
H43C H 0.723634 0.339416 0.470605 0.102 Uiso 1 1 calc R U . . .
C44 C 0.3450(4) -0.0671(2) 0.2729(3) 0.1087(14) Uani 1 1 d . . . . .
H44A H 0.366128 -0.108636 0.225625 0.163 Uiso 1 1 calc R U . . .
H44B H 0.254367 -0.090809 0.254995 0.163 Uiso 1 1 calc R U . . .
H44C H 0.377216 -0.078420 0.326223 0.163 Uiso 1 1 calc R U . . .
C45 C 0.3052(3) 0.2614(2) 0.2347(2) 0.0742(8) Uani 1 1 d . . . . .
H45A H 0.221907 0.206108 0.197641 0.111 Uiso 1 1 calc R U . . .
H45B H 0.342723 0.293572 0.198917 0.111 Uiso 1 1 calc R U . . .
H45C H 0.299006 0.317285 0.281911 0.111 Uiso 1 1 calc R U . . .
C46 C 0.5282(2) 0.63049(18) 0.40825(15) 0.0468(6) Uani 1 1 d . . . . .
C47 C 0.5377(3) 0.72816(19) 0.46465(17) 0.0571(7) Uani 1 1 d . . . . .
H47 H 0.599412 0.763560 0.521976 0.069 Uiso 1 1 calc R U . . .
C48 C 0.4571(3) 0.7747(2) 0.4377(2) 0.0669(8) Uani 1 1 d . . . . .
H48 H 0.465136 0.842487 0.476436 0.080 Uiso 1 1 calc R U . . .
C49 C 0.3661(3) 0.7238(2) 0.3555(2) 0.0664(8) Uani 1 1 d . . . . .
H49 H 0.310471 0.755493 0.337833 0.080 Uiso 1 1 calc R U . . .
C50 C 0.3561(3) 0.6266(2) 0.2992(2) 0.0708(8) Uani 1 1 d . . . . .
H50 H 0.293781 0.591240 0.242143 0.085 Uiso 1 1 calc R U . . .
C51 C 0.4359(3) 0.5802(2) 0.32526(17) 0.0624(7) Uani 1 1 d . . . . .
H51 H 0.427835 0.512779 0.285861 0.075 Uiso 1 1 calc R U . . .
C52 C 0.8083(2) 0.55357(16) 0.27746(14) 0.0409(5) Uani 1 1 d . . . . .
C53 C 0.7712(2) 0.57880(17) 0.20471(15) 0.0434(5) Uani 1 1 d . . . . .
C54 C 0.8570(2) 0.61022(18) 0.16568(16) 0.0487(6) Uani 1 1 d . . . . .
H54 H 0.832105 0.627612 0.116508 0.058 Uiso 1 1 calc R U . . .
C55 C 0.9772(2) 0.61679(18) 0.19645(16) 0.0495(6) Uani 1 1 d . . . . .
C56 C 1.0115(2) 0.59178(19) 0.26829(16) 0.0512(6) Uani 1 1 d . . . . .
H56 H 1.094109 0.596274 0.290151 0.061 Uiso 1 1 calc R U . . .
C57 C 0.9292(2) 0.56010(18) 0.30997(15) 0.0465(6) Uani 1 1 d . . . . .
C58 C 0.6394(2) 0.5688(2) 0.16748(18) 0.0578(6) Uani 1 1 d . . . . .
H58A H 0.622155 0.619455 0.211641 0.087 Uiso 1 1 calc R U . . .
H58B H 0.581514 0.495268 0.151619 0.087 Uiso 1 1 calc R U . . .
H58C H 0.628749 0.585257 0.115002 0.087 Uiso 1 1 calc R U . . .
C59 C 1.0665(3) 0.6479(3) 0.1507(2) 0.0741(8) Uani 1 1 d . . . . .
H59A H 1.039828 0.590053 0.092789 0.111 Uiso 1 1 calc R U . . .
H59B H 1.150289 0.659731 0.186122 0.111 Uiso 1 1 calc R U . . .
H59C H 1.067428 0.714179 0.143559 0.111 Uiso 1 1 calc R U . . .
C60 C 0.9722(2) 0.5334(2) 0.38790(17) 0.0642(7) Uani 1 1 d . . . . .
H60A H 0.973608 0.586765 0.440750 0.096 Uiso 1 1 calc R U . . .
H60B H 1.055997 0.534208 0.396190 0.096 Uiso 1 1 calc R U . . .
H60C H 0.914894 0.461732 0.377442 0.096 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'
N N 0.0061 0.0033 '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
C1 N1 C6 121.25(19) . . ?
C5 N1 C1 117.99(18) . . ?
C5 N1 C6 120.74(18) . . ?
N1 C1 C7 117.61(18) . . ?
C2 C1 N1 121.1(2) . . ?
C2 C1 C7 121.2(2) . . ?
C1 C2 H2 118.1 . . ?
C1 C2 C3 123.8(2) . . ?
C3 C2 H2 118.1 . . ?
C2 C3 H3 108.5 . . ?
C2 C3 C4 107.94(18) . . ?
C2 C3 C16 111.23(19) . . ?
C4 C3 H3 108.5 . . ?
C4 C3 C16 112.05(19) . . ?
C16 C3 H3 108.5 . . ?
C3 C4 H4 118.0 . . ?
C5 C4 C3 123.9(2) . . ?
C5 C4 H4 118.0 . . ?
N1 C5 C22 116.51(19) . . ?
C4 C5 N1 121.3(2) . . ?
C4 C5 C22 122.1(2) . . ?
N1 C6 H6A 109.5 . . ?
N1 C6 H6B 109.5 . . ?
N1 C6 H6C 109.5 . . ?
H6A C6 H6B 109.5 . . ?
H6A C6 H6C 109.5 . . ?
H6B C6 H6C 109.5 . . ?
C8 C7 C1 119.8(2) . . ?
C12 C7 C1 119.9(2) . . ?
C12 C7 C8 120.2(2) . . ?
C7 C8 C13 121.1(2) . . ?
C9 C8 C7 119.0(2) . . ?
C9 C8 C13 120.0(2) . . ?
C8 C9 H9 119.0 . . ?
C10 C9 C8 122.0(2) . . ?
C10 C9 H9 119.0 . . ?
C9 C10 C11 117.8(2) . . ?
C9 C10 C14 121.3(3) . . ?
C11 C10 C14 120.8(3) . . ?
C10 C11 H11 118.9 . . ?
C10 C11 C12 122.3(3) . . ?
C12 C11 H11 118.9 . . ?
C7 C12 C15 121.5(2) . . ?
C11 C12 C7 118.7(2) . . ?
C11 C12 C15 119.8(2) . . ?
C8 C13 H13A 109.5 . . ?
C8 C13 H13B 109.5 . . ?
C8 C13 H13C 109.5 . . ?
H13A C13 H13B 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
C10 C14 H14A 109.5 . . ?
C10 C14 H14B 109.5 . . ?
C10 C14 H14C 109.5 . . ?
H14A C14 H14B 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C12 C15 H15A 109.5 . . ?
C12 C15 H15B 109.5 . . ?
C12 C15 H15C 109.5 . . ?
H15A C15 H15B 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
C17 C16 C3 121.8(2) . . ?
C21 C16 C3 119.8(2) . . ?
C21 C16 C17 118.4(2) . . ?
C16 C17 H17 119.9 . . ?
C16 C17 C18 120.1(3) . . ?
C18 C17 H17 119.9 . . ?
C17 C18 H18 119.8 . . ?
C19 C18 C17 120.4(3) . . ?
C19 C18 H18 119.8 . . ?
C18 C19 H19 120.0 . . ?
C18 C19 C20 119.9(3) . . ?
C20 C19 H19 120.0 . . ?
C19 C20 H20 120.1 . . ?
C19 C20 C21 119.8(3) . . ?
C21 C20 H20 120.1 . . ?
C16 C21 H21 119.3 . . ?
C20 C21 C16 121.4(2) . . ?
C20 C21 H21 119.3 . . ?
C23 C22 C5 120.5(2) . . ?
C23 C22 C27 119.9(2) . . ?
C27 C22 C5 119.7(2) . . ?
C22 C23 C28 120.9(2) . . ?
C24 C23 C22 118.8(2) . . ?
C24 C23 C28 120.2(3) . . ?
C23 C24 H24 118.9 . . ?
C25 C24 C23 122.3(3) . . ?
C25 C24 H24 118.9 . . ?
C24 C25 C29 121.5(3) . . ?
C26 C25 C24 117.8(2) . . ?
C26 C25 C29 120.7(3) . . ?
C25 C26 H26 118.8 . . ?
C25 C26 C27 122.5(3) . . ?
C27 C26 H26 118.8 . . ?
C22 C27 C30 121.2(2) . . ?
C26 C27 C22 118.8(3) . . ?
C26 C27 C30 120.1(2) . . ?
C23 C28 H28A 109.5 . . ?
C23 C28 H28B 109.5 . . ?
C23 C28 H28C 109.5 . . ?
H28A C28 H28B 109.5 . . ?
H28A C28 H28C 109.5 . . ?
H28B C28 H28C 109.5 . . ?
C25 C29 H29A 109.5 . . ?
C25 C29 H29B 109.5 . . ?
C25 C29 H29C 109.5 . . ?
H29A C29 H29B 109.5 . . ?
H29A C29 H29C 109.5 . . ?
H29B C29 H29C 109.5 . . ?
C27 C30 H30A 109.5 . . ?
C27 C30 H30B 109.5 . . ?
C27 C30 H30C 109.5 . . ?
H30A C30 H30B 109.5 . . ?
H30A C30 H30C 109.5 . . ?
H30B C30 H30C 109.5 . . ?
C31 N2 C35 117.74(17) . . ?
C31 N2 C36 121.02(18) . . ?
C35 N2 C36 121.19(18) . . ?
N2 C31 C37 117.19(18) . . ?
C32 C31 N2 121.6(2) . . ?
C32 C31 C37 121.12(19) . . ?
C31 C32 H32 117.7 . . ?
C31 C32 C33 124.5(2) . . ?
C33 C32 H32 117.7 . . ?
C32 C33 H33 108.5 . . ?
C32 C33 C46 114.2(2) . . ?
C34 C33 C32 107.93(18) . . ?
C34 C33 H33 108.5 . . ?
C34 C33 C46 109.04(19) . . ?
C46 C33 H33 108.5 . . ?
C33 C34 H34 117.8 . . ?
C35 C34 C33 124.4(2) . . ?
C35 C34 H34 117.8 . . ?
N2 C35 C52 117.72(18) . . ?
C34 C35 N2 121.7(2) . . ?
C34 C35 C52 120.6(2) . . ?
N2 C36 H36A 109.5 . . ?
N2 C36 H36B 109.5 . . ?
N2 C36 H36C 109.5 . . ?
H36A C36 H36B 109.5 . . ?
H36A C36 H36C 109.5 . . ?
H36B C36 H36C 109.5 . . ?
C38 C37 C31 119.1(2) . . ?
C38 C37 C42 119.8(2) . . ?
C42 C37 C31 121.1(2) . . ?
C37 C38 C39 119.0(3) . . ?
C37 C38 C43 121.3(2) . . ?
C39 C38 C43 119.7(3) . . ?
C38 C39 H39 119.1 . . ?
C40 C39 C38 121.7(3) . . ?
C40 C39 H39 119.1 . . ?
C39 C40 C44 120.3(3) . . ?
C41 C40 C39 118.2(3) . . ?
C41 C40 C44 121.6(3) . . ?
C40 C41 H41 118.7 . . ?
C40 C41 C42 122.6(3) . . ?
C42 C41 H41 118.7 . . ?
C37 C42 C45 121.5(2) . . ?
C41 C42 C37 118.7(3) . . ?
C41 C42 C45 119.9(3) . . ?
C38 C43 H43A 109.5 . . ?
C38 C43 H43B 109.5 . . ?
C38 C43 H43C 109.5 . . ?
H43A C43 H43B 109.5 . . ?
H43A C43 H43C 109.5 . . ?
H43B C43 H43C 109.5 . . ?
C40 C44 H44A 109.5 . . ?
C40 C44 H44B 109.5 . . ?
C40 C44 H44C 109.5 . . ?
H44A C44 H44B 109.5 . . ?
H44A C44 H44C 109.5 . . ?
H44B C44 H44C 109.5 . . ?
C42 C45 H45A 109.5 . . ?
C42 C45 H45B 109.5 . . ?
C42 C45 H45C 109.5 . . ?
H45A C45 H45B 109.5 . . ?
H45A C45 H45C 109.5 . . ?
H45B C45 H45C 109.5 . . ?
C47 C46 C33 121.5(2) . . ?
C47 C46 C51 118.5(2) . . ?
C51 C46 C33 120.0(2) . . ?
C46 C47 H47 119.9 . . ?
C46 C47 C48 120.1(3) . . ?
C48 C47 H47 119.9 . . ?
C47 C48 H48 119.7 . . ?
C49 C48 C47 120.7(3) . . ?
C49 C48 H48 119.7 . . ?
C48 C49 H49 120.3 . . ?
C48 C49 C50 119.4(3) . . ?
C50 C49 H49 120.3 . . ?
C49 C50 H50 119.9 . . ?
C49 C50 C51 120.2(3) . . ?
C51 C50 H50 119.9 . . ?
C46 C51 H51 119.5 . . ?
C50 C51 C46 121.0(2) . . ?
C50 C51 H51 119.5 . . ?
C53 C52 C35 119.7(2) . . ?
C57 C52 C35 120.0(2) . . ?
C57 C52 C53 120.3(2) . . ?
C52 C53 C58 120.6(2) . . ?
C54 C53 C52 119.0(2) . . ?
C54 C53 C58 120.4(2) . . ?
C53 C54 H54 119.1 . . ?
C55 C54 C53 121.8(2) . . ?
C55 C54 H54 119.1 . . ?
C54 C55 C59 120.3(2) . . ?
C56 C55 C54 118.1(2) . . ?
C56 C55 C59 121.5(2) . . ?
C55 C56 H56 118.8 . . ?
C55 C56 C57 122.3(2) . . ?
C57 C56 H56 118.8 . . ?
C52 C57 C56 118.5(2) . . ?
C52 C57 C60 121.7(2) . . ?
C56 C57 C60 119.8(2) . . ?
C53 C58 H58A 109.5 . . ?
C53 C58 H58B 109.5 . . ?
C53 C58 H58C 109.5 . . ?
H58A C58 H58B 109.5 . . ?
H58A C58 H58C 109.5 . . ?
H58B C58 H58C 109.5 . . ?
C55 C59 H59A 109.5 . . ?
C55 C59 H59B 109.5 . . ?
C55 C59 H59C 109.5 . . ?
H59A C59 H59B 109.5 . . ?
H59A C59 H59C 109.5 . . ?
H59B C59 H59C 109.5 . . ?
C57 C60 H60A 109.5 . . ?
C57 C60 H60B 109.5 . . ?
C57 C60 H60C 109.5 . . ?
H60A C60 H60B 109.5 . . ?
H60A C60 H60C 109.5 . . ?
H60B C60 H60C 109.5 . . ?
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 C1 1.405(3) . ?
N1 C5 1.400(3) . ?
N1 C6 1.449(3) . ?
C1 C2 1.338(3) . ?
C1 C7 1.496(3) . ?
C2 H2 0.9500 . ?
C2 C3 1.503(3) . ?
C3 H3 1.0000 . ?
C3 C4 1.504(3) . ?
C3 C16 1.530(3) . ?
C4 H4 0.9500 . ?
C4 C5 1.334(3) . ?
C5 C22 1.501(3) . ?
C6 H6A 0.9800 . ?
C6 H6B 0.9800 . ?
C6 H6C 0.9800 . ?
C7 C8 1.401(3) . ?
C7 C12 1.398(3) . ?
C8 C9 1.391(3) . ?
C8 C13 1.500(3) . ?
C9 H9 0.9500 . ?
C9 C10 1.386(4) . ?
C10 C11 1.388(4) . ?
C10 C14 1.513(4) . ?
C11 H11 0.9500 . ?
C11 C12 1.392(3) . ?
C12 C15 1.511(3) . ?
C13 H13A 0.9800 . ?
C13 H13B 0.9800 . ?
C13 H13C 0.9800 . ?
C14 H14A 0.9800 . ?
C14 H14B 0.9800 . ?
C14 H14C 0.9800 . ?
C15 H15A 0.9800 . ?
C15 H15B 0.9800 . ?
C15 H15C 0.9800 . ?
C16 C17 1.387(3) . ?
C16 C21 1.383(3) . ?
C17 H17 0.9500 . ?
C17 C18 1.402(4) . ?
C18 H18 0.9500 . ?
C18 C19 1.364(4) . ?
C19 H19 0.9500 . ?
C19 C20 1.380(4) . ?
C20 H20 0.9500 . ?
C20 C21 1.382(3) . ?
C21 H21 0.9500 . ?
C22 C23 1.398(3) . ?
C22 C27 1.399(3) . ?
C23 C24 1.396(4) . ?
C23 C28 1.509(4) . ?
C24 H24 0.9500 . ?
C24 C25 1.382(4) . ?
C25 C26 1.374(4) . ?
C25 C29 1.513(4) . ?
C26 H26 0.9500 . ?
C26 C27 1.396(3) . ?
C27 C30 1.495(4) . ?
C28 H28A 0.9800 . ?
C28 H28B 0.9800 . ?
C28 H28C 0.9800 . ?
C29 H29A 0.9800 . ?
C29 H29B 0.9800 . ?
C29 H29C 0.9800 . ?
C30 H30A 0.9800 . ?
C30 H30B 0.9800 . ?
C30 H30C 0.9800 . ?
N2 C31 1.399(3) . ?
N2 C35 1.405(3) . ?
N2 C36 1.454(3) . ?
C31 C32 1.332(3) . ?
C31 C37 1.496(3) . ?
C32 H32 0.9500 . ?
C32 C33 1.509(3) . ?
C33 H33 1.0000 . ?
C33 C34 1.502(3) . ?
C33 C46 1.520(3) . ?
C34 H34 0.9500 . ?
C34 C35 1.331(3) . ?
C35 C52 1.498(3) . ?
C36 H36A 0.9800 . ?
C36 H36B 0.9800 . ?
C36 H36C 0.9800 . ?
C37 C38 1.396(3) . ?
C37 C42 1.401(3) . ?
C38 C39 1.397(4) . ?
C38 C43 1.499(4) . ?
C39 H39 0.9500 . ?
C39 C40 1.380(4) . ?
C40 C41 1.371(4) . ?
C40 C44 1.520(4) . ?
C41 H41 0.9500 . ?
C41 C42 1.390(4) . ?
C42 C45 1.511(4) . ?
C43 H43A 0.9800 . ?
C43 H43B 0.9800 . ?
C43 H43C 0.9800 . ?
C44 H44A 0.9800 . ?
C44 H44B 0.9800 . ?
C44 H44C 0.9800 . ?
C45 H45A 0.9800 . ?
C45 H45B 0.9800 . ?
C45 H45C 0.9800 . ?
C46 C47 1.382(3) . ?
C46 C51 1.390(3) . ?
C47 H47 0.9500 . ?
C47 C48 1.390(4) . ?
C48 H48 0.9500 . ?
C48 C49 1.373(4) . ?
C49 H49 0.9500 . ?
C49 C50 1.374(4) . ?
C50 H50 0.9500 . ?
C50 C51 1.377(4) . ?
C51 H51 0.9500 . ?
C52 C53 1.402(3) . ?
C52 C57 1.393(3) . ?
C53 C54 1.392(3) . ?
C53 C58 1.508(3) . ?
C54 H54 0.9500 . ?
C54 C55 1.381(3) . ?
C55 C56 1.380(3) . ?
C55 C59 1.511(3) . ?
C56 H56 0.9500 . ?
C56 C57 1.397(3) . ?
C57 C60 1.507(3) . ?
C58 H58A 0.9800 . ?
C58 H58B 0.9800 . ?
C58 H58C 0.9800 . ?
C59 H59A 0.9800 . ?
C59 H59B 0.9800 . ?
C59 H59C 0.9800 . ?
C60 H60A 0.9800 . ?
C60 H60B 0.9800 . ?
C60 H60C 0.9800 . ?
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
N1 C1 C2 C3 7.3(4) . . . . ?
N1 C1 C7 C8 76.7(3) . . . . ?
N1 C1 C7 C12 -104.6(2) . . . . ?
N1 C5 C22 C23 94.5(3) . . . . ?
N1 C5 C22 C27 -85.4(3) . . . . ?
C1 N1 C5 C4 -9.9(3) . . . . ?
C1 N1 C5 C22 167.1(2) . . . . ?
C1 C2 C3 C4 -19.9(3) . . . . ?
C1 C2 C3 C16 103.4(3) . . . . ?
C1 C7 C8 C9 178.0(2) . . . . ?
C1 C7 C8 C13 -1.6(3) . . . . ?
C1 C7 C12 C11 -178.5(2) . . . . ?
C1 C7 C12 C15 3.2(3) . . . . ?
C2 C1 C7 C8 -101.4(3) . . . . ?
C2 C1 C7 C12 77.4(3) . . . . ?
C2 C3 C4 C5 19.1(3) . . . . ?
C2 C3 C16 C17 115.1(2) . . . . ?
C2 C3 C16 C21 -64.2(3) . . . . ?
C3 C4 C5 N1 -5.6(4) . . . . ?
C3 C4 C5 C22 177.5(2) . . . . ?
C3 C16 C17 C18 179.2(2) . . . . ?
C3 C16 C21 C20 -179.3(2) . . . . ?
C4 C3 C16 C17 -124.0(2) . . . . ?
C4 C3 C16 C21 56.8(3) . . . . ?
C4 C5 C22 C23 -88.5(3) . . . . ?
C4 C5 C22 C27 91.6(3) . . . . ?
C5 N1 C1 C2 9.1(3) . . . . ?
C5 N1 C1 C7 -168.9(2) . . . . ?
C5 C22 C23 C24 178.8(2) . . . . ?
C5 C22 C23 C28 -0.9(4) . . . . ?
C5 C22 C27 C26 -179.4(2) . . . . ?
C5 C22 C27 C30 -0.4(4) . . . . ?
C6 N1 C1 C2 -169.3(2) . . . . ?
C6 N1 C1 C7 12.7(3) . . . . ?
C6 N1 C5 C4 168.5(2) . . . . ?
C6 N1 C5 C22 -14.4(3) . . . . ?
C7 C1 C2 C3 -174.8(2) . . . . ?
C7 C8 C9 C10 0.9(3) . . . . ?
C8 C7 C12 C11 0.2(3) . . . . ?
C8 C7 C12 C15 -178.1(2) . . . . ?
C8 C9 C10 C11 -0.7(4) . . . . ?
C8 C9 C10 C14 179.6(2) . . . . ?
C9 C10 C11 C12 0.1(4) . . . . ?
C10 C11 C12 C7 0.1(4) . . . . ?
C10 C11 C12 C15 178.4(2) . . . . ?
C12 C7 C8 C9 -0.7(3) . . . . ?
C12 C7 C8 C13 179.7(2) . . . . ?
C13 C8 C9 C10 -179.4(2) . . . . ?
C14 C10 C11 C12 179.9(2) . . . . ?
C16 C3 C4 C5 -103.7(3) . . . . ?
C16 C17 C18 C19 0.8(4) . . . . ?
C17 C16 C21 C20 1.4(4) . . . . ?
C17 C18 C19 C20 0.0(4) . . . . ?
C18 C19 C20 C21 -0.1(4) . . . . ?
C19 C20 C21 C16 -0.6(4) . . . . ?
C21 C16 C17 C18 -1.5(3) . . . . ?
C22 C23 C24 C25 0.9(4) . . . . ?
C23 C22 C27 C26 0.7(4) . . . . ?
C23 C22 C27 C30 179.6(3) . . . . ?
C23 C24 C25 C26 0.1(4) . . . . ?
C23 C24 C25 C29 -179.4(3) . . . . ?
C24 C25 C26 C27 -0.8(4) . . . . ?
C25 C26 C27 C22 0.4(4) . . . . ?
C25 C26 C27 C30 -178.6(3) . . . . ?
C27 C22 C23 C24 -1.3(4) . . . . ?
C27 C22 C23 C28 179.0(3) . . . . ?
C28 C23 C24 C25 -179.4(3) . . . . ?
C29 C25 C26 C27 178.8(3) . . . . ?
N2 C31 C32 C33 2.8(4) . . . . ?
N2 C31 C37 C38 79.2(3) . . . . ?
N2 C31 C37 C42 -102.3(3) . . . . ?
N2 C35 C52 C53 92.0(3) . . . . ?
N2 C35 C52 C57 -91.0(3) . . . . ?
C31 N2 C35 C34 -6.8(3) . . . . ?
C31 N2 C35 C52 172.52(19) . . . . ?
C31 C32 C33 C34 -13.2(3) . . . . ?
C31 C32 C33 C46 108.3(3) . . . . ?
C31 C37 C38 C39 -179.9(2) . . . . ?
C31 C37 C38 C43 2.1(3) . . . . ?
C31 C37 C42 C41 -178.7(2) . . . . ?
C31 C37 C42 C45 2.4(3) . . . . ?
C32 C31 C37 C38 -97.4(3) . . . . ?
C32 C31 C37 C42 81.0(3) . . . . ?
C32 C33 C34 C35 14.6(3) . . . . ?
C32 C33 C46 C47 138.0(2) . . . . ?
C32 C33 C46 C51 -45.6(3) . . . . ?
C33 C34 C35 N2 -5.7(4) . . . . ?
C33 C34 C35 C52 175.0(2) . . . . ?
C33 C46 C47 C48 175.6(2) . . . . ?
C33 C46 C51 C50 -176.1(2) . . . . ?
C34 C33 C46 C47 -101.2(2) . . . . ?
C34 C33 C46 C51 75.2(3) . . . . ?
C34 C35 C52 C53 -88.7(3) . . . . ?
C34 C35 C52 C57 88.2(3) . . . . ?
C35 N2 C31 C32 8.2(3) . . . . ?
C35 N2 C31 C37 -168.47(19) . . . . ?
C35 C52 C53 C54 177.02(19) . . . . ?
C35 C52 C53 C58 -4.9(3) . . . . ?
C35 C52 C57 C56 -177.2(2) . . . . ?
C35 C52 C57 C60 3.2(3) . . . . ?
C36 N2 C31 C32 -169.5(2) . . . . ?
C36 N2 C31 C37 13.8(3) . . . . ?
C36 N2 C35 C34 170.9(2) . . . . ?
C36 N2 C35 C52 -9.8(3) . . . . ?
C37 C31 C32 C33 179.3(2) . . . . ?
C37 C38 C39 C40 -1.6(4) . . . . ?
C38 C37 C42 C41 -0.3(3) . . . . ?
C38 C37 C42 C45 -179.2(2) . . . . ?
C38 C39 C40 C41 0.3(4) . . . . ?
C38 C39 C40 C44 -179.9(2) . . . . ?
C39 C40 C41 C42 1.1(4) . . . . ?
C40 C41 C42 C37 -1.1(4) . . . . ?
C40 C41 C42 C45 177.9(3) . . . . ?
C42 C37 C38 C39 1.6(3) . . . . ?
C42 C37 C38 C43 -176.4(2) . . . . ?
C43 C38 C39 C40 176.4(2) . . . . ?
C44 C40 C41 C42 -178.7(3) . . . . ?
C46 C33 C34 C35 -110.0(3) . . . . ?
C46 C47 C48 C49 1.1(4) . . . . ?
C47 C46 C51 C50 0.4(4) . . . . ?
C47 C48 C49 C50 -1.0(4) . . . . ?
C48 C49 C50 C51 0.6(4) . . . . ?
C49 C50 C51 C46 -0.3(5) . . . . ?
C51 C46 C47 C48 -0.8(4) . . . . ?
C52 C53 C54 C55 0.2(3) . . . . ?
C53 C52 C57 C56 -0.2(3) . . . . ?
C53 C52 C57 C60 -179.9(2) . . . . ?
C53 C54 C55 C56 -0.4(3) . . . . ?
C53 C54 C55 C59 178.1(2) . . . . ?
C54 C55 C56 C57 0.2(4) . . . . ?
C55 C56 C57 C52 0.1(4) . . . . ?
C55 C56 C57 C60 179.7(2) . . . . ?
C57 C52 C53 C54 0.1(3) . . . . ?
C57 C52 C53 C58 178.2(2) . . . . ?
C58 C53 C54 C55 -177.9(2) . . . . ?
C59 C55 C56 C57 -178.3(2) . . . . ?
