# Electronic Supplementary Material (ESI) for Physical Chemistry Chemical Physics.
# This journal is © the Owner Societies 2022

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
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data_20220328_sv20_mo_90k_auto
_database_code_depnum_ccdc_archive 'CCDC 2176622'
loop_
_audit_author_name
_audit_author_address
'Sanehiro Muromachi'
;National Institute of Advanced Industrial Science and Technology (AIST)
Japan
;
_audit_update_record             
;
2022-06-02 deposited with the CCDC.	2022-07-07 downloaded from the CCDC.
;
_audit_creation_date             2022-04-05
_audit_creation_method           
;
Olex2 1.3-ac4
(compiled 2019.04.23 svn.r3594 for Rigaku Oxford Diffraction, GUI svn.r5739)
;
_shelx_SHELXL_version_number     2016/6
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         
'0.22(Br), 0.38(O), H12.59 O7.24, H0.9 O0.5, H3.27 O1.5, 0.23(C17 H38 N)'
_chemical_formula_sum            'C3.65 H16.27 Br0.21 N0.22 O9.66'
_chemical_formula_weight         234.73
_chemical_melting_point          ?
_chemical_oxdiff_formula         (C4H9)3C5H11NBr(H2O)38
_chemical_oxdiff_usercomment     'N4445-3-HYD hydrate'
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 '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           51
_space_group_name_H-M_alt        'P m m a'
_space_group_name_Hall           '-P 2a 2a'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z'
'x+1/2, -y, -z'
'-x, y, -z'
'-x, -y, -z'
'x-1/2, y, -z'
'-x-1/2, y, z'
'x, -y, z'

_cell_length_a                   21.0695(10)
_cell_length_b                   12.6077(6)
_cell_length_c                   12.0415(6)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     3198.7(3)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    5064
_cell_measurement_temperature    90.00(16)
_cell_measurement_theta_max      31.3360
_cell_measurement_theta_min      1.9430
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.621
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.96376
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.41.104a (Rigaku Oxford Diffraction, 2021)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   .
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    0.975
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       prism
_exptl_crystal_F_000             995
_exptl_crystal_preparation       ?
_exptl_crystal_recrystallization_method ?
_exptl_crystal_size_max          0.05
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.05
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0617
_diffrn_reflns_av_unetI/netI     0.0580
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.826
_diffrn_reflns_limit_h_max       28
_diffrn_reflns_limit_h_min       -22
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            20300
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.826
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         31.024
_diffrn_reflns_theta_min         1.948
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      90.00(16)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.826
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -36.00   0.00   0.50   17.74    --   -4.27 -76.00  57.00   72
  2  ω    -72.00 -43.00   0.50   17.74    --   -4.27 -76.00  57.00   58
  3  ω    -20.00  22.00   0.50   17.74    --   -4.27 -99.00 150.00   84
  4  ω    -28.00  -3.00   0.50   17.74    --   -4.27  79.00 -62.00   50
  5  ω    -20.00  40.00   0.50   17.74    --    6.85 -99.00 -60.00  120
;
_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      0.0141684000
_diffrn_orient_matrix_UB_12      0.0273815000
_diffrn_orient_matrix_UB_13      -0.0451027000
_diffrn_orient_matrix_UB_21      -0.0241813000
_diffrn_orient_matrix_UB_22      0.0390591000
_diffrn_orient_matrix_UB_23      0.0027247000
_diffrn_orient_matrix_UB_31      0.0186603000
_diffrn_orient_matrix_UB_32      0.0298332000
_diffrn_orient_matrix_UB_33      0.0377714000
_diffrn_oxdiff_digest_frames     
;
01ea679cf95e7796c0116bd8c54f7acad3000251021
;
_diffrn_oxdiff_digest_hkl        
;
0121ef92cb60643db8d402326c5ec9b91ed242
;
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3374
_reflns_number_total             4514
_reflns_odcompleteness_completeness 99.89
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_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 1.171.41.104a (Rigaku OD, 2021)'
_computing_data_collection       'CrysAlisPro 1.171.41.104a (Rigaku OD, 2021)'
_computing_data_reduction        'CrysAlisPro 1.171.41.104a (Rigaku OD, 2021)'
_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         0.437
_refine_diff_density_min         -0.455
_refine_diff_density_rms         0.062
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.083
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     346
_refine_ls_number_reflns         4514
_refine_ls_number_restraints     29
_refine_ls_R_factor_all          0.0748
_refine_ls_R_factor_gt           0.0493
_refine_ls_restrained_S_all      1.081
_refine_ls_shift/su_max          0.039
_refine_ls_shift/su_mean         0.002
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0340P)²+2.5572P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1117
_refine_ls_wR_factor_ref         0.1188
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All C(H,H,H,H,H) groups, All O(H) groups, All O(H,H)
  groups, All O(H,H,H) groups, All O(H,H,H,H) groups
2. Restrained distances
 O2-H2A = O2-H2B
 0.87 with sigma of 0.02
 O10-H10A = O10-H10B
 0.87 with sigma of 0.02
 O11-H11A = O11-H11B
 0.87 with sigma of 0.02
 O12-H12A = O12-H12B
 0.87 with sigma of 0.02
 O13-H13A = O13-H13B
 0.87 with sigma of 0.02
 O14-H14A = O14-H14B
 0.87 with sigma of 0.02
 O15-H15A = O15-H15B
 0.87 with sigma of 0.02
 O16-H16A = O16-H16B
 0.87 with sigma of 0.02
 O17-H17A = O17-H17B
 0.87 with sigma of 0.02
 H13A-H13B
 1.38 with sigma of 0.04
 H2A-H2B
 1.38 with sigma of 0.04
 H17A-H17B
 1.38 with sigma of 0.04
 H11A-H11B
 1.38 with sigma of 0.04
 H15A-H15B
 1.38 with sigma of 0.04
 H10A-H10B
 1.38 with sigma of 0.04
 H12A-H12B
 1.38 with sigma of 0.04
 H14A-H14B
 1.38 with sigma of 0.04
 H16A-H16B
 1.38 with sigma of 0.04
3. Uiso/Uaniso restraints and constraints
Uiso(C1B) = Uiso(C1D)
Uiso(C2B) = Uiso(C2D)
Uiso(C3B) = Uiso(C3D)
Uiso(C4B) = Uiso(C4D)
Uanis(C1A) = Uanis(C1C)
Uanis(C2A) = Uanis(C2C)
Uanis(C3A) = Uanis(C3C)
Uanis(C4A) = Uanis(C4C)
4. Others
 1*[Sof(O21A)+Sof(H21A)+Sof(H21B)]+1*[Sof(O21B)]+1*[Sof(O21C)]=1 with esd of 0.1
 1*[Sof(O20A)]+1*[Sof(O20B)]+1*[Sof(O20C)]=1 with esd of 0.01
 Sof(ON1)=0.25*(1-FVAR(2))
 Sof(N1)=Sof(C1A)=Sof(H1AA)=Sof(H1AB)=Sof(C2A)=Sof(H2AA)=Sof(H2AB)=Sof(C3A)=
 Sof(H3AA)=Sof(H3AB)=Sof(C4A)=Sof(H4AA)=Sof(H4AB)=Sof(H4AC)=Sof(C1B)=Sof(H1BA)=
 Sof(H1BB)=Sof(C2B)=Sof(H2BA)=Sof(H2BB)=Sof(C3B)=Sof(H3BA)=Sof(H3BB)=Sof(C4B)=
 Sof(H4BA)=Sof(H4BB)=Sof(H4BC)=Sof(C1C)=Sof(H1CA)=Sof(H1CB)=Sof(C2C)=Sof(H2CA)=
 Sof(H2CB)=Sof(C3C)=Sof(H3CA)=Sof(H3CB)=Sof(C4C)=Sof(H4CA)=Sof(H4CB)=Sof(H4CC)=
 Sof(C1D)=Sof(H1DA)=Sof(H1DB)=Sof(C2D)=Sof(H2DA)=Sof(H2DB)=Sof(C3D)=Sof(H3DA)=
 Sof(H3DB)=Sof(C4D)=Sof(H4DA)=Sof(H4DB)=Sof(C5D)=Sof(H5DA)=Sof(H5DB)=Sof(H5DC)=
 0.25*FVAR(2)
 Sof(H21A)=Sof(H21B)=0.12495*FVAR(3)
 Sof(O21A)=0.5*FVAR(3)
 Fixed Sof: H18A(0.25) H18B(0.25) H20B(0.25) H2A(0.5) H2B(0.5) H2C(0.5)
 H2D(0.5) H10A(0.5) H10B(0.5) H10C(0.5) H10D(0.5) H11A(0.5) H11B(0.5) H11C(0.5)
 H11D(0.5) H12C(0.25) H14B(0.5) H14C(0.5)
5.a Secondary CH2 refined with riding coordinates:
 C1A(H1AA,H1AB), C2A(H2AA,H2AB), C3A(H3AA,H3AB), C1B(H1BA,H1BB), C2B(H2BA,
 H2BB), C3B(H3BA,H3BB), C1C(H1CA,H1CB), C2C(H2CA,H2CB), C3C(H3CA,H3CB),
 C1D(H1DA,H1DB), C2D(H2DA,H2DB), C3D(H3DA,H3DB), C4D(H4DA,H4DB)
5.b Idealised Me refined as rotating group:
 C4A(H4AA,H4AB,H4AC), C4B(H4BA,H4BB,H4BC), C4C(H4CA,H4CB,H4CC), C5D(H5DA,H5DB,
 H5DC)
;
_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 0.250000 0.500000 -0.02935(3) 0.02035(6) Uiso 0.6976(7) 4 d S T P A 2
Br2 Br 0.250000 0.500000 -0.00601(18) 0.0210(4) Uiso 0.1030(7) 4 d S T P B 3
Br3 Br 0.250000 0.500000 -0.0484(2) 0.0129(5) Uiso 0.0779(6) 4 d S T P C 4
O18A O 0.6386(2) 0.500000 1.1323(4) 0.0176(10) Uiso 0.202(3) 2 d S T P D 5
O18B O 0.60286(6) 0.500000 1.12456(10) 0.0292(3) Uiso 0.972(3) 2 d S T P E 6
H18A H 0.589(3) 0.438(5) 1.103(5) 0.044 Uiso 0.25 1 d R . . F 6
H18B H 0.6428(19) 0.500000 1.084(3) 0.044 Uiso 0.5 2 d RS T P G 6
O21A O 0.750000 0.2048(2) 0.6646(2) 0.0380(6) Uiso 0.518(3) 2 d S T P H 7
H21A H 0.750000 0.250(15) 0.734(14) 0.057 Uiso 0.1294(8) 2 d RS T P H 7
H21B H 0.709(11) 0.21(2) 0.63(2) 0.057 Uiso 0.0647(4) 1 d R . . H 7
O21B O 0.750000 0.2407(2) 0.6538(2) 0.0279(6) Uiso 0.444(3) 2 d S T P I 8
O21C O 0.750000 0.2924(14) 0.6358(15) 0.039(4) Uiso 0.078(3) 2 d S T P J 9
O20A O 0.42721(8) 0.500000 0.64746(14) 0.0283(4) Uiso 0.717(3) 2 d S T P K 10
H20B H 0.4118(19) 0.500000 0.720(3) 0.042 Uiso 0.5 2 d RS T P L 10
O20B O 0.4088(3) 0.500000 0.6402(5) 0.0133(11) Uiso 0.177(2) 2 d S T P M 11
O20C O 0.8632(7) 0.500000 0.3652(12) 0.055(4) Uiso 0.110(3) 2 d S T P N 12
ON1 O 0.750000 0.500000 0.4715(13) 0.007(3) Uiso 0.0823(19) 4 d S T P O 13
O2 O 0.64143(4) 0.18023(6) 0.93465(7) 0.0260(2) Uani 1 1 d D . . . .
H2A H 0.6770(6) 0.2119(15) 0.9233(19) 0.039 Uiso 0.5 1 d DR . . . .
H2B H 0.6233(8) 0.1630(18) 0.8737(10) 0.039 Uiso 0.5 1 d DR . . . .
H2C H 0.6129(13) 0.218(2) 0.964(2) 0.039 Uiso 0.5 1 d R . . . .
H2D H 0.6541(13) 0.137(2) 0.967(2) 0.039 Uiso 0.5 1 d R . . . .
O10 O 0.55729(4) 0.30205(6) 1.05798(7) 0.0266(2) Uani 1 1 d D . . . .
H10A H 0.5859(6) 0.2636(14) 1.0247(16) 0.040 Uiso 0.5 1 d DR . . . .
H10B H 0.5245(6) 0.3063(19) 1.0148(14) 0.040 Uiso 0.5 1 d DR . . . .
H10C H 0.5538(13) 0.270(2) 1.117(2) 0.040 Uiso 0.5 1 d R . . . .
H10D H 0.5730(12) 0.374(2) 1.079(2) 0.040 Uiso 0.5 1 d R . . . .
O11 O 0.57929(4) 0.10866(7) 0.74853(6) 0.0260(2) Uani 1 1 d D . . . .
H11A H 0.5997(7) 0.1287(19) 0.8062(11) 0.039 Uiso 0.5 1 d DR . . . .
H11B H 0.5409(5) 0.129(2) 0.7485(18) 0.039 Uiso 0.5 1 d DR . . . .
H11C H 0.5994(13) 0.126(2) 0.692(2) 0.039 Uiso 0.5 1 d R . . . .
H11D H 0.5809(13) 0.053(2) 0.750(2) 0.039 Uiso 0.5 1 d R . . . .
O12 O 0.44411(4) 0.29862(7) 0.56090(7) 0.0276(2) Uani 1 1 d D . . . .
H12A H 0.4471(10) 0.2602(13) 0.6211(10) 0.041 Uiso 0.59(2) 1 d DR . . . .
H12B H 0.4144(7) 0.2619(14) 0.5276(13) 0.041 Uiso 0.56(2) 1 d DR . . . .
H12C H 0.483(2) 0.300(4) 0.516(5) 0.041 Uiso 0.25 1 d R . . . .
O13 O 0.68363(5) 0.000000 0.04162(9) 0.0240(3) Uani 1 2 d DS T P . .
H13A H 0.6637(10) 0.000000 0.1047(10) 0.036 Uiso 0.54(4) 2 d DRS T P . .
H13B H 0.6697(10) 0.0566(10) 0.0082(13) 0.036 Uiso 0.49(2) 1 d DR . . . .
H13C H 0.7210(18) 0.000000 0.052(3) 0.036 Uiso 0.45(4) 2 d RS T P . .
O14 O 0.63969(4) 0.17171(7) 0.55756(7) 0.0289(2) Uani 1 1 d D . . . .
H14A H 0.6162(8) 0.156(2) 0.6147(12) 0.043 Uiso 0.35(2) 1 d DR . . . .
H14B H 0.6767(5) 0.187(2) 0.5864(17) 0.043 Uiso 0.5 1 d DR . . . .
H14C H 0.6499(13) 0.120(2) 0.515(2) 0.043 Uiso 0.5 1 d R . . . .
H14D H 0.6150(12) 0.207(2) 0.537(2) 0.043 Uiso 0.56(2) 1 d R . . . .
O15 O 0.61887(5) 0.000000 0.24026(9) 0.0250(3) Uani 1 2 d DS T P . .
H15A H 0.6464(7) 0.000000 0.2944(10) 0.038 Uiso 0.68(4) 2 d DRS T P . .
H15B H 0.6436(7) 0.000000 0.1829(10) 0.038 Uiso 0.78(4) 2 d DRS T P . .
H15C H 0.5960(10) 0.0473(17) 0.2433(15) 0.038 Uiso 0.63(2) 1 d R . . . .
O16 O 0.68381(5) 0.000000 0.43757(9) 0.0255(3) Uani 1 2 d DS T P . .
H16A H 0.6647(8) 0.000000 0.3742(10) 0.038 Uiso 0.59(4) 2 d DRS T P . .
H16B H 0.7243(5) 0.000000 0.429(3) 0.038 Uiso 0.44(3) 2 d DRS T P . .
H16C H 0.6692(15) 0.048(2) 0.460(3) 0.038 Uiso 0.40(2) 1 d R . . . .
O17 O 0.45676(4) 0.17997(7) 0.75296(6) 0.0258(2) Uani 1 1 d D . . . .
H17A H 0.4943(6) 0.1536(19) 0.752(3) 0.039 Uiso 0.31(3) 1 d DR . . . .
H17B H 0.4517(11) 0.2131(15) 0.8154(10) 0.039 Uiso 0.46(2) 1 d DR . . . .
H17C H 0.4518(16) 0.210(3) 0.697(3) 0.039 Uiso 0.40(2) 1 d R . . . .
O19 O 0.750000 0.28677(10) 0.87635(10) 0.0307(3) Uani 1 2 d S T P . .
H19A H 0.750000 0.350(3) 0.907(3) 0.046 Uiso 0.67(4) 2 d RS T P . .
H19B H 0.712(3) 0.253(5) 0.904(5) 0.046 Uiso 0.22(3) 1 d R . . . .
N1 N 0.7439(2) 0.5077(4) 0.4954(2) 0.0247(6) Uiso 0.2294(5) 1 d . . . O -1
C1A C 0.7722(2) 0.4220(4) 0.4288(4) 0.0210(7) Uani 0.2294(5) 1 d . . . O -1
H1AA H 0.787855 0.367034 0.480793 0.025 Uiso 0.2294(5) 1 calc R . . O -1
H1AB H 0.809729 0.451466 0.390145 0.025 Uiso 0.2294(5) 1 calc R . . O -1
C2A C 0.7314(2) 0.3679(4) 0.3435(4) 0.0272(9) Uani 0.2294(5) 1 d . . . O -1
H2AA H 0.717488 0.420736 0.287767 0.033 Uiso 0.2294(5) 1 calc R . . O -1
H2AB H 0.693064 0.339142 0.380173 0.033 Uiso 0.2294(5) 1 calc R . . O -1
C3A C 0.7668(2) 0.2764(4) 0.2836(5) 0.0335(8) Uani 0.2294(5) 1 d . . . O -1
H3AA H 0.804702 0.306639 0.246716 0.040 Uiso 0.2294(5) 1 calc R . . O -1
H3AB H 0.781991 0.225981 0.340651 0.040 Uiso 0.2294(5) 1 calc R . . O -1
C4A C 0.7304(2) 0.2159(4) 0.1996(5) 0.0350(8) Uani 0.2294(5) 1 d . . . O -1
H4AA H 0.691125 0.189250 0.233078 0.053 Uiso 0.2294(5) 1 calc GR . . O -1
H4AB H 0.755993 0.155995 0.173347 0.053 Uiso 0.2294(5) 1 calc GR . . O -1
H4AC H 0.720074 0.262284 0.136902 0.053 Uiso 0.2294(5) 1 calc GR . . O -1
C1B C 0.6900(2) 0.4674(3) 0.5697(4) 0.0245(7) Uiso 0.2294(5) 1 d . . . O -1
H1BA H 0.654800 0.490260 0.520661 0.029 Uiso 0.2294(5) 1 calc R . . O -1
H1BB H 0.695117 0.391301 0.551346 0.029 Uiso 0.2294(5) 1 calc R . . O -1
C2B C 0.6593(2) 0.4547(4) 0.6482(4) 0.0240(6) Uiso 0.2294(5) 1 d . . . O -1
H2BA H 0.691412 0.435931 0.704963 0.029 Uiso 0.2294(5) 1 calc R . . O -1
H2BB H 0.637107 0.387382 0.631571 0.029 Uiso 0.2294(5) 1 calc R . . O -1
C3B C 0.6093(2) 0.5162(4) 0.7169(4) 0.0305(8) Uiso 0.2294(5) 1 d . . . O -1
H3BA H 0.629843 0.577849 0.753054 0.037 Uiso 0.2294(5) 1 calc R . . O -1
H3BB H 0.575891 0.543400 0.666609 0.037 Uiso 0.2294(5) 1 calc R . . O -1
C4B C 0.5798(3) 0.4481(4) 0.8031(5) 0.0319(8) Uiso 0.2294(5) 1 d . . . O -1
H4BA H 0.557727 0.388816 0.767301 0.048 Uiso 0.2294(5) 1 calc GR . . O -1
H4BB H 0.549363 0.489969 0.846244 0.048 Uiso 0.2294(5) 1 calc GR . . O -1
H4BC H 0.612829 0.420493 0.852549 0.048 Uiso 0.2294(5) 1 calc GR . . O -1
C1C C 0.7154(2) 0.5962(4) 0.4205(4) 0.0210(7) Uani 0.2294(5) 1 d . . . O -1
H1CA H 0.678033 0.566951 0.381123 0.025 Uiso 0.2294(5) 1 calc R . . O -1
H1CB H 0.700192 0.654528 0.468733 0.025 Uiso 0.2294(5) 1 calc R . . O -1
C2C C 0.7607(2) 0.6421(3) 0.3351(3) 0.0272(9) Uani 0.2294(5) 1 d . . . O -1
H2CA H 0.797053 0.676359 0.372855 0.033 Uiso 0.2294(5) 1 calc R . . O -1
H2CB H 0.777209 0.584948 0.286747 0.033 Uiso 0.2294(5) 1 calc R . . O -1
C3C C 0.7255(3) 0.7219(5) 0.2671(5) 0.0335(8) Uani 0.2294(5) 1 d . . . O -1
H3CA H 0.707339 0.777134 0.316209 0.040 Uiso 0.2294(5) 1 calc R . . O -1
H3CB H 0.690071 0.686817 0.227423 0.040 Uiso 0.2294(5) 1 calc R . . O -1
C4C C 0.7706(2) 0.7734(4) 0.1828(5) 0.0350(8) Uani 0.2294(5) 1 d . . . O -1
H4CA H 0.801463 0.817855 0.222091 0.053 Uiso 0.2294(5) 1 calc GR . . O -1
H4CB H 0.746147 0.817310 0.131015 0.053 Uiso 0.2294(5) 1 calc GR . . O -1
H4CC H 0.793051 0.717966 0.141419 0.053 Uiso 0.2294(5) 1 calc GR . . O -1
C1D C 0.7958(2) 0.5607(4) 0.5657(4) 0.0245(7) Uiso 0.2294(5) 1 d . . . O -1
H1DA H 0.830435 0.582857 0.515197 0.029 Uiso 0.2294(5) 1 calc R . . O -1
H1DB H 0.777743 0.625886 0.598877 0.029 Uiso 0.2294(5) 1 calc R . . O -1
C2D C 0.82435(16) 0.4959(12) 0.6572(3) 0.0240(6) Uiso 0.2294(5) 1 d . . . O -1
H2DA H 0.809004 0.537592 0.721525 0.029 Uiso 0.2294(5) 1 calc R . . O -1
H2DB H 0.795249 0.434290 0.654507 0.029 Uiso 0.2294(5) 1 calc R . . O -1
C3D C 0.8791(3) 0.4444(4) 0.7098(5) 0.0305(8) Uiso 0.2294(5) 1 d . . . O -1
H3DA H 0.866104 0.371503 0.729932 0.037 Uiso 0.2294(5) 1 calc R . . O -1
H3DB H 0.912644 0.437855 0.652514 0.037 Uiso 0.2294(5) 1 calc R . . O -1
C4D C 0.90828(19) 0.4918(7) 0.8079(4) 0.0319(8) Uiso 0.2294(5) 1 d . . . O -1
H4DA H 0.944360 0.447634 0.833122 0.038 Uiso 0.2294(5) 1 calc R . . O -1
H4DB H 0.876896 0.496022 0.868875 0.038 Uiso 0.2294(5) 1 calc R . . O -1
C5D C 0.9322(3) 0.6060(5) 0.7767(5) 0.0415(14) Uiso 0.2294(5) 1 d . . . O -1
H5DA H 0.958750 0.602136 0.709954 0.062 Uiso 0.2294(5) 1 calc GR . . O -1
H5DB H 0.957171 0.635004 0.838293 0.062 Uiso 0.2294(5) 1 calc GR . . O -1
H5DC H 0.895678 0.652099 0.762363 0.062 Uiso 0.2294(5) 1 calc GR . . O -1
H20A H 0.4197(10) 0.4706(19) 0.6331(18) 0.062 Uiso 0.65(2) 1 d R . . . .
H17D H 0.4308(15) 0.130(3) 0.753(2) 0.062 Uiso 0.54(3) 1 d R . . . .
H12D H 0.4371(15) 0.378(3) 0.588(3) 0.032(9) Uiso 0.38(3) 1 d . . . . .


_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
N1 C1A 1.472(7) . ?
N1 C1B 1.532(6) . ?
N1 C1C 1.555(6) . ?
N1 C1D 1.536(6) . ?
C1A C2A 1.503(7) . ?
C2A C3A 1.551(7) . ?
C3A C4A 1.480(8) . ?
C1B C2B 1.156(7) . ?
C2B C3B 1.548(7) . ?
C3B C4B 1.483(7) . ?
C1C C2C 1.518(6) . ?
C2C C3C 1.495(7) . ?
C3C C4C 1.535(8) . ?
C1D C2D 1.498(10) . ?
C2D C3D 1.468(9) . ?
C3D C4D 1.459(8) . ?
C4D C5D 1.571(11) . ?

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
C1A N1 C1B 112.0(4) . . ?
C1A N1 C1C 111.5(3) . . ?
C1A N1 C1D 109.3(4) . . ?
C1B N1 C1C 106.9(4) . . ?
C1B N1 C1D 110.6(3) . . ?
C1D N1 C1C 106.4(4) . . ?
N1 C1A C2A 118.3(4) . . ?
C1A C2A C3A 112.4(4) . . ?
C4A C3A C2A 116.9(4) . . ?
C2B C1B N1 159.5(5) . . ?
C1B C2B C3B 138.4(5) . . ?
C4B C3B C2B 111.6(4) . . ?
C2C C1C N1 115.1(4) . . ?
C3C C2C C1C 108.4(4) . . ?
C2C C3C C4C 109.8(4) . . ?
C2D C1D N1 117.0(6) . . ?
C3D C2D C1D 150.9(5) . . ?
C4D C3D C2D 119.9(6) . . ?
C3D C4D C5D 108.5(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
;
_oxdiff_exptl_absorpt_empirical_full_max 1.136
_oxdiff_exptl_absorpt_empirical_full_min 0.885
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_20220328_sv20_mo_90k_auto_CCDC1
_database_code_depnum_ccdc_archive 'CCDC 2176623'
loop_
_audit_author_name
_audit_author_address
'Sanehiro Muromachi'
;National Institute of Advanced Industrial Science and Technology (AIST)
Japan
;
_audit_update_record             
;
2022-06-02 deposited with the CCDC.	2022-07-07 downloaded from the CCDC.
;
_audit_creation_date             2022-05-13
_audit_creation_method           
;
Olex2 1.3-ac4
(compiled 2019.04.23 svn.r3594 for Rigaku Oxford Diffraction, GUI svn.r5739)
;
_shelx_SHELXL_version_number     2016/6
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         
'0.22(Br), 0.39(O), H9.16 O8.81, H0.25 O0.5, 0.25(C17 H38 N)'
_chemical_formula_sum            'C3.65 H16.27 Br0.21 N0.22 O9.66'
_chemical_formula_weight         234.73
_chemical_melting_point          ?
_chemical_oxdiff_formula         (C4H9)3C5H11NBr(H2O)38
_chemical_oxdiff_usercomment     'N4445-3-HYD hydrate'
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 '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           51
_space_group_name_H-M_alt        'P m m a'
_space_group_name_Hall           '-P 2a 2a'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z'
'x+1/2, -y, -z'
'-x, y, -z'
'-x, -y, -z'
'x-1/2, y, -z'
'-x-1/2, y, z'
'x, -y, z'

_cell_length_a                   21.0695(10)
_cell_length_b                   12.6077(6)
_cell_length_c                   12.0415(6)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     3198.7(3)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    5064
_cell_measurement_temperature    90.00(16)
_cell_measurement_theta_max      31.3360
_cell_measurement_theta_min      1.9430
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.621
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.96376
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.41.104a (Rigaku Oxford Diffraction, 2021)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   .
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    0.975
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       prism
_exptl_crystal_F_000             995
_exptl_crystal_preparation       ?
_exptl_crystal_recrystallization_method ?
_exptl_crystal_size_max          0.05
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.05
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0617
_diffrn_reflns_av_unetI/netI     0.0580
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.826
_diffrn_reflns_limit_h_max       28
_diffrn_reflns_limit_h_min       -22
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            20300
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.826
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         31.024
_diffrn_reflns_theta_min         1.948
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      90.00(16)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.826
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -36.00   0.00   0.50   17.74    --   -4.27 -76.00  57.00   72
  2  ω    -72.00 -43.00   0.50   17.74    --   -4.27 -76.00  57.00   58
  3  ω    -20.00  22.00   0.50   17.74    --   -4.27 -99.00 150.00   84
  4  ω    -28.00  -3.00   0.50   17.74    --   -4.27  79.00 -62.00   50
  5  ω    -20.00  40.00   0.50   17.74    --    6.85 -99.00 -60.00  120
;
_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      0.0141684000
_diffrn_orient_matrix_UB_12      0.0273815000
_diffrn_orient_matrix_UB_13      -0.0451027000
_diffrn_orient_matrix_UB_21      -0.0241813000
_diffrn_orient_matrix_UB_22      0.0390591000
_diffrn_orient_matrix_UB_23      0.0027247000
_diffrn_orient_matrix_UB_31      0.0186603000
_diffrn_orient_matrix_UB_32      0.0298332000
_diffrn_orient_matrix_UB_33      0.0377714000
_diffrn_oxdiff_digest_frames     
;
01ea679cf95e7796c0116bd8c54f7acad3000251021
;
_diffrn_oxdiff_digest_hkl        
;
0121ef92cb60643db8d402326c5ec9b91ed242
;
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3374
_reflns_number_total             4514
_reflns_odcompleteness_completeness 99.89
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_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 1.171.41.104a (Rigaku OD, 2021)'
_computing_data_collection       'CrysAlisPro 1.171.41.104a (Rigaku OD, 2021)'
_computing_data_reduction        'CrysAlisPro 1.171.41.104a (Rigaku OD, 2021)'
_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         0.715
_refine_diff_density_min         -0.457
_refine_diff_density_rms         0.073
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.105
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     307
_refine_ls_number_reflns         4514
_refine_ls_number_restraints     29
_refine_ls_R_factor_all          0.0825
_refine_ls_R_factor_gt           0.0573
_refine_ls_restrained_S_all      1.102
_refine_ls_shift/su_max          0.062
_refine_ls_shift/su_mean         0.002
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0718P)²+2.8456P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1549
_refine_ls_wR_factor_ref         0.1639
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups, All O(H,H) groups, All O(H,H,H)
  groups, All O(H,H,H,H) groups
2. Restrained distances
 O2-H2A = O2-H2B
 0.87 with sigma of 0.02
 O10-H10A = O10-H10B
 0.87 with sigma of 0.02
 O11-H11A = O11-H11B
 0.87 with sigma of 0.02
 O12-H12A = O12-H12B
 0.87 with sigma of 0.02
 O13-H13A = O13-H13B
 0.87 with sigma of 0.02
 O14-H14A = O14-H14B
 0.87 with sigma of 0.02
 O15-H15A = O15-H15B
 0.87 with sigma of 0.02
 O16-H16A = O16-H16B
 0.87 with sigma of 0.02
 O17-H17A = O17-H17B
 0.87 with sigma of 0.02
 H13A-H13B
 1.38 with sigma of 0.04
 H2A-H2B
 1.38 with sigma of 0.04
 H17A-H17B
 1.38 with sigma of 0.04
 H11A-H11B
 1.38 with sigma of 0.04
 H15A-H15B
 1.38 with sigma of 0.04
 H10A-H10B
 1.38 with sigma of 0.04
 H12A-H12B
 1.38 with sigma of 0.04
 H14A-H14B
 1.38 with sigma of 0.04
 H16A-H16B
 1.38 with sigma of 0.04
3. Uiso/Uaniso restraints and constraints
Uiso(C1B) = Uiso(C1D)
Uiso(C2B) = Uiso(C2D)
Uiso(C3B) = Uiso(C3D)
Uiso(C4B) = Uiso(C4D)
Uanis(C1A) = Uanis(C1C)
Uanis(C2A) = Uanis(C2C)
Uanis(C3A) = Uanis(C3C)
Uanis(C4A) = Uanis(C4C)
4. Others
 1*[Sof(O21A)+Sof(H21A)+Sof(H21B)]+1*[Sof(O21B)]=1 with esd of 0.1
 1*[Sof(O20A)]+1*[Sof(O20B)]=1 with esd of 0.1
 Sof(H21A)=Sof(H21B)=0.12495*FVAR(2)
 Sof(O21A)=0.5*FVAR(2)
 Fixed Sof: H18A(0.25) H18B(0.25) H20A(0.25) H2A(0.25) H2B(0.25) H2C(0.25)
 H2D(0.25) H10A(0.25) H10B(0.25) H10C(0.25) H10D(0.25) H11A(0.25) H11B(0.25)
 H11C(0.25) H11D(0.25) H12A(0.25) H12B(0.25) H12C(0.25) H12D(0.25) H13A(0.25)
 H13B(0.25) H13C(0.25) H14A(0.25) H14B(0.25) H14C(0.25) H14D(0.25) H15A(0.25)
 H15B(0.25) H15C(0.25) H16A(0.25) H16B(0.25) H16C(0.25) H17A(0.25) H17B(0.25)
 H17C(0.25) H19A(0.25) H19B(0.25) N1(0.25) C1A(0.25) H1AA(0.25) H1AB(0.25)
 C2A(0.25) H2AA(0.25) H2AB(0.25) C3A(0.25) H3AA(0.25) H3AB(0.25) C4A(0.25)
 H4AA(0.25) H4AB(0.25) H4AC(0.25) C1B(0.25) H1BA(0.25) H1BB(0.25) C2B(0.25)
 H2BA(0.25) H2BB(0.25) C3B(0.25) H3BA(0.25) H3BB(0.25) C4B(0.25) H4BA(0.25)
 H4BB(0.25) H4BC(0.25) C1C(0.25) H1CA(0.25) H1CB(0.25) C2C(0.25) H2CA(0.25)
 H2CB(0.25) C3C(0.25) H3CA(0.25) H3CB(0.25) C4C(0.25) H4CA(0.25) H4CB(0.25)
 H4CC(0.25) C1D(0.25) H1DA(0.25) H1DB(0.25) C2D(0.25) H2DA(0.25) H2DB(0.25)
 C3D(0.25) H3DA(0.25) H3DB(0.25) C4D(0.25) H4DA(0.25) H4DB(0.25) C5D(0.25)
 H5DA(0.25) H5DB(0.25) H5DC(0.25)
5.a Secondary CH2 refined with riding coordinates:
 C1A(H1AA,H1AB), C2A(H2AA,H2AB), C3A(H3AA,H3AB), C1B(H1BA,H1BB), C2B(H2BA,
 H2BB), C3B(H3BA,H3BB), C1C(H1CA,H1CB), C2C(H2CA,H2CB), C3C(H3CA,H3CB),
 C1D(H1DA,H1DB), C2D(H2DA,H2DB), C3D(H3DA,H3DB), C4D(H4DA,H4DB)
5.b Idealised Me refined as rotating group:
 C4A(H4AA,H4AB,H4AC), C4B(H4BA,H4BB,H4BC), C4C(H4CA,H4CB,H4CC), C5D(H5DA,H5DB,
 H5DC)
;
_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 0.250000 0.500000 -0.02937(3) 0.02107(7) Uiso 0.7050(8) 4 d S T P A 2
Br2 Br 0.250000 0.500000 -0.0060(2) 0.0169(5) Uiso 0.0952(8) 4 d S T P B 3
Br3 Br 0.250000 0.500000 -0.0479(2) 0.0096(5) Uiso 0.0737(7) 4 d S T P C 4
O18A O 0.6387(3) 0.500000 1.1322(5) 0.0175(12) Uiso 0.200(3) 2 d S T P D 5
O18B O 0.60284(7) 0.500000 1.12441(12) 0.0304(3) Uiso 0.991(4) 2 d S T P E 6
H18A H 0.583(3) 0.407(6) 1.093(6) 0.046 Uiso 0.25 1 d R . . F 6
H18B H 0.639(2) 0.500000 1.078(5) 0.046 Uiso 0.5 2 d RS T P G 6
O21A O 0.750000 0.2096(2) 0.6627(2) 0.0389(6) Uiso 0.636(4) 2 d S T P H 7
H21A H 0.750000 0.261(17) 0.750(13) 0.058 Uiso 0.1588(10) 2 d RS T P H 7
H21B H 0.699(12) 0.21(2) 0.62(2) 0.058 Uiso 0.0794(5) 1 d R . . H 7
O21B O 0.750000 0.2491(3) 0.6517(3) 0.0373(9) Uiso 0.417(4) 2 d S T P I 8
O20A O 0.42407(8) 0.500000 0.64576(14) 0.0390(4) Uiso 0.990(4) 2 d S T P J 10
H20A H 0.405(3) 0.500000 0.744(4) 0.058 Uiso 0.5 2 d RS T P K 10
O20B O 0.3781(9) 0.500000 0.6353(16) 0.093(5) Uiso 0.158(5) 2 d S T P L 11
O2 O 0.64138(4) 0.18020(8) 0.93474(8) 0.0264(2) Uani 1 1 d D . . . .
H2A H 0.6747(7) 0.2193(16) 0.923(3) 0.040 Uiso 0.25 1 d DR . . . .
H2B H 0.6235(10) 0.168(3) 0.8719(11) 0.040 Uiso 0.25 1 d DR . . . .
H2C H 0.608(3) 0.229(6) 0.980(6) 0.040 Uiso 0.25 1 d R . . . .
H2D H 0.662(3) 0.163(6) 0.967(5) 0.040 Uiso 0.25 1 d R . . . .
O10 O 0.55725(4) 0.30186(8) 1.05799(8) 0.0269(2) Uani 1 1 d D . . . .
H10A H 0.5853(7) 0.2634(17) 1.023(2) 0.040 Uiso 0.25 1 d DR . . . .
H10B H 0.5248(6) 0.306(4) 1.0137(16) 0.040 Uiso 0.25 1 d DR . . . .
H10C H 0.561(3) 0.270(6) 1.121(6) 0.040 Uiso 0.25 1 d R . . . .
H10D H 0.579(3) 0.338(6) 1.072(6) 0.040 Uiso 0.25 1 d R . . . .
O11 O 0.57932(5) 0.10872(8) 0.74851(8) 0.0262(2) Uani 1 1 d D . . . .
H11A H 0.5994(9) 0.134(2) 0.8057(13) 0.039 Uiso 0.25 1 d DR . . . .
H11B H 0.5411(6) 0.134(2) 0.749(3) 0.039 Uiso 0.25 1 d DR . . . .
H11C H 0.598(3) 0.131(6) 0.683(6) 0.039 Uiso 0.25 1 d R . . . .
H11D H 0.581(4) 0.056(6) 0.748(5) 0.039 Uiso 0.25 1 d R . . . .
O12 O 0.44399(5) 0.29835(8) 0.56109(8) 0.0278(2) Uani 1 1 d D . . . .
H12A H 0.4458(19) 0.2640(19) 0.6249(11) 0.042 Uiso 0.25 1 d DR . . . .
H12B H 0.4130(8) 0.2628(19) 0.5294(17) 0.042 Uiso 0.25 1 d DR . . . .
H12C H 0.478(3) 0.289(6) 0.528(6) 0.042 Uiso 0.25 1 d R . . . .
H12D H 0.429(3) 0.345(6) 0.585(6) 0.042 Uiso 0.25 1 d R . . . .
O13 O 0.68355(6) 0.000000 0.04142(11) 0.0241(3) Uani 1 2 d DS T P . .
H13A H 0.6624(10) 0.000000 0.1036(11) 0.036 Uiso 0.5 2 d DRS T P . .
H13B H 0.6706(16) 0.0585(11) 0.0090(16) 0.036 Uiso 0.25 1 d DR . . . .
H13C H 0.719(2) 0.000000 0.045(4) 0.036 Uiso 0.5 2 d RS T P . .
O14 O 0.63958(5) 0.17190(8) 0.55735(8) 0.0291(2) Uani 1 1 d D . . . .
H14A H 0.6121(7) 0.162(4) 0.6089(14) 0.044 Uiso 0.25 1 d DR . . . .
H14B H 0.6754(6) 0.189(3) 0.588(2) 0.044 Uiso 0.25 1 d DR . . . .
H14C H 0.646(3) 0.139(6) 0.513(6) 0.044 Uiso 0.25 1 d R . . . .
H14D H 0.609(3) 0.222(6) 0.511(6) 0.044 Uiso 0.25 1 d R . . . .
O15 O 0.61858(7) 0.000000 0.24028(11) 0.0252(3) Uani 1 2 d DS T P . .
H15A H 0.6448(9) 0.000000 0.2955(11) 0.038 Uiso 0.5 2 d DRS T P . .
H15B H 0.6413(10) 0.000000 0.1809(10) 0.038 Uiso 0.5 2 d DRS T P . .
H15C H 0.594(3) 0.054(6) 0.243(5) 0.038 Uiso 0.25 1 d R . . . .
O16 O 0.68364(6) 0.000000 0.43786(11) 0.0255(3) Uani 1 2 d DS T P . .
H16A H 0.6649(9) 0.000000 0.3744(11) 0.038 Uiso 0.5 2 d DRS T P . .
H16B H 0.7241(5) 0.000000 0.431(3) 0.038 Uiso 0.5 2 d DRS T P . .
H16C H 0.663(3) 0.065(6) 0.460(5) 0.038 Uiso 0.25 1 d R . . . .
O17 O 0.45661(5) 0.18022(8) 0.75276(7) 0.0262(2) Uani 1 1 d D . . . .
H17A H 0.4933(6) 0.1505(18) 0.754(3) 0.039 Uiso 0.25 1 d DR . . . .
H17B H 0.4511(15) 0.2159(17) 0.8137(12) 0.039 Uiso 0.25 1 d DR . . . .
H17C H 0.426(3) 0.130(6) 0.752(5) 0.039 Uiso 0.25 1 d R . . . .
O19 O 0.750000 0.28679(12) 0.87632(12) 0.0306(4) Uani 1 2 d S T P . .
H19A H 0.750000 0.349(4) 0.905(4) 0.046 Uiso 0.5 2 d RS T P . .
H19B H 0.709(3) 0.256(6) 0.901(6) 0.046 Uiso 0.25 1 d R . . . .
N1 N 0.7540(3) 0.498(2) 0.4926(2) 0.0298(6) Uiso 0.25 1 d . . . M -1
C1A C 0.7739(3) 0.4206(5) 0.4292(5) 0.0292(8) Uani 0.25 1 d . . . M -1
H1AA H 0.787617 0.362274 0.478749 0.035 Uiso 0.25 1 calc R . . M -1
H1AB H 0.812351 0.446161 0.390098 0.035 Uiso 0.25 1 calc R . . M -1
C2A C 0.7294(3) 0.3721(4) 0.3408(5) 0.0283(11) Uani 0.25 1 d . . . M -1
H2AA H 0.717796 0.426733 0.285328 0.034 Uiso 0.25 1 calc R . . M -1
H2AB H 0.689932 0.346560 0.376572 0.034 Uiso 0.25 1 calc R . . M -1
C3A C 0.7649(2) 0.2744(5) 0.2798(6) 0.0378(10) Uani 0.25 1 d . . . M -1
H3AA H 0.803115 0.302809 0.242530 0.045 Uiso 0.25 1 calc R . . M -1
H3AB H 0.779575 0.224625 0.337987 0.045 Uiso 0.25 1 calc R . . M -1
C4A C 0.7304(3) 0.2160(5) 0.2014(5) 0.0388(10) Uani 0.25 1 d . . . M -1
H4AA H 0.693565 0.183203 0.237415 0.058 Uiso 0.25 1 calc GR . . M -1
H4AB H 0.757531 0.160592 0.169772 0.058 Uiso 0.25 1 calc GR . . M -1
H4AC H 0.715860 0.263355 0.142029 0.058 Uiso 0.25 1 calc GR . . M -1
C1B C 0.6902(3) 0.4672(4) 0.5691(5) 0.0289(8) Uiso 0.25 1 d . . . M -1
H1BA H 0.659714 0.513382 0.529448 0.035 Uiso 0.25 1 calc R . . M -1
H1BB H 0.682723 0.396391 0.536174 0.035 Uiso 0.25 1 calc R . . M -1
C2B C 0.6597(3) 0.4546(5) 0.6482(5) 0.0298(8) Uiso 0.25 1 d . . . M -1
H2BA H 0.691952 0.436385 0.704964 0.036 Uiso 0.25 1 calc R . . M -1
H2BB H 0.637556 0.387134 0.632209 0.036 Uiso 0.25 1 calc R . . M -1
C3B C 0.6095(3) 0.5174(5) 0.7166(5) 0.0353(9) Uiso 0.25 1 d . . . M -1
H3BA H 0.630126 0.578278 0.753998 0.042 Uiso 0.25 1 calc R . . M -1
H3BB H 0.576376 0.545381 0.666246 0.042 Uiso 0.25 1 calc R . . M -1
C4B C 0.5793(3) 0.4455(5) 0.8028(6) 0.0368(9) Uiso 0.25 1 d . . . M -1
H4BA H 0.555723 0.388880 0.765359 0.055 Uiso 0.25 1 calc GR . . M -1
H4BB H 0.550229 0.486966 0.849165 0.055 Uiso 0.25 1 calc GR . . M -1
H4BC H 0.612505 0.414298 0.849524 0.055 Uiso 0.25 1 calc GR . . M -1
C1C C 0.7153(3) 0.5967(4) 0.4201(5) 0.0292(8) Uani 0.25 1 d . . . M -1
H1CA H 0.678335 0.566275 0.380509 0.035 Uiso 0.25 1 calc R . . M -1
H1CB H 0.699570 0.651302 0.472353 0.035 Uiso 0.25 1 calc R . . M -1
C2C C 0.7600(3) 0.6464(4) 0.3379(4) 0.0283(11) Uani 0.25 1 d . . . M -1
H2CA H 0.794329 0.684941 0.377076 0.034 Uiso 0.25 1 calc R . . M -1
H2CB H 0.779461 0.591359 0.290163 0.034 Uiso 0.25 1 calc R . . M -1
C3C C 0.7224(3) 0.7198(6) 0.2710(6) 0.0378(10) Uani 0.25 1 d . . . M -1
H3CA H 0.703275 0.775245 0.318602 0.045 Uiso 0.25 1 calc R . . M -1
H3CB H 0.687954 0.681436 0.232193 0.045 Uiso 0.25 1 calc R . . M -1
C4C C 0.7715(3) 0.7738(5) 0.1801(5) 0.0388(10) Uani 0.25 1 d . . . M -1
H4CA H 0.805203 0.811793 0.219627 0.058 Uiso 0.25 1 calc GR . . M -1
H4CB H 0.748094 0.823572 0.132878 0.058 Uiso 0.25 1 calc GR . . M -1
H4CC H 0.790290 0.718034 0.133924 0.058 Uiso 0.25 1 calc GR . . M -1
C1D C 0.7955(3) 0.5628(5) 0.5663(5) 0.0289(8) Uiso 0.25 1 d . . . M -1
H1DA H 0.830076 0.594597 0.521551 0.035 Uiso 0.25 1 calc R . . M -1
H1DB H 0.770404 0.621352 0.598971 0.035 Uiso 0.25 1 calc R . . M -1
C2D C 0.8237(2) 0.498(2) 0.6574(4) 0.0298(8) Uiso 0.25 1 d . . . M -1
H2DA H 0.810487 0.541845 0.721463 0.036 Uiso 0.25 1 calc R . . M -1
H2DB H 0.792967 0.438504 0.657304 0.036 Uiso 0.25 1 calc R . . M -1
C3D C 0.8786(3) 0.4422(5) 0.7098(6) 0.0353(9) Uiso 0.25 1 d . . . M -1
H3DA H 0.864413 0.369954 0.730282 0.042 Uiso 0.25 1 calc R . . M -1
H3DB H 0.911971 0.434175 0.652532 0.042 Uiso 0.25 1 calc R . . M -1
C4D C 0.9080(2) 0.4898(7) 0.8080(4) 0.0368(9) Uiso 0.25 1 d . . . M -1
H4DA H 0.944208 0.445721 0.832954 0.044 Uiso 0.25 1 calc R . . M -1
H4DB H 0.876785 0.493857 0.869246 0.044 Uiso 0.25 1 calc R . . M -1
C5D C 0.9327(4) 0.6086(6) 0.7758(7) 0.0474(17) Uiso 0.25 1 d . . . M -1
H5DA H 0.960382 0.604639 0.710434 0.071 Uiso 0.25 1 calc GR . . M -1
H5DB H 0.956489 0.638542 0.838327 0.071 Uiso 0.25 1 calc GR . . M -1
H5DC H 0.896181 0.653982 0.759165 0.071 Uiso 0.25 1 calc GR . . M -1


_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
N1 C1A 1.31(2) . ?
N1 C1B 1.675(10) . ?
N1 C1C 1.72(2) . ?
N1 C1D 1.489(16) . ?
C1A C2A 1.546(8) . ?
C2A C3A 1.617(8) . ?
C3A C4A 1.401(9) . ?
C1B C2B 1.159(8) . ?
C2B C3B 1.557(8) . ?
C3B C4B 1.517(9) . ?
C1C C2C 1.504(8) . ?
C2C C3C 1.461(8) . ?
C3C C4C 1.652(9) . ?
C1D C2D 1.493(18) . ?
C2D C3D 1.492(16) . ?
C3D C4D 1.463(9) . ?
C4D C5D 1.633(12) . ?

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
C1A N1 C1B 113.8(16) . . ?
C1A N1 C1C 113.2(4) . . ?
C1A N1 C1D 124.5(7) . . ?
C1B N1 C1C 93.9(6) . . ?
C1D N1 C1B 105.8(5) . . ?
C1D N1 C1C 100.7(15) . . ?
N1 C1A C2A 120.1(5) . . ?
C1A C2A C3A 109.5(4) . . ?
C4A C3A C2A 117.8(5) . . ?
C2B C1B N1 158.1(6) . . ?
C1B C2B C3B 137.8(6) . . ?
C4B C3B C2B 110.1(5) . . ?
C2C C1C N1 109.7(5) . . ?
C3C C2C C1C 106.7(5) . . ?
C2C C3C C4C 106.7(5) . . ?
C2D C1D N1 111.8(13) . . ?
C3D C2D C1D 151.3(6) . . ?
C4D C3D C2D 118.5(10) . . ?
C3D C4D C5D 108.6(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
;
_oxdiff_exptl_absorpt_empirical_full_max 1.136
_oxdiff_exptl_absorpt_empirical_full_min 0.885
