data_mn04-qu
_audit_creation_date               2019-08-15
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number       '2018/3'
_audit_contact_author_address      ?
_audit_contact_author_email        ?
_audit_contact_author_name         ''
_audit_contact_author_phone        ?
_publ_contact_author_id_orcid      ?
_publ_section_references
;
Dolomanov, O.V., Bourhis, L.J., Gildea, R.J, Howard, J.A.K. & Puschmann, H.
 (2009), J. Appl. Cryst. 42, 339-341.

Sheldrick, G.M. (2015). Acta Cryst. A71, 3-8.

Sheldrick, G.M. (2015). Acta Cryst. C71, 3-8.
;
_chemical_name_common              ?
_chemical_name_systematic          ?
_chemical_formula_moiety           'Br, C22 H29 N2 O2, C3 H8 O'
_chemical_formula_sum              'C25 H37 Br N2 O3'
_chemical_formula_weight           493.47
_chemical_absolute_configuration   syn
_chemical_melting_point            ?
_chemical_oxdiff_formula           C25H38BrN2O3
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'
 'Br' 'Br' -0.6763 1.2805
 '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'

_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.
;
_space_group_crystal_system        'orthorhombic'
_space_group_IT_number             19
_space_group_name_H-M_alt          'P 21 21 21'
_space_group_name_Hall             'P 2ac 2ab'
loop_
  _space_group_symop_operation_xyz
 'x, y, z'
 '-x+1/2, -y, z+1/2'
 '-x, y+1/2, -z+1/2'
 'x+1/2, -y+1/2, -z'

_cell_length_a                     8.25467(2)
_cell_length_b                     13.60583(4)
_cell_length_c                     22.29025(7)
_cell_angle_alpha                  90
_cell_angle_beta                   90
_cell_angle_gamma                  90
_cell_volume                       2503.453(12)
_cell_formula_units_Z              4
_cell_measurement_reflns_used      31209
_cell_measurement_temperature      100.00(10)
_cell_measurement_theta_max        76.1160
_cell_measurement_theta_min        3.2450
_shelx_estimated_absorpt_T_max     ?
_shelx_estimated_absorpt_T_min     ?
_exptl_absorpt_coefficient_mu      2.449
_exptl_absorpt_correction_T_max    0.985
_exptl_absorpt_correction_T_min    0.656
_exptl_absorpt_correction_type     gaussian
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.40.53 (Rigaku Oxford Diffraction, 2019)
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_absorpt_special_details     ?
_exptl_crystal_colour              'clear colourless'
_exptl_crystal_density_diffrn      1.309
_exptl_crystal_density_meas        ?
_exptl_crystal_density_method      ?
_exptl_crystal_description         block
_exptl_crystal_F_000               1040
loop_
  _exptl_crystal_face_index_h
  _exptl_crystal_face_index_k
  _exptl_crystal_face_index_l
  _exptl_crystal_face_perp_dist
 5 -3 -5 0.1527
 -3 -5 8 0.0972
 -5 3 5 0.0802
 -2 8 -3 0.1369
 3 6 -8 0.1112
 -1 -6 -10 0.0566
 2 -8 2 0.1115
 2 4 12 0.0538
 -2 8 0 0.1401
 0 0 1 0.0700
 2 5 2 0.0931
 5 2 5 0.1156
 -2 -2 -5 0.0718

_exptl_crystal_size_max            0.288
_exptl_crystal_size_mid            0.215
_exptl_crystal_size_min            0.141
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
 4.6298 -3.1315 -5.1717 -0.0634 0.7966 0.6012
 -2.8696 -5.4032 8.4182 0.0697 -0.8957 0.4392
 -4.6572 2.8615 5.4070 0.0649 -0.8171 -0.5729
 -1.5762 8.1962 -3.3001 -0.0080 0.1191 -0.9929
 2.5170 5.9523 -8.2448 -0.0662 0.8520 -0.5193
 -0.9600 -6.0772 -10.1713 0.8820 0.1639 0.4419
 2.0802 -8.0257 2.2108 0.0076 0.0027 1.0000
 1.6798 4.2610 11.8354 -0.9663 -0.1792 -0.1847
 -1.7176 8.3632 -0.2011 -0.1634 -0.0316 -0.9861
 0.0000 0.0000 1.0000 -0.0525 -0.0435 0.0110
 2.0000 5.0000 2.0000 -0.5127 0.3112 -0.3459
 5.0000 2.0000 5.0000 -0.8470 0.5278 0.2135
 -2.0000 -2.0000 -5.0000 0.5460 -0.1091 0.0047

_exptl_transmission_factor_max     ?
_exptl_transmission_factor_min     ?
_diffrn_reflns_av_R_equivalents    0.0158
_diffrn_reflns_av_unetI/netI       0.0075
_diffrn_reflns_Laue_measured_fraction_full  0.998
_diffrn_reflns_Laue_measured_fraction_max  0.998
_diffrn_reflns_limit_h_max         10
_diffrn_reflns_limit_h_min         -10
_diffrn_reflns_limit_k_max         13
_diffrn_reflns_limit_k_min         -17
_diffrn_reflns_limit_l_max         28
_diffrn_reflns_limit_l_min         -27
_diffrn_reflns_number              32407
_diffrn_reflns_point_group_measured_fraction_full  0.999
_diffrn_reflns_point_group_measured_fraction_max  0.998
_diffrn_reflns_theta_full          67.684
_diffrn_reflns_theta_max           76.367
_diffrn_reflns_theta_min           3.806
_diffrn_ambient_environment        N~2~
_diffrn_ambient_temperature        100.00(10)
_diffrn_detector                   'CCD plate'
_diffrn_detector_area_resol_mean   10.0000
_diffrn_detector_type              HyPix
_diffrn_measured_fraction_theta_full  0.998
_diffrn_measured_fraction_theta_max  0.998
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
--------------------------------------------------------------------------
  1  ω    -27.00  20.00   0.50    0.50    --  -47.57  19.00 -60.00   94
  2  ω     62.00  87.00   0.50    0.50    --   47.57 166.00-129.00   50
  3  ω     94.00 124.00   0.50    3.00    --  104.75 166.00-129.00   60
  4  ω    108.00 134.00   0.50    3.00    --  104.75 125.00 -90.00   52
  5  ω    140.00 176.00   0.50    3.00    --  104.75 125.00 -30.00   72
  6  ω    152.00 178.00   0.50    3.00    --  104.75  77.00  30.00   52
  7  ω    149.00 178.00   0.50    3.00    --  104.75  15.00   0.00   58
  8  ω    140.00 177.00   0.50    3.00    --  104.75  15.00  30.00   74
  9  ω    123.00 148.00   0.50    3.00    --  104.75  77.00  30.00   50
 10  ω    117.00 177.00   0.50    3.00    --  104.75  45.00  60.00  120
 11  ω    120.00 146.00   0.50    3.00    --  104.75  30.00 150.00   52
 12  ω    134.00 160.00   0.50    3.00    --  104.75  79.00 175.32   52
 13  ω    107.00 132.00   0.50    3.00    --  104.75 115.00  84.00   50
 14  ω     81.00 112.00   0.50    3.00    --  104.75  79.00 175.32   62
 15  ω     98.00 124.00   0.50    3.00    --  104.75  15.00  30.00   52
 16  ω    116.00 142.00   0.50    3.00    --  104.75  15.00   0.00   52
 17  ω     95.00 120.00   0.50    3.00    --  104.75  45.00 -90.00   50
 18  ω    132.00 168.00   0.50    3.00    --  104.75  45.00 -90.00   72
 19  ω    117.00 143.00   0.50    3.00    --  104.75  30.00 -90.00   52
 20  ω     82.00 178.00   0.50    3.00    --  104.75 125.00-120.00  192
 21  ω     81.00 134.00   0.50    3.00    --  104.75 125.00 -30.00  106
 22  ω     46.00  71.00   0.50    3.00    --  104.75 -61.00  60.00   50
 23  ω     81.00 106.00   0.50    3.00    --  104.75 -94.00   0.00   50
 24  ω     69.00  95.00   0.50    3.00    --  104.75-101.00  -4.17   52
 25  ω     58.00 110.00   0.50    3.00    --  104.75-125.00   0.00  104
 26  ω     77.00 112.00   0.50    3.00    --  104.75-125.00 -90.00   70
 27  ω     65.00  91.00   0.50    0.50    --   47.57-166.00-151.00   52
 28  ω     38.00  68.00   0.50    3.00    --  104.75-125.00 -90.00   60
 29  ω     42.00  92.00   0.50    3.00    --  104.75 -94.00 -30.00  100
 30  ω     48.00  74.00   0.50    3.00    --  104.75 -77.00 -90.00   52
 31  ω     47.00  73.00   0.50    3.00    --  104.75-115.00  -5.00   52
 32  ω     54.00  93.00   0.50    3.00    --  104.75 -78.00   9.89   78
 33  ω     50.00 102.00   0.50    3.00    --  104.75 -77.00  90.00  104
 34  ω     46.00  71.00   0.50    3.00    --  104.75 -61.00 150.00   50
 35  ω     32.00  73.00   0.50    3.00    --  104.75 -77.00 150.00   82
 36  ω     13.00  51.00   0.50    0.50    --   47.57-115.00  -5.00   76
 37  ω     33.00  63.00   0.50    3.00    --  104.75 -61.00 -30.00   60
 38  ω     38.00  64.00   0.50    3.00    --  104.75 -94.00   0.00   52
 39  ω     33.00 102.00   0.50    3.00    --  104.75 -77.00 -30.00  138
 40  ω     37.00  70.00   0.50    3.00    --  104.75 -61.00 -90.00   66
 41  ω     36.00  62.00   0.50    3.00    --  104.75 -94.00-180.00   52
 42  ω     72.00  98.00   0.50    3.00    --  104.75 -94.00-180.00   52
 43  ω     64.00  90.00   0.50    3.00    --  104.75-125.00-180.00   52
 44  ω     39.00 109.00   0.50    3.00    --  104.75-125.00 -60.00  140
 45  ω    -15.00  27.00   0.50    0.50    --  -47.57  19.00 150.00   84
 46  ω    -89.00  -7.00   0.50    0.50    --  -47.57 115.00  84.00  164
 47  ω   -102.00 -77.00   0.50    0.50    --  -47.57 166.00-129.00   50
 48  ω   -111.00 -86.00   0.50    3.00    -- -102.00 166.00-129.00   50
 49  ω   -117.00 -91.00   0.50    3.00    -- -102.00 -54.00  27.36   52
 50  ω   -132.00-107.00   0.50    3.00    -- -102.00-115.00  -5.00   50
 51  ω   -119.00 -75.00   0.50    0.50    --  -47.57-125.00  60.00   88
 52  ω   -108.00 -83.00   0.50    0.50    --  -47.57-166.00-151.00   50
;
_diffrn_measurement_device         'four-circle diffractometer'
_diffrn_measurement_device_type    'XtaLAB Synergy R, DW system, HyPix'
_diffrn_measurement_method         'ω scans'
_diffrn_orient_matrix_type        
 'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11        -0.1003366000
_diffrn_orient_matrix_UB_12        -0.0414097000
_diffrn_orient_matrix_UB_13        -0.0524987000
_diffrn_orient_matrix_UB_21        0.1395525000
_diffrn_orient_matrix_UB_22        0.0238392000
_diffrn_orient_matrix_UB_23        -0.0435272000
_diffrn_orient_matrix_UB_31        0.0727385000
_diffrn_orient_matrix_UB_32        -0.1026989000
_diffrn_orient_matrix_UB_33        0.0110478000
_diffrn_oxdiff_digest_frames
;
017f9d8c534767791e2de28ac1297791f7037064425
;
_diffrn_oxdiff_digest_hkl
;
0198959e70421707cff3e410bd2edcdc09cd60
;
_diffrn_radiation_monochromator    mirror
_diffrn_radiation_probe            x-ray
_diffrn_radiation_type             CuK\a
_diffrn_radiation_wavelength       1.54184
_diffrn_source                     'Rotating-anode X-ray tube'
_diffrn_source_type                'Rigaku (Cu) X-ray Source'
_reflns_Friedel_coverage           0.758
_reflns_Friedel_fraction_full      1.000
_reflns_Friedel_fraction_max       0.997
_reflns_number_gt                  5237
_reflns_number_total               5240
_reflns_odcompleteness_completeness  99.05
_reflns_odcompleteness_iscentric   1
_reflns_odcompleteness_theta       76.86
_reflns_special_details
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression       'I > 2σ(I)'
_computing_cell_refinement         'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_computing_data_collection         'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_computing_data_reduction          'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_computing_molecular_graphics      'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material    'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement    'ShelXL (Sheldrick, 2015)'
_computing_structure_solution      'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max           0.194
_refine_diff_density_min           -0.162
_refine_diff_density_rms           0.036
_refine_ls_abs_structure_details
;
 Flack x determined using 2254 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack     -0.022(3)
_refine_ls_extinction_coef         0.00098(10)
_refine_ls_extinction_expression  
 'Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^'
_refine_ls_extinction_method       'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref     1.062
_refine_ls_hydrogen_treatment      mixed
_refine_ls_matrix_type             full
_refine_ls_number_parameters       295
_refine_ls_number_reflns           5240
_refine_ls_number_restraints       0
_refine_ls_R_factor_all            0.0166
_refine_ls_R_factor_gt             0.0166
_refine_ls_restrained_S_all        1.062
_refine_ls_shift/su_max            0.002
_refine_ls_shift/su_mean           0.000
_refine_ls_structure_factor_coef   Fsqd
_refine_ls_weighting_details      
 'w=1/[σ²(Fo²)+(0.0233P)²+0.8545P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme        calc
_refine_ls_wR_factor_gt            0.0440
_refine_ls_wR_factor_ref           0.0440
_refine_special_details            ?
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2.a Ternary CH refined with riding coordinates:
 C11(H11), C12(H12), C14(H14), C15(H15), C24(H24)
2.b Secondary CH2 refined with riding coordinates:
 C13(H13A,H13B), C16(H16A,H16B), C17(H17A,H17B), C18(H18A,H18B), C21(H21A,H21B)
2.c Aromatic/amide H refined with riding coordinates:
 C3(H3), C4(H4), C6(H6), C7(H7), C10(H10), C19(H19)
2.d Idealised Me refined as rotating group:
 C1(H1A,H1B,H1C), C22(H22A,H22B,H22C), C23(H23A,H23B,H23C), C25(H25A,H25B,H25C)
2.e Idealised tetrahedral OH refined as rotating group:
 O2(H2), O3(H3A)
;
_atom_sites_solution_hydrogens     mixed
_atom_sites_solution_primary       dual
_atom_sites_solution_secondary     ?
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
 Br1 Br 0.78753(2) 0.59171(2) 0.55891(2) 0.01707(6) Uani 1 1 d . . . . .
 O1 O 0.44609(18) 0.43775(10) 0.71564(6) 0.0236(3) Uani 1 1 d . . . . .
 O2 O 0.55867(15) 0.44297(9) 0.42353(5) 0.0156(2) Uani 1 1 d . . . . .
 H2 H 0.649480 0.422280 0.431456 0.023 Uiso 1 1 calc GR . . . .
 O3 O 0.84694(18) 0.67505(11) 0.69836(6) 0.0238(3) Uani 1 1 d . . . . .
 H3A H 0.818405 0.654554 0.665417 0.036 Uiso 1 1 calc GR . . . .
 N1 N 0.33612(19) 0.15594(11) 0.54248(7) 0.0169(3) Uani 1 1 d . . . . .
 N2 N 0.30584(17) 0.60629(10) 0.45665(6) 0.0125(3) Uani 1 1 d . . . . .
 C1 C 0.5350(3) 0.52534(18) 0.70312(10) 0.0313(5) Uani 1 1 d . . . . .
 H1A H 0.629450 0.509326 0.679945 0.047 Uiso 1 1 calc GR . . . .
 H1B H 0.567487 0.555582 0.740133 0.047 Uiso 1 1 calc GR . . . .
 H1C H 0.468043 0.570023 0.680867 0.047 Uiso 1 1 calc GR . . . .
 C2 C 0.4160(2) 0.37598(14) 0.66874(8) 0.0181(4) Uani 1 1 d . . . . .
 C3 C 0.3553(2) 0.28261(15) 0.68599(8) 0.0208(4) Uani 1 1 d . . . . .
 H3 H 0.333256 0.269586 0.726130 0.025 Uiso 1 1 calc R . . . .
 C4 C 0.3294(2) 0.21223(14) 0.64380(8) 0.0196(4) Uani 1 1 d . . . . .
 H4 H 0.291633 0.150709 0.655413 0.024 Uiso 1 1 calc R . . . .
 C5 C 0.3594(2) 0.23162(13) 0.58197(8) 0.0155(3) Uani 1 1 d . . . . .
 C6 C 0.3697(2) 0.17243(13) 0.48527(8) 0.0173(3) Uani 1 1 d . . . . .
 H6 H 0.360904 0.120499 0.458342 0.021 Uiso 1 1 calc R . . . .
 C7 C 0.4180(2) 0.26467(13) 0.46336(8) 0.0166(3) Uani 1 1 d . . . . .
 H7 H 0.440620 0.272345 0.422752 0.020 Uiso 1 1 calc R . . . .
 C8 C 0.4322(2) 0.34368(13) 0.50142(8) 0.0143(3) Uani 1 1 d . . . . .
 C9 C 0.41113(19) 0.32668(13) 0.56431(8) 0.0140(3) Uani 1 1 d . . . . .
 C10 C 0.4423(2) 0.39875(14) 0.60930(8) 0.0165(3) Uani 1 1 d . . . . .
 H10 H 0.480176 0.460695 0.598602 0.020 Uiso 1 1 calc R . . . .
 C11 C 0.4644(2) 0.44635(13) 0.47659(8) 0.0136(3) Uani 1 1 d . . . . .
 H11 H 0.521017 0.485602 0.506919 0.016 Uiso 1 1 calc R . . . .
 C12 C 0.2981(2) 0.49420(12) 0.46263(7) 0.0127(3) Uani 1 1 d . . . . .
 H12 H 0.226308 0.479536 0.496497 0.015 Uiso 1 1 calc R . . . .
 C13 C 0.2148(2) 0.45373(12) 0.40522(7) 0.0152(3) Uani 1 1 d . . . . .
 H13A H 0.276872 0.398826 0.389673 0.018 Uiso 1 1 calc R . . . .
 H13B H 0.107254 0.430084 0.415205 0.018 Uiso 1 1 calc R . . . .
 C14 C 0.2020(2) 0.53383(13) 0.35704(7) 0.0158(3) Uani 1 1 d . . . . .
 H14 H 0.163236 0.505436 0.319275 0.019 Uiso 1 1 calc R . . . .
 C15 C 0.0865(2) 0.61580(13) 0.37797(8) 0.0164(4) Uani 1 1 d . . . . .
 H15 H 0.104622 0.673732 0.352723 0.020 Uiso 1 1 calc R . . . .
 C16 C 0.1350(2) 0.64178(13) 0.44272(9) 0.0157(3) Uani 1 1 d . . . . .
 H16A H 0.129436 0.712431 0.448164 0.019 Uiso 1 1 calc R . . . .
 H16B H 0.059281 0.611593 0.470438 0.019 Uiso 1 1 calc R . . . .
 C17 C 0.4149(2) 0.63682(13) 0.40517(8) 0.0144(3) Uani 1 1 d . . . . .
 H17A H 0.526899 0.623002 0.415314 0.017 Uiso 1 1 calc R . . . .
 H17B H 0.404544 0.706946 0.398314 0.017 Uiso 1 1 calc R . . . .
 C18 C 0.3683(2) 0.58068(14) 0.34793(8) 0.0168(3) Uani 1 1 d . . . . .
 H18A H 0.365028 0.625440 0.314076 0.020 Uiso 1 1 calc R . . . .
 H18B H 0.448135 0.530197 0.339593 0.020 Uiso 1 1 calc R . . . .
 C19 C -0.0897(2) 0.58806(17) 0.37392(9) 0.0220(4) Uani 1 1 d . . . . .
 H19 H -0.132751 0.546776 0.403096 0.026 Uiso 1 1 calc R . . . .
 C20 C -0.1857(2) 0.61987(18) 0.33070(10) 0.0293(5) Uani 1 1 d . . . . .
 H20A H -0.301(3) 0.597(2) 0.3286(12) 0.034(7) Uiso 1 1 d . . . . .
 H20B H -0.141(4) 0.663(2) 0.3027(14) 0.044(8) Uiso 1 1 d . . . . .
 C21 C 0.3654(2) 0.65768(13) 0.51257(8) 0.0162(3) Uani 1 1 d . . . . .
 H21A H 0.372912 0.727505 0.504239 0.019 Uiso 1 1 calc R . . . .
 H21B H 0.473884 0.634361 0.521381 0.019 Uiso 1 1 calc R . . . .
 C22 C 0.2615(2) 0.64356(14) 0.56795(8) 0.0222(4) Uani 1 1 d . . . . .
 H22A H 0.152921 0.664915 0.559666 0.033 Uiso 1 1 calc GR . . . .
 H22B H 0.305220 0.681540 0.600438 0.033 Uiso 1 1 calc GR . . . .
 H22C H 0.260481 0.575300 0.578839 0.033 Uiso 1 1 calc GR . . . .
 C23 C 1.0390(3) 0.5406(2) 0.70412(11) 0.0389(6) Uani 1 1 d . . . . .
 H23A H 0.971000 0.508162 0.732905 0.058 Uiso 1 1 calc GR . . . .
 H23B H 1.150416 0.525507 0.712421 0.058 Uiso 1 1 calc GR . . . .
 H23C H 1.011898 0.518340 0.664507 0.058 Uiso 1 1 calc GR . . . .
 C24 C 1.0135(3) 0.65064(18) 0.70813(9) 0.0260(4) Uani 1 1 d . . . . .
 H24 H 1.079152 0.682673 0.677163 0.031 Uiso 1 1 calc R . . . .
 C25 C 1.0609(3) 0.6919(2) 0.76883(10) 0.0343(5) Uani 1 1 d . . . . .
 H25A H 1.036417 0.760798 0.770108 0.051 Uiso 1 1 calc GR . . . .
 H25B H 1.174932 0.682396 0.775091 0.051 Uiso 1 1 calc GR . . . .
 H25C H 1.001491 0.658475 0.799740 0.051 Uiso 1 1 calc GR . . . .


_geom_special_details
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
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
 O1 C1 1.427(3) . ?
 O1 C2 1.364(2) . ?
 O2 H2 0.8200 . ?
 O2 C11 1.417(2) . ?
 O3 H3A 0.8200 . ?
 O3 C24 1.431(3) . ?
 N1 C5 1.368(2) . ?
 N1 C6 1.324(2) . ?
 N2 C12 1.532(2) . ?
 N2 C16 1.523(2) . ?
 N2 C17 1.517(2) . ?
 N2 C21 1.511(2) . ?
 C1 H1A 0.9600 . ?
 C1 H1B 0.9600 . ?
 C1 H1C 0.9600 . ?
 C2 C3 1.419(3) . ?
 C2 C10 1.378(2) . ?
 C3 H3 0.9300 . ?
 C3 C4 1.359(3) . ?
 C4 H4 0.9300 . ?
 C4 C5 1.425(3) . ?
 C5 C9 1.418(2) . ?
 C6 H6 0.9300 . ?
 C6 C7 1.405(3) . ?
 C7 H7 0.9300 . ?
 C7 C8 1.374(3) . ?
 C8 C9 1.431(2) . ?
 C8 C11 1.526(2) . ?
 C9 C10 1.426(2) . ?
 C10 H10 0.9300 . ?
 C11 H11 0.9800 . ?
 C11 C12 1.551(2) . ?
 C12 H12 0.9800 . ?
 C12 C13 1.553(2) . ?
 C13 H13A 0.9700 . ?
 C13 H13B 0.9700 . ?
 C13 C14 1.534(2) . ?
 C14 H14 0.9800 . ?
 C14 C15 1.539(2) . ?
 C14 C18 1.527(2) . ?
 C15 H15 0.9800 . ?
 C15 C16 1.539(3) . ?
 C15 C19 1.506(2) . ?
 C16 H16A 0.9700 . ?
 C16 H16B 0.9700 . ?
 C17 H17A 0.9700 . ?
 C17 H17B 0.9700 . ?
 C17 C18 1.536(2) . ?
 C18 H18A 0.9700 . ?
 C18 H18B 0.9700 . ?
 C19 H19 0.9300 . ?
 C19 C20 1.321(3) . ?
 C20 H20A 1.01(3) . ?
 C20 H20B 0.93(3) . ?
 C21 H21A 0.9700 . ?
 C21 H21B 0.9700 . ?
 C21 C22 1.516(3) . ?
 C22 H22A 0.9600 . ?
 C22 H22B 0.9600 . ?
 C22 H22C 0.9600 . ?
 C23 H23A 0.9600 . ?
 C23 H23B 0.9600 . ?
 C23 H23C 0.9600 . ?
 C23 C24 1.515(3) . ?
 C24 H24 0.9800 . ?
 C24 C25 1.516(3) . ?
 C25 H25A 0.9600 . ?
 C25 H25B 0.9600 . ?
 C25 H25C 0.9600 . ?

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 O1 C1 117.27(15) . . ?
 C11 O2 H2 109.5 . . ?
 C24 O3 H3A 109.5 . . ?
 C6 N1 C5 117.56(16) . . ?
 C16 N2 C12 107.13(13) . . ?
 C17 N2 C12 111.31(13) . . ?
 C17 N2 C16 107.98(12) . . ?
 C21 N2 C12 113.73(12) . . ?
 C21 N2 C16 108.83(13) . . ?
 C21 N2 C17 107.70(13) . . ?
 O1 C1 H1A 109.5 . . ?
 O1 C1 H1B 109.5 . . ?
 O1 C1 H1C 109.5 . . ?
 H1A C1 H1B 109.5 . . ?
 H1A C1 H1C 109.5 . . ?
 H1B C1 H1C 109.5 . . ?
 O1 C2 C3 114.09(16) . . ?
 O1 C2 C10 124.73(17) . . ?
 C10 C2 C3 121.18(17) . . ?
 C2 C3 H3 120.0 . . ?
 C4 C3 C2 119.92(17) . . ?
 C4 C3 H3 120.0 . . ?
 C3 C4 H4 119.6 . . ?
 C3 C4 C5 120.76(17) . . ?
 C5 C4 H4 119.6 . . ?
 N1 C5 C4 117.29(16) . . ?
 N1 C5 C9 123.38(16) . . ?
 C9 C5 C4 119.33(17) . . ?
 N1 C6 H6 118.5 . . ?
 N1 C6 C7 123.08(17) . . ?
 C7 C6 H6 118.5 . . ?
 C6 C7 H7 119.7 . . ?
 C8 C7 C6 120.55(17) . . ?
 C8 C7 H7 119.7 . . ?
 C7 C8 C9 117.89(16) . . ?
 C7 C8 C11 120.46(15) . . ?
 C9 C8 C11 121.62(15) . . ?
 C5 C9 C8 117.13(16) . . ?
 C5 C9 C10 119.10(16) . . ?
 C10 C9 C8 123.76(16) . . ?
 C2 C10 C9 119.55(17) . . ?
 C2 C10 H10 120.2 . . ?
 C9 C10 H10 120.2 . . ?
 O2 C11 C8 111.64(14) . . ?
 O2 C11 H11 109.4 . . ?
 O2 C11 C12 109.41(13) . . ?
 C8 C11 H11 109.4 . . ?
 C8 C11 C12 107.63(14) . . ?
 C12 C11 H11 109.4 . . ?
 N2 C12 C11 113.45(14) . . ?
 N2 C12 H12 107.2 . . ?
 N2 C12 C13 107.44(13) . . ?
 C11 C12 H12 107.2 . . ?
 C11 C12 C13 114.09(14) . . ?
 C13 C12 H12 107.2 . . ?
 C12 C13 H13A 109.5 . . ?
 C12 C13 H13B 109.5 . . ?
 H13A C13 H13B 108.1 . . ?
 C14 C13 C12 110.82(13) . . ?
 C14 C13 H13A 109.5 . . ?
 C14 C13 H13B 109.5 . . ?
 C13 C14 H14 110.1 . . ?
 C13 C14 C15 110.19(14) . . ?
 C15 C14 H14 110.1 . . ?
 C18 C14 C13 109.15(15) . . ?
 C18 C14 H14 110.1 . . ?
 C18 C14 C15 107.13(14) . . ?
 C14 C15 H15 108.3 . . ?
 C16 C15 C14 106.84(14) . . ?
 C16 C15 H15 108.3 . . ?
 C19 C15 C14 113.48(15) . . ?
 C19 C15 H15 108.3 . . ?
 C19 C15 C16 111.41(15) . . ?
 N2 C16 C15 111.05(14) . . ?
 N2 C16 H16A 109.4 . . ?
 N2 C16 H16B 109.4 . . ?
 C15 C16 H16A 109.4 . . ?
 C15 C16 H16B 109.4 . . ?
 H16A C16 H16B 108.0 . . ?
 N2 C17 H17A 109.6 . . ?
 N2 C17 H17B 109.6 . . ?
 N2 C17 C18 110.08(14) . . ?
 H17A C17 H17B 108.2 . . ?
 C18 C17 H17A 109.6 . . ?
 C18 C17 H17B 109.6 . . ?
 C14 C18 C17 108.81(14) . . ?
 C14 C18 H18A 109.9 . . ?
 C14 C18 H18B 109.9 . . ?
 C17 C18 H18A 109.9 . . ?
 C17 C18 H18B 109.9 . . ?
 H18A C18 H18B 108.3 . . ?
 C15 C19 H19 118.6 . . ?
 C20 C19 C15 122.79(19) . . ?
 C20 C19 H19 118.6 . . ?
 C19 C20 H20A 120.1(15) . . ?
 C19 C20 H20B 117(2) . . ?
 H20A C20 H20B 123(3) . . ?
 N2 C21 H21A 108.4 . . ?
 N2 C21 H21B 108.4 . . ?
 N2 C21 C22 115.40(15) . . ?
 H21A C21 H21B 107.5 . . ?
 C22 C21 H21A 108.4 . . ?
 C22 C21 H21B 108.4 . . ?
 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 . . ?
 H23A C23 H23B 109.5 . . ?
 H23A C23 H23C 109.5 . . ?
 H23B C23 H23C 109.5 . . ?
 C24 C23 H23A 109.5 . . ?
 C24 C23 H23B 109.5 . . ?
 C24 C23 H23C 109.5 . . ?
 O3 C24 C23 110.8(2) . . ?
 O3 C24 H24 108.7 . . ?
 O3 C24 C25 107.35(18) . . ?
 C23 C24 H24 108.7 . . ?
 C23 C24 C25 112.5(2) . . ?
 C25 C24 H24 108.7 . . ?
 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 . . ?

_olex2_submission_special_instructions  'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
- Detector area scaling
;
_oxdiff_exptl_absorpt_empirical_full_max  1.468
_oxdiff_exptl_absorpt_empirical_full_min  0.726
