#------------------------------------------------------------------------------
#$Date: 2024-10-04 20:22:16 +0200 (Fri 04 de Oct de 2024) $
#$Revision: 295056 $
#$URL: svn://www.crystallography.net/cod/cif/7/71/71/7717157.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_7717157
loop_
_publ_author_name
'Calder, Ethan D. E.'
'Male, Louise'
'Jupp, Andrew R.'
_publ_section_title
;
 Accessing five- and seven-membered phosphorus-based heterocycles
 via cycloaddition reactions of azophosphines.
;
_journal_issue                   36
_journal_name_full
'Dalton transactions (Cambridge, England : 2003)'
_journal_page_first              15032
_journal_page_last               15039
_journal_paper_doi               10.1039/d4dt02248c
_journal_volume                  53
_journal_year                    2024
_chemical_formula_moiety         'C37 H53 N2 O8 P'
_chemical_formula_sum            'C37 H53 N2 O8 P'
_chemical_formula_weight         684.78
_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             2024-05-01
_audit_creation_method
;
Olex2 1.5
(compiled 2024.02.16 svn.r378c4104 for OlexSys, GUI svn.r6928)
;
_audit_update_record
;
2024-05-17 deposited with the CCDC.	2024-08-07 downloaded from the CCDC.
;
_cell_angle_alpha                110.174(3)
_cell_angle_beta                 93.849(3)
_cell_angle_gamma                98.359(3)
_cell_formula_units_Z            2
_cell_length_a                   11.0797(3)
_cell_length_b                   12.5123(4)
_cell_length_c                   13.9655(5)
_cell_measurement_reflns_used    15826
_cell_measurement_temperature    99.98(13)
_cell_measurement_theta_max      72.6790
_cell_measurement_theta_min      3.7510
_cell_volume                     1783.60(11)
_computing_cell_refinement       'CrysAlisPro 1.171.42.73a (Rigaku OD, 2022)'
_computing_data_collection       'CrysAlisPro 1.171.42.73a (Rigaku OD, 2022)'
_computing_data_reduction        'CrysAlisPro 1.171.42.73a (Rigaku OD, 2022)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2019/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      99.98(13)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.3537
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.986
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -69.00  32.00   1.00    3.41    --  -41.27  57.00 150.00  101
  2  ω    -87.00  -6.00   1.00    3.41    --  -41.27 125.00-150.00   81
  3  ω   -113.00 -13.00   1.00    3.41    --  -41.27 -57.00   0.00  100
  4  ω   -113.00 -13.00   1.00    3.41    --  -41.27 -57.00-120.00  100
  5  ω     29.00 108.00   1.00   13.64    --  102.80-111.00  60.00   79
  6  ω     31.00 132.00   1.00   13.64    --  102.80 -61.00 -60.00  101
  7  ω     31.00 132.00   1.00   13.64    --  102.80 -61.00 150.00  101
  8  ω    104.00 176.00   1.00   13.64    --  102.80 111.00-150.00   72
  9  ω     27.00 131.00   1.00   13.64    --  102.80 -30.00  90.00  104
 10  ω    103.00 178.00   1.00   13.64    --  102.80  77.00  60.00   75
 11  ω     29.00 108.00   1.00   13.64    --  102.80-111.00-180.00   79
 12  ω     29.00 108.00   1.00   13.64    --  102.80-111.00 -30.00   79
 13  ω     29.00 108.00   1.00   13.64    --  102.80-111.00 -90.00   79
 14  ω    103.00 178.00   1.00   13.64    --  102.80  77.00 -90.00   75
 15  ω     50.00 178.00   1.00   13.64    --  102.80  15.00  60.00  128
 16  ω    103.00 178.00   1.00   13.64    --  102.80  80.00 110.00   75
 17  ω     29.00 108.00   1.00   13.64    --  102.80-111.00 150.00   79
 18  ω   -113.00 -13.00   1.00    3.41    --  -41.27 -57.00  60.00  100
 19  ω   -113.00 -13.00   1.00    3.41    --  -41.27 -57.00 120.00  100
 20  ω   -113.00 -13.00   1.00    3.41    --  -41.27 -57.00 -60.00  100
 21  ω    -33.00  66.00   1.00    3.41    --   41.27 -38.00 -30.00   99
 22  ω     13.00 114.00   1.00    3.41    --   41.27  57.00 -90.00  101
 23  ω     74.00 175.00   1.00   13.64    --  102.80  61.00 -90.00  101
 24  ω     74.00 175.00   1.00   13.64    --  102.80  61.00 150.00  101
 25  ω     75.00 178.00   1.00   13.64    --  102.80  30.00-150.00  103
 26  ω     77.00 176.00   1.00   13.64    --  102.80  45.00-120.00   99
 27  ω     74.00 175.00   1.00   13.64    --  102.80  61.00  60.00  101
 28  ω     74.00 175.00   1.00   13.64    --  102.80  61.00 -60.00  101
 29  ω     74.00 175.00   1.00   13.64    --  102.80  61.00  90.00  101
 30  ω     74.00 171.00   1.00   13.64    --  102.80  61.00  30.00   97
 31  ω     74.00 175.00   1.00   13.64    --  102.80  61.00 120.00  101
;
_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      0.1254232000
_diffrn_orient_matrix_UB_12      0.0309494000
_diffrn_orient_matrix_UB_13      0.0668839000
_diffrn_orient_matrix_UB_21      -0.0593259000
_diffrn_orient_matrix_UB_22      -0.0497010000
_diffrn_orient_matrix_UB_23      0.0759442000
_diffrn_orient_matrix_UB_31      0.0286375000
_diffrn_orient_matrix_UB_32      -0.1198059000
_diffrn_orient_matrix_UB_33      -0.0615971000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0464
_diffrn_reflns_av_unetI/netI     0.0330
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.986
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            33249
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.986
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         72.745
_diffrn_reflns_theta_min         3.826
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    1.123
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.823
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.42.73a (Rigaku Oxford Diffraction, 2022)
Numerical absorption correction based on gaussian integration over
a multifaceted crystal model
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    1.275
_exptl_crystal_description       block
_exptl_crystal_F_000             736
_exptl_crystal_preparation       'Slow evaporation of hexane'
_exptl_crystal_size_max          0.171
_exptl_crystal_size_mid          0.103
_exptl_crystal_size_min          0.075
_refine_diff_density_max         0.287
_refine_diff_density_min         -0.385
_refine_diff_density_rms         0.045
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.027
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     440
_refine_ls_number_reflns         7013
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.027
_refine_ls_R_factor_all          0.0480
_refine_ls_R_factor_gt           0.0384
_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)+(0.0405P)²+0.8367P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0915
_refine_ls_wR_factor_ref         0.0981
_reflns_Friedel_coverage         0.000
_reflns_number_gt                5955
_reflns_number_total             7013
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d4dt02248c2.cif
_cod_data_source_block           edec_098_c_gaussian
_cod_original_cell_volume        1783.60(10)
_cod_database_code               7717157
_shelx_shelxl_version_number     2019/3
_chemical_oxdiff_formula         'C11 H10 N O'
_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   0.920
_shelx_estimated_absorpt_t_min   0.831
_reflns_odcompleteness_completeness 99.95
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_olex2_refinement_description
;
1.a Ternary CH refined with riding coordinates:
 C26(H26), C32(H32)
1.b Secondary CH2 refined with riding coordinates:
 C31(H31A,H31B), C30(H30A,H30B), C29(H29A,H29B), C28(H28A,H28B), C27(H27A,
 H27B), C33(H33A,H33B), C34(H34A,H34B), C35(H35A,H35B), C36(H36A,H36B),
 C37(H37A,H37B), C18(H18A,H18B), C20(H20A,H20B), C22(H22A,H22B), C24(H24A,H24B)
1.c Aromatic/amide H refined with riding coordinates:
 C3(H3), C5(H5)
1.d Idealised Me refined as rotating group:
 C7(H7A,H7B,H7C), C8(H8A,H8B,H8C), C9(H9A,H9B,H9C), C19(H19A,H19B,H19C),
 C21(H21A,H21B,H21C), C23(H23A,H23B,H23C), C25(H25A,H25B,H25C)
;
_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 1.364
_oxdiff_exptl_absorpt_empirical_full_min 0.734
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 0.75509(14) 0.22906(13) 0.43625(11) 0.0203(3) Uani 1 1 d . . . . .
C2 C 0.66421(14) 0.17340(13) 0.47672(12) 0.0221(3) Uani 1 1 d . . . . .
C3 C 0.69119(15) 0.17768(14) 0.57690(12) 0.0246(3) Uani 1 1 d . . . . .
H3 H 0.630870 0.140532 0.605897 0.030 Uiso 1 1 calc R U . . .
C4 C 0.80380(15) 0.23467(14) 0.63617(12) 0.0244(3) Uani 1 1 d . . . . .
C5 C 0.89136(14) 0.28912(14) 0.59307(12) 0.0242(3) Uani 1 1 d . . . . .
H5 H 0.968493 0.327961 0.632642 0.029 Uiso 1 1 calc R U . . .
C6 C 0.86881(14) 0.28811(13) 0.49333(12) 0.0223(3) Uani 1 1 d . . . . .
C7 C 0.54311(15) 0.10816(15) 0.41379(13) 0.0282(3) Uani 1 1 d . . . . .
H7A H 0.557924 0.047443 0.351499 0.042 Uiso 1 1 calc R U . . .
H7B H 0.499019 0.161661 0.394556 0.042 Uiso 1 1 calc R U . . .
H7C H 0.493566 0.072908 0.454351 0.042 Uiso 1 1 calc R U . . .
C8 C 0.96533(15) 0.34847(15) 0.44944(13) 0.0287(4) Uani 1 1 d . . . . .
H8A H 1.029287 0.399105 0.504870 0.043 Uiso 1 1 calc R U . . .
H8B H 0.927496 0.394869 0.416106 0.043 Uiso 1 1 calc R U . . .
H8C H 1.002099 0.290757 0.398731 0.043 Uiso 1 1 calc R U . . .
C9 C 0.83119(17) 0.23678(16) 0.74423(13) 0.0309(4) Uani 1 1 d . . . . .
H9A H 0.786917 0.291311 0.790571 0.046 Uiso 1 1 calc R U . . .
H9B H 0.919781 0.261214 0.766630 0.046 Uiso 1 1 calc R U . . .
H9C H 0.804650 0.159181 0.745623 0.046 Uiso 1 1 calc R U . . .
C26 C 0.93061(13) 0.33347(13) 0.08936(11) 0.0206(3) Uani 1 1 d . . . . .
H26 H 0.920882 0.399086 0.065874 0.025 Uiso 1 1 calc R U . . .
C31 C 0.97854(14) 0.24429(14) 0.00063(12) 0.0245(3) Uani 1 1 d . . . . .
H31A H 0.998197 0.180435 0.021928 0.029 Uiso 1 1 calc R U . . .
H31B H 0.914427 0.211161 -0.059735 0.029 Uiso 1 1 calc R U . . .
C30 C 1.09427(15) 0.30366(16) -0.02809(14) 0.0302(4) Uani 1 1 d . . . . .
H30A H 1.128182 0.245014 -0.081768 0.036 Uiso 1 1 calc R U . . .
H30B H 1.071667 0.360905 -0.057184 0.036 Uiso 1 1 calc R U . . .
C29 C 1.19269(15) 0.36464(15) 0.06412(15) 0.0317(4) Uani 1 1 d . . . . .
H29A H 1.225792 0.306020 0.085767 0.038 Uiso 1 1 calc R U . . .
H29B H 1.261191 0.409074 0.043845 0.038 Uiso 1 1 calc R U . . .
C28 C 1.14215(14) 0.44631(15) 0.15420(13) 0.0288(4) Uani 1 1 d . . . . .
H28A H 1.119291 0.510951 0.135691 0.035 Uiso 1 1 calc R U . . .
H28B H 1.206826 0.479377 0.214160 0.035 Uiso 1 1 calc R U . . .
C27 C 1.02937(14) 0.38388(15) 0.18352(12) 0.0250(3) Uani 1 1 d . . . . .
H27A H 0.997537 0.438876 0.241625 0.030 Uiso 1 1 calc R U . . .
H27B H 1.051955 0.321041 0.204962 0.030 Uiso 1 1 calc R U . . .
C32 C 0.66807(13) 0.25126(13) 0.00896(11) 0.0200(3) Uani 1 1 d . . . . .
H32 H 0.701693 0.200423 -0.051667 0.024 Uiso 1 1 calc R U . . .
C33 C 0.64752(15) 0.36045(14) -0.01236(12) 0.0257(3) Uani 1 1 d . . . . .
H33A H 0.615852 0.413467 0.047135 0.031 Uiso 1 1 calc R U . . .
H33B H 0.726611 0.401325 -0.021933 0.031 Uiso 1 1 calc R U . . .
C34 C 0.55521(16) 0.32697(16) -0.10918(13) 0.0304(4) Uani 1 1 d . . . . .
H34A H 0.538800 0.398006 -0.119851 0.036 Uiso 1 1 calc R U . . .
H34B H 0.591130 0.280900 -0.169663 0.036 Uiso 1 1 calc R U . . .
C35 C 0.43482(16) 0.25694(18) -0.10055(14) 0.0361(4) Uani 1 1 d . . . . .
H35A H 0.394014 0.306198 -0.045255 0.043 Uiso 1 1 calc R U . . .
H35B H 0.379510 0.232436 -0.165915 0.043 Uiso 1 1 calc R U . . .
C36 C 0.45577(15) 0.15072(17) -0.07714(14) 0.0336(4) Uani 1 1 d . . . . .
H36A H 0.488075 0.097299 -0.135964 0.040 Uiso 1 1 calc R U . . .
H36B H 0.376421 0.109798 -0.068062 0.040 Uiso 1 1 calc R U . . .
C37 C 0.54646(14) 0.18350(15) 0.02001(13) 0.0264(3) Uani 1 1 d . . . . .
H37A H 0.561329 0.112559 0.031659 0.032 Uiso 1 1 calc R U . . .
H37B H 0.511276 0.231357 0.080107 0.032 Uiso 1 1 calc R U . . .
C10 C 0.78097(13) 0.16055(13) 0.25480(11) 0.0197(3) Uani 1 1 d . . . . .
C11 C 0.78643(13) 0.16173(13) 0.15660(11) 0.0200(3) Uani 1 1 d . . . . .
C12 C 0.64781(13) 0.36658(13) 0.28320(11) 0.0195(3) Uani 1 1 d . . . . .
C13 C 0.74400(13) 0.39562(13) 0.22698(11) 0.0201(3) Uani 1 1 d . . . . .
C14 C 0.82328(14) 0.06192(13) 0.28156(11) 0.0214(3) Uani 1 1 d . . . . .
C15 C 0.81743(13) 0.05701(13) 0.08010(12) 0.0211(3) Uani 1 1 d . . . . .
C16 C 0.53551(13) 0.42555(13) 0.28855(11) 0.0211(3) Uani 1 1 d . . . . .
C17 C 0.77879(13) 0.51424(13) 0.23679(11) 0.0209(3) Uani 1 1 d . . . . .
C18 C 0.99099(19) -0.00352(17) 0.34066(17) 0.0419(5) Uani 1 1 d . . . . .
H18A H 1.003034 -0.067509 0.278474 0.050 Uiso 1 1 calc R U . . .
H18B H 0.932629 -0.035478 0.378818 0.050 Uiso 1 1 calc R U . . .
C19 C 1.11066(19) 0.05242(19) 0.40678(16) 0.0434(5) Uani 1 1 d . . . . .
H19A H 1.167576 0.083637 0.368156 0.065 Uiso 1 1 calc R U . . .
H19B H 1.145626 -0.005001 0.427571 0.065 Uiso 1 1 calc R U . . .
H19C H 1.097487 0.115421 0.468080 0.065 Uiso 1 1 calc R U . . .
C20 C 0.79797(18) -0.05549(15) -0.09889(13) 0.0320(4) Uani 1 1 d . . . . .
H20A H 0.796959 -0.122186 -0.076024 0.038 Uiso 1 1 calc R U . . .
H20B H 0.879600 -0.037573 -0.120216 0.038 Uiso 1 1 calc R U . . .
C21 C 0.69830(19) -0.08318(18) -0.18679(14) 0.0394(4) Uani 1 1 d . . . . .
H21A H 0.710250 -0.151557 -0.243784 0.059 Uiso 1 1 calc R U . . .
H21B H 0.701711 -0.017230 -0.209771 0.059 Uiso 1 1 calc R U . . .
H21C H 0.617973 -0.098785 -0.164132 0.059 Uiso 1 1 calc R U . . .
C22 C 0.40069(14) 0.52518(15) 0.39787(12) 0.0244(3) Uani 1 1 d . . . . .
H22A H 0.385414 0.553288 0.340806 0.029 Uiso 1 1 calc R U . . .
H22B H 0.416671 0.592770 0.463117 0.029 Uiso 1 1 calc R U . . .
C23 C 0.28911(15) 0.44175(16) 0.40004(14) 0.0320(4) Uani 1 1 d . . . . .
H23A H 0.273544 0.374872 0.335436 0.048 Uiso 1 1 calc R U . . .
H23B H 0.217616 0.480448 0.408365 0.048 Uiso 1 1 calc R U . . .
H23C H 0.303588 0.415675 0.457727 0.048 Uiso 1 1 calc R U . . .
C24 C 0.75115(15) 0.70723(14) 0.32839(13) 0.0261(3) Uani 1 1 d . . . . .
H24A H 0.749314 0.715262 0.260252 0.031 Uiso 1 1 calc R U . . .
H24B H 0.832646 0.746276 0.368208 0.031 Uiso 1 1 calc R U . . .
C25 C 0.65130(16) 0.76072(15) 0.38435(14) 0.0320(4) Uani 1 1 d . . . . .
H25A H 0.571307 0.722967 0.343321 0.048 Uiso 1 1 calc R U . . .
H25B H 0.664659 0.843470 0.395329 0.048 Uiso 1 1 calc R U . . .
H25C H 0.652745 0.750642 0.450941 0.048 Uiso 1 1 calc R U . . .
N1 N 0.73166(11) 0.23008(11) 0.33329(10) 0.0203(3) Uani 1 1 d . . . . .
N2 N 0.63523(11) 0.29179(11) 0.32825(10) 0.0210(3) Uani 1 1 d . . . . .
O1 O 0.75228(11) -0.02117(10) 0.28016(9) 0.0276(2) Uani 1 1 d . . . . .
O2 O 0.94346(10) 0.08475(10) 0.31208(9) 0.0265(2) Uani 1 1 d . . . . .
O3 O 0.87129(11) -0.01225(10) 0.09877(9) 0.0276(2) Uani 1 1 d . . . . .
O4 O 0.77348(10) 0.04461(10) -0.01603(8) 0.0255(2) Uani 1 1 d . . . . .
O5 O 0.47932(11) 0.42901(11) 0.21306(9) 0.0292(3) Uani 1 1 d . . . . .
O6 O 0.50770(9) 0.46842(10) 0.38403(8) 0.0229(2) Uani 1 1 d . . . . .
O7 O 0.84727(11) 0.55334(10) 0.18672(9) 0.0287(3) Uani 1 1 d . . . . .
O8 O 0.72984(10) 0.58636(9) 0.31630(8) 0.0248(2) Uani 1 1 d . . . . .
P1 P 0.78069(3) 0.28636(3) 0.12245(3) 0.01786(9) 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 0.0181 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'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
P P 0.2955 0.4335 '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
5 4 2 0.0381
-4 -5 -2 0.0600
-7 4 0 0.0464
7 -3 0 0.0714
2 -7 6 0.0360
0 -4 9 0.0510
-3 8 -4 0.0443
-2 7 -6 0.0355
1 1 -9 0.0675
3 -5 -4 0.0914
4 6 -5 0.0390
6 -2 -5 0.0892
-4 -3 -4 0.0674
1 7 -6 0.0330
3 4 -8 0.0561
-7 -2 2 0.0643
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 120.17(13) . . ?
C6 C1 C2 122.18(14) . . ?
C6 C1 N1 117.63(13) . . ?
C1 C2 C7 121.66(13) . . ?
C3 C2 C1 117.47(14) . . ?
C3 C2 C7 120.85(14) . . ?
C2 C3 H3 118.9 . . ?
C2 C3 C4 122.23(14) . . ?
C4 C3 H3 118.9 . . ?
C3 C4 C9 121.12(15) . . ?
C5 C4 C3 118.42(14) . . ?
C5 C4 C9 120.45(15) . . ?
C4 C5 H5 119.2 . . ?
C4 C5 C6 121.69(14) . . ?
C6 C5 H5 119.2 . . ?
C1 C6 C8 121.74(14) . . ?
C5 C6 C1 118.01(14) . . ?
C5 C6 C8 120.25(14) . . ?
C2 C7 H7A 109.5 . . ?
C2 C7 H7B 109.5 . . ?
C2 C7 H7C 109.5 . . ?
H7A C7 H7B 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
C6 C8 H8A 109.5 . . ?
C6 C8 H8B 109.5 . . ?
C6 C8 H8C 109.5 . . ?
H8A C8 H8B 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
C4 C9 H9A 109.5 . . ?
C4 C9 H9B 109.5 . . ?
C4 C9 H9C 109.5 . . ?
H9A C9 H9B 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
C31 C26 H26 105.9 . . ?
C31 C26 P1 116.43(10) . . ?
C27 C26 H26 105.9 . . ?
C27 C26 C31 109.88(13) . . ?
C27 C26 P1 112.15(10) . . ?
P1 C26 H26 105.9 . . ?
C26 C31 H31A 109.8 . . ?
C26 C31 H31B 109.8 . . ?
H31A C31 H31B 108.2 . . ?
C30 C31 C26 109.38(13) . . ?
C30 C31 H31A 109.8 . . ?
C30 C31 H31B 109.8 . . ?
C31 C30 H30A 109.2 . . ?
C31 C30 H30B 109.2 . . ?
H30A C30 H30B 107.9 . . ?
C29 C30 C31 112.18(14) . . ?
C29 C30 H30A 109.2 . . ?
C29 C30 H30B 109.2 . . ?
C30 C29 H29A 109.3 . . ?
C30 C29 H29B 109.3 . . ?
H29A C29 H29B 107.9 . . ?
C28 C29 C30 111.80(14) . . ?
C28 C29 H29A 109.3 . . ?
C28 C29 H29B 109.3 . . ?
C29 C28 H28A 109.3 . . ?
C29 C28 H28B 109.3 . . ?
C29 C28 C27 111.51(14) . . ?
H28A C28 H28B 108.0 . . ?
C27 C28 H28A 109.3 . . ?
C27 C28 H28B 109.3 . . ?
C26 C27 H27A 110.0 . . ?
C26 C27 H27B 110.0 . . ?
C28 C27 C26 108.27(12) . . ?
C28 C27 H27A 110.0 . . ?
C28 C27 H27B 110.0 . . ?
H27A C27 H27B 108.4 . . ?
C33 C32 H32 107.7 . . ?
C33 C32 P1 111.68(10) . . ?
C37 C32 H32 107.7 . . ?
C37 C32 C33 110.93(13) . . ?
C37 C32 P1 110.86(10) . . ?
P1 C32 H32 107.7 . . ?
C32 C33 H33A 109.7 . . ?
C32 C33 H33B 109.7 . . ?
H33A C33 H33B 108.2 . . ?
C34 C33 C32 109.97(13) . . ?
C34 C33 H33A 109.7 . . ?
C34 C33 H33B 109.7 . . ?
C33 C34 H34A 109.3 . . ?
C33 C34 H34B 109.3 . . ?
H34A C34 H34B 108.0 . . ?
C35 C34 C33 111.44(14) . . ?
C35 C34 H34A 109.3 . . ?
C35 C34 H34B 109.3 . . ?
C34 C35 H35A 109.3 . . ?
C34 C35 H35B 109.3 . . ?
H35A C35 H35B 108.0 . . ?
C36 C35 C34 111.51(14) . . ?
C36 C35 H35A 109.3 . . ?
C36 C35 H35B 109.3 . . ?
C35 C36 H36A 109.4 . . ?
C35 C36 H36B 109.4 . . ?
C35 C36 C37 111.35(15) . . ?
H36A C36 H36B 108.0 . . ?
C37 C36 H36A 109.4 . . ?
C37 C36 H36B 109.4 . . ?
C32 C37 H37A 109.7 . . ?
C32 C37 H37B 109.7 . . ?
C36 C37 C32 110.04(13) . . ?
C36 C37 H37A 109.7 . . ?
C36 C37 H37B 109.7 . . ?
H37A C37 H37B 108.2 . . ?
C11 C10 C14 119.32(14) . . ?
N1 C10 C11 129.25(14) . . ?
N1 C10 C14 111.12(12) . . ?
C10 C11 C15 116.08(13) . . ?
C10 C11 P1 124.37(12) . . ?
C15 C11 P1 118.91(11) . . ?
C13 C12 C16 118.29(13) . . ?
N2 C12 C13 130.65(14) . . ?
N2 C12 C16 110.96(12) . . ?
C12 C13 P1 118.85(11) . . ?
C17 C13 C12 118.51(14) . . ?
C17 C13 P1 119.72(11) . . ?
O1 C14 C10 122.25(14) . . ?
O1 C14 O2 126.03(14) . . ?
O2 C14 C10 111.57(12) . . ?
O3 C15 C11 126.11(14) . . ?
O3 C15 O4 122.73(14) . . ?
O4 C15 C11 111.12(13) . . ?
O5 C16 C12 122.29(14) . . ?
O5 C16 O6 125.50(14) . . ?
O6 C16 C12 112.19(12) . . ?
O7 C17 C13 127.79(15) . . ?
O7 C17 O8 120.80(14) . . ?
O8 C17 C13 111.34(12) . . ?
H18A C18 H18B 108.5 . . ?
C19 C18 H18A 110.3 . . ?
C19 C18 H18B 110.3 . . ?
O2 C18 H18A 110.3 . . ?
O2 C18 H18B 110.3 . . ?
O2 C18 C19 107.24(16) . . ?
C18 C19 H19A 109.5 . . ?
C18 C19 H19B 109.5 . . ?
C18 C19 H19C 109.5 . . ?
H19A C19 H19B 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
H20A C20 H20B 108.6 . . ?
C21 C20 H20A 110.3 . . ?
C21 C20 H20B 110.3 . . ?
O4 C20 H20A 110.3 . . ?
O4 C20 H20B 110.3 . . ?
O4 C20 C21 106.86(14) . . ?
C20 C21 H21A 109.5 . . ?
C20 C21 H21B 109.5 . . ?
C20 C21 H21C 109.5 . . ?
H21A C21 H21B 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
H22A C22 H22B 108.1 . . ?
C23 C22 H22A 109.6 . . ?
C23 C22 H22B 109.6 . . ?
O6 C22 H22A 109.6 . . ?
O6 C22 H22B 109.6 . . ?
O6 C22 C23 110.19(13) . . ?
C22 C23 H23A 109.5 . . ?
C22 C23 H23B 109.5 . . ?
C22 C23 H23C 109.5 . . ?
H23A C23 H23B 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 109.5 . . ?
H24A C24 H24B 108.5 . . ?
C25 C24 H24A 110.2 . . ?
C25 C24 H24B 110.2 . . ?
O8 C24 H24A 110.2 . . ?
O8 C24 H24B 110.2 . . ?
O8 C24 C25 107.63(13) . . ?
C24 C25 H25A 109.5 . . ?
C24 C25 H25B 109.5 . . ?
C24 C25 H25C 109.5 . . ?
H25A C25 H25B 109.5 . . ?
H25A C25 H25C 109.5 . . ?
H25B C25 H25C 109.5 . . ?
C10 N1 C1 120.67(12) . . ?
C10 N1 N2 128.13(12) . . ?
N2 N1 C1 109.88(11) . . ?
C12 N2 N1 119.18(12) . . ?
C14 O2 C18 115.20(13) . . ?
C15 O4 C20 116.61(13) . . ?
C16 O6 C22 116.83(12) . . ?
C17 O8 C24 116.09(12) . . ?
C26 P1 C32 107.34(7) . . ?
C11 P1 C26 108.95(7) . . ?
C11 P1 C32 110.77(7) . . ?
C13 P1 C26 110.15(7) . . ?
C13 P1 C32 110.90(7) . . ?
C13 P1 C11 108.71(7) . . ?
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 1.401(2) . ?
C1 C6 1.399(2) . ?
C1 N1 1.4487(18) . ?
C2 C3 1.392(2) . ?
C2 C7 1.506(2) . ?
C3 H3 0.9500 . ?
C3 C4 1.395(2) . ?
C4 C5 1.392(2) . ?
C4 C9 1.510(2) . ?
C5 H5 0.9500 . ?
C5 C6 1.394(2) . ?
C6 C8 1.504(2) . ?
C7 H7A 0.9800 . ?
C7 H7B 0.9800 . ?
C7 H7C 0.9800 . ?
C8 H8A 0.9800 . ?
C8 H8B 0.9800 . ?
C8 H8C 0.9800 . ?
C9 H9A 0.9800 . ?
C9 H9B 0.9800 . ?
C9 H9C 0.9800 . ?
C26 H26 1.0000 . ?
C26 C31 1.539(2) . ?
C26 C27 1.536(2) . ?
C26 P1 1.8239(14) . ?
C31 H31A 0.9900 . ?
C31 H31B 0.9900 . ?
C31 C30 1.534(2) . ?
C30 H30A 0.9900 . ?
C30 H30B 0.9900 . ?
C30 C29 1.524(3) . ?
C29 H29A 0.9900 . ?
C29 H29B 0.9900 . ?
C29 C28 1.521(3) . ?
C28 H28A 0.9900 . ?
C28 H28B 0.9900 . ?
C28 C27 1.531(2) . ?
C27 H27A 0.9900 . ?
C27 H27B 0.9900 . ?
C32 H32 1.0000 . ?
C32 C33 1.539(2) . ?
C32 C37 1.531(2) . ?
C32 P1 1.8321(15) . ?
C33 H33A 0.9900 . ?
C33 H33B 0.9900 . ?
C33 C34 1.533(2) . ?
C34 H34A 0.9900 . ?
C34 H34B 0.9900 . ?
C34 C35 1.522(2) . ?
C35 H35A 0.9900 . ?
C35 H35B 0.9900 . ?
C35 C36 1.519(3) . ?
C36 H36A 0.9900 . ?
C36 H36B 0.9900 . ?
C36 C37 1.527(2) . ?
C37 H37A 0.9900 . ?
C37 H37B 0.9900 . ?
C10 C11 1.382(2) . ?
C10 C14 1.531(2) . ?
C10 N1 1.348(2) . ?
C11 C15 1.480(2) . ?
C11 P1 1.7892(15) . ?
C12 C13 1.443(2) . ?
C12 C16 1.530(2) . ?
C12 N2 1.2926(19) . ?
C13 C17 1.434(2) . ?
C13 P1 1.7407(16) . ?
C14 O1 1.2025(19) . ?
C14 O2 1.3288(19) . ?
C15 O3 1.2084(19) . ?
C15 O4 1.3455(18) . ?
C16 O5 1.2049(19) . ?
C16 O6 1.3307(18) . ?
C17 O7 1.2261(18) . ?
C17 O8 1.3687(19) . ?
C18 H18A 0.9900 . ?
C18 H18B 0.9900 . ?
C18 C19 1.490(3) . ?
C18 O2 1.450(2) . ?
C19 H19A 0.9800 . ?
C19 H19B 0.9800 . ?
C19 H19C 0.9800 . ?
C20 H20A 0.9900 . ?
C20 H20B 0.9900 . ?
C20 C21 1.503(3) . ?
C20 O4 1.457(2) . ?
C21 H21A 0.9800 . ?
C21 H21B 0.9800 . ?
C21 H21C 0.9800 . ?
C22 H22A 0.9900 . ?
C22 H22B 0.9900 . ?
C22 C23 1.507(2) . ?
C22 O6 1.4588(18) . ?
C23 H23A 0.9800 . ?
C23 H23B 0.9800 . ?
C23 H23C 0.9800 . ?
C24 H24A 0.9900 . ?
C24 H24B 0.9900 . ?
C24 C25 1.501(2) . ?
C24 O8 1.4443(19) . ?
C25 H25A 0.9800 . ?
C25 H25B 0.9800 . ?
C25 H25C 0.9800 . ?
N1 N2 1.4177(18) . ?
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 N1 N2 C12 134.32(14) . . . . ?
C2 C1 C6 C5 1.0(2) . . . . ?
C2 C1 C6 C8 -179.46(15) . . . . ?
C2 C1 N1 C10 -104.02(17) . . . . ?
C2 C1 N1 N2 63.88(18) . . . . ?
C2 C3 C4 C5 0.2(2) . . . . ?
C2 C3 C4 C9 -179.28(15) . . . . ?
C3 C4 C5 C6 0.2(2) . . . . ?
C4 C5 C6 C1 -0.8(2) . . . . ?
C4 C5 C6 C8 179.64(15) . . . . ?
C6 C1 C2 C3 -0.6(2) . . . . ?
C6 C1 C2 C7 -178.79(15) . . . . ?
C6 C1 N1 C10 77.93(18) . . . . ?
C6 C1 N1 N2 -114.18(15) . . . . ?
C7 C2 C3 C4 178.20(15) . . . . ?
C9 C4 C5 C6 179.70(15) . . . . ?
C26 C31 C30 C29 54.92(18) . . . . ?
C31 C26 C27 C28 62.01(17) . . . . ?
C31 C26 P1 C32 -61.45(13) . . . . ?
C31 C26 P1 C11 58.55(13) . . . . ?
C31 C26 P1 C13 177.72(11) . . . . ?
C31 C30 C29 C28 -52.38(19) . . . . ?
C30 C29 C28 C27 54.54(18) . . . . ?
C29 C28 C27 C26 -58.99(18) . . . . ?
C27 C26 C31 C30 -60.14(16) . . . . ?
C27 C26 P1 C32 170.79(11) . . . . ?
C27 C26 P1 C11 -69.21(13) . . . . ?
C27 C26 P1 C13 49.96(13) . . . . ?
C32 C33 C34 C35 55.62(19) . . . . ?
C33 C32 C37 C36 57.68(18) . . . . ?
C33 C32 P1 C26 -69.61(12) . . . . ?
C33 C32 P1 C11 171.56(10) . . . . ?
C33 C32 P1 C13 50.76(12) . . . . ?
C33 C34 C35 C36 -55.3(2) . . . . ?
C34 C35 C36 C37 55.8(2) . . . . ?
C35 C36 C37 C32 -56.73(19) . . . . ?
C37 C32 C33 C34 -57.13(17) . . . . ?
C37 C32 P1 C26 166.13(11) . . . . ?
C37 C32 P1 C11 47.30(13) . . . . ?
C37 C32 P1 C13 -73.51(13) . . . . ?
C10 C11 C15 O3 -22.7(2) . . . . ?
C10 C11 C15 O4 154.97(13) . . . . ?
C10 C11 P1 C26 111.10(13) . . . . ?
C10 C11 P1 C32 -131.05(13) . . . . ?
C10 C11 P1 C13 -8.96(15) . . . . ?
C10 C14 O2 C18 178.99(14) . . . . ?
C10 N1 N2 C12 -58.9(2) . . . . ?
C11 C10 C14 O1 -97.26(18) . . . . ?
C11 C10 C14 O2 86.94(16) . . . . ?
C11 C10 N1 C1 -168.40(14) . . . . ?
C11 C10 N1 N2 26.1(2) . . . . ?
C11 C15 O4 C20 179.93(12) . . . . ?
C12 C13 C17 O7 -170.80(15) . . . . ?
C12 C13 C17 O8 12.32(19) . . . . ?
C12 C13 P1 C26 -163.02(11) . . . . ?
C12 C13 P1 C32 78.30(13) . . . . ?
C12 C13 P1 C11 -43.72(13) . . . . ?
C12 C16 O6 C22 -179.09(12) . . . . ?
C13 C12 C16 O5 49.9(2) . . . . ?
C13 C12 C16 O6 -131.51(14) . . . . ?
C13 C12 N2 N1 5.3(2) . . . . ?
C13 C17 O8 C24 -175.44(13) . . . . ?
C14 C10 C11 C15 8.20(19) . . . . ?
C14 C10 C11 P1 -162.46(11) . . . . ?
C14 C10 N1 C1 18.11(18) . . . . ?
C14 C10 N1 N2 -147.37(13) . . . . ?
C15 C11 P1 C26 -59.31(13) . . . . ?
C15 C11 P1 C32 58.54(13) . . . . ?
C15 C11 P1 C13 -179.37(11) . . . . ?
C16 C12 C13 C17 40.8(2) . . . . ?
C16 C12 C13 P1 -119.87(13) . . . . ?
C16 C12 N2 N1 -178.53(12) . . . . ?
C17 C13 P1 C26 36.58(14) . . . . ?
C17 C13 P1 C32 -82.10(13) . . . . ?
C17 C13 P1 C11 155.88(12) . . . . ?
C19 C18 O2 C14 -159.64(16) . . . . ?
C21 C20 O4 C15 154.47(14) . . . . ?
C23 C22 O6 C16 96.30(15) . . . . ?
C25 C24 O8 C17 156.07(13) . . . . ?
N1 C1 C2 C3 -178.56(14) . . . . ?
N1 C1 C2 C7 3.2(2) . . . . ?
N1 C1 C6 C5 179.00(14) . . . . ?
N1 C1 C6 C8 -1.4(2) . . . . ?
N1 C10 C11 C15 -164.84(14) . . . . ?
N1 C10 C11 P1 24.5(2) . . . . ?
N1 C10 C14 O1 76.96(18) . . . . ?
N1 C10 C14 O2 -98.83(14) . . . . ?
N2 C12 C13 C17 -143.26(16) . . . . ?
N2 C12 C13 P1 56.1(2) . . . . ?
N2 C12 C16 O5 -126.79(16) . . . . ?
N2 C12 C16 O6 51.76(17) . . . . ?
O1 C14 O2 C18 3.4(2) . . . . ?
O3 C15 O4 C20 -2.3(2) . . . . ?
O5 C16 O6 C22 -0.6(2) . . . . ?
O7 C17 O8 C24 7.4(2) . . . . ?
P1 C26 C31 C30 171.00(11) . . . . ?
P1 C26 C27 C28 -166.82(11) . . . . ?
P1 C32 C33 C34 178.65(11) . . . . ?
P1 C32 C37 C36 -177.63(12) . . . . ?
P1 C11 C15 O3 148.49(13) . . . . ?
P1 C11 C15 O4 -33.84(16) . . . . ?
P1 C13 C17 O7 -10.3(2) . . . . ?
P1 C13 C17 O8 172.79(10) . . . . ?
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
4.7085 3.6825 2.1366 0.8474 -0.3001 -0.4379
-3.7543 -4.5478 -2.3277 -0.7673 0.2720 0.5807
-6.7607 3.7136 0.4183 -0.7050 0.2483 -0.6643
7.0636 -2.6710 0.0312 0.8054 -0.2839 0.5204
1.8908 -7.1260 6.4777 0.4499 0.7339 0.5089
0.3110 -3.7973 8.9471 0.5199 0.8498 -0.0873
-2.5191 7.8817 -3.7904 -0.3255 -0.5301 -0.7829
-2.0202 7.3285 -6.0654 -0.4322 -0.7050 -0.5622
0.8382 0.7122 -8.7503 -0.4581 -0.7497 0.4777
2.5367 -5.2142 -4.3563 -0.1346 -0.2222 0.9657
4.1265 5.6457 -4.8236 0.3697 -0.8917 -0.2611
5.5078 -1.8105 -5.4434 0.2707 -0.6502 0.7099
-4.4725 -2.7280 -3.7415 -0.8956 0.1168 0.4292
1.2529 7.1995 -6.0294 -0.0233 -0.8900 -0.4553
3.1092 3.9824 -8.0514 -0.0253 -0.9938 0.1079
-6.7873 -1.5431 1.6496 -0.7887 0.6046 -0.1111
