# Electronic Supplementary Material (ESI) for Organic Chemistry Frontiers.
# This journal is © the Partner Organisations 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. 
# 
#######################################################################

data_ZM-2-20220413
_database_code_depnum_ccdc_archive 'CCDC 1844840'
loop_
_audit_author_name
_audit_author_address
'Man Zhu'
;Henan Normal University
China
;
_audit_update_record             
;
2022-07-01 deposited with the CCDC.	2022-08-31 downloaded from the CCDC.
;
_audit_creation_date             2022-04-13
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_chemical_name_systematic        ?
_chemical_formula_moiety         'C11 H12 O3'
_chemical_formula_sum            'C11 H12 O3'
_chemical_formula_weight         192.22
_chemical_oxdiff_formula         'C1 H1 O1 N1'
loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_Cromer_Mann_a1
_atom_type_scat_Cromer_Mann_a2
_atom_type_scat_Cromer_Mann_a3
_atom_type_scat_Cromer_Mann_a4
_atom_type_scat_Cromer_Mann_b1
_atom_type_scat_Cromer_Mann_b2
_atom_type_scat_Cromer_Mann_b3
_atom_type_scat_Cromer_Mann_b4
_atom_type_scat_Cromer_Mann_c
_atom_type_scat_source
_atom_type_scat_dispersion_source
H 0.00000 0.00000 0.49300 0.32291 0.14019 0.04081 10.51090 26.12570 3.14236
57.79970 0.0030380000826
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
C 0.01920 0.00962 2.31000 1.02000 1.58860 0.86500 20.84390 10.20750 0.56870
51.65120 0.215599998832
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
O 0.05239 0.03377 3.04850 2.28680 1.54630 0.86700 13.27710 5.70110 0.32390
32.90890 0.250800013542
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 x,y,z
2 -x,y+1/2,-z+1/2
3 -x,-y,-z
4 x,-y-1/2,z-1/2

_symmetry_Int_Tables_number      14
_cell_length_a                   10.3910(3)
_cell_length_b                   8.8427(3)
_cell_length_c                   10.6292(3)
_cell_angle_alpha                90
_cell_angle_beta                 98.559(3)
_cell_angle_gamma                90
_cell_volume                     965.78(5)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    1853
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      71.2720
_cell_measurement_theta_min      6.5290
_exptl_absorpt_coefficient_mu    0.791
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.82200
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.42a (Rigaku Oxford Diffraction, 2019)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear light black'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    black
_exptl_crystal_density_diffrn    1.3219
_exptl_crystal_description       block
_exptl_crystal_F_000             409.4299
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.25
_diffrn_reflns_av_R_equivalents  0.0173
_diffrn_reflns_av_unetI/netI     0.0236
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            3834
_diffrn_reflns_theta_full        71.2185
_diffrn_reflns_theta_max         71.22
_diffrn_reflns_theta_min         4.30
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 8.0521
_diffrn_detector_type            EosS2
_diffrn_measured_fraction_theta_full 0.9818
_diffrn_measured_fraction_theta_max 0.9818
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω   -102.00 -16.00   1.00    1.00    --  -35.62 -28.00 -42.00   86
  2  ω    -32.00  -2.00   1.00    1.00    --  -35.62  28.00 119.00   30
  3  ω     36.00  61.00   1.00    1.00    --   35.62  28.00 119.00   25
  4  ω     13.00  38.00   1.00    1.00    --   35.62 -28.00 -42.00   25
  5  ω    110.00 151.00   1.00    2.81    --  107.12  28.00 119.00   41
  6  ω     40.00 129.00   1.00    2.81    --  107.12 -28.00 -42.00   89
  7  ω     73.00  99.00   1.00    1.00    --   35.62 178.00   0.00   26
  8  ω     69.00 107.00   1.00    1.00    --   35.62 178.00  60.00   38
  9  ω    -36.00  65.00   1.00    1.00    --   35.62 -19.00-150.00  101
 10  ω     60.00 107.00   1.00    1.00    --   35.62 178.00 -30.00   47
 11  ω     49.00 100.00   1.00    2.81    --  107.12 -95.00-120.00   51
 12  ω     50.00 130.00   1.00    2.81    --  107.12 -77.00   0.00   80
 13  ω     39.00 123.00   1.00    2.81    --  107.12 -45.00-120.00   84
 14  ω     49.00 103.00   1.00    2.81    --  107.12 -95.00  90.00   54
 15  ω     94.00 128.00   1.00    2.81    --  107.12  45.00 -30.00   34
 16  ω    142.00 167.00   1.00    2.81    --  107.12  45.00 -30.00   25
 17  ω     65.00 108.00   1.00    2.81    --  107.12 -95.00 -60.00   43
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, EosS2'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0233552000
_diffrn_orient_matrix_UB_12      -0.0458928000
_diffrn_orient_matrix_UB_13      0.1413834000
_diffrn_orient_matrix_UB_21      0.1412960000
_diffrn_orient_matrix_UB_22      -0.0434016000
_diffrn_orient_matrix_UB_23      -0.0117415000
_diffrn_orient_matrix_UB_31      0.0442764000
_diffrn_orient_matrix_UB_32      0.1624260000
_diffrn_orient_matrix_UB_33      0.0367341000
_diffrn_oxdiff_digest_frames     
;
0122856c094943feaaefc0b3b4dafa76af000309655
;
_diffrn_oxdiff_digest_hkl        
;
01369e165a23818c83e98569ec91ed43e30524
;
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_reflns_Friedel_coverage         0.0
_reflns_limit_h_max              12
_reflns_limit_h_min              -12
_reflns_limit_k_max              10
_reflns_limit_k_min              0
_reflns_limit_l_max              12
_reflns_limit_l_min              0
_reflns_number_gt                1565
_reflns_number_total             1838
_reflns_odcompleteness_completeness 99.73
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_reflns_threshold_expression     I>=2u(I)
_computing_cell_refinement       'CrysAlisPro 1.171.40.42a (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.40.42a (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.42a (Rigaku OD, 2019)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'olex2.refine (Bourhis et al., 2015)'
_computing_structure_solution    'olex2.solve (Bourhis et al., 2015)'
_refine_diff_density_max         0.2452
_refine_diff_density_min         -0.1808
_refine_diff_density_rms         0.0403
_refine_ls_d_res_high            0.8143
_refine_ls_d_res_low             10.2753
_refine_ls_goodness_of_fit_ref   1.0600
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_constraints    15
_refine_ls_number_parameters     143
_refine_ls_number_reflns         1838
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0502
_refine_ls_R_factor_gt           0.0440
_refine_ls_restrained_S_all      1.0600
_refine_ls_shift/su_max          0.0000
_refine_ls_shift/su_mean         0.0000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0631P)²+0.1452P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1194
_refine_ls_wR_factor_ref         0.1251
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2.a Ternary CH refined with riding coordinates:
 C1(H1), C10(H10)
2.b Secondary CH2 refined with riding coordinates:
 C11(H11a,H11b)
2.c Aromatic/amide H refined with riding coordinates:
 C7(H7), C4(H4), C6(H6), C5(H5)
;
_atom_sites_solution_primary     iterative
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_refinement_flags_posn
O12 O -0.02346(13) 0.3005(2) 0.30168(13) 0.0723(4) Uani 1.000000 .
O14 O 0.23122(13) 0.52343(16) 0.66260(14) 0.0748(4) Uani 1.000000 .
O13 O 0.12762(15) 0.15975(17) 0.61406(14) 0.0712(4) Uani 1.000000 .
C8 C 0.42030(15) 0.39301(18) 0.61759(14) 0.0473(4) Uani 1.000000 .
C3 C 0.44136(15) 0.28080(18) 0.53272(15) 0.0476(4) Uani 1.000000 .
C9 C 0.28240(16) 0.43421(18) 0.59888(15) 0.0494(4) Uani 1.000000 .
C1 C 0.21381(15) 0.34467(18) 0.48689(15) 0.0471(4) Uani 1.000000 .
H1 H 0.18940(15) 0.41512(18) 0.41619(15) 0.0565(4) Uiso 1.000000 R
C10 C 0.09035(15) 0.27164(19) 0.51814(16) 0.0505(4) Uani 1.000000 .
H10 H 0.03676(15) 0.34866(19) 0.55173(16) 0.0606(5) Uiso 1.000000 R
C2 C 0.31693(17) 0.2361(2) 0.44911(18) 0.0562(4) Uani 1.000000 .
C7 C 0.52141(18) 0.4522(2) 0.70429(16) 0.0604(5) Uani 1.000000 .
H7 H 0.50615(18) 0.5285(2) 0.76045(16) 0.0725(6) Uiso 1.000000 R
C4 C 0.56647(17) 0.2254(2) 0.53316(18) 0.0608(5) Uani 1.000000 .
H4 H 0.58264(17) 0.1507(2) 0.47590(18) 0.0729(6) Uiso 1.000000 R
C6 C 0.64426(18) 0.3948(3) 0.70462(17) 0.0676(5) Uani 1.000000 .
H6 H 0.71326(18) 0.4316(3) 0.76230(17) 0.0811(7) Uiso 1.000000 R
C5 C 0.66581(17) 0.2826(3) 0.61952(19) 0.0673(5) Uani 1.000000 .
H5 H 0.74962(17) 0.2451(3) 0.62088(19) 0.0808(7) Uiso 1.000000 R
C11 C 0.01203(17) 0.1975(2) 0.40317(19) 0.0638(5) Uani 1.000000 .
H11a H -0.06619(17) 0.1538(2) 0.42771(19) 0.0766(6) Uiso 1.000000 R
H11b H 0.06272(17) 0.1160(2) 0.37411(19) 0.0766(6) Uiso 1.000000 R
H13 H 0.068(3) 0.168(3) 0.680(3) 0.106(9) Uiso 1.000000 .
H12 H -0.085(3) 0.367(3) 0.322(3) 0.112(10) Uiso 1.000000 .
H2a H 0.291(2) 0.131(2) 0.465(2) 0.071(6) Uiso 1.000000 .
H2b H 0.325(2) 0.245(2) 0.359(2) 0.068(6) Uiso 1.000000 .


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
O12 C11 1.418(2) . ?
O12 H12 0.92(3) . ?
O14 C9 1.213(2) . ?
O13 C10 1.432(2) . ?
O13 H13 1.00(3) . ?
C8 C3 1.380(2) . ?
C8 C9 1.463(2) . ?
C8 C7 1.392(2) . ?
C3 C2 1.509(2) . ?
C3 C4 1.389(2) . ?
C9 C1 1.516(2) . ?
C1 H1 0.9800 . ?
C1 C10 1.517(2) . ?
C1 C2 1.536(2) . ?
C10 H10 0.9800 . ?
C10 C11 1.513(2) . ?
C2 H2a 0.99(2) . ?
C2 H2b 0.98(2) . ?
C7 H7 0.9300 . ?
C7 C6 1.373(3) . ?
C4 H4 0.9300 . ?
C4 C5 1.372(3) . ?
C6 H6 0.9300 . ?
C6 C5 1.383(3) . ?
C5 H5 0.9300 . ?
C11 H11a 0.9700 . ?
C11 H11b 0.9700 . ?

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
H12 O12 C11 109.9(18) . . ?
H13 O13 C10 108.5(16) . . ?
C9 C8 C3 109.72(14) . . ?
C7 C8 C3 121.69(16) . . ?
C7 C8 C9 128.58(16) . . ?
C2 C3 C8 111.60(14) . . ?
C4 C3 C8 119.40(16) . . ?
C4 C3 C2 128.99(16) . . ?
C8 C9 O14 126.02(16) . . ?
C1 C9 O14 125.73(15) . . ?
C1 C9 C8 108.25(13) . . ?
H1 C1 C9 107.93(9) . . ?
C10 C1 C9 111.38(13) . . ?
C10 C1 H1 107.93(9) . . ?
C2 C1 C9 105.48(13) . . ?
C2 C1 H1 107.93(9) . . ?
C2 C1 C10 115.90(14) . . ?
C1 C10 O13 107.59(13) . . ?
H10 C10 O13 109.20(9) . . ?
H10 C10 C1 109.20(9) . . ?
C11 C10 O13 109.37(15) . . ?
C11 C10 C1 112.24(14) . . ?
C11 C10 H10 109.20(10) . . ?
C1 C2 C3 104.61(13) . . ?
H2a C2 C3 112.4(12) . . ?
H2a C2 C1 108.8(13) . . ?
H2b C2 C3 111.1(12) . . ?
H2b C2 C1 111.9(13) . . ?
H2b C2 H2a 108.0(18) . . ?
H7 C7 C8 120.90(11) . . ?
C6 C7 C8 118.19(19) . . ?
C6 C7 H7 120.90(12) . . ?
H4 C4 C3 120.57(11) . . ?
C5 C4 C3 118.86(19) . . ?
C5 C4 H4 120.57(12) . . ?
H6 C6 C7 119.86(12) . . ?
C5 C6 C7 120.29(17) . . ?
C5 C6 H6 119.86(11) . . ?
C6 C5 C4 121.55(17) . . ?
H5 C5 C4 119.23(12) . . ?
H5 C5 C6 119.23(11) . . ?
C10 C11 O12 112.58(16) . . ?
H11a C11 O12 109.08(9) . . ?
H11a C11 C10 109.08(10) . . ?
H11b C11 O12 109.08(10) . . ?
H11b C11 C10 109.08(10) . . ?
H11b C11 H11a 107.8 . . ?

_olex2_date_sample_data_collection 2022-04-13
_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 1.197
_oxdiff_exptl_absorpt_empirical_full_min 0.782
####################################################################### 
# 
# 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_1_sq
_database_code_depnum_ccdc_archive 'CCDC 2190949'
loop_
_audit_author_name
_audit_author_address
'Man Zhu'
;Henan Normal University
China
;
_audit_update_record             
;
2022-07-18 deposited with the CCDC.	2022-08-31 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C15 H21 N O2'
_chemical_formula_sum            'C15 H21 N O2'
_chemical_formula_weight         247.33

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'

_space_group_crystal_system      trigonal
_space_group_IT_number           148
_space_group_name_H-M_alt        'R -3 :H'
_space_group_name_Hall           '-R 3'

_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.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-y, x-y, z'
'-x+y, -x, z'
'x+2/3, y+1/3, z+1/3'
'-y+2/3, x-y+1/3, z+1/3'
'-x+y+2/3, -x+1/3, z+1/3'
'x+1/3, y+2/3, z+2/3'
'-y+1/3, x-y+2/3, z+2/3'
'-x+y+1/3, -x+2/3, z+2/3'
'-x, -y, -z'
'y, -x+y, -z'
'x-y, x, -z'
'-x+2/3, -y+1/3, -z+1/3'
'y+2/3, -x+y+1/3, -z+1/3'
'x-y+2/3, x+1/3, -z+1/3'
'-x+1/3, -y+2/3, -z+2/3'
'y+1/3, -x+y+2/3, -z+2/3'
'x-y+1/3, x+2/3, -z+2/3'

_cell_length_a                   30.683(2)
_cell_length_b                   30.683(2)
_cell_length_c                   9.8677(17)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                120
_cell_volume                     8045.5(17)
_cell_formula_units_Z            18
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    2257
_cell_measurement_theta_min      4.7640
_cell_measurement_theta_max      71.1010

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    0.919
_exptl_crystal_F_000             2412
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.230
_exptl_crystal_size_mid          0.210
_exptl_crystal_size_min          0.180
_exptl_absorpt_coefficient_mu    0.480
_shelx_estimated_absorpt_T_min   0.898
_shelx_estimated_absorpt_T_max   0.919
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  0.895
_exptl_absorpt_correction_T_max  0.917
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, EosS2'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            7442
_diffrn_reflns_av_unetI/netI     0.1028
_diffrn_reflns_av_R_equivalents  0.0940
_diffrn_reflns_limit_h_min       -22
_diffrn_reflns_limit_h_max       37
_diffrn_reflns_limit_k_min       -28
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_theta_min         4.993
_diffrn_reflns_theta_max         73.682
_diffrn_reflns_theta_full        67.679
_diffrn_measured_fraction_theta_max 0.947
_diffrn_measured_fraction_theta_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.947
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.947
_diffrn_reflns_point_group_measured_fraction_full 0.996
_reflns_number_total             3440
_reflns_number_gt                2242
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 Structure factors included contributions from the .fab file.
 
 _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.
;

_computing_data_collection       'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_computing_cell_refinement       'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_computing_structure_solution    'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1000P)²+45.0000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3440
_refine_ls_number_parameters     167
_refine_ls_number_restraints     30
_refine_ls_R_factor_all          0.1390
_refine_ls_R_factor_gt           0.0952
_refine_ls_wR_factor_ref         0.2894
_refine_ls_wR_factor_gt          0.2361
_refine_ls_goodness_of_fit_ref   1.039
_refine_ls_restrained_S_all      1.081
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

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
O1 O 0.37869(9) 0.09744(9) 0.3436(2) 0.0418(6) Uani 1 1 d . . . . .
N1 N 0.40328(11) 0.13971(11) 0.4349(2) 0.0383(7) Uani 1 1 d . . . . .
O2 O 0.24925(11) 0.02586(11) 0.2348(3) 0.0602(8) Uani 1 1 d . . . . .
H2 H 0.234326 -0.000686 0.192705 0.090 Uiso 1 1 calc R U . . .
C11 C 0.36231(14) 0.14286(13) 0.5049(3) 0.0396(8) Uani 1 1 d . . . . .
H11 H 0.369367 0.177717 0.508031 0.048 Uiso 1 1 calc R U . . .
C2 C 0.32905(14) 0.08916(14) 0.3077(3) 0.0430(8) Uani 1 1 d . . . . .
H2A H 0.331981 0.109055 0.227025 0.052 Uiso 1 1 calc R U . . .
C12 C 0.44013(15) 0.18636(14) 0.3596(3) 0.0480(9) Uani 1 1 d . . . . .
C10 C 0.35349(16) 0.12073(14) 0.6451(3) 0.0490(9) Uani 1 1 d . . . . .
C0AA C 0.29740(15) 0.03429(14) 0.2743(4) 0.0478(9) Uani 1 1 d . . . . .
H0AA H 0.312599 0.025419 0.201040 0.057 Uiso 1 1 calc R U . . .
H0AB H 0.294407 0.013935 0.352747 0.057 Uiso 1 1 calc R U . . .
C15 C 0.41592(18) 0.20396(17) 0.2546(4) 0.0624(11) Uani 1 1 d . . . . .
H15A H 0.402456 0.179921 0.182111 0.094 Uiso 1 1 calc R U . . .
H15B H 0.440752 0.236053 0.219246 0.094 Uiso 1 1 calc R U . . .
H15C H 0.389284 0.207005 0.296215 0.094 Uiso 1 1 calc R U . . .
C13 C 0.46807(17) 0.22626(17) 0.4673(4) 0.0636(11) Uani 1 1 d . . . . .
H13A H 0.445530 0.235620 0.508073 0.095 Uiso 1 1 calc R U . . .
H13B H 0.495707 0.255299 0.426230 0.095 Uiso 1 1 calc R U . . .
H13C H 0.480607 0.213034 0.535473 0.095 Uiso 1 1 calc R U . . .
C3 C 0.31228(16) 0.10871(18) 0.4270(4) 0.0595(11) Uani 1 1 d . . . . .
H3 H 0.298509 0.129378 0.393087 0.071 Uiso 1 1 calc R U . . .
C14 C 0.47669(18) 0.17320(19) 0.2914(5) 0.0707(13) Uani 1 1 d . . . . .
H14A H 0.489668 0.159678 0.357527 0.106 Uiso 1 1 calc R U . . .
H14B H 0.503985 0.202984 0.252078 0.106 Uiso 1 1 calc R U . . .
H14C H 0.459440 0.148669 0.221695 0.106 Uiso 1 1 calc R U . . .
C9 C 0.3863(2) 0.1362(2) 0.7529(4) 0.0681(13) Uani 1 1 d . . . . .
H9 H 0.418593 0.163753 0.744845 0.082 Uiso 1 1 calc R U . . .
C5 C 0.30543(19) 0.07916(16) 0.6570(5) 0.0700(14) Uani 1 1 d . U . . .
C4 C 0.2760(2) 0.0710(2) 0.5284(5) 0.102(2) Uani 1 1 d . U . . .
H4A H 0.247852 0.076356 0.543843 0.122 Uiso 1 1 calc R U . . .
H4B H 0.263176 0.036905 0.495402 0.122 Uiso 1 1 calc R U . . .
C8 C 0.3699(3) 0.1095(3) 0.8755(5) 0.0887(17) Uani 1 1 d . U . . .
H8 H 0.390962 0.119662 0.950726 0.106 Uiso 1 1 calc R U . . .
C7 C 0.3228(3) 0.0686(3) 0.8829(6) 0.099(2) Uani 1 1 d . U . . .
H7 H 0.312600 0.050852 0.964061 0.119 Uiso 1 1 calc R U . . .
C6 C 0.2902(3) 0.0526(2) 0.7776(6) 0.102(2) Uani 1 1 d . U . . .
H6 H 0.258348 0.024506 0.786073 0.122 Uiso 1 1 calc R U . . .


_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 N1 1.444(3) . ?
O1 C2 1.457(4) . ?
N1 C11 1.479(4) . ?
N1 C12 1.504(4) . ?
O2 C0AA 1.421(5) . ?
C11 C10 1.505(4) . ?
C11 C3 1.561(5) . ?
C2 C0AA 1.500(5) . ?
C2 C3 1.523(5) . ?
C12 C13 1.521(6) . ?
C12 C15 1.523(5) . ?
C12 C14 1.526(6) . ?
C10 C9 1.375(6) . ?
C10 C5 1.391(6) . ?
C3 C4 1.514(7) . ?
C9 C8 1.406(7) . ?
C5 C6 1.384(7) . ?
C5 C4 1.504(8) . ?
C8 C7 1.362(10) . ?
C7 C6 1.352(10) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N1 O1 C2 109.8(2) . . ?
O1 N1 C11 105.7(2) . . ?
O1 N1 C12 110.7(2) . . ?
C11 N1 C12 115.3(3) . . ?
N1 C11 C10 111.5(3) . . ?
N1 C11 C3 108.0(3) . . ?
C10 C11 C3 104.8(3) . . ?
O1 C2 C0AA 106.4(3) . . ?
O1 C2 C3 105.9(3) . . ?
C0AA C2 C3 117.1(3) . . ?
N1 C12 C13 105.9(3) . . ?
N1 C12 C15 114.0(3) . . ?
C13 C12 C15 111.6(3) . . ?
N1 C12 C14 105.6(3) . . ?
C13 C12 C14 109.1(4) . . ?
C15 C12 C14 110.3(3) . . ?
C9 C10 C5 120.6(4) . . ?
C9 C10 C11 128.3(4) . . ?
C5 C10 C11 111.1(4) . . ?
O2 C0AA C2 107.2(3) . . ?
C4 C3 C2 118.2(4) . . ?
C4 C3 C11 106.7(4) . . ?
C2 C3 C11 103.4(3) . . ?
C10 C9 C8 118.5(5) . . ?
C6 C5 C10 120.2(5) . . ?
C6 C5 C4 129.0(5) . . ?
C10 C5 C4 110.8(4) . . ?
C5 C4 C3 106.2(4) . . ?
C7 C8 C9 119.3(6) . . ?
C6 C7 C8 122.9(5) . . ?
C7 C6 C5 118.5(6) . . ?

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
C2 O1 N1 C11 25.7(3) . . . . ?
C2 O1 N1 C12 -99.8(3) . . . . ?
O1 N1 C11 C10 101.2(3) . . . . ?
C12 N1 C11 C10 -136.2(3) . . . . ?
O1 N1 C11 C3 -13.4(3) . . . . ?
C12 N1 C11 C3 109.2(3) . . . . ?
N1 O1 C2 C0AA -152.9(3) . . . . ?
N1 O1 C2 C3 -27.7(4) . . . . ?
O1 N1 C12 C13 -173.1(3) . . . . ?
C11 N1 C12 C13 67.0(4) . . . . ?
O1 N1 C12 C15 63.8(4) . . . . ?
C11 N1 C12 C15 -56.1(4) . . . . ?
O1 N1 C12 C14 -57.5(4) . . . . ?
C11 N1 C12 C14 -177.3(3) . . . . ?
N1 C11 C10 C9 62.0(5) . . . . ?
C3 C11 C10 C9 178.6(4) . . . . ?
N1 C11 C10 C5 -117.0(4) . . . . ?
C3 C11 C10 C5 -0.4(4) . . . . ?
O1 C2 C0AA O2 -178.1(3) . . . . ?
C3 C2 C0AA O2 63.7(4) . . . . ?
O1 C2 C3 C4 -100.0(4) . . . . ?
C0AA C2 C3 C4 18.4(6) . . . . ?
O1 C2 C3 C11 17.6(4) . . . . ?
C0AA C2 C3 C11 136.0(3) . . . . ?
N1 C11 C3 C4 122.8(4) . . . . ?
C10 C11 C3 C4 3.8(5) . . . . ?
N1 C11 C3 C2 -2.7(4) . . . . ?
C10 C11 C3 C2 -121.7(3) . . . . ?
C5 C10 C9 C8 -0.8(6) . . . . ?
C11 C10 C9 C8 -179.7(4) . . . . ?
C9 C10 C5 C6 -0.5(7) . . . . ?
C11 C10 C5 C6 178.6(4) . . . . ?
C9 C10 C5 C4 177.6(4) . . . . ?
C11 C10 C5 C4 -3.3(5) . . . . ?
C6 C5 C4 C3 -176.4(5) . . . . ?
C10 C5 C4 C3 5.7(6) . . . . ?
C2 C3 C4 C5 110.3(4) . . . . ?
C11 C3 C4 C5 -5.6(6) . . . . ?
C10 C9 C8 C7 1.6(7) . . . . ?
C9 C8 C7 C6 -1.2(9) . . . . ?
C8 C7 C6 C5 -0.1(9) . . . . ?
C10 C5 C6 C7 1.0(8) . . . . ?
C4 C5 C6 C7 -176.8(6) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
O2 H2 N1 0.82 2.05 2.871(4) 175.3 8_544 yes

_refine_diff_density_max         0.413
_refine_diff_density_min         -0.527
_refine_diff_density_rms         0.080



####################################################################### 
# 
# 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_zm-1-20220413
_database_code_depnum_ccdc_archive 'CCDC 2190477'
loop_
_audit_author_name
_audit_author_address
'Man Zhu'
;Henan Normal University
China
;
_audit_update_record             
;
2022-07-15 deposited with the CCDC.	2022-08-31 downloaded from the CCDC.
;
_audit_creation_date             2022-07-14
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        1
_chemical_formula_moiety         '4(C2 H4 O2), 4(C15 H23 N O2), [+ solvents]'
_chemical_formula_sum            'C68 H108 N4 O16'
_chemical_formula_weight         1237.58
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C1 H1 O1 N1'
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'

_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      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/n 1'
_space_group_name_Hall           '-P 2yn'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   9.0611(2)
_cell_length_b                   9.8268(2)
_cell_length_c                   38.9367(6)
_cell_angle_alpha                90
_cell_angle_beta                 93.796(2)
_cell_angle_gamma                90
_cell_volume                     3459.38(12)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    6049
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      71.4180
_cell_measurement_theta_min      4.5530
_shelx_estimated_absorpt_T_max   0.728
_shelx_estimated_absorpt_T_min   0.728
_exptl_absorpt_coefficient_mu    0.679
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.42520
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.42a (Rigaku Oxford Diffraction, 2019)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.188
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1344
_exptl_crystal_preparation       ?
_exptl_crystal_recrystallization_method ?
_exptl_crystal_size_max          0.5
_exptl_crystal_size_mid          0.5
_exptl_crystal_size_min          0.5
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0408
_diffrn_reflns_av_unetI/netI     0.0573
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.976
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       4
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       47
_diffrn_reflns_limit_l_min       -47
_diffrn_reflns_number            14315
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.976
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         71.475
_diffrn_reflns_theta_min         4.552
_diffrn_ambient_temperature      298(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 8.0521
_diffrn_detector_type            EosS2
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.976
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -42.00  32.00   1.00    1.81    --  -35.62  12.00 -76.00   74
  2  ω   -103.00 -69.00   1.00    1.81    --  -35.62 -12.00 110.00   34
  3  ω     -1.00  24.00   1.00    1.81    --   35.62 -12.00 110.00   25
  4  ω     24.00  49.00   1.00    1.81    --   35.62  12.00 -76.00   25
  5  ω     68.00 177.00   1.00    7.24    --  107.12  12.00 -76.00  109
  6  ω     37.00  76.00   1.00    7.24    --  107.12 -12.00 110.00   39
  7  ω    -21.00  32.00   1.00    1.81    --  -35.62  57.00-180.00   53
  8  ω    -52.00  29.00   1.00    1.81    --  -35.62  57.00 120.00   81
  9  ω     77.00 103.00   1.00    1.81    --   35.62-178.00  60.00   26
 10  ω      3.00  66.00   1.00    1.81    --   35.62 -99.00  30.00   63
 11  ω     61.00  88.00   1.00    1.81    --   35.62 178.00 150.00   27
 12  ω     47.00 106.00   1.00    7.24    --  107.12 -95.00  30.00   59
 13  ω     41.00  74.00   1.00    7.24    --  107.12 -95.00 -90.00   33
 14  ω    113.00 139.00   1.00    7.24    --  107.12  45.00 150.00   26
 15  ω     84.00 120.00   1.00    7.24    --  107.12 -61.00-150.00   36
 16  ω     98.00 128.00   1.00    7.24    --  107.12 -30.00  30.00   30
 17  ω     41.00  72.00   1.00    7.24    --  107.12 -61.00-150.00   31
 18  ω     38.00  91.00   1.00    7.24    --  107.12 -30.00  30.00   53
 19  ω     82.00 108.00   1.00    7.24    --  107.12 -95.00 -60.00   26
 20  ω     38.00 126.00   1.00    7.24    --  107.12 -30.00 -90.00   88
 21  ω    107.00 133.00   1.00    7.24    --  107.12 -77.00-120.00   26
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, EosS2'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0748790000
_diffrn_orient_matrix_UB_12      -0.0234168000
_diffrn_orient_matrix_UB_13      -0.0339144000
_diffrn_orient_matrix_UB_21      0.1520102000
_diffrn_orient_matrix_UB_22      -0.0074800000
_diffrn_orient_matrix_UB_23      0.0201380000
_diffrn_orient_matrix_UB_31      -0.0185474000
_diffrn_orient_matrix_UB_32      -0.1547351000
_diffrn_orient_matrix_UB_33      0.0041417000
_diffrn_oxdiff_digest_frames     
;
01934db35a488818080e89b3d823c3eaa901006c4cc
;
_diffrn_oxdiff_digest_hkl        
;
017bb2c39f81305988472597bb548abdbc4dc9
;
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                4974
_reflns_number_total             6581
_reflns_odcompleteness_completeness 99.91
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 Structure factors included contributions from the .fab file.
 
 _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 1.171.40.42a (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.40.42a (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.42a (Rigaku OD, 2019)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'olex2.refine (Bourhis et al., 2015)'
_computing_structure_solution    'olex2.solve (Bourhis et al., 2015)'
_refine_diff_density_max         0.621
_refine_diff_density_min         -0.505
_refine_diff_density_rms         0.061
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.055
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     422
_refine_ls_number_reflns         6581
_refine_ls_number_restraints     9
_refine_ls_R_factor_all          0.1150
_refine_ls_R_factor_gt           0.0838
_refine_ls_restrained_S_all      1.061
_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)+(0.0639P)²+8.7995P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2223
_refine_ls_wR_factor_ref         0.2347
_refine_special_details          ?
_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, All O(H) groups
2. Restrained distances
 H35-H43
 2.1 with sigma of 0.02
 H1_$1-H16_$2
 2.1 with sigma of 0.02
 H16_$2-O16_$2
 0.82 with sigma of 0.02
3. Uiso/Uaniso restraints and constraints
Uanis(C28) \\sim Ueq: with sigma of 0.01 and sigma for terminal atoms of 0.02
4.a Ternary CH refined with riding coordinates:
 C5(H5), C24(H24), C14(H14), C13(H13), C23(H23), C32(H32)
4.b Secondary CH2 refined with riding coordinates:
 C6(H6a,H6b), C15(H15a,H15b), C33(H33a,H33b), C31(H31a,H31b)
4.c Aromatic/amide H refined with riding coordinates:
 C11(H11), C8(H8), C26(H26), C9(H9), C10(H10), C29(H29), C27(H27), C28(H28)
4.d Tetrahedral OH refined with riding coordinates:
 O1(H1), O43(H43)
4.e Idealised Me refined as rotating group:
 C40(H40a,H40b,H40c), C38(H38a,H38b,H38c), C39(H39a,H39b,H39c), C22(H22a,H22b,
 H22c), C20(H20a,H20b,H20c), C4(H4a,H4b,H4c), C21(H21a,H21b,H21c), C44(H44a,
 H44b,H44c)
4.f Idealised tetrahedral OH refined as rotating group:
 O35(H35), O34(H34)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     iterative
_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
O1 O 0.3077(3) 0.0944(3) 0.57480(7) 0.0459(7) Uani 1 1 d . . . . .
H1 H 0.321248 0.011930 0.574887 0.069 Uiso 1 1 calc DR . . . .
O17 O 0.4226(3) 0.5470(3) 0.60836(7) 0.0443(7) Uani 1 1 d . . . . .
N18 N 0.4756(3) 0.3234(3) 0.56984(7) 0.0308(6) Uani 1 1 d . . . . .
N36 N 0.2169(3) 0.3448(3) 0.67809(7) 0.0278(6) Uani 1 1 d . . . . .
H36 H 0.217(4) 0.302(4) 0.6603(10) 0.033 Uiso 1 1 d R . . . .
O16 O 0.3416(4) 0.8340(3) 0.55138(8) 0.0583(9) Uani 1 1 d D . . . .
O3 O 0.2221(4) 0.2257(3) 0.61419(8) 0.0637(9) Uani 1 1 d . . . . .
O35 O 0.4562(4) 0.4931(4) 0.68856(8) 0.0758(12) Uani 1 1 d . . . . .
H35 H 0.525454 0.544290 0.685317 0.114 Uiso 1 1 calc DGR . . . .
O41 O 0.7805(4) 0.7328(4) 0.69050(10) 0.0732(10) Uani 1 1 d . . . . .
O43 O 0.6439(4) 0.6162(4) 0.65290(9) 0.0736(10) Uani 1 1 d . . . . .
H43 H 0.691937 0.546196 0.650891 0.110 Uiso 1 1 calc DR . . . .
O34 O 0.6444(5) 0.6145(4) 0.74521(10) 0.0813(12) Uani 1 1 d . . . . .
H34 H 0.684698 0.645044 0.728611 0.122 Uiso 1 1 calc GR . . . .
C12 C 0.3092(4) 0.3329(4) 0.51659(8) 0.0333(8) Uani 1 1 d . . . . .
C2 C 0.2128(4) 0.1238(3) 0.59558(9) 0.0369(8) Uani 1 1 d . . . . .
C5 C 0.3493(4) 0.5382(3) 0.54801(8) 0.0318(7) Uani 1 1 d . . . . .
H5 H 0.344513 0.596340 0.527519 0.038 Uiso 1 1 calc R . . . .
C37 C 0.0707(4) 0.4217(4) 0.67853(9) 0.0332(8) Uani 1 1 d . . . . .
C24 C 0.2654(4) 0.2614(4) 0.70958(8) 0.0326(8) Uani 1 1 d . . . . .
H24 H 0.194662 0.272355 0.727367 0.039 Uiso 1 1 calc R . . . .
C14 C 0.4218(4) 0.6224(4) 0.57700(9) 0.0371(8) Uani 1 1 d . . . . .
H14 H 0.524210 0.641561 0.571870 0.045 Uiso 1 1 calc R . . . .
C13 C 0.4295(4) 0.4055(3) 0.53805(8) 0.0299(7) Uani 1 1 d . . . . .
H13 H 0.514340 0.425476 0.524545 0.036 Uiso 1 1 calc R . . . .
C7 C 0.1715(4) 0.3786(4) 0.52579(9) 0.0366(8) Uani 1 1 d . . . . .
C23 C 0.4239(4) 0.2974(4) 0.72442(9) 0.0392(9) Uani 1 1 d . . . . .
H23 H 0.428237 0.272065 0.748810 0.047 Uiso 1 1 calc R . . . .
C25 C 0.2786(5) 0.1131(4) 0.70014(9) 0.0416(9) Uani 1 1 d . . . . .
C19 C 0.6351(4) 0.2737(4) 0.57412(10) 0.0435(9) Uani 1 1 d . . . . .
C32 C 0.4678(5) 0.4468(4) 0.72324(10) 0.0450(9) Uani 1 1 d . . . . .
H32 H 0.396059 0.498288 0.735818 0.054 Uiso 1 1 calc R . . . .
C6 C 0.1903(4) 0.4887(4) 0.55233(9) 0.0372(8) Uani 1 1 d . . . . .
H6A H 0.179906 0.453145 0.575292 0.045 Uiso 1 1 calc R . . . .
H6B H 0.119138 0.561308 0.547815 0.045 Uiso 1 1 calc R . . . .
C40 C 0.0594(5) 0.5028(5) 0.64516(10) 0.0500(10) Uani 1 1 d . . . . .
H40A H 0.143190 0.562304 0.644498 0.075 Uiso 1 1 calc GR . . . .
H40B H -0.029807 0.555720 0.643984 0.075 Uiso 1 1 calc GR . . . .
H40C H 0.057757 0.441427 0.625953 0.075 Uiso 1 1 calc GR . . . .
C42 C 0.7290(5) 0.7117(4) 0.66090(13) 0.0504(10) Uani 1 1 d . . . . .
C11 C 0.3211(5) 0.2329(4) 0.49200(11) 0.0500(10) Uani 1 1 d . . . . .
H11 H 0.413218 0.203443 0.485844 0.060 Uiso 1 1 calc R . . . .
C15 C 0.3423(5) 0.7564(4) 0.58200(10) 0.0468(10) Uani 1 1 d . . . . .
H15A H 0.241521 0.738914 0.587757 0.056 Uiso 1 1 calc R . . . .
H15B H 0.392016 0.806683 0.600831 0.056 Uiso 1 1 calc R . . . .
C38 C 0.0771(5) 0.5172(4) 0.70927(10) 0.0509(11) Uani 1 1 d . . . . .
H38A H 0.079671 0.464912 0.730128 0.076 Uiso 1 1 calc GR . . . .
H38B H -0.008706 0.574698 0.707977 0.076 Uiso 1 1 calc GR . . . .
H38C H 0.164547 0.572388 0.709145 0.076 Uiso 1 1 calc GR . . . .
C8 C 0.0439(5) 0.3204(5) 0.51064(12) 0.0529(11) Uani 1 1 d . . . . .
H8 H -0.048414 0.349182 0.516845 0.064 Uiso 1 1 calc R . . . .
C33 C 0.6198(5) 0.4739(5) 0.74060(11) 0.0561(12) Uani 1 1 d . . . . .
H33A H 0.628298 0.428732 0.762795 0.067 Uiso 1 1 calc R . . . .
H33B H 0.694774 0.436479 0.726628 0.067 Uiso 1 1 calc R . . . .
C30 C 0.4267(5) 0.0777(5) 0.69883(11) 0.0527(11) Uani 1 1 d . . . . .
C39 C -0.0555(5) 0.3218(5) 0.67966(13) 0.0555(11) Uani 1 1 d . . . . .
H39A H -0.048802 0.255812 0.661649 0.083 Uiso 1 1 calc GR . . . .
H39B H -0.147818 0.369594 0.676489 0.083 Uiso 1 1 calc GR . . . .
H39C H -0.050148 0.276516 0.701549 0.083 Uiso 1 1 calc GR . . . .
C22 C 0.6641(5) 0.1789(5) 0.54459(13) 0.0600(12) Uani 1 1 d . . . . .
H22A H 0.592109 0.107020 0.543531 0.090 Uiso 1 1 calc GR . . . .
H22B H 0.761372 0.140662 0.548186 0.090 Uiso 1 1 calc GR . . . .
H22C H 0.657065 0.228842 0.523359 0.090 Uiso 1 1 calc GR . . . .
C31 C 0.5245(5) 0.1965(5) 0.70688(12) 0.0593(12) Uani 1 1 d . . . . .
H31A H 0.560090 0.235251 0.686054 0.071 Uiso 1 1 calc R . . . .
H31B H 0.608557 0.170890 0.722225 0.071 Uiso 1 1 calc R . . . .
C26 C 0.1675(6) 0.0192(4) 0.69360(12) 0.0589(12) Uani 1 1 d . . . . .
H26 H 0.068816 0.044376 0.694364 0.071 Uiso 1 1 calc R . . . .
C9 C 0.0548(6) 0.2203(5) 0.48647(14) 0.0682(14) Uani 1 1 d . . . . .
H9 H -0.030776 0.180537 0.476476 0.082 Uiso 1 1 calc R . . . .
C20 C 0.7395(5) 0.3954(5) 0.57546(14) 0.0624(13) Uani 1 1 d . . . . .
H20A H 0.728947 0.443851 0.554029 0.094 Uiso 1 1 calc GR . . . .
H20B H 0.839604 0.364275 0.579344 0.094 Uiso 1 1 calc GR . . . .
H20C H 0.715654 0.454847 0.593871 0.094 Uiso 1 1 calc GR . . . .
C10 C 0.1918(6) 0.1772(5) 0.47667(13) 0.0658(14) Uani 1 1 d . . . . .
H10 H 0.197151 0.110884 0.459771 0.079 Uiso 1 1 calc R . . . .
C4 C 0.0802(6) 0.0335(5) 0.59688(16) 0.0720(15) Uani 1 1 d . . . . .
H4A H 0.019212 0.042655 0.575890 0.108 Uiso 1 1 calc GR . . . .
H4B H 0.024584 0.059240 0.615997 0.108 Uiso 1 1 calc GR . . . .
H4C H 0.111731 -0.059397 0.599590 0.108 Uiso 1 1 calc GR . . . .
C21 C 0.6450(6) 0.1987(6) 0.60856(14) 0.0728(15) Uani 1 1 d . . . . .
H21A H 0.619208 0.259670 0.626473 0.109 Uiso 1 1 calc GR . . . .
H21B H 0.744188 0.166340 0.613431 0.109 Uiso 1 1 calc GR . . . .
H21C H 0.577992 0.122950 0.607431 0.109 Uiso 1 1 calc GR . . . .
C29 C 0.4622(8) -0.0566(6) 0.69144(14) 0.0819(19) Uani 1 1 d . . . . .
H29 H 0.560591 -0.082903 0.690889 0.098 Uiso 1 1 calc R . . . .
C27 C 0.2054(9) -0.1138(5) 0.68582(15) 0.0829(18) Uani 1 1 d . . . . .
H27 H 0.131340 -0.178031 0.681212 0.099 Uiso 1 1 calc R . . . .
C28 C 0.3496(9) -0.1510(5) 0.68489(16) 0.0872(19) Uani 1 1 d . U . . .
H28 H 0.373186 -0.240565 0.679811 0.105 Uiso 1 1 calc R . . . .
C44 C 0.7705(7) 0.8048(6) 0.63267(18) 0.093(2) Uani 1 1 d . . . . .
H44A H 0.685575 0.856732 0.624497 0.140 Uiso 1 1 calc GR . . . .
H44B H 0.805305 0.752030 0.614101 0.140 Uiso 1 1 calc GR . . . .
H44C H 0.847326 0.865462 0.641324 0.140 Uiso 1 1 calc GR . . . .
H18 H 0.423(5) 0.247(5) 0.5715(11) 0.049(12) Uiso 1 1 d . . . . .
H16 H 0.369(17) 0.878(3) 0.5353(17) 0.37(9) Uiso 1 1 d D . . . .
H17 H 0.492(6) 0.580(6) 0.6212(14) 0.075(17) Uiso 1 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
O1 H1 0.8200 . ?
O1 C2 1.253(4) . ?
O17 C14 1.428(4) . ?
O17 H17 0.84(5) . ?
N18 C13 1.513(4) . ?
N18 C19 1.524(4) . ?
N18 H18 0.90(5) . ?
N36 H36 0.81(4) . ?
N36 C37 1.526(4) . ?
N36 C24 1.516(4) . ?
O16 C15 1.415(5) . ?
O16 H16 0.81(2) . ?
O3 C2 1.236(4) . ?
O35 H35 0.8200 . ?
O35 C32 1.423(5) . ?
O41 C42 1.232(6) . ?
O43 H43 0.8200 . ?
O43 C42 1.241(5) . ?
O34 H34 0.8200 . ?
O34 C33 1.409(6) . ?
C12 C13 1.508(5) . ?
C12 C7 1.395(5) . ?
C12 C11 1.381(5) . ?
C2 C4 1.497(6) . ?
C5 H5 0.9800 . ?
C5 C14 1.514(5) . ?
C5 C13 1.555(4) . ?
C5 C6 1.541(5) . ?
C37 C40 1.522(5) . ?
C37 C38 1.519(5) . ?
C37 C39 1.510(6) . ?
C24 H24 0.9800 . ?
C24 C23 1.553(5) . ?
C24 C25 1.510(5) . ?
C14 H14 0.9800 . ?
C14 C15 1.519(5) . ?
C13 H13 0.9800 . ?
C7 C6 1.498(5) . ?
C7 C8 1.386(6) . ?
C23 H23 0.9800 . ?
C23 C32 1.523(6) . ?
C23 C31 1.537(5) . ?
C25 C30 1.390(6) . ?
C25 C26 1.377(6) . ?
C19 C22 1.517(6) . ?
C19 C20 1.524(6) . ?
C19 C21 1.528(6) . ?
C32 H32 0.9800 . ?
C32 C33 1.517(6) . ?
C6 H6A 0.9700 . ?
C6 H6B 0.9700 . ?
C40 H40A 0.9600 . ?
C40 H40B 0.9600 . ?
C40 H40C 0.9600 . ?
C42 C44 1.498(7) . ?
C11 H11 0.9300 . ?
C11 C10 1.391(6) . ?
C15 H15A 0.9700 . ?
C15 H15B 0.9700 . ?
C38 H38A 0.9600 . ?
C38 H38B 0.9600 . ?
C38 H38C 0.9600 . ?
C8 H8 0.9300 . ?
C8 C9 1.370(6) . ?
C33 H33A 0.9700 . ?
C33 H33B 0.9700 . ?
C30 C31 1.486(7) . ?
C30 C29 1.393(7) . ?
C39 H39A 0.9600 . ?
C39 H39B 0.9600 . ?
C39 H39C 0.9600 . ?
C22 H22A 0.9600 . ?
C22 H22B 0.9600 . ?
C22 H22C 0.9600 . ?
C31 H31A 0.9700 . ?
C31 H31B 0.9700 . ?
C26 H26 0.9300 . ?
C26 C27 1.390(7) . ?
C9 H9 0.9300 . ?
C9 C10 1.389(7) . ?
C20 H20A 0.9600 . ?
C20 H20B 0.9600 . ?
C20 H20C 0.9600 . ?
C10 H10 0.9300 . ?
C4 H4A 0.9600 . ?
C4 H4B 0.9600 . ?
C4 H4C 0.9600 . ?
C21 H21A 0.9600 . ?
C21 H21B 0.9600 . ?
C21 H21C 0.9600 . ?
C29 H29 0.9300 . ?
C29 C28 1.390(9) . ?
C27 H27 0.9300 . ?
C27 C28 1.360(9) . ?
C28 H28 0.9300 . ?
C44 H44A 0.9600 . ?
C44 H44B 0.9600 . ?
C44 H44C 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 H1 109.5 . . ?
C14 O17 H17 106(4) . . ?
C13 N18 C19 118.0(3) . . ?
C13 N18 H18 113(3) . . ?
C19 N18 H18 103(3) . . ?
C37 N36 H36 108(3) . . ?
C24 N36 H36 113(3) . . ?
C24 N36 C37 117.6(3) . . ?
C15 O16 H16 162(10) . . ?
C32 O35 H35 109.5 . . ?
C42 O43 H43 109.5 . . ?
C33 O34 H34 109.5 . . ?
C7 C12 C13 109.3(3) . . ?
C11 C12 C13 129.3(3) . . ?
C11 C12 C7 121.3(4) . . ?
O1 C2 C4 118.2(3) . . ?
O3 C2 O1 122.8(4) . . ?
O3 C2 C4 119.0(4) . . ?
C14 C5 H5 106.4 . . ?
C14 C5 C13 117.2(3) . . ?
C14 C5 C6 117.0(3) . . ?
C13 C5 H5 106.4 . . ?
C6 C5 H5 106.4 . . ?
C6 C5 C13 102.6(3) . . ?
C40 C37 N36 105.0(3) . . ?
C38 C37 N36 109.1(3) . . ?
C38 C37 C40 110.3(3) . . ?
C39 C37 N36 109.7(3) . . ?
C39 C37 C40 110.9(3) . . ?
C39 C37 C38 111.6(3) . . ?
N36 C24 H24 110.1 . . ?
N36 C24 C23 112.9(3) . . ?
C23 C24 H24 110.1 . . ?
C25 C24 N36 110.4(3) . . ?
C25 C24 H24 110.1 . . ?
C25 C24 C23 102.9(3) . . ?
O17 C14 C5 109.3(3) . . ?
O17 C14 H14 108.8 . . ?
O17 C14 C15 108.4(3) . . ?
C5 C14 H14 108.9 . . ?
C5 C14 C15 112.5(3) . . ?
C15 C14 H14 108.8 . . ?
N18 C13 C5 110.6(3) . . ?
N18 C13 H13 111.2 . . ?
C12 C13 N18 110.6(3) . . ?
C12 C13 C5 101.7(3) . . ?
C12 C13 H13 111.2 . . ?
C5 C13 H13 111.2 . . ?
C12 C7 C6 110.3(3) . . ?
C8 C7 C12 119.5(4) . . ?
C8 C7 C6 130.2(4) . . ?
C24 C23 H23 106.3 . . ?
C32 C23 C24 116.5(3) . . ?
C32 C23 H23 106.3 . . ?
C32 C23 C31 116.4(4) . . ?
C31 C23 C24 104.4(3) . . ?
C31 C23 H23 106.3 . . ?
C30 C25 C24 110.0(4) . . ?
C26 C25 C24 128.5(4) . . ?
C26 C25 C30 121.4(4) . . ?
N18 C19 C20 109.5(3) . . ?
N18 C19 C21 104.5(3) . . ?
C22 C19 N18 108.9(3) . . ?
C22 C19 C20 111.7(4) . . ?
C22 C19 C21 111.4(4) . . ?
C20 C19 C21 110.4(4) . . ?
O35 C32 C23 109.5(3) . . ?
O35 C32 H32 107.4 . . ?
O35 C32 C33 112.0(3) . . ?
C23 C32 H32 107.4 . . ?
C33 C32 C23 112.8(4) . . ?
C33 C32 H32 107.4 . . ?
C5 C6 H6A 111.3 . . ?
C5 C6 H6B 111.3 . . ?
C7 C6 C5 102.5(3) . . ?
C7 C6 H6A 111.3 . . ?
C7 C6 H6B 111.3 . . ?
H6A C6 H6B 109.2 . . ?
C37 C40 H40A 109.5 . . ?
C37 C40 H40B 109.5 . . ?
C37 C40 H40C 109.5 . . ?
H40A C40 H40B 109.5 . . ?
H40A C40 H40C 109.5 . . ?
H40B C40 H40C 109.5 . . ?
O41 C42 O43 123.6(5) . . ?
O41 C42 C44 119.1(5) . . ?
O43 C42 C44 117.4(5) . . ?
C12 C11 H11 120.8 . . ?
C12 C11 C10 118.4(4) . . ?
C10 C11 H11 120.8 . . ?
O16 C15 C14 109.6(3) . . ?
O16 C15 H15A 109.8 . . ?
O16 C15 H15B 109.8 . . ?
C14 C15 H15A 109.8 . . ?
C14 C15 H15B 109.8 . . ?
H15A C15 H15B 108.2 . . ?
C37 C38 H38A 109.5 . . ?
C37 C38 H38B 109.5 . . ?
C37 C38 H38C 109.5 . . ?
H38A C38 H38B 109.5 . . ?
H38A C38 H38C 109.5 . . ?
H38B C38 H38C 109.5 . . ?
C7 C8 H8 120.2 . . ?
C9 C8 C7 119.5(4) . . ?
C9 C8 H8 120.2 . . ?
O34 C33 C32 111.1(4) . . ?
O34 C33 H33A 109.4 . . ?
O34 C33 H33B 109.4 . . ?
C32 C33 H33A 109.4 . . ?
C32 C33 H33B 109.4 . . ?
H33A C33 H33B 108.0 . . ?
C25 C30 C31 111.0(4) . . ?
C25 C30 C29 118.8(5) . . ?
C29 C30 C31 130.2(5) . . ?
C37 C39 H39A 109.5 . . ?
C37 C39 H39B 109.5 . . ?
C37 C39 H39C 109.5 . . ?
H39A C39 H39B 109.5 . . ?
H39A C39 H39C 109.5 . . ?
H39B C39 H39C 109.5 . . ?
C19 C22 H22A 109.5 . . ?
C19 C22 H22B 109.5 . . ?
C19 C22 H22C 109.5 . . ?
H22A C22 H22B 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
C23 C31 H31A 111.0 . . ?
C23 C31 H31B 111.0 . . ?
C30 C31 C23 103.7(4) . . ?
C30 C31 H31A 111.0 . . ?
C30 C31 H31B 111.0 . . ?
H31A C31 H31B 109.0 . . ?
C25 C26 H26 120.6 . . ?
C25 C26 C27 118.8(5) . . ?
C27 C26 H26 120.6 . . ?
C8 C9 H9 119.5 . . ?
C8 C9 C10 120.9(5) . . ?
C10 C9 H9 119.5 . . ?
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 . . ?
C11 C10 H10 119.8 . . ?
C9 C10 C11 120.4(4) . . ?
C9 C10 H10 119.8 . . ?
C2 C4 H4A 109.5 . . ?
C2 C4 H4B 109.5 . . ?
C2 C4 H4C 109.5 . . ?
H4A C4 H4B 109.5 . . ?
H4A C4 H4C 109.5 . . ?
H4B C4 H4C 109.5 . . ?
C19 C21 H21A 109.5 . . ?
C19 C21 H21B 109.5 . . ?
C19 C21 H21C 109.5 . . ?
H21A C21 H21B 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
C30 C29 H29 120.2 . . ?
C28 C29 C30 119.6(6) . . ?
C28 C29 H29 120.2 . . ?
C26 C27 H27 119.7 . . ?
C28 C27 C26 120.7(6) . . ?
C28 C27 H27 119.7 . . ?
C29 C28 H28 119.7 . . ?
C27 C28 C29 120.7(5) . . ?
C27 C28 H28 119.7 . . ?
C42 C44 H44A 109.5 . . ?
C42 C44 H44B 109.5 . . ?
C42 C44 H44C 109.5 . . ?
H44A C44 H44B 109.5 . . ?
H44A C44 H44C 109.5 . . ?
H44B C44 H44C 109.5 . . ?

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
O17 C14 C15 O16 179.3(3) . . . . ?
N36 C24 C23 C32 37.2(4) . . . . ?
N36 C24 C23 C31 -92.6(3) . . . . ?
N36 C24 C25 C30 104.1(4) . . . . ?
N36 C24 C25 C26 -76.3(5) . . . . ?
O35 C32 C33 O34 67.8(5) . . . . ?
C12 C7 C6 C5 20.0(4) . . . . ?
C12 C7 C8 C9 -1.0(6) . . . . ?
C12 C11 C10 C9 -1.1(8) . . . . ?
C5 C14 C15 O16 -59.7(5) . . . . ?
C37 N36 C24 C23 -126.4(3) . . . . ?
C37 N36 C24 C25 119.0(3) . . . . ?
C24 N36 C37 C40 175.7(3) . . . . ?
C24 N36 C37 C38 57.6(4) . . . . ?
C24 N36 C37 C39 -65.0(4) . . . . ?
C24 C23 C32 O35 -58.8(4) . . . . ?
C24 C23 C32 C33 175.8(3) . . . . ?
C24 C23 C31 C30 -26.8(4) . . . . ?
C24 C25 C30 C31 -0.4(5) . . . . ?
C24 C25 C30 C29 178.2(4) . . . . ?
C24 C25 C26 C27 -179.0(4) . . . . ?
C14 C5 C13 N18 47.5(4) . . . . ?
C14 C5 C13 C12 165.0(3) . . . . ?
C14 C5 C6 C7 -163.6(3) . . . . ?
C13 N18 C19 C22 -62.0(4) . . . . ?
C13 N18 C19 C20 60.5(4) . . . . ?
C13 N18 C19 C21 178.8(3) . . . . ?
C13 C12 C7 C6 3.0(4) . . . . ?
C13 C12 C7 C8 -176.6(3) . . . . ?
C13 C12 C11 C10 177.2(4) . . . . ?
C13 C5 C14 O17 -65.4(4) . . . . ?
C13 C5 C14 C15 174.1(3) . . . . ?
C13 C5 C6 C7 -33.8(3) . . . . ?
C7 C12 C13 N18 93.2(3) . . . . ?
C7 C12 C13 C5 -24.3(4) . . . . ?
C7 C12 C11 C10 -0.6(6) . . . . ?
C7 C8 C9 C10 -0.7(8) . . . . ?
C23 C24 C25 C30 -16.6(4) . . . . ?
C23 C24 C25 C26 162.9(4) . . . . ?
C23 C32 C33 O34 -168.1(4) . . . . ?
C25 C24 C23 C32 156.2(3) . . . . ?
C25 C24 C23 C31 26.4(4) . . . . ?
C25 C30 C31 C23 17.4(5) . . . . ?
C25 C30 C29 C28 1.3(7) . . . . ?
C25 C26 C27 C28 0.4(8) . . . . ?
C19 N18 C13 C12 118.1(3) . . . . ?
C19 N18 C13 C5 -130.0(3) . . . . ?
C32 C23 C31 C30 -156.6(3) . . . . ?
C6 C5 C14 O17 57.1(4) . . . . ?
C6 C5 C14 C15 -63.4(4) . . . . ?
C6 C5 C13 N18 -82.2(3) . . . . ?
C6 C5 C13 C12 35.3(3) . . . . ?
C6 C7 C8 C9 179.6(4) . . . . ?
C11 C12 C13 N18 -84.8(5) . . . . ?
C11 C12 C13 C5 157.7(4) . . . . ?
C11 C12 C7 C6 -178.9(4) . . . . ?
C11 C12 C7 C8 1.6(6) . . . . ?
C8 C7 C6 C5 -160.6(4) . . . . ?
C8 C9 C10 C11 1.7(8) . . . . ?
C30 C25 C26 C27 0.5(7) . . . . ?
C30 C29 C28 C27 -0.4(9) . . . . ?
C31 C23 C32 O35 65.1(5) . . . . ?
C31 C23 C32 C33 -60.3(5) . . . . ?
C31 C30 C29 C28 179.6(5) . . . . ?
C26 C25 C30 C31 -180.0(4) . . . . ?
C26 C25 C30 C29 -1.4(6) . . . . ?
C26 C27 C28 C29 -0.5(9) . . . . ?
C29 C30 C31 C23 -160.9(5) . . . . ?

_smtbx_masks_special_details     ?
loop_
_smtbx_masks_void_nr
_smtbx_masks_void_average_x
_smtbx_masks_void_average_y
_smtbx_masks_void_average_z
_smtbx_masks_void_volume
_smtbx_masks_void_count_electrons
_smtbx_masks_void_content
1 0.213 -0.050 0.321 11.5 0.5 '1 ?'
2 0.287 0.450 0.179 11.5 0.5 '1 ?'
3 0.713 0.550 0.821 11.5 0.5 '1 ?'
4 0.787 0.050 0.679 11.5 0.5 '1 ?'

_smtbx_masks_void_probe_radius   1.2
_smtbx_masks_void_truncation_radius 1.2
_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 2.012
_oxdiff_exptl_absorpt_empirical_full_min 0.338
####################################################################### 
# 
# 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_ZM-2-20220510
_database_code_depnum_ccdc_archive 'CCDC 2183361'
loop_
_audit_author_name
_audit_author_address
'Man Zhu'
;Henan Normal University
China
;
_audit_update_record             
;
2022-07-01 deposited with the CCDC.	2022-08-31 downloaded from the CCDC.
;
_audit_creation_date             2022-06-01
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_chemical_formula_moiety         'C14 H15 Br N2 O2'
_chemical_formula_sum            'C14 H15 Br N2 O2'
_chemical_formula_weight         323.19
_chemical_oxdiff_formula         'C1 H1 O1 N1'
loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_Cromer_Mann_a1
_atom_type_scat_Cromer_Mann_a2
_atom_type_scat_Cromer_Mann_a3
_atom_type_scat_Cromer_Mann_a4
_atom_type_scat_Cromer_Mann_b1
_atom_type_scat_Cromer_Mann_b2
_atom_type_scat_Cromer_Mann_b3
_atom_type_scat_Cromer_Mann_b4
_atom_type_scat_Cromer_Mann_c
_atom_type_scat_source
_atom_type_scat_dispersion_source
H 0.00000 0.00000 0.49300 0.32291 0.14019 0.04081 10.51090 26.12570 3.14236
57.79970 0.0030380000826
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
C 0.01920 0.00962 2.31000 1.02000 1.58860 0.86500 20.84390 10.20750 0.56870
51.65120 0.215599998832
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
Br -0.67402 1.33011 17.17890 5.23580 5.63770 3.98510 2.17230 16.57960 0.26090
41.43280 2.95569992065
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
O 0.05239 0.03377 3.04850 2.28680 1.54630 0.86700 13.27710 5.70110 0.32390
32.90890 0.250800013542
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
N 0.03256 0.01839 12.21260 3.13220 2.01250 1.16630 0.00570 9.89330 28.99750
0.58260 -11.5290002823
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 x,y,z
2 -x,y+1/2,-z+1/2
3 -x,-y,-z
4 x,-y-1/2,z-1/2

_symmetry_Int_Tables_number      14
_cell_length_a                   7.18110(10)
_cell_length_b                   21.3904(4)
_cell_length_c                   9.2071(2)
_cell_angle_alpha                90
_cell_angle_beta                 107.427(2)
_cell_angle_gamma                90
_cell_volume                     1349.36(5)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    4315
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      71.3730
_cell_measurement_theta_min      5.4150
_exptl_absorpt_coefficient_mu    4.157
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.37212
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.53 (Rigaku Oxford Diffraction, 2019)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.5908
_exptl_crystal_description       block
_exptl_crystal_F_000             654.9662
_exptl_crystal_size_max          0.1
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.1
_diffrn_reflns_av_R_equivalents  0.0255
_diffrn_reflns_av_unetI/netI     0.0252
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       25
_diffrn_reflns_limit_k_min       -25
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            6467
_diffrn_reflns_theta_full        71.4485
_diffrn_reflns_theta_max         71.45
_diffrn_reflns_theta_min         4.13
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 8.0521
_diffrn_detector_type            EosS2
_diffrn_measured_fraction_theta_full 0.9833
_diffrn_measured_fraction_theta_max 0.9833
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -97.00 -11.00   1.00    1.00    --  -35.62 140.00 128.00   86
  2  ω    -92.00  -6.00   1.00    1.00    --  -35.62 130.00 -45.00   86
  3  ω     27.00  92.00   1.00    1.00    --   35.62-130.00-117.00   65
  4  ω     38.00 122.00   1.00    1.00    --  107.12-130.00-117.00   84
  5  ω     90.00 126.00   1.00    1.00    --  107.12 140.00 128.00   36
  6  ω    122.00 148.00   1.00    1.00    --  107.12 130.00 -45.00   26
  7  ω     60.00  85.00   1.00    1.00    --  107.12-140.00  68.00   25
  8  ω   -102.00 -24.00   1.00    1.00    --  -35.62 -57.00  60.00   78
  9  ω     68.00  99.00   1.00    1.00    --   35.62  19.00  30.00   31
 10  ω      7.00  48.00   1.00    1.00    --   35.62  19.00  30.00   41
 11  ω     18.00 104.00   1.00    1.00    --   35.62  38.00-180.00   86
 12  ω     41.00 108.00   1.00    1.00    --  107.12 -95.00-150.00   67
 13  ω    131.00 175.00   1.00    1.00    --  107.12  30.00-120.00   44
 14  ω     93.00 118.00   1.00    1.00    --  107.12  30.00-120.00   25
 15  ω     85.00 111.00   1.00    1.00    --  107.12-111.00  60.00   26
 16  ω     38.00  83.00   1.00    1.00    --  107.12-111.00  60.00   45
 17  ω     95.00 173.00   1.00    1.00    --  107.12  45.00 -30.00   78
 18  ω     55.00 130.00   1.00    1.00    --  107.12 -77.00  30.00   75
 19  ω     38.00 120.00   1.00    1.00    --  107.12 -30.00-180.00   82
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, EosS2'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0198394000
_diffrn_orient_matrix_UB_12      0.0107611000
_diffrn_orient_matrix_UB_13      0.1694189000
_diffrn_orient_matrix_UB_21      -0.0045309000
_diffrn_orient_matrix_UB_22      -0.0711880000
_diffrn_orient_matrix_UB_23      0.0244680000
_diffrn_orient_matrix_UB_31      0.2238516000
_diffrn_orient_matrix_UB_32      -0.0024340000
_diffrn_orient_matrix_UB_33      0.0382329000
_diffrn_oxdiff_digest_frames     
;
0194d9f01b12901c2c137af717b2fb818901132a77d
;
_diffrn_oxdiff_digest_hkl        
;
010171482d3c82aa318aaa3d09163dd09590a4
;
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_reflns_Friedel_coverage         0.0
_reflns_limit_h_max              8
_reflns_limit_h_min              -8
_reflns_limit_k_max              25
_reflns_limit_k_min              0
_reflns_limit_l_max              11
_reflns_limit_l_min              0
_reflns_number_gt                2324
_reflns_number_total             2583
_reflns_odcompleteness_completeness 99.92
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_reflns_threshold_expression     I>=2u(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  'olex2.refine (Bourhis et al., 2015)'
_computing_structure_solution    'olex2.solve (Bourhis et al., 2015)'
_refine_diff_density_max         0.6408
_refine_diff_density_min         -1.0485
_refine_diff_density_rms         0.1267
_refine_ls_d_res_high            0.8132
_refine_ls_d_res_low             10.6952
_refine_ls_goodness_of_fit_ref   1.0438
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_constraints    26
_refine_ls_number_parameters     173
_refine_ls_number_reflns         2583
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0539
_refine_ls_R_factor_gt           0.0503
_refine_ls_restrained_S_all      1.0438
_refine_ls_shift/su_max          0.0000
_refine_ls_shift/su_mean         0.0000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0767P)²+1.2766P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1361
_refine_ls_wR_factor_ref         0.1403
_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 O(H) groups
2.a Ternary CH refined with riding coordinates:
 C1(H1), C9(H9), C10(H10)
2.b Secondary CH2 refined with riding coordinates:
 C8(H8a,H8b), C13(H13a,H13b), C14(H14a,H14b), C16(H16a,H16b)
2.c Aromatic/amide H refined with riding coordinates:
 C3(H3), C4(H4), C6(H6)
2.d Idealised tetrahedral OH refined as rotating group:
 O17(H17)
;
_atom_sites_solution_primary     iterative
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_refinement_flags_posn
Br19 Br 1.13844(7) 0.41142(2) 0.12000(5) 0.0676(2) Uani 1.000000 .
O18 O 0.3682(4) 0.30001(14) 0.8573(3) 0.0589(7) Uani 1.000000 .
N15 N 0.6888(4) 0.31504(12) 0.6363(3) 0.0380(5) Uani 1.000000 .
N11 N 0.5706(4) 0.33769(13) 0.7269(3) 0.0417(6) Uani 1.000000 .
O17 O 0.3398(5) 0.42793(17) 0.8682(4) 0.0793(10) Uani 1.000000 .
H17 H 0.321(4) 0.3903(2) 0.874(8) 0.1189(15) Uiso 1.000000 GR
C1 C 0.8481(4) 0.36135(16) 0.6706(3) 0.0415(7) Uani 1.000000 .
H1 H 0.9468(4) 0.35338(16) 0.7684(3) 0.0498(8) Uiso 1.000000 R
C5 C 1.0520(5) 0.39373(17) 0.2910(4) 0.0437(7) Uani 1.000000 .
C3 C 1.0730(4) 0.32952(17) 0.5085(4) 0.0465(8) Uani 1.000000 .
H3 H 1.1250(4) 0.29551(17) 0.5703(4) 0.0558(9) Uiso 1.000000 R
C4 C 1.1324(5) 0.34297(17) 0.3814(4) 0.0491(8) Uani 1.000000 .
H4 H 1.2252(5) 0.31810(17) 0.3574(4) 0.0589(10) Uiso 1.000000 R
C2 C 0.9357(4) 0.36749(16) 0.5415(3) 0.0401(7) Uani 1.000000 .
C6 C 0.9135(5) 0.43192(17) 0.3231(4) 0.0472(8) Uani 1.000000 .
H6 H 0.8605(5) 0.46576(17) 0.2611(4) 0.0566(9) Uiso 1.000000 R
C12 C 0.4878(5) 0.29236(17) 0.7864(3) 0.0454(7) Uani 1.000000 .
C7 C 0.8562(5) 0.41814(15) 0.4508(4) 0.0424(7) Uani 1.000000 .
C9 C 0.7390(5) 0.42352(16) 0.6697(4) 0.0448(8) Uani 1.000000 .
H9 H 0.8187(5) 0.45185(16) 0.7473(4) 0.0538(9) Uiso 1.000000 R
C10 C 0.5505(5) 0.40542(15) 0.7090(4) 0.0433(7) Uani 1.000000 .
H10 H 0.4370(5) 0.41485(15) 0.6216(4) 0.0520(9) Uiso 1.000000 R
C8 C 0.7085(5) 0.45124(17) 0.5093(4) 0.0511(8) Uani 1.000000 .
H8a H 0.7313(5) 0.49599(17) 0.5148(4) 0.0613(10) Uiso 1.000000 R
H8b H 0.5770(5) 0.44325(17) 0.4442(4) 0.0613(10) Uiso 1.000000 R
C13 C 0.5613(6) 0.23166(18) 0.7437(5) 0.0578(9) Uani 1.000000 .
H13a H 0.5974(6) 0.20313(18) 0.8295(5) 0.0694(11) Uiso 1.000000 R
H13b H 0.4641(6) 0.21187(18) 0.6598(5) 0.0694(11) Uiso 1.000000 R
C14 C 0.7394(6) 0.25137(18) 0.6971(5) 0.0575(9) Uani 1.000000 .
H14a H 0.7597(6) 0.22363(18) 0.6199(5) 0.0690(11) Uiso 1.000000 R
H14b H 0.8561(6) 0.25170(18) 0.7840(5) 0.0690(11) Uiso 1.000000 R
C16 C 0.5265(7) 0.4379(2) 0.8499(5) 0.0658(11) Uani 1.000000 .
H16a H 0.5470(7) 0.4825(2) 0.8422(5) 0.0789(14) Uiso 1.000000 R
H16b H 0.6255(7) 0.4225(2) 0.9393(5) 0.0789(14) Uiso 1.000000 R


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
Br19 C5 1.895(3) . ?
O18 C12 1.235(4) . ?
N15 N11 1.441(3) . ?
N15 C1 1.474(4) . ?
N15 C14 1.476(4) . ?
N11 C12 1.338(4) . ?
N11 C10 1.460(4) . ?
O17 H17 0.8200 . ?
O17 C16 1.417(5) . ?
C1 H1 0.9800 . ?
C1 C2 1.508(4) . ?
C1 C9 1.542(5) . ?
C5 C4 1.385(5) . ?
C5 C6 1.386(5) . ?
C3 H3 0.9300 . ?
C3 C4 1.390(5) . ?
C3 C2 1.380(4) . ?
C4 H4 0.9300 . ?
C2 C7 1.382(5) . ?
C6 H6 0.9300 . ?
C6 C7 1.389(5) . ?
C12 C13 1.498(5) . ?
C7 C8 1.503(4) . ?
C9 H9 0.9800 . ?
C9 C10 1.551(4) . ?
C9 C8 1.544(5) . ?
C10 H10 0.9800 . ?
C10 C16 1.526(5) . ?
C8 H8a 0.9700 . ?
C8 H8b 0.9700 . ?
C13 H13a 0.9700 . ?
C13 H13b 0.9700 . ?
C13 C14 1.525(5) . ?
C14 H14a 0.9700 . ?
C14 H14b 0.9700 . ?
C16 H16a 0.9700 . ?
C16 H16b 0.9700 . ?

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
C1 N15 N11 101.8(2) . . ?
C14 N15 N11 102.2(2) . . ?
C14 N15 C1 116.9(3) . . ?
C12 N11 N15 113.9(3) . . ?
C10 N11 N15 108.9(2) . . ?
C10 N11 C12 136.4(3) . . ?
C16 O17 H17 109.5 . . ?
H1 C1 N15 112.43(16) . . ?
C2 C1 N15 111.7(2) . . ?
C2 C1 H1 112.43(16) . . ?
C9 C1 N15 102.6(2) . . ?
C9 C1 H1 112.43(17) . . ?
C9 C1 C2 104.6(3) . . ?
C4 C5 Br19 118.4(2) . . ?
C6 C5 Br19 119.6(3) . . ?
C6 C5 C4 122.0(3) . . ?
C4 C3 H3 120.6(2) . . ?
C2 C3 H3 120.6(2) . . ?
C2 C3 C4 118.9(3) . . ?
C3 C4 C5 119.4(3) . . ?
H4 C4 C5 120.30(18) . . ?
H4 C4 C3 120.3(2) . . ?
C3 C2 C1 128.1(3) . . ?
C7 C2 C1 110.5(3) . . ?
C7 C2 C3 121.4(3) . . ?
H6 C6 C5 121.0(2) . . ?
C7 C6 C5 118.0(3) . . ?
C7 C6 H6 121.0(2) . . ?
N11 C12 O18 125.8(3) . . ?
C13 C12 O18 127.5(3) . . ?
C13 C12 N11 106.6(3) . . ?
C6 C7 C2 120.3(3) . . ?
C8 C7 C2 111.1(3) . . ?
C8 C7 C6 128.5(3) . . ?
H9 C9 C1 110.14(17) . . ?
C10 C9 C1 105.1(3) . . ?
C10 C9 H9 110.14(17) . . ?
C8 C9 C1 105.2(3) . . ?
C8 C9 H9 110.14(19) . . ?
C8 C9 C10 115.8(3) . . ?
C9 C10 N11 102.2(3) . . ?
H10 C10 N11 109.05(18) . . ?
H10 C10 C9 109.05(19) . . ?
C16 C10 N11 112.9(3) . . ?
C16 C10 C9 114.4(3) . . ?
C16 C10 H10 109.0(2) . . ?
C9 C8 C7 104.4(3) . . ?
H8a C8 C7 110.88(18) . . ?
H8a C8 C9 110.88(19) . . ?
H8b C8 C7 110.9(2) . . ?
H8b C8 C9 110.88(19) . . ?
H8b C8 H8a 108.9 . . ?
H13a C13 C12 111.16(18) . . ?
H13b C13 C12 111.2(2) . . ?
H13b C13 H13a 109.1 . . ?
C14 C13 C12 103.0(3) . . ?
C14 C13 H13a 111.16(19) . . ?
C14 C13 H13b 111.2(2) . . ?
C13 C14 N15 103.3(3) . . ?
H14a C14 N15 111.10(19) . . ?
H14a C14 C13 111.1(2) . . ?
H14b C14 N15 111.1(2) . . ?
H14b C14 C13 111.1(2) . . ?
H14b C14 H14a 109.1 . . ?
C10 C16 O17 112.6(3) . . ?
H16a C16 O17 109.1(3) . . ?
H16a C16 C10 109.1(2) . . ?
H16b C16 O17 109.1(3) . . ?
H16b C16 C10 109.1(2) . . ?
H16b C16 H16a 107.8 . . ?

_olex2_date_sample_data_collection 2022-05-10
_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 2.081
_oxdiff_exptl_absorpt_empirical_full_min 0.652
