#------------------------------------------------------------------------------
#$Date: 2020-06-20 04:00:44 +0300 (Sat, 20 Jun 2020) $
#$Revision: 253282 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/55/83/1558374.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_1558374
loop_
_publ_author_name
'Guo, Rui'
'Jiang, Jingxing'
'Hu, Chenyang'
'Liu, Liu Leo'
'Cui, Ping'
'Zhao, Meihua'
'Ke, Zhuofeng'
'Tung, Chen-Ho'
'Kong, Lingbing'
_publ_section_title
;
 BNN-1,3-dipoles: isolation and intramolecular cycloaddition with
 unactivated arenes
;
_journal_name_full               'Chemical Science'
_journal_paper_doi               10.1039/D0SC02162H
_journal_year                    2020
_chemical_formula_moiety         'C59 H70 B2 N4, C7 H8'
_chemical_formula_sum            'C66 H78 B2 N4'
_chemical_formula_weight         948.94
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2020-05-19
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2020-05-25 deposited with the CCDC.	2020-06-19 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 98.1553(9)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   11.75034(11)
_cell_length_b                   23.8044(3)
_cell_length_c                   19.95734(18)
_cell_measurement_reflns_used    14527
_cell_measurement_temperature    173.00(10)
_cell_measurement_theta_max      76.0010
_cell_measurement_theta_min      2.8590
_cell_volume                     5525.81(10)
_computing_cell_refinement       'CrysAlisPro 1.171.40.19a (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.40.19a (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.40.19a (Rigaku OD, 2018)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      173.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.989
_diffrn_measured_fraction_theta_max 0.989
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -63.00  24.00   1.00    0.11    --  -48.45  58.00 133.00   87
  2  ω    -10.00  43.00   1.00    0.11    --   48.45 -58.00  -7.00   53
  3  ω     83.00 110.00   1.00    0.11    --   48.45  58.00 133.00   27
  4  ω    -94.00 -62.00   1.00    0.90    --  -86.25  58.00 133.00   32
  5  ω   -139.00-114.00   1.00    0.90    --  -86.25 -58.00  -7.00   25
  6  ω    -50.00 -23.00   1.00    0.90    --  -86.25  58.00 133.00   27
  7  ω     91.00 178.00   1.00    0.90    --  106.49  58.00 133.00   87
  8  ω     36.00 122.00   1.00    0.90    --  106.49 -58.00  -7.00   86
  9  ω   -120.00 -78.00   1.00    0.11    --  -48.45-125.00 150.00   42
 10  ω   -119.00 -34.00   1.00    0.11    --  -48.45 -58.00  -7.00   85
 11  ω     34.00  92.00   1.00    0.90    --  106.49 -94.00 -60.00   58
 12  ω     34.00 108.00   1.00    0.90    --  106.49 -94.00 -30.00   74
 13  ω     93.00 178.00   1.00    0.90    --  106.49  15.00 -90.00   85
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0864826000
_diffrn_orient_matrix_UB_12      -0.0203941000
_diffrn_orient_matrix_UB_13      -0.0603788000
_diffrn_orient_matrix_UB_21      -0.0552750000
_diffrn_orient_matrix_UB_22      -0.0394808000
_diffrn_orient_matrix_UB_23      0.0474448000
_diffrn_orient_matrix_UB_31      -0.0836086000
_diffrn_orient_matrix_UB_32      0.0471071000
_diffrn_orient_matrix_UB_33      0.0136757000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0359
_diffrn_reflns_av_unetI/netI     0.0352
_diffrn_reflns_Laue_measured_fraction_full 0.989
_diffrn_reflns_Laue_measured_fraction_max 0.989
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       28
_diffrn_reflns_limit_k_min       -26
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            31156
_diffrn_reflns_point_group_measured_fraction_full 0.989
_diffrn_reflns_point_group_measured_fraction_max 0.989
_diffrn_reflns_theta_full        66.600
_diffrn_reflns_theta_max         66.600
_diffrn_reflns_theta_min         2.907
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.489
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.65582
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.40.19a (Rigaku Oxford Diffraction, 2018)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.141
_exptl_crystal_description       plate
_exptl_crystal_F_000             2048
_exptl_crystal_size_max          0.5
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.2
_refine_diff_density_max         0.281
_refine_diff_density_min         -0.205
_refine_diff_density_rms         0.040
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.019
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     668
_refine_ls_number_reflns         9650
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.019
_refine_ls_R_factor_all          0.0568
_refine_ls_R_factor_gt           0.0440
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0588P)²+2.0949P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1119
_refine_ls_wR_factor_ref         0.1211
_reflns_Friedel_coverage         0.000
_reflns_number_gt                8200
_reflns_number_total             9650
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d0sc02162h2.cif
_cod_data_source_block           klb-4
_cod_original_cell_volume        5525.81(9)
_cod_database_code               1558374
_shelx_shelxl_version_number     2014/7
_chemical_oxdiff_formula         CBNBr
_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   0.908
_shelx_estimated_absorpt_t_min   0.792
_reflns_odcompleteness_completeness 95.37
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_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:
 C35(H35), C52(H52), C55(H55)
2.b Aromatic/amide H refined with riding coordinates:
 C27(H27), C28(H28), C29(H29), C33(H33), C20(H20), C44(H44), C3(H3), C5(H5),
 C18(H18), C9(H9), C4(H4), C11(H11), C42(H42), C61(H61), C65(H65), C64(H64),
 C63(H63), C62(H62)
2.c Idealised Me refined as rotating group:
 C37(H37A,H37B,H37C), C22(H22A,H22B,H22C), C39(H39A,H39B,H39C), C53(H53A,H53B,
 H53C), C24(H24A,H24B,H24C), C47(H47A,H47B,H47C), C46(H46A,H46B,H46C), C54(H54A,
 H54B,H54C), C56(H56A,H56B,H56C), C58(H58A,H58B,H58C), C13(H13A,H13B,H13C),
 C59(H59A,H59B,H59C), C38(H38A,H38B,H38C), C23(H23A,H23B,H23C), C15(H15A,H15B,
 H15C), C14(H14A,H14B,H14C), C57(H57A,H57B,H57C), C48(H48A,H48B,H48C), C66(H66A,
 H66B,H66C)
;
_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
;
_oxdiff_exptl_absorpt_empirical_full_max 1.435
_oxdiff_exptl_absorpt_empirical_full_min 0.654
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -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
N2 N 0.60317(9) 0.68893(5) 0.65884(6) 0.0208(2) Uani 1 1 d . . . . .
N1 N 0.56262(10) 0.74379(5) 0.64341(6) 0.0230(3) Uani 1 1 d . . . . .
N3 N 0.33304(10) 0.67493(5) 0.70390(6) 0.0244(3) Uani 1 1 d . . . . .
N4 N 0.34077(10) 0.64268(5) 0.60356(6) 0.0257(3) Uani 1 1 d . . . . .
C30 C 0.68680(12) 0.57678(6) 0.64171(7) 0.0246(3) Uani 1 1 d . . . . .
C49 C 0.40368(12) 0.65229(6) 0.66423(7) 0.0218(3) Uani 1 1 d . . . . .
C26 C 0.56823(12) 0.53781(6) 0.72010(7) 0.0246(3) Uani 1 1 d . . . . .
C25 C 0.59870(11) 0.58426(6) 0.68292(7) 0.0226(3) Uani 1 1 d . . . . .
C35 C 0.75986(12) 0.73523(6) 0.61304(7) 0.0232(3) Uani 1 1 d . . . . .
H35 H 0.8254 0.7524 0.6416 0.028 Uiso 1 1 calc R . . . .
C31 C 0.72507(12) 0.62701(6) 0.60677(7) 0.0240(3) Uani 1 1 d . . . . .
C40 C 0.48932(12) 0.54014(6) 0.77326(7) 0.0254(3) Uani 1 1 d . . . . .
C36 C 0.72796(11) 0.68069(6) 0.64824(7) 0.0219(3) Uani 1 1 d . . . . .
C1 C 0.63565(12) 0.84030(6) 0.60338(7) 0.0243(3) Uani 1 1 d . . . . .
C2 C 0.72051(13) 0.87830(6) 0.63463(7) 0.0266(3) Uani 1 1 d . . . . .
C16 C 0.82283(13) 0.86002(6) 0.68360(7) 0.0257(3) Uani 1 1 d . . . . .
C6 C 0.54096(13) 0.86460(6) 0.56161(7) 0.0278(3) Uani 1 1 d . . . . .
C21 C 0.80774(13) 0.83883(6) 0.74770(8) 0.0272(3) Uani 1 1 d . . . . .
C27 C 0.61897(13) 0.48543(6) 0.71275(8) 0.0290(3) Uani 1 1 d . . . . .
H27 H 0.5964 0.4547 0.7364 0.035 Uiso 1 1 calc R . . . .
C28 C 0.70192(13) 0.47860(6) 0.67097(8) 0.0311(3) Uani 1 1 d . . . . .
H28 H 0.7340 0.4434 0.6659 0.037 Uiso 1 1 calc R . . . .
C7 C 0.44015(13) 0.83267(6) 0.52529(8) 0.0283(3) Uani 1 1 d . . . . .
C50 C 0.22349(12) 0.68134(7) 0.66732(8) 0.0309(3) Uani 1 1 d . . . . .
C34 C 0.79165(13) 0.72817(6) 0.54367(8) 0.0279(3) Uani 1 1 d . . . . .
C29 C 0.73704(13) 0.52450(6) 0.63659(8) 0.0291(3) Uani 1 1 d . . . . .
H29 H 0.7950 0.5202 0.6097 0.035 Uiso 1 1 calc R . . . .
C52 C 0.37435(13) 0.69126(7) 0.77493(7) 0.0285(3) Uani 1 1 d . . . . .
H52 H 0.4501 0.6739 0.7870 0.034 Uiso 1 1 calc R . . . .
C45 C 0.53182(13) 0.56019(6) 0.83818(8) 0.0298(3) Uani 1 1 d . . . . .
C17 C 0.93561(13) 0.86964(6) 0.66933(8) 0.0294(3) Uani 1 1 d . . . . .
C37 C 0.80159(12) 0.67545(6) 0.71756(8) 0.0274(3) Uani 1 1 d . . . . .
H37A H 0.7948 0.7092 0.7431 0.041 Uiso 1 1 calc GR . . . .
H37B H 0.8805 0.6700 0.7117 0.041 Uiso 1 1 calc GR . . . .
H37C H 0.7757 0.6440 0.7414 0.041 Uiso 1 1 calc GR . . . .
C32 C 0.74223(14) 0.62767(6) 0.54140(8) 0.0308(3) Uani 1 1 d . . . . .
C33 C 0.78042(14) 0.67897(7) 0.51136(8) 0.0328(3) Uani 1 1 d . . . . .
H33 H 0.7979 0.6773 0.4674 0.039 Uiso 1 1 calc R . . . .
C41 C 0.38100(13) 0.51447(7) 0.76184(8) 0.0301(3) Uani 1 1 d . . . . .
C20 C 0.90406(14) 0.82657(6) 0.79450(8) 0.0326(3) Uani 1 1 d . . . . .
H20 H 0.8934 0.8121 0.8364 0.039 Uiso 1 1 calc R . . . .
C8 C 0.43716(14) 0.81739(7) 0.45711(8) 0.0332(3) Uani 1 1 d . . . . .
C55 C 0.39482(14) 0.62115(7) 0.54541(8) 0.0324(3) Uani 1 1 d . . . . .
H55 H 0.4708 0.6068 0.5643 0.039 Uiso 1 1 calc R . . . .
C12 C 0.34123(13) 0.82579(7) 0.55637(8) 0.0322(3) Uani 1 1 d . . . . .
C44 C 0.46487(15) 0.55426(7) 0.89014(8) 0.0362(4) Uani 1 1 d . . . . .
H44 H 0.4929 0.5680 0.9330 0.043 Uiso 1 1 calc R . . . .
C51 C 0.22851(13) 0.66084(7) 0.60463(8) 0.0312(3) Uani 1 1 d . . . . .
C3 C 0.71004(15) 0.93604(7) 0.62395(8) 0.0345(4) Uani 1 1 d . . . . .
H3 H 0.7666 0.9599 0.6452 0.041 Uiso 1 1 calc R . . . .
C5 C 0.53364(15) 0.92270(7) 0.55168(9) 0.0365(4) Uani 1 1 d . . . . .
H5 H 0.4708 0.9375 0.5237 0.044 Uiso 1 1 calc R . . . .
C18 C 1.02855(14) 0.85690(7) 0.71805(9) 0.0347(4) Uani 1 1 d . . . . .
H18 H 1.1025 0.8632 0.7082 0.042 Uiso 1 1 calc R . . . .
C10 C 0.23591(14) 0.79127(7) 0.45085(9) 0.0370(4) Uani 1 1 d . . . . .
C19 C 1.01503(14) 0.83514(7) 0.78102(9) 0.0356(4) Uani 1 1 d . . . . .
C9 C 0.33491(15) 0.79728(7) 0.42122(8) 0.0367(4) Uani 1 1 d . . . . .
H9 H 0.3331 0.7876 0.3759 0.044 Uiso 1 1 calc R . . . .
C4 C 0.61730(16) 0.95844(7) 0.58241(9) 0.0400(4) Uani 1 1 d . . . . .
H4 H 0.6114 0.9970 0.5753 0.048 Uiso 1 1 calc R . . . .
C11 C 0.24125(14) 0.80482(7) 0.51871(9) 0.0377(4) Uani 1 1 d . . . . .
H11 H 0.1763 0.7998 0.5398 0.045 Uiso 1 1 calc R . . . .
C42 C 0.31746(14) 0.50903(7) 0.81559(9) 0.0364(4) Uani 1 1 d . . . . .
H42 H 0.2458 0.4918 0.8080 0.044 Uiso 1 1 calc R . . . .
C22 C 0.69071(14) 0.83202(7) 0.76858(8) 0.0352(4) Uani 1 1 d . . . . .
H22A H 0.6425 0.8627 0.7510 0.053 Uiso 1 1 calc GR . . . .
H22B H 0.6974 0.8317 0.8171 0.053 Uiso 1 1 calc GR . . . .
H22C H 0.6574 0.7973 0.7510 0.053 Uiso 1 1 calc GR . . . .
C39 C 0.84108(15) 0.77843(7) 0.51290(9) 0.0378(4) Uani 1 1 d . . . . .
H39A H 0.7880 0.8092 0.5115 0.057 Uiso 1 1 calc GR . . . .
H39B H 0.8546 0.7695 0.4678 0.057 Uiso 1 1 calc GR . . . .
H39C H 0.9124 0.7887 0.5398 0.057 Uiso 1 1 calc GR . . . .
C53 C 0.39242(15) 0.75418(7) 0.78009(9) 0.0364(4) Uani 1 1 d . . . . .
H53A H 0.4473 0.7654 0.7513 0.055 Uiso 1 1 calc GR . . . .
H53B H 0.4207 0.7641 0.8261 0.055 Uiso 1 1 calc GR . . . .
H53C H 0.3207 0.7730 0.7661 0.055 Uiso 1 1 calc GR . . . .
C43 C 0.35808(15) 0.52862(7) 0.87997(9) 0.0386(4) Uani 1 1 d . . . . .
C24 C 0.95996(16) 0.89672(7) 0.60462(9) 0.0393(4) Uani 1 1 d . . . . .
H24A H 0.8967 0.8900 0.5695 0.059 Uiso 1 1 calc GR . . . .
H24B H 1.0289 0.8810 0.5917 0.059 Uiso 1 1 calc GR . . . .
H24C H 0.9698 0.9364 0.6115 0.059 Uiso 1 1 calc GR . . . .
C47 C 0.33408(15) 0.49136(8) 0.69321(9) 0.0412(4) Uani 1 1 d . . . . .
H47A H 0.3220 0.5216 0.6611 0.062 Uiso 1 1 calc GR . . . .
H47B H 0.2624 0.4727 0.6957 0.062 Uiso 1 1 calc GR . . . .
H47C H 0.3880 0.4651 0.6791 0.062 Uiso 1 1 calc GR . . . .
C46 C 0.65031(15) 0.58539(7) 0.85311(9) 0.0382(4) Uani 1 1 d . . . . .
H46A H 0.7054 0.5600 0.8385 0.057 Uiso 1 1 calc GR . . . .
H46B H 0.6689 0.5918 0.9009 0.057 Uiso 1 1 calc GR . . . .
H46C H 0.6522 0.6204 0.8294 0.057 Uiso 1 1 calc GR . . . .
C54 C 0.29786(16) 0.66802(8) 0.82366(9) 0.0392(4) Uani 1 1 d . . . . .
H54A H 0.2296 0.6905 0.8214 0.059 Uiso 1 1 calc GR . . . .
H54B H 0.3386 0.6689 0.8689 0.059 Uiso 1 1 calc GR . . . .
H54C H 0.2771 0.6300 0.8115 0.059 Uiso 1 1 calc GR . . . .
C56 C 0.41482(18) 0.66839(8) 0.49811(9) 0.0449(4) Uani 1 1 d . . . . .
H56A H 0.3422 0.6818 0.4757 0.067 Uiso 1 1 calc GR . . . .
H56B H 0.4602 0.6550 0.4650 0.067 Uiso 1 1 calc GR . . . .
H56C H 0.4548 0.6984 0.5235 0.067 Uiso 1 1 calc GR . . . .
B2 B 0.53937(13) 0.64367(7) 0.67623(8) 0.0212(3) Uani 1 1 d . . . . .
C58 C 0.12322(14) 0.70718(9) 0.69406(10) 0.0475(5) Uani 1 1 d . . . . .
H58A H 0.0990 0.6831 0.7280 0.071 Uiso 1 1 calc GR . . . .
H58B H 0.0611 0.7120 0.6577 0.071 Uiso 1 1 calc GR . . . .
H58C H 0.1451 0.7431 0.7137 0.071 Uiso 1 1 calc GR . . . .
C13 C 0.34159(16) 0.84225(9) 0.62900(9) 0.0461(4) Uani 1 1 d . . . . .
H13A H 0.4082 0.8267 0.6561 0.069 Uiso 1 1 calc GR . . . .
H13B H 0.2735 0.8281 0.6446 0.069 Uiso 1 1 calc GR . . . .
H13C H 0.3434 0.8824 0.6328 0.069 Uiso 1 1 calc GR . . . .
C59 C 0.13441(16) 0.65781(9) 0.54585(10) 0.0478(5) Uani 1 1 d . . . . .
H59A H 0.1611 0.6731 0.5064 0.072 Uiso 1 1 calc GR . . . .
H59B H 0.0694 0.6790 0.5558 0.072 Uiso 1 1 calc GR . . . .
H59C H 0.1123 0.6193 0.5375 0.072 Uiso 1 1 calc GR . . . .
B1 B 0.64648(14) 0.77441(7) 0.61802(8) 0.0229(3) Uani 1 1 d . . . . .
C38 C 0.7216(2) 0.57770(8) 0.49479(9) 0.0485(5) Uani 1 1 d . . . . .
H38A H 0.7925 0.5578 0.4942 0.073 Uiso 1 1 calc GR . . . .
H38B H 0.6930 0.5903 0.4499 0.073 Uiso 1 1 calc GR . . . .
H38C H 0.6663 0.5532 0.5106 0.073 Uiso 1 1 calc GR . . . .
C23 C 1.11662(17) 0.82329(9) 0.83428(10) 0.0518(5) Uani 1 1 d . . . . .
H23A H 1.0985 0.8341 0.8779 0.078 Uiso 1 1 calc GR . . . .
H23B H 1.1819 0.8443 0.8244 0.078 Uiso 1 1 calc GR . . . .
H23C H 1.1341 0.7839 0.8345 0.078 Uiso 1 1 calc GR . . . .
C15 C 0.54162(17) 0.82337(10) 0.42221(10) 0.0510(5) Uani 1 1 d . . . . .
H15A H 0.5711 0.8609 0.4284 0.077 Uiso 1 1 calc GR . . . .
H15B H 0.5211 0.8159 0.3747 0.077 Uiso 1 1 calc GR . . . .
H15C H 0.5993 0.7971 0.4412 0.077 Uiso 1 1 calc GR . . . .
C14 C 0.12500(17) 0.77167(9) 0.40997(11) 0.0520(5) Uani 1 1 d . . . . .
H14A H 0.1299 0.7757 0.3626 0.078 Uiso 1 1 calc GR . . . .
H14B H 0.0624 0.7939 0.4214 0.078 Uiso 1 1 calc GR . . . .
H14C H 0.1123 0.7329 0.4199 0.078 Uiso 1 1 calc GR . . . .
C60 C 1.01821(16) 0.51313(10) 0.71901(12) 0.0551(5) Uani 1 1 d . . . . .
C57 C 0.3294(2) 0.57225(9) 0.50998(11) 0.0604(6) Uani 1 1 d . . . . .
H57A H 0.3078 0.5466 0.5431 0.091 Uiso 1 1 calc GR . . . .
H57B H 0.3772 0.5532 0.4821 0.091 Uiso 1 1 calc GR . . . .
H57C H 0.2615 0.5859 0.4823 0.091 Uiso 1 1 calc GR . . . .
C48 C 0.2877(2) 0.52159(11) 0.93739(11) 0.0629(6) Uani 1 1 d . . . . .
H48A H 0.3372 0.5103 0.9776 0.094 Uiso 1 1 calc GR . . . .
H48B H 0.2300 0.4934 0.9255 0.094 Uiso 1 1 calc GR . . . .
H48C H 0.2515 0.5566 0.9454 0.094 Uiso 1 1 calc GR . . . .
C61 C 1.01598(18) 0.45582(10) 0.72582(14) 0.0628(6) Uani 1 1 d . . . . .
H61 H 1.0077 0.4401 0.7675 0.075 Uiso 1 1 calc R . . . .
C65 C 1.03255(19) 0.53557(12) 0.65708(13) 0.0662(6) Uani 1 1 d . . . . .
H65 H 1.0354 0.5744 0.6520 0.079 Uiso 1 1 calc R . . . .
C66 C 1.0039(2) 0.55085(11) 0.77853(14) 0.0718(7) Uani 1 1 d . . . . .
H66A H 0.9240 0.5596 0.7778 0.108 Uiso 1 1 calc GR . . . .
H66B H 1.0466 0.5849 0.7755 0.108 Uiso 1 1 calc GR . . . .
H66C H 1.0321 0.5319 0.8200 0.108 Uiso 1 1 calc GR . . . .
C64 C 1.0426(2) 0.50152(14) 0.60299(14) 0.0744(7) Uani 1 1 d . . . . .
H64 H 1.0527 0.5175 0.5617 0.089 Uiso 1 1 calc R . . . .
C63 C 1.0380(2) 0.44415(15) 0.60888(16) 0.0849(9) Uani 1 1 d . . . . .
H63 H 1.0428 0.4212 0.5716 0.102 Uiso 1 1 calc R . . . .
C62 C 1.0260(2) 0.42096(13) 0.67096(18) 0.0826(8) Uani 1 1 d . . . . .
H62 H 1.0247 0.3821 0.6761 0.099 Uiso 1 1 calc R . . . .
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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'
B B 0.0090 0.0039 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 '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
N1 N2 C36 113.03(10) . . ?
B2 N2 N1 126.69(11) . . ?
B2 N2 C36 120.05(11) . . ?
B1 N1 N2 109.46(11) . . ?
C49 N3 C50 109.76(12) . . ?
C49 N3 C52 121.61(12) . . ?
C50 N3 C52 128.60(12) . . ?
C49 N4 C55 121.23(12) . . ?
C49 N4 C51 109.54(12) . . ?
C51 N4 C55 128.94(13) . . ?
C25 C30 C31 117.67(12) . . ?
C29 C30 C25 120.49(13) . . ?
C29 C30 C31 121.81(13) . . ?
N3 C49 N4 107.03(12) . . ?
N3 C49 B2 130.90(12) . . ?
N4 C49 B2 121.62(12) . . ?
C25 C26 C40 124.85(13) . . ?
C27 C26 C25 120.10(13) . . ?
C27 C26 C40 114.88(13) . . ?
C30 C25 B2 114.43(12) . . ?
C26 C25 C30 117.88(13) . . ?
C26 C25 B2 127.48(13) . . ?
C36 C35 H35 107.8 . . ?
C36 C35 B1 101.44(11) . . ?
C34 C35 H35 107.8 . . ?
C34 C35 C36 115.79(12) . . ?
C34 C35 B1 115.59(12) . . ?
B1 C35 H35 107.8 . . ?
C30 C31 C36 113.95(12) . . ?
C32 C31 C30 124.08(13) . . ?
C32 C31 C36 121.48(13) . . ?
C45 C40 C26 119.25(13) . . ?
C41 C40 C26 120.36(13) . . ?
C41 C40 C45 119.61(14) . . ?
N2 C36 C35 104.77(10) . . ?
N2 C36 C37 108.49(11) . . ?
C31 C36 N2 103.65(10) . . ?
C31 C36 C35 116.50(12) . . ?
C31 C36 C37 112.96(12) . . ?
C37 C36 C35 109.69(11) . . ?
C2 C1 B1 120.76(12) . . ?
C6 C1 C2 116.21(13) . . ?
C6 C1 B1 122.99(13) . . ?
C1 C2 C16 123.19(13) . . ?
C3 C2 C1 121.25(14) . . ?
C3 C2 C16 115.49(13) . . ?
C21 C16 C2 120.14(13) . . ?
C21 C16 C17 118.90(14) . . ?
C17 C16 C2 120.58(13) . . ?
C1 C6 C7 125.22(13) . . ?
C5 C6 C1 121.00(14) . . ?
C5 C6 C7 113.77(13) . . ?
C16 C21 C22 121.92(14) . . ?
C20 C21 C16 119.27(14) . . ?
C20 C21 C22 118.72(14) . . ?
C26 C27 H27 119.4 . . ?
C28 C27 C26 121.12(14) . . ?
C28 C27 H27 119.4 . . ?
C27 C28 H28 120.2 . . ?
C27 C28 C29 119.51(14) . . ?
C29 C28 H28 120.2 . . ?
C8 C7 C6 120.51(14) . . ?
C12 C7 C6 119.41(14) . . ?
C12 C7 C8 119.34(14) . . ?
N3 C50 C58 125.05(15) . . ?
C51 C50 N3 106.65(13) . . ?
C51 C50 C58 128.29(15) . . ?
C35 C34 C39 116.90(13) . . ?
C33 C34 C35 121.72(14) . . ?
C33 C34 C39 121.34(14) . . ?
C30 C29 H29 119.6 . . ?
C28 C29 C30 120.78(14) . . ?
C28 C29 H29 119.6 . . ?
N3 C52 H52 106.7 . . ?
N3 C52 C53 110.36(13) . . ?
N3 C52 C54 111.91(13) . . ?
C53 C52 H52 106.7 . . ?
C53 C52 C54 113.99(13) . . ?
C54 C52 H52 106.7 . . ?
C40 C45 C46 121.03(14) . . ?
C44 C45 C40 119.16(15) . . ?
C44 C45 C46 119.74(15) . . ?
C16 C17 C24 122.66(14) . . ?
C18 C17 C16 119.36(15) . . ?
C18 C17 C24 117.87(15) . . ?
C36 C37 H37A 109.5 . . ?
C36 C37 H37B 109.5 . . ?
C36 C37 H37C 109.5 . . ?
H37A C37 H37B 109.5 . . ?
H37A C37 H37C 109.5 . . ?
H37B C37 H37C 109.5 . . ?
C31 C32 C33 120.28(14) . . ?
C31 C32 C38 123.69(15) . . ?
C33 C32 C38 116.01(14) . . ?
C34 C33 C32 123.46(14) . . ?
C34 C33 H33 118.3 . . ?
C32 C33 H33 118.3 . . ?
C40 C41 C47 120.93(14) . . ?
C42 C41 C40 119.19(15) . . ?
C42 C41 C47 119.86(15) . . ?
C21 C20 H20 118.7 . . ?
C19 C20 C21 122.51(15) . . ?
C19 C20 H20 118.7 . . ?
C7 C8 C15 121.02(15) . . ?
C9 C8 C7 119.23(15) . . ?
C9 C8 C15 119.74(15) . . ?
N4 C55 H55 106.6 . . ?
N4 C55 C56 110.64(13) . . ?
N4 C55 C57 112.56(15) . . ?
C56 C55 H55 106.6 . . ?
C56 C55 C57 113.26(15) . . ?
C57 C55 H55 106.6 . . ?
C7 C12 C13 120.51(15) . . ?
C11 C12 C7 119.42(15) . . ?
C11 C12 C13 120.05(15) . . ?
C45 C44 H44 119.0 . . ?
C43 C44 C45 122.05(15) . . ?
C43 C44 H44 119.0 . . ?
N4 C51 C59 124.76(15) . . ?
C50 C51 N4 107.00(13) . . ?
C50 C51 C59 128.24(15) . . ?
C2 C3 H3 119.4 . . ?
C4 C3 C2 121.21(15) . . ?
C4 C3 H3 119.4 . . ?
C6 C5 H5 119.3 . . ?
C4 C5 C6 121.50(15) . . ?
C4 C5 H5 119.3 . . ?
C17 C18 H18 118.8 . . ?
C17 C18 C19 122.36(15) . . ?
C19 C18 H18 118.8 . . ?
C9 C10 C14 120.93(17) . . ?
C11 C10 C9 117.98(15) . . ?
C11 C10 C14 121.08(17) . . ?
C20 C19 C18 117.58(15) . . ?
C20 C19 C23 120.59(17) . . ?
C18 C19 C23 121.78(17) . . ?
C8 C9 H9 119.0 . . ?
C10 C9 C8 122.09(15) . . ?
C10 C9 H9 119.0 . . ?
C3 C4 H4 120.6 . . ?
C5 C4 C3 118.83(15) . . ?
C5 C4 H4 120.6 . . ?
C12 C11 H11 119.1 . . ?
C10 C11 C12 121.89(16) . . ?
C10 C11 H11 119.1 . . ?
C41 C42 H42 119.0 . . ?
C43 C42 C41 121.94(16) . . ?
C43 C42 H42 119.0 . . ?
C21 C22 H22A 109.5 . . ?
C21 C22 H22B 109.5 . . ?
C21 C22 H22C 109.5 . . ?
H22A C22 H22B 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
C34 C39 H39A 109.5 . . ?
C34 C39 H39B 109.5 . . ?
C34 C39 H39C 109.5 . . ?
H39A C39 H39B 109.5 . . ?
H39A C39 H39C 109.5 . . ?
H39B C39 H39C 109.5 . . ?
C52 C53 H53A 109.5 . . ?
C52 C53 H53B 109.5 . . ?
C52 C53 H53C 109.5 . . ?
H53A C53 H53B 109.5 . . ?
H53A C53 H53C 109.5 . . ?
H53B C53 H53C 109.5 . . ?
C44 C43 C42 118.04(15) . . ?
C44 C43 C48 121.23(17) . . ?
C42 C43 C48 120.73(18) . . ?
C17 C24 H24A 109.5 . . ?
C17 C24 H24B 109.5 . . ?
C17 C24 H24C 109.5 . . ?
H24A C24 H24B 109.5 . . ?
H24A C24 H24C 109.5 . . ?
H24B C24 H24C 109.5 . . ?
C41 C47 H47A 109.5 . . ?
C41 C47 H47B 109.5 . . ?
C41 C47 H47C 109.5 . . ?
H47A C47 H47B 109.5 . . ?
H47A C47 H47C 109.5 . . ?
H47B C47 H47C 109.5 . . ?
C45 C46 H46A 109.5 . . ?
C45 C46 H46B 109.5 . . ?
C45 C46 H46C 109.5 . . ?
H46A C46 H46B 109.5 . . ?
H46A C46 H46C 109.5 . . ?
H46B C46 H46C 109.5 . . ?
C52 C54 H54A 109.5 . . ?
C52 C54 H54B 109.5 . . ?
C52 C54 H54C 109.5 . . ?
H54A C54 H54B 109.5 . . ?
H54A C54 H54C 109.5 . . ?
H54B C54 H54C 109.5 . . ?
C55 C56 H56A 109.5 . . ?
C55 C56 H56B 109.5 . . ?
C55 C56 H56C 109.5 . . ?
H56A C56 H56B 109.5 . . ?
H56A C56 H56C 109.5 . . ?
H56B C56 H56C 109.5 . . ?
N2 B2 C49 115.37(12) . . ?
N2 B2 C25 118.12(12) . . ?
C25 B2 C49 123.42(12) . . ?
C50 C58 H58A 109.5 . . ?
C50 C58 H58B 109.5 . . ?
C50 C58 H58C 109.5 . . ?
H58A C58 H58B 109.5 . . ?
H58A C58 H58C 109.5 . . ?
H58B C58 H58C 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 . . ?
C51 C59 H59A 109.5 . . ?
C51 C59 H59B 109.5 . . ?
C51 C59 H59C 109.5 . . ?
H59A C59 H59B 109.5 . . ?
H59A C59 H59C 109.5 . . ?
H59B C59 H59C 109.5 . . ?
N1 B1 C35 110.52(12) . . ?
N1 B1 C1 122.95(13) . . ?
C1 B1 C35 126.26(12) . . ?
C32 C38 H38A 109.5 . . ?
C32 C38 H38B 109.5 . . ?
C32 C38 H38C 109.5 . . ?
H38A C38 H38B 109.5 . . ?
H38A C38 H38C 109.5 . . ?
H38B C38 H38C 109.5 . . ?
C19 C23 H23A 109.5 . . ?
C19 C23 H23B 109.5 . . ?
C19 C23 H23C 109.5 . . ?
H23A C23 H23B 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 109.5 . . ?
C8 C15 H15A 109.5 . . ?
C8 C15 H15B 109.5 . . ?
C8 C15 H15C 109.5 . . ?
H15A C15 H15B 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 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 . . ?
C61 C60 C65 118.7(2) . . ?
C61 C60 C66 120.3(2) . . ?
C65 C60 C66 120.9(2) . . ?
C55 C57 H57A 109.5 . . ?
C55 C57 H57B 109.5 . . ?
C55 C57 H57C 109.5 . . ?
H57A C57 H57B 109.5 . . ?
H57A C57 H57C 109.5 . . ?
H57B C57 H57C 109.5 . . ?
C43 C48 H48A 109.5 . . ?
C43 C48 H48B 109.5 . . ?
C43 C48 H48C 109.5 . . ?
H48A C48 H48B 109.5 . . ?
H48A C48 H48C 109.5 . . ?
H48B C48 H48C 109.5 . . ?
C60 C61 H61 119.7 . . ?
C60 C61 C62 120.7(3) . . ?
C62 C61 H61 119.7 . . ?
C60 C65 H65 119.6 . . ?
C64 C65 C60 120.9(3) . . ?
C64 C65 H65 119.6 . . ?
C60 C66 H66A 109.5 . . ?
C60 C66 H66B 109.5 . . ?
C60 C66 H66C 109.5 . . ?
H66A C66 H66B 109.5 . . ?
H66A C66 H66C 109.5 . . ?
H66B C66 H66C 109.5 . . ?
C65 C64 H64 119.6 . . ?
C65 C64 C63 120.9(3) . . ?
C63 C64 H64 119.6 . . ?
C64 C63 H63 120.5 . . ?
C64 C63 C62 119.0(3) . . ?
C62 C63 H63 120.5 . . ?
C61 C62 H62 120.1 . . ?
C63 C62 C61 119.9(3) . . ?
C63 C62 H62 120.1 . . ?
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
N2 N1 1.4091(16) . ?
N2 C36 1.5235(17) . ?
N2 B2 1.384(2) . ?
N1 B1 1.379(2) . ?
N3 C49 1.3390(18) . ?
N3 C50 1.3951(19) . ?
N3 C52 1.4837(19) . ?
N4 C49 1.3458(19) . ?
N4 C55 1.4906(19) . ?
N4 C51 1.391(2) . ?
C30 C25 1.422(2) . ?
C30 C31 1.486(2) . ?
C30 C29 1.387(2) . ?
C49 B2 1.592(2) . ?
C26 C25 1.406(2) . ?
C26 C40 1.506(2) . ?
C26 C27 1.399(2) . ?
C25 B2 1.574(2) . ?
C35 H35 0.9800 . ?
C35 C36 1.5472(19) . ?
C35 C34 1.494(2) . ?
C35 B1 1.641(2) . ?
C31 C36 1.5202(19) . ?
C31 C32 1.348(2) . ?
C40 C45 1.404(2) . ?
C40 C41 1.401(2) . ?
C36 C37 1.529(2) . ?
C1 C2 1.423(2) . ?
C1 C6 1.416(2) . ?
C1 B1 1.597(2) . ?
C2 C16 1.502(2) . ?
C2 C3 1.394(2) . ?
C16 C21 1.409(2) . ?
C16 C17 1.413(2) . ?
C6 C7 1.504(2) . ?
C6 C5 1.398(2) . ?
C21 C20 1.392(2) . ?
C21 C22 1.501(2) . ?
C27 H27 0.9300 . ?
C27 C28 1.379(2) . ?
C28 H28 0.9300 . ?
C28 C29 1.384(2) . ?
C7 C8 1.404(2) . ?
C7 C12 1.403(2) . ?
C50 C51 1.352(2) . ?
C50 C58 1.493(2) . ?
C34 C33 1.334(2) . ?
C34 C39 1.499(2) . ?
C29 H29 0.9300 . ?
C52 H52 0.9800 . ?
C52 C53 1.514(2) . ?
C52 C54 1.519(2) . ?
C45 C44 1.395(2) . ?
C45 C46 1.507(2) . ?
C17 C18 1.389(2) . ?
C17 C24 1.507(2) . ?
C37 H37A 0.9600 . ?
C37 H37B 0.9600 . ?
C37 H37C 0.9600 . ?
C32 C33 1.459(2) . ?
C32 C38 1.508(2) . ?
C33 H33 0.9300 . ?
C41 C42 1.397(2) . ?
C41 C47 1.506(2) . ?
C20 H20 0.9300 . ?
C20 C19 1.383(2) . ?
C8 C9 1.393(2) . ?
C8 C15 1.502(2) . ?
C55 H55 0.9800 . ?
C55 C56 1.508(2) . ?
C55 C57 1.514(3) . ?
C12 C11 1.394(2) . ?
C12 C13 1.501(2) . ?
C44 H44 0.9300 . ?
C44 C43 1.384(3) . ?
C51 C59 1.495(2) . ?
C3 H3 0.9300 . ?
C3 C4 1.379(2) . ?
C5 H5 0.9300 . ?
C5 C4 1.377(3) . ?
C18 H18 0.9300 . ?
C18 C19 1.389(3) . ?
C10 C9 1.385(3) . ?
C10 C11 1.385(3) . ?
C10 C14 1.510(2) . ?
C19 C23 1.508(2) . ?
C9 H9 0.9300 . ?
C4 H4 0.9300 . ?
C11 H11 0.9300 . ?
C42 H42 0.9300 . ?
C42 C43 1.386(3) . ?
C22 H22A 0.9600 . ?
C22 H22B 0.9600 . ?
C22 H22C 0.9600 . ?
C39 H39A 0.9600 . ?
C39 H39B 0.9600 . ?
C39 H39C 0.9600 . ?
C53 H53A 0.9600 . ?
C53 H53B 0.9600 . ?
C53 H53C 0.9600 . ?
C43 C48 1.514(2) . ?
C24 H24A 0.9600 . ?
C24 H24B 0.9600 . ?
C24 H24C 0.9600 . ?
C47 H47A 0.9600 . ?
C47 H47B 0.9600 . ?
C47 H47C 0.9600 . ?
C46 H46A 0.9600 . ?
C46 H46B 0.9600 . ?
C46 H46C 0.9600 . ?
C54 H54A 0.9600 . ?
C54 H54B 0.9600 . ?
C54 H54C 0.9600 . ?
C56 H56A 0.9600 . ?
C56 H56B 0.9600 . ?
C56 H56C 0.9600 . ?
C58 H58A 0.9600 . ?
C58 H58B 0.9600 . ?
C58 H58C 0.9600 . ?
C13 H13A 0.9600 . ?
C13 H13B 0.9600 . ?
C13 H13C 0.9600 . ?
C59 H59A 0.9600 . ?
C59 H59B 0.9600 . ?
C59 H59C 0.9600 . ?
C38 H38A 0.9600 . ?
C38 H38B 0.9600 . ?
C38 H38C 0.9600 . ?
C23 H23A 0.9600 . ?
C23 H23B 0.9600 . ?
C23 H23C 0.9600 . ?
C15 H15A 0.9600 . ?
C15 H15B 0.9600 . ?
C15 H15C 0.9600 . ?
C14 H14A 0.9600 . ?
C14 H14B 0.9600 . ?
C14 H14C 0.9600 . ?
C60 C61 1.372(3) . ?
C60 C65 1.378(3) . ?
C60 C66 1.517(4) . ?
C57 H57A 0.9600 . ?
C57 H57B 0.9600 . ?
C57 H57C 0.9600 . ?
C48 H48A 0.9600 . ?
C48 H48B 0.9600 . ?
C48 H48C 0.9600 . ?
C61 H61 0.9300 . ?
C61 C62 1.392(4) . ?
C65 H65 0.9300 . ?
C65 C64 1.368(4) . ?
C66 H66A 0.9600 . ?
C66 H66B 0.9600 . ?
C66 H66C 0.9600 . ?
C64 H64 0.9300 . ?
C64 C63 1.372(4) . ?
C63 H63 0.9300 . ?
C63 C62 1.382(4) . ?
C62 H62 0.9300 . ?
