#------------------------------------------------------------------------------
#$Date: 2022-02-04 21:55:13 +0200 (Fri, 04 Feb 2022) $
#$Revision: 272725 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/06/11/7061150.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_7061150
loop_
_publ_author_name
'Kubota, Yasuhiro'
'Koide, Kenta'
'Mizuno, Yuka'
'Nakazawa, Masato'
'Inuzuka, Toshiyasu'
'Funabiki, Kazumasa'
'Sato, Hiroyasu'
'Matsui, Masaki'
_publ_section_title
;
 Synthesis and fluorescence properties of unsymmetrical
 1,4-dihydropyrrolo[3,2-b]pyrrole dyes
;
_journal_issue                   4
_journal_name_full               'New Journal of Chemistry'
_journal_page_first              1533
_journal_page_last               1542
_journal_paper_doi               10.1039/D1NJ04663B
_journal_volume                  46
_journal_year                    2022
_chemical_formula_moiety         'C20 H25 N3 O2'
_chemical_formula_sum            'C20 H25 N3 O2'
_chemical_formula_weight         339.43
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2021-11-22
_audit_creation_method
;
Olex2 1.5
(compiled 2021.11.18 svn.ra9532c28 for OlexSys, GUI svn.r6427)
;
_audit_update_record
;
2021-11-24 deposited with the CCDC.	2021-12-02 downloaded from the CCDC.
;
_cell_angle_alpha                90.747(3)
_cell_angle_beta                 96.017(3)
_cell_angle_gamma                93.379(2)
_cell_formula_units_Z            4
_cell_length_a                   10.6244(3)
_cell_length_b                   12.3177(3)
_cell_length_c                   14.0897(6)
_cell_measurement_reflns_used    14435
_cell_measurement_temperature    99.9(6)
_cell_measurement_theta_max      75.1560
_cell_measurement_theta_min      3.1490
_cell_volume                     1830.20(10)
_computing_cell_refinement       'CrysAlisPro 1.171.42.35a (Rigaku OD, 2021)'
_computing_data_collection       'CrysAlisPro 1.171.42.35a (Rigaku OD, 2021)'
_computing_data_reduction        'CrysAlisPro 1.171.42.35a (Rigaku OD, 2021)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      99.9(6)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            'HyPix-Arc 150'
_diffrn_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.944
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     33.00  95.00   0.50    0.50    --   67.84   0.00 150.00  124
  2  ω     48.00  73.00   0.50    0.50    --   67.84-135.00-115.00   50
  3  ω     41.00  66.00   0.50    0.50    --   69.39-135.00-115.00   50
  4  ω     46.00 109.00   0.50    0.50    --   67.84  15.00-120.00  126
  5  ω     33.00  94.00   0.50    0.50    --   67.84   0.00-150.00  122
  6  ω     37.00  82.00   0.50    0.50    --   69.39-134.00  64.00   90
  7  ω     28.00  63.00   0.50    0.50    --   67.84-125.00 120.00   70
  8  ω     39.00  64.00   0.50    0.50    --   67.84-134.00  64.00   50
  9  ω     32.00  77.00   0.50    0.50    --   67.84-125.00  30.00   90
 10  ω     32.00  96.00   0.50    0.50    --   69.39-125.00   0.00  128
 11  ω   -119.00 -76.00   0.50    0.50    --  -80.25-135.00-115.00   86
 12  ω   -106.00 -57.00   0.50    0.50    --  -80.25 -15.00 -90.00   98
 13  ω   -111.00 -84.00   0.50    0.50    --  -69.93 -15.00-180.00   54
 14  ω    -78.00 -43.00   0.50    0.50    --  -69.93 -15.00-180.00   70
 15  ω   -102.00 -55.00   0.50    0.50    --  -80.25 -15.00-180.00   94
 16  ω    -88.00 -61.00   0.50    0.50    --  -80.25 -15.00-150.00   54
 17  ω    -86.00 -58.00   0.50    0.50    --  -80.25 -15.00   0.00   56
 18  ω   -122.00 -92.00   0.50    0.50    --  -80.25 -15.00   0.00   60
 19  ω    -89.00 -59.00   0.50    0.50    --  -80.25 -15.00 120.00   60
 20  ω    -98.00 -71.00   0.50    0.50    --  -80.25   0.00 -90.00   54
 21  ω    -85.00 -52.00   0.50    0.50    --  -69.93   0.00-150.00   66
 22  ω    -80.00 -53.00   0.50    0.50    --  -80.25   0.00-150.00   54
 23  ω   -111.00 -53.00   0.50    0.50    --  -80.25 135.00 -49.00  116
 24  ω    -88.00 -63.00   0.50    0.50    --  -68.75 135.00 -49.00   50
 25  ω    -80.00 -51.00   0.50    0.50    --  -68.75 125.00-180.00   58
 26  ω    -95.00 -65.00   0.50    0.50    --  -68.75 125.00  30.00   60
 27  ω    -88.00 -63.00   0.50    0.50    --  -68.75 134.00 130.00   50
 28  ω   -100.00 -70.00   0.50    0.50    --  -69.93 134.00 130.00   60
 29  ω   -110.00 -70.00   0.50    0.50    --  -80.25 134.00 130.00   80
 30  ω    -92.00 -32.00   0.50    0.50    --  -68.75 125.00  90.00  120
 31  ω   -103.00 -41.00   0.50    0.50    --  -80.25 125.00 120.00  124
 32  ω   -106.00 -38.00   0.50    0.50    --  -80.25 125.00  60.00  136
 33  ω    -96.00 -45.00   0.50    0.50    --  -69.93 125.00   0.00  102
 34  ω   -106.00 -45.00   0.50    0.50    --  -80.25 125.00 -90.00  122
 35  ω    -95.00 -62.00   0.50    0.50    --  -68.75 125.00-120.00   66
 36  ω    -66.00 -41.00   0.50    0.50    --  -80.25 125.00-150.00   50
 37  ω   -103.00 -39.00   0.50    0.50    --  -80.25 125.00-180.00  128
 38  ω   -106.00 -80.00   0.50    0.50    --  -80.25 125.00-120.00   52
 39  ω   -100.00 -35.00   0.50    0.50    --  -75.44 123.00-142.40  130
 40  ω   -102.00 -76.00   0.50    0.50    --  -80.25 125.00   0.00   52
 41  ω    -63.00 -38.00   0.50    0.50    --  -80.25 125.00   0.00   50
 42  ω    -63.00 -33.00   0.50    0.50    --  -75.44 124.00  63.79   60
 43  ω   -100.00 -75.00   0.50    0.50    --  -75.44 124.00  63.79   50
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'ROD, Synergy Custom system, HyPix-Arc 150'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0471372000
_diffrn_orient_matrix_UB_12      0.1143233000
_diffrn_orient_matrix_UB_13      0.0146007000
_diffrn_orient_matrix_UB_21      -0.0223624000
_diffrn_orient_matrix_UB_22      0.0127016000
_diffrn_orient_matrix_UB_23      -0.1089913000
_diffrn_orient_matrix_UB_31      -0.1364399000
_diffrn_orient_matrix_UB_32      -0.0497150000
_diffrn_orient_matrix_UB_33      0.0003660000
_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  0.0415
_diffrn_reflns_av_unetI/netI     0.0274
_diffrn_reflns_Laue_measured_fraction_full 0.992
_diffrn_reflns_Laue_measured_fraction_max 0.944
_diffrn_reflns_limit_h_max       10
_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            26401
_diffrn_reflns_point_group_measured_fraction_full 0.992
_diffrn_reflns_point_group_measured_fraction_max 0.944
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         76.496
_diffrn_reflns_theta_min         3.154
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'Rigaku (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.643
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.61031
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.42.35a (Rigaku Oxford Diffraction, 2021)
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    1.232
_exptl_crystal_description       plate
_exptl_crystal_F_000             728
_exptl_crystal_size_max          0.173
_exptl_crystal_size_mid          0.102
_exptl_crystal_size_min          0.017
_refine_diff_density_max         0.336
_refine_diff_density_min         -0.341
_refine_diff_density_rms         0.068
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.080
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     459
_refine_ls_number_reflns         7268
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.080
_refine_ls_R_factor_all          0.0663
_refine_ls_R_factor_gt           0.0612
_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)+(0.1065P)²+0.6744P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1649
_refine_ls_wR_factor_ref         0.1694
_reflns_Friedel_coverage         0.000
_reflns_number_gt                6589
_reflns_number_total             7268
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d1nj04663b2.cif
_cod_data_source_block           p5
_cod_depositor_comments
'Adding full bibliography for 7061149--7061150.cif.'
_cod_database_code               7061150
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'C H 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   0.987
_shelx_estimated_absorpt_t_min   0.899
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C19(H19A,H19B), C17'(H17C,H17D), C19'(H19C,H19D), C9(H9A,H9B), C9'(H9'A,H9'B),
  C17(H17A,H17B)
2.b Aromatic/amide H refined with riding coordinates:
 N1'(H1'), N1(H1), C6'(H6'), C12(H12), C16(H16), C15'(H15'), C15(H15),
 C3'(H3'), C6(H6), C13(H13), C3(H3), C13'(H13'), C16'(H16'), C12'(H12')
2.c Idealised Me refined as rotating group:
 C1'(H1'A,H1'B,H1'C), C1(H1A,H1B,H1C), C18'(H18D,H18E,H18F), C20(H20A,H20B,
 H20C), C10(H10A,H10B,H10C), C20'(H20D,H20E,H20F), C10'(H10D,H10E,H10F),
 C18(H18A,H18B,H18C)
;
_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 1.713
_oxdiff_exptl_absorpt_empirical_full_min 0.591
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
O2 O 0.67155(12) 0.10851(10) 0.28992(8) 0.0284(3) Uani 1 1 d . . . . .
O1 O 0.57328(12) -0.00554(10) 0.38585(9) 0.0310(3) Uani 1 1 d . . . . .
O1' O 1.36547(12) 0.81112(10) 1.11470(9) 0.0309(3) Uani 1 1 d . . . . .
O2' O 1.15583(12) 0.79247(11) 1.13403(9) 0.0339(3) Uani 1 1 d . . . . .
N2 N 0.64838(13) 0.43412(11) 0.56233(10) 0.0239(3) Uani 1 1 d . . . . .
N1' N 1.31392(13) 0.67706(11) 0.94656(10) 0.0240(3) Uani 1 1 d . . . . .
H1' H 1.395317 0.696873 0.955003 0.029 Uiso 1 1 calc R U . . .
N1 N 0.56918(13) 0.16172(12) 0.52096(10) 0.0253(3) Uani 1 1 d . . . . .
H1 H 0.537820 0.099657 0.541425 0.030 Uiso 1 1 calc R U . . .
N2' N 1.06588(13) 0.52945(12) 0.81909(10) 0.0241(3) Uani 1 1 d . . . . .
N3 N 0.59255(13) 0.73245(12) 0.95000(10) 0.0254(3) Uani 1 1 d . . . . .
N00A N 1.06887(14) 0.16129(12) 0.47661(10) 0.0275(3) Uani 1 1 d . . . . .
C7 C 0.58057(15) 0.25880(14) 0.56944(12) 0.0237(3) Uani 1 1 d . . . . .
C11 C 0.60328(15) 0.50073(14) 0.72493(12) 0.0236(3) Uani 1 1 d . . . . .
C14 C 0.60069(15) 0.65768(13) 0.87579(12) 0.0237(3) Uani 1 1 d . . . . .
C7' C 1.25487(15) 0.60963(14) 0.87565(12) 0.0236(3) Uani 1 1 d . . . . .
C4' C 1.12597(15) 0.59954(14) 0.88763(12) 0.0247(3) Uani 1 1 d . . . . .
C5 C 0.60305(15) 0.41645(14) 0.65045(12) 0.0233(3) Uani 1 1 d . . . . .
C4 C 0.63477(15) 0.33630(14) 0.51264(12) 0.0238(3) Uani 1 1 d . . . . .
C6' C 1.27601(15) 0.54309(14) 0.79708(12) 0.0252(3) Uani 1 1 d . . . . .
H6' H 1.354398 0.533670 0.772122 0.030 Uiso 1 1 calc R U . . .
C12 C 0.58643(15) 0.61070(14) 0.70650(12) 0.0254(3) Uani 1 1 d . . . . .
H12 H 0.575693 0.633630 0.642196 0.030 Uiso 1 1 calc R U . . .
C8 C 0.61651(15) 0.08583(14) 0.36972(12) 0.0254(3) Uani 1 1 d . . . . .
C16 C 0.61675(15) 0.47154(14) 0.82114(12) 0.0246(3) Uani 1 1 d . . . . .
H16 H 0.626759 0.397397 0.836259 0.030 Uiso 1 1 calc R U . . .
C15' C 1.20447(15) 0.25493(14) 0.60652(12) 0.0252(3) Uani 1 1 d . . . . .
H15' H 1.269200 0.206068 0.600388 0.030 Uiso 1 1 calc R U . . .
C15 C 0.61602(15) 0.54648(14) 0.89470(12) 0.0252(3) Uani 1 1 d . . . . .
H15 H 0.625938 0.523075 0.958884 0.030 Uiso 1 1 calc R U . . .
C5' C 1.15786(15) 0.49431(14) 0.76400(12) 0.0246(3) Uani 1 1 d . . . . .
C2' C 1.22229(16) 0.70865(14) 1.00289(12) 0.0252(3) Uani 1 1 d . . . . .
C11' C 1.13096(15) 0.41114(14) 0.68843(12) 0.0246(3) Uani 1 1 d . . . . .
C14' C 1.09164(15) 0.24417(14) 0.54331(12) 0.0245(3) Uani 1 1 d . . . . .
C8' C 1.25807(16) 0.77571(13) 1.08743(12) 0.0253(3) Uani 1 1 d . . . . .
C3' C 1.10407(16) 0.66233(14) 0.96796(12) 0.0262(4) Uani 1 1 d . . . . .
H3' H 1.025434 0.671025 0.992781 0.031 Uiso 1 1 calc R U . . .
C6 C 0.56038(15) 0.30808(14) 0.65695(12) 0.0244(3) Uani 1 1 d . . . . .
H6 H 0.525142 0.274456 0.709265 0.029 Uiso 1 1 calc R U . . .
C2 C 0.61585(15) 0.17811(14) 0.43356(12) 0.0246(3) Uani 1 1 d . . . . .
C13 C 0.58498(16) 0.68703(14) 0.77956(12) 0.0262(4) Uani 1 1 d . . . . .
H13 H 0.573101 0.760828 0.764116 0.031 Uiso 1 1 calc R U . . .
C19 C 0.64684(16) 0.70825(14) 1.04692(12) 0.0266(4) Uani 1 1 d . . . . .
H19A H 0.605465 0.639239 1.066572 0.032 Uiso 1 1 calc R U . . .
H19B H 0.626305 0.766440 1.090878 0.032 Uiso 1 1 calc R U . . .
C3 C 0.65874(15) 0.28677(14) 0.42626(12) 0.0241(3) Uani 1 1 d . . . . .
H3 H 0.695841 0.319889 0.374506 0.029 Uiso 1 1 calc R U . . .
C13' C 1.00096(16) 0.32226(15) 0.55409(13) 0.0283(4) Uani 1 1 d . . . . .
H13' H 0.924681 0.319209 0.512170 0.034 Uiso 1 1 calc R U . . .
C16' C 1.22230(15) 0.33476(14) 0.67669(12) 0.0249(3) Uani 1 1 d . . . . .
H16' H 1.298595 0.338576 0.718601 0.030 Uiso 1 1 calc R U . . .
C17' C 0.96474(17) 0.16491(15) 0.40048(13) 0.0290(4) Uani 1 1 d . . . . .
H17C H 0.885613 0.176003 0.429740 0.035 Uiso 1 1 calc R U . . .
H17D H 0.954060 0.093474 0.366678 0.035 Uiso 1 1 calc R U . . .
C1' C 0.93230(16) 0.49460(15) 0.81411(13) 0.0294(4) Uani 1 1 d . . . . .
H1'A H 0.902925 0.502415 0.877356 0.044 Uiso 1 1 calc R U . . .
H1'B H 0.920389 0.418245 0.792932 0.044 Uiso 1 1 calc R U . . .
H1'C H 0.883455 0.539638 0.768672 0.044 Uiso 1 1 calc R U . . .
C12' C 1.02114(16) 0.40240(14) 0.62403(12) 0.0277(4) Uani 1 1 d . . . . .
H12' H 0.958362 0.453478 0.628688 0.033 Uiso 1 1 calc R U . . .
C1 C 0.70526(17) 0.53320(14) 0.52572(13) 0.0283(4) Uani 1 1 d . . . . .
H1A H 0.638414 0.576524 0.495231 0.043 Uiso 1 1 calc R U . . .
H1B H 0.762671 0.514382 0.478783 0.043 Uiso 1 1 calc R U . . .
H1C H 0.753003 0.575438 0.578478 0.043 Uiso 1 1 calc R U . . .
C19' C 1.16009(17) 0.07841(14) 0.46782(13) 0.0294(4) Uani 1 1 d . . . . .
H19C H 1.113190 0.009274 0.445848 0.035 Uiso 1 1 calc R U . . .
H19D H 1.204628 0.066285 0.531756 0.035 Uiso 1 1 calc R U . . .
C18' C 0.98201(19) 0.25331(17) 0.32742(14) 0.0369(4) Uani 1 1 d . . . . .
H18D H 0.905645 0.253381 0.281916 0.055 Uiso 1 1 calc R U . . .
H18E H 1.055177 0.239074 0.293174 0.055 Uiso 1 1 calc R U . . .
H18F H 0.996310 0.324312 0.360211 0.055 Uiso 1 1 calc R U . . .
C9 C 0.68482(19) 0.01494(15) 0.22880(13) 0.0318(4) Uani 1 1 d . . . . .
H9A H 0.600363 -0.016110 0.201844 0.038 Uiso 1 1 calc R U . . .
H9B H 0.729121 -0.041933 0.265731 0.038 Uiso 1 1 calc R U . . .
C9' C 1.17759(19) 0.84194(16) 1.22831(13) 0.0341(4) Uani 1 1 d . . . . .
H9'A H 1.238270 0.906153 1.228798 0.041 Uiso 1 1 calc R U . . .
H9'B H 1.212261 0.789352 1.275205 0.041 Uiso 1 1 calc R U . . .
C20 C 0.79023(17) 0.69824(17) 1.05860(14) 0.0333(4) Uani 1 1 d . . . . .
H20A H 0.811547 0.637968 1.018316 0.050 Uiso 1 1 calc R U . . .
H20B H 0.818570 0.684239 1.125525 0.050 Uiso 1 1 calc R U . . .
H20C H 0.832555 0.766081 1.039453 0.050 Uiso 1 1 calc R U . . .
C17 C 0.5850(2) 0.84822(15) 0.92755(14) 0.0361(4) Uani 1 1 d . . . . .
H17A H 0.558053 0.886425 0.983564 0.043 Uiso 1 1 calc R U . . .
H17B H 0.517918 0.854734 0.873970 0.043 Uiso 1 1 calc R U . . .
C10 C 0.7607(2) 0.05383(17) 0.15002(14) 0.0396(5) Uani 1 1 d . . . . .
H10A H 0.771224 -0.007371 0.107008 0.059 Uiso 1 1 calc R U . . .
H10B H 0.844132 0.083960 0.177584 0.059 Uiso 1 1 calc R U . . .
H10C H 0.715976 0.110206 0.114172 0.059 Uiso 1 1 calc R U . . .
C20' C 1.25845(19) 0.10670(18) 0.39949(15) 0.0400(5) Uani 1 1 d . . . . .
H20D H 1.215656 0.116446 0.335367 0.060 Uiso 1 1 calc R U . . .
H20E H 1.316134 0.047650 0.397817 0.060 Uiso 1 1 calc R U . . .
H20F H 1.306866 0.174219 0.421280 0.060 Uiso 1 1 calc R U . . .
C10' C 1.0501(2) 0.8752(2) 1.25199(16) 0.0466(5) Uani 1 1 d . . . . .
H10D H 1.020980 0.932339 1.208701 0.070 Uiso 1 1 calc R U . . .
H10E H 1.057446 0.902779 1.318015 0.070 Uiso 1 1 calc R U . . .
H10F H 0.988995 0.812122 1.244646 0.070 Uiso 1 1 calc R U . . .
C18 C 0.7058(3) 0.90664(18) 0.90103(16) 0.0487(6) Uani 1 1 d . . . . .
H18A H 0.735546 0.868641 0.846842 0.073 Uiso 1 1 calc R U . . .
H18B H 0.771065 0.907492 0.955675 0.073 Uiso 1 1 calc R U . . .
H18C H 0.688857 0.981502 0.883455 0.073 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 0.0181 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'
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
1 -1 9 0.0086
-1 1 -9 0.0086
-6 -3 3 0.0907
-3 -7 0 0.0780
-6 4 2 0.0458
6 -4 -2 0.0561
7 1 -1 0.0455
-3 7 2 0.0684
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
C8 O2 C9 114.87(14) . . ?
C8' O2' C9' 117.77(14) . . ?
C5 N2 C1 129.20(14) . . ?
C4 N2 C5 107.35(14) . . ?
C4 N2 C1 123.42(14) . . ?
C7' N1' H1' 126.2 . . ?
C7' N1' C2' 107.64(14) . . ?
C2' N1' H1' 126.2 . . ?
C7 N1 H1 126.1 . . ?
C7 N1 C2 107.83(14) . . ?
C2 N1 H1 126.1 . . ?
C4' N2' C5' 107.25(13) . . ?
C4' N2' C1' 123.69(14) . . ?
C5' N2' C1' 128.86(14) . . ?
C14 N3 C19 119.44(13) . . ?
C14 N3 C17 118.86(14) . . ?
C19 N3 C17 116.12(14) . . ?
C14' N00A C17' 120.40(14) . . ?
C14' N00A C19' 121.45(14) . . ?
C17' N00A C19' 117.13(14) . . ?
N1 C7 C4 108.14(14) . . ?
N1 C7 C6 142.75(16) . . ?
C4 C7 C6 109.08(15) . . ?
C12 C11 C5 124.01(15) . . ?
C12 C11 C16 116.48(15) . . ?
C16 C11 C5 119.48(15) . . ?
N3 C14 C15 120.83(15) . . ?
N3 C14 C13 122.10(15) . . ?
C13 C14 C15 116.91(15) . . ?
N1' C7' C4' 108.02(14) . . ?
N1' C7' C6' 143.60(15) . . ?
C4' C7' C6' 108.31(15) . . ?
N2' C4' C7' 108.87(14) . . ?
N2' C4' C3' 142.07(15) . . ?
C7' C4' C3' 109.01(15) . . ?
N2 C5 C11 124.07(15) . . ?
C6 C5 N2 110.04(15) . . ?
C6 C5 C11 125.88(15) . . ?
N2 C4 C7 108.17(14) . . ?
N2 C4 C3 142.48(16) . . ?
C7 C4 C3 109.33(15) . . ?
C7' C6' H6' 127.2 . . ?
C5' C6' C7' 105.50(14) . . ?
C5' C6' H6' 127.2 . . ?
C11 C12 H12 119.1 . . ?
C13 C12 C11 121.81(15) . . ?
C13 C12 H12 119.1 . . ?
O2 C8 C2 113.70(15) . . ?
O1 C8 O2 122.21(16) . . ?
O1 C8 C2 124.08(16) . . ?
C11 C16 H16 118.8 . . ?
C15 C16 C11 122.46(15) . . ?
C15 C16 H16 118.8 . . ?
C14' C15' H15' 119.3 . . ?
C16' C15' H15' 119.3 . . ?
C16' C15' C14' 121.31(15) . . ?
C14 C15 H15 119.6 . . ?
C16 C15 C14 120.87(15) . . ?
C16 C15 H15 119.6 . . ?
N2' C5' C11' 123.04(15) . . ?
C6' C5' N2' 110.06(15) . . ?
C6' C5' C11' 126.71(15) . . ?
N1' C2' C8' 120.25(15) . . ?
C3' C2' N1' 110.32(15) . . ?
C3' C2' C8' 129.34(15) . . ?
C16' C11' C5' 118.78(15) . . ?
C12' C11' C5' 124.77(15) . . ?
C12' C11' C16' 116.43(15) . . ?
N00A C14' C15' 122.19(15) . . ?
N00A C14' C13' 121.37(15) . . ?
C15' C14' C13' 116.42(15) . . ?
O1' C8' O2' 124.07(16) . . ?
O1' C8' C2' 125.31(15) . . ?
O2' C8' C2' 110.60(15) . . ?
C4' C3' H3' 127.5 . . ?
C2' C3' C4' 105.00(14) . . ?
C2' C3' H3' 127.5 . . ?
C7 C6 H6 127.3 . . ?
C5 C6 C7 105.36(15) . . ?
C5 C6 H6 127.3 . . ?
N1 C2 C8 118.25(15) . . ?
N1 C2 C3 110.04(14) . . ?
C3 C2 C8 131.68(16) . . ?
C14 C13 H13 119.3 . . ?
C12 C13 C14 121.47(15) . . ?
C12 C13 H13 119.3 . . ?
N3 C19 H19A 108.5 . . ?
N3 C19 H19B 108.5 . . ?
N3 C19 C20 114.97(14) . . ?
H19A C19 H19B 107.5 . . ?
C20 C19 H19A 108.5 . . ?
C20 C19 H19B 108.5 . . ?
C4 C3 H3 127.7 . . ?
C2 C3 C4 104.66(15) . . ?
C2 C3 H3 127.7 . . ?
C14' C13' H13' 119.3 . . ?
C12' C13' C14' 121.41(16) . . ?
C12' C13' H13' 119.3 . . ?
C15' C16' C11' 122.16(15) . . ?
C15' C16' H16' 118.9 . . ?
C11' C16' H16' 118.9 . . ?
N00A C17' H17C 108.5 . . ?
N00A C17' H17D 108.5 . . ?
N00A C17' C18' 114.89(15) . . ?
H17C C17' H17D 107.5 . . ?
C18' C17' H17C 108.5 . . ?
C18' C17' H17D 108.5 . . ?
N2' C1' H1'A 109.5 . . ?
N2' C1' H1'B 109.5 . . ?
N2' C1' H1'C 109.5 . . ?
H1'A C1' H1'B 109.5 . . ?
H1'A C1' H1'C 109.5 . . ?
H1'B C1' H1'C 109.5 . . ?
C11' C12' H12' 118.9 . . ?
C13' C12' C11' 122.22(15) . . ?
C13' C12' H12' 118.9 . . ?
N2 C1 H1A 109.5 . . ?
N2 C1 H1B 109.5 . . ?
N2 C1 H1C 109.5 . . ?
H1A C1 H1B 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
N00A C19' H19C 108.7 . . ?
N00A C19' H19D 108.7 . . ?
N00A C19' C20' 114.38(15) . . ?
H19C C19' H19D 107.6 . . ?
C20' C19' H19C 108.7 . . ?
C20' C19' H19D 108.7 . . ?
C17' C18' H18D 109.5 . . ?
C17' C18' H18E 109.5 . . ?
C17' C18' H18F 109.5 . . ?
H18D C18' H18E 109.5 . . ?
H18D C18' H18F 109.5 . . ?
H18E C18' H18F 109.5 . . ?
O2 C9 H9A 110.3 . . ?
O2 C9 H9B 110.3 . . ?
O2 C9 C10 107.19(15) . . ?
H9A C9 H9B 108.5 . . ?
C10 C9 H9A 110.3 . . ?
C10 C9 H9B 110.3 . . ?
O2' C9' H9'A 110.6 . . ?
O2' C9' H9'B 110.6 . . ?
O2' C9' C10' 105.82(16) . . ?
H9'A C9' H9'B 108.7 . . ?
C10' C9' H9'A 110.6 . . ?
C10' C9' H9'B 110.6 . . ?
C19 C20 H20A 109.5 . . ?
C19 C20 H20B 109.5 . . ?
C19 C20 H20C 109.5 . . ?
H20A C20 H20B 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
N3 C17 H17A 108.2 . . ?
N3 C17 H17B 108.2 . . ?
N3 C17 C18 116.25(17) . . ?
H17A C17 H17B 107.4 . . ?
C18 C17 H17A 108.2 . . ?
C18 C17 H17B 108.2 . . ?
C9 C10 H10A 109.5 . . ?
C9 C10 H10B 109.5 . . ?
C9 C10 H10C 109.5 . . ?
H10A C10 H10B 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
C19' C20' H20D 109.5 . . ?
C19' C20' H20E 109.5 . . ?
C19' C20' H20F 109.5 . . ?
H20D C20' H20E 109.5 . . ?
H20D C20' H20F 109.5 . . ?
H20E C20' H20F 109.5 . . ?
C9' C10' H10D 109.5 . . ?
C9' C10' H10E 109.5 . . ?
C9' C10' H10F 109.5 . . ?
H10D C10' H10E 109.5 . . ?
H10D C10' H10F 109.5 . . ?
H10E C10' H10F 109.5 . . ?
C17 C18 H18A 109.5 . . ?
C17 C18 H18B 109.5 . . ?
C17 C18 H18C 109.5 . . ?
H18A C18 H18B 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 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
O2 C8 1.346(2) . ?
O2 C9 1.452(2) . ?
O1 C8 1.223(2) . ?
O1' C8' 1.219(2) . ?
O2' C8' 1.351(2) . ?
O2' C9' 1.445(2) . ?
N2 C5 1.393(2) . ?
N2 C4 1.378(2) . ?
N2 C1 1.454(2) . ?
N1' H1' 0.8800 . ?
N1' C7' 1.366(2) . ?
N1' C2' 1.388(2) . ?
N1 H1 0.8800 . ?
N1 C7 1.362(2) . ?
N1 C2 1.388(2) . ?
N2' C4' 1.367(2) . ?
N2' C5' 1.395(2) . ?
N2' C1' 1.453(2) . ?
N3 C14 1.397(2) . ?
N3 C19 1.467(2) . ?
N3 C17 1.470(2) . ?
N00A C14' 1.372(2) . ?
N00A C17' 1.461(2) . ?
N00A C19' 1.461(2) . ?
C7 C4 1.391(2) . ?
C7 C6 1.409(2) . ?
C11 C5 1.466(2) . ?
C11 C12 1.401(2) . ?
C11 C16 1.402(2) . ?
C14 C15 1.414(2) . ?
C14 C13 1.403(2) . ?
C7' C4' 1.396(2) . ?
C7' C6' 1.413(2) . ?
C4' C3' 1.410(2) . ?
C5 C6 1.392(2) . ?
C4 C3 1.408(2) . ?
C6' H6' 0.9500 . ?
C6' C5' 1.391(2) . ?
C12 H12 0.9500 . ?
C12 C13 1.387(2) . ?
C8 C2 1.441(2) . ?
C16 H16 0.9500 . ?
C16 C15 1.380(2) . ?
C15' H15' 0.9500 . ?
C15' C14' 1.415(2) . ?
C15' C16' 1.376(2) . ?
C15 H15 0.9500 . ?
C5' C11' 1.462(2) . ?
C2' C8' 1.445(2) . ?
C2' C3' 1.387(2) . ?
C11' C16' 1.411(2) . ?
C11' C12' 1.399(2) . ?
C14' C13' 1.419(2) . ?
C3' H3' 0.9500 . ?
C6 H6 0.9500 . ?
C2 C3 1.397(2) . ?
C13 H13 0.9500 . ?
C19 H19A 0.9900 . ?
C19 H19B 0.9900 . ?
C19 C20 1.527(2) . ?
C3 H3 0.9500 . ?
C13' H13' 0.9500 . ?
C13' C12' 1.377(2) . ?
C16' H16' 0.9500 . ?
C17' H17C 0.9900 . ?
C17' H17D 0.9900 . ?
C17' C18' 1.525(3) . ?
C1' H1'A 0.9800 . ?
C1' H1'B 0.9800 . ?
C1' H1'C 0.9800 . ?
C12' H12' 0.9500 . ?
C1 H1A 0.9800 . ?
C1 H1B 0.9800 . ?
C1 H1C 0.9800 . ?
C19' H19C 0.9900 . ?
C19' H19D 0.9900 . ?
C19' C20' 1.522(3) . ?
C18' H18D 0.9800 . ?
C18' H18E 0.9800 . ?
C18' H18F 0.9800 . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C9 C10 1.506(3) . ?
C9' H9'A 0.9900 . ?
C9' H9'B 0.9900 . ?
C9' C10' 1.507(3) . ?
C20 H20A 0.9800 . ?
C20 H20B 0.9800 . ?
C20 H20C 0.9800 . ?
C17 H17A 0.9900 . ?
C17 H17B 0.9900 . ?
C17 C18 1.518(3) . ?
C10 H10A 0.9800 . ?
C10 H10B 0.9800 . ?
C10 H10C 0.9800 . ?
C20' H20D 0.9800 . ?
C20' H20E 0.9800 . ?
C20' H20F 0.9800 . ?
C10' H10D 0.9800 . ?
C10' H10E 0.9800 . ?
C10' H10F 0.9800 . ?
C18 H18A 0.9800 . ?
C18 H18B 0.9800 . ?
C18 H18C 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
O2 C8 C2 N1 -175.61(13) . . . . ?
O2 C8 C2 C3 2.0(3) . . . . ?
O1 C8 C2 N1 3.4(2) . . . . ?
O1 C8 C2 C3 -179.02(17) . . . . ?
N2 C5 C6 C7 -0.12(18) . . . . ?
N2 C4 C3 C2 178.5(2) . . . . ?
N1' C7' C4' N2' -178.03(13) . . . . ?
N1' C7' C4' C3' 0.06(19) . . . . ?
N1' C7' C6' C5' 176.3(2) . . . . ?
N1' C2' C8' O1' 1.7(3) . . . . ?
N1' C2' C8' O2' -177.02(14) . . . . ?
N1' C2' C3' C4' 0.47(19) . . . . ?
N1 C7 C4 N2 -178.95(13) . . . . ?
N1 C7 C4 C3 -0.26(18) . . . . ?
N1 C7 C6 C5 178.0(2) . . . . ?
N1 C2 C3 C4 -0.69(17) . . . . ?
N2' C4' C3' C2' 176.7(2) . . . . ?
N2' C5' C11' C16' -141.50(17) . . . . ?
N2' C5' C11' C12' 40.1(3) . . . . ?
N3 C14 C15 C16 176.24(15) . . . . ?
N3 C14 C13 C12 -176.43(15) . . . . ?
N00A C14' C13' C12' 176.86(17) . . . . ?
C7 N1 C2 C8 178.65(14) . . . . ?
C7 N1 C2 C3 0.55(18) . . . . ?
C7 C4 C3 C2 0.58(17) . . . . ?
C11 C5 C6 C7 -179.15(14) . . . . ?
C11 C12 C13 C14 0.2(3) . . . . ?
C11 C16 C15 C14 0.4(2) . . . . ?
C14 N3 C19 C20 63.0(2) . . . . ?
C14 N3 C17 C18 -72.3(2) . . . . ?
C7' N1' C2' C8' 176.43(14) . . . . ?
C7' N1' C2' C3' -0.45(19) . . . . ?
C7' C4' C3' C2' -0.32(19) . . . . ?
C7' C6' C5' N2' 0.46(19) . . . . ?
C7' C6' C5' C11' -174.60(16) . . . . ?
C4' N2' C5' C6' -0.62(19) . . . . ?
C4' N2' C5' C11' 174.65(15) . . . . ?
C4' C7' C6' C5' -0.13(19) . . . . ?
C5 N2 C4 C7 0.39(17) . . . . ?
C5 N2 C4 C3 -177.6(2) . . . . ?
C5 C11 C12 C13 178.73(15) . . . . ?
C5 C11 C16 C15 -179.09(15) . . . . ?
C4 N2 C5 C11 178.88(14) . . . . ?
C4 N2 C5 C6 -0.17(18) . . . . ?
C4 C7 C6 C5 0.37(18) . . . . ?
C6' C7' C4' N2' -0.25(19) . . . . ?
C6' C7' C4' C3' 177.84(14) . . . . ?
C6' C5' C11' C16' 33.0(3) . . . . ?
C6' C5' C11' C12' -145.44(18) . . . . ?
C12 C11 C5 N2 33.4(2) . . . . ?
C12 C11 C5 C6 -147.69(17) . . . . ?
C12 C11 C16 C15 -1.2(2) . . . . ?
C8 O2 C9 C10 -173.73(15) . . . . ?
C8 C2 C3 C4 -178.45(17) . . . . ?
C16 C11 C5 N2 -148.82(16) . . . . ?
C16 C11 C5 C6 30.1(2) . . . . ?
C16 C11 C12 C13 0.9(2) . . . . ?
C15' C14' C13' C12' -1.5(3) . . . . ?
C15 C14 C13 C12 -1.0(2) . . . . ?
C5' N2' C4' C7' 0.53(19) . . . . ?
C5' N2' C4' C3' -176.5(2) . . . . ?
C5' C11' C16' C15' -179.23(16) . . . . ?
C5' C11' C12' C13' 179.93(17) . . . . ?
C2' N1' C7' C4' 0.23(18) . . . . ?
C2' N1' C7' C6' -176.2(2) . . . . ?
C14' N00A C17' C18' 67.9(2) . . . . ?
C14' N00A C19' C20' -89.4(2) . . . . ?
C14' C15' C16' C11' -1.2(3) . . . . ?
C14' C13' C12' C11' -0.4(3) . . . . ?
C8' O2' C9' C10' 166.54(17) . . . . ?
C8' C2' C3' C4' -176.04(17) . . . . ?
C3' C2' C8' O1' 177.93(17) . . . . ?
C3' C2' C8' O2' -0.8(3) . . . . ?
C6 C7 C4 N2 -0.48(18) . . . . ?
C6 C7 C4 C3 178.21(13) . . . . ?
C2 N1 C7 C4 -0.17(18) . . . . ?
C2 N1 C7 C6 -177.8(2) . . . . ?
C13 C14 C15 C16 0.7(2) . . . . ?
C19 N3 C14 C15 23.4(2) . . . . ?
C19 N3 C14 C13 -161.33(16) . . . . ?
C19 N3 C17 C18 81.3(2) . . . . ?
C16' C15' C14' N00A -176.06(16) . . . . ?
C16' C15' C14' C13' 2.3(2) . . . . ?
C16' C11' C12' C13' 1.5(3) . . . . ?
C17' N00A C14' C15' -167.51(16) . . . . ?
C17' N00A C14' C13' 14.2(3) . . . . ?
C17' N00A C19' C20' 79.1(2) . . . . ?
C1' N2' C4' C7' 175.85(15) . . . . ?
C1' N2' C4' C3' -1.2(3) . . . . ?
C1' N2' C5' C6' -175.62(16) . . . . ?
C1' N2' C5' C11' -0.3(3) . . . . ?
C12' C11' C16' C15' -0.7(3) . . . . ?
C1 N2 C5 C11 1.1(3) . . . . ?
C1 N2 C5 C6 -177.90(15) . . . . ?
C1 N2 C4 C7 178.29(14) . . . . ?
C1 N2 C4 C3 0.3(3) . . . . ?
C19' N00A C14' C15' 0.6(3) . . . . ?
C19' N00A C14' C13' -177.66(16) . . . . ?
C19' N00A C17' C18' -100.73(18) . . . . ?
C9 O2 C8 O1 -4.8(2) . . . . ?
C9 O2 C8 C2 174.19(14) . . . . ?
C9' O2' C8' O1' -9.1(3) . . . . ?
C9' O2' C8' C2' 169.61(15) . . . . ?
C17 N3 C14 C15 176.05(16) . . . . ?
C17 N3 C14 C13 -8.7(2) . . . . ?
C17 N3 C19 C20 -90.40(19) . . . . ?
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
1.2066 -0.8444 8.7604 -0.0255 -0.9925 -0.1194
-1.2066 0.8444 -8.7604 0.0255 0.9925 0.1194
-6.1371 -2.8978 2.6359 -0.0035 -0.1869 0.9824
-2.9509 -6.9652 -0.3700 -0.6626 0.0178 0.7488
-6.1962 3.7933 1.8825 0.7532 -0.0184 0.6575
6.0412 -4.1303 -1.8978 -0.7847 0.0193 -0.6196
6.7383 1.2181 -1.2757 -0.1970 0.0038 -0.9804
-2.9302 7.3146 1.6882 0.9990 -0.0256 0.0368
