# Electronic Supplementary Material (ESI) for Chemical Science.
# This journal is © The Royal Society of Chemistry 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_liuhonghao_0726_auto
_database_code_depnum_ccdc_archive 'CCDC 2101150'
loop_
_audit_author_name
_audit_author_address
lhc
;Lanzhou University
China
;
_audit_update_record             
;
2021-08-03 deposited with the CCDC.	2022-04-12 downloaded from the CCDC.
;
_audit_creation_date             2021-07-28
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6032)
;
_shelx_SHELXL_version_number     2018/1
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C26 H35 N5 O2'
_chemical_formula_sum            'C26 H35 N5 O2'
_chemical_formula_weight         449.59
_chemical_melting_point          ?
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/c 1'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   10.3083(3)
_cell_length_b                   24.7520(7)
_cell_length_c                   10.4153(4)
_cell_angle_alpha                90
_cell_angle_beta                 108.265(4)
_cell_angle_gamma                90
_cell_volume                     2523.58(16)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    6631
_cell_measurement_temperature    303.04(10)
_cell_measurement_theta_max      75.3820
_cell_measurement_theta_min      1.7860
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.608
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.90035
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.41.105a (Rigaku Oxford Diffraction, 2021)
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    1.183
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             968
_exptl_crystal_size_max          0.11
_exptl_crystal_size_mid          0.07
_exptl_crystal_size_min          0.05
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0428
_diffrn_reflns_av_unetI/netI     0.0411
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.965
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       26
_diffrn_reflns_limit_k_min       -30
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            19037
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.965
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         76.252
_diffrn_reflns_theta_min         3.571
_diffrn_ambient_environment      air
_diffrn_ambient_temperature      303.04(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.965
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    114.00 175.00   0.50    1.00    --  104.25  45.00 -60.00  122
  2  ω     94.00 174.00   0.50    1.00    --  104.25  22.00  73.00  160
  3  ω     50.00 121.00   0.50    0.20    --   46.32  22.00  73.00  142
  4  ω   -115.00 -90.00   0.50    0.20    --  -46.32-125.00  90.00   50
  5  ω   -111.00 -81.00   0.50    0.20    --  -46.32-175.00  40.00   60
  6  ω    -69.00 -44.00   0.50    0.20    --  -46.32-175.00  40.00   50
  7  ω    -91.00 -57.00   0.50    1.00    -- -102.00 114.00 -89.00   68
  8  ω    -25.00  29.00   0.50    0.20    --  -46.32  19.00-180.00  108
  9  ω     32.00 103.00   0.50    1.00    --  104.25-125.00-120.00  142
 10  ω     42.00  68.00   0.50    1.00    --  104.25-108.00  83.00   52
 11  ω     34.00  95.00   0.50    1.00    --  104.25 -94.00 120.00  122
 12  ω     33.00  62.00   0.50    1.00    --  104.25 -61.00  60.00   58
 13  ω    -79.00 -29.00   0.50    0.20    -- -102.00 103.00-120.00  100
 14  ω   -110.00 -84.00   0.50    0.20    --  -46.32-125.00-180.00   52
 15  ω   -115.00 -85.00   0.50    0.20    --  -46.32-125.00 -90.00   60
 16  ω   -119.00 -94.00   0.50    0.20    --  -46.32-125.00  30.00   50
 17  ω     -6.00  29.00   0.50    0.20    --   46.32 -19.00 -60.00   70
 18  ω    -19.00  19.00   0.50    0.20    --   46.32 -19.00-120.00   76
 19  ω    -69.00 -29.00   0.50    0.20    -- -102.00  61.00   0.00   80
 20  ω    -63.00 -31.00   0.50    0.20    -- -102.00  61.00  30.00   64
 21  ω    -69.00 -44.00   0.50    0.20    -- -102.00  61.00 -90.00   50
 22  ω    -68.00 -42.00   0.50    0.20    -- -102.00  61.00  60.00   52
 23  ω    137.00 166.00   0.50    0.20    --  104.25  77.00 150.00   58
 24  ω     89.00 126.00   0.50    0.20    --  104.25  77.00 150.00   74
 25  ω    137.00 163.00   0.50    0.20    --  104.25  30.00 -90.00   52
 26  ω     39.00  64.00   0.50    0.20    --  104.25 -61.00   0.00   50
 27  ω     43.00  98.00   0.50    0.20    --  104.25 -94.00 150.00  110
 28  ω     40.00  65.00   0.50    0.20    --  104.25 -61.00 150.00   50
 29  ω     44.00  70.00   0.50    0.20    --  104.25 -61.00-180.00   52
 30  ω     36.00  63.00   0.50    0.20    --  104.25 -61.00 -90.00   54
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy R, DW system, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0200522000
_diffrn_orient_matrix_UB_12      0.0172238000
_diffrn_orient_matrix_UB_13      0.1471070000
_diffrn_orient_matrix_UB_21      -0.1557050000
_diffrn_orient_matrix_UB_22      -0.0019864000
_diffrn_orient_matrix_UB_23      -0.0273808000
_diffrn_orient_matrix_UB_31      0.0108550000
_diffrn_orient_matrix_UB_32      -0.0597865000
_diffrn_orient_matrix_UB_33      0.0432208000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'Rigaku (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3610
_reflns_number_total             5099
_reflns_odcompleteness_completeness 99.74
_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.
 
 _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 1.171.41.105a (Rigaku OD, 2021)'
_computing_data_collection       'CrysAlisPro 1.171.41.105a (Rigaku OD, 2021)'
_computing_data_reduction        'CrysAlisPro 1.171.41.105a (Rigaku OD, 2021)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/1 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT  (Sheldrick, 2015)'
_refine_diff_density_max         0.344
_refine_diff_density_min         -0.218
_refine_diff_density_rms         0.034
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.046
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     321
_refine_ls_number_reflns         5099
_refine_ls_number_restraints     24
_refine_ls_R_factor_all          0.0830
_refine_ls_R_factor_gt           0.0625
_refine_ls_restrained_S_all      1.045
_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)+(0.1021P)²+0.3891P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1861
_refine_ls_wR_factor_ref         0.2029
_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
2. Uiso/Uaniso restraints and constraints
Uanis(C2) \\sim Ueq, Uanis(C00O) \\sim Ueq, Uanis(C00M) \\sim Ueq, Uanis(C1)
\\sim Ueq: with sigma of 0.01 and sigma for terminal atoms of 0.02
3. Others
 Fixed Sof: C00M(0.8) H00A(0.8) H00C(0.8) C00O(0.8) H00D(0.8) H00E(0.8)
 C1(0.2) H1A(0.2) H1B(0.2) C2(0.2) H2A(0.2) H2B(0.2)
4.a Ternary CH refined with riding coordinates:
 C00H(H00H)
4.b Secondary CH2 refined with riding coordinates:
 C00M(H00A,H00C), C00O(H00D,H00E), C00S(H00U,H00V), C00T(H00W,H00X), C00U(H00Y,
 H), C00X(H1,HE), C1(H1A,H1B), C2(H2A,H2B)
4.c Aromatic/amide H refined with riding coordinates:
 N004(H004), C00B(H00B), C00I(H00I), C00J(H00J), C00K(H00K), C00L(H00L),
 C00N(H00N)
4.d Idealised Me refined as rotating group:
 C00P(H00F,H00G,H00M), C00Q(H00O,H00P,H00Q), C00R(H00R,H00S,H00T), C00V(H00Z,
 HA,HB), C00W(H00,HC,HD)
;
_atom_sites_solution_hydrogens   geom
_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
O001 O 1.06490(15) 0.32320(7) 0.47124(17) 0.0812(5) Uani 1 1 d . . . . .
O002 O 0.45403(18) 0.70383(7) 0.51859(18) 0.0932(5) Uani 1 1 d . . . . .
N003 N 0.55101(18) 0.62150(7) 0.5084(2) 0.0779(5) Uani 1 1 d . . . . .
N004 N 0.90194(18) 0.33866(8) 0.56982(19) 0.0742(5) Uani 1 1 d . . . . .
H004 H 0.825270 0.354677 0.559295 0.089 Uiso 1 1 calc R U . . .
N005 N 0.33637(18) 0.57429(9) 0.4500(2) 0.0852(6) Uani 1 1 d . . . . .
N006 N 0.65509(19) 0.57447(8) 0.3824(2) 0.0856(6) Uani 1 1 d . . . . .
N007 N 0.32721(19) 0.50069(8) 0.2962(2) 0.0858(6) Uani 1 1 d . . . . .
C008 C 0.5259(2) 0.55325(8) 0.3655(2) 0.0695(5) Uani 1 1 d . . . . .
C009 C 0.4538(2) 0.51043(8) 0.2898(2) 0.0692(5) Uani 1 1 d . . . . .
C00A C 0.4612(2) 0.58270(9) 0.4424(2) 0.0712(5) Uani 1 1 d . . . . .
C00B C 0.6441(2) 0.47333(8) 0.2164(2) 0.0686(5) Uani 1 1 d . . . . .
H00B H 0.703905 0.494508 0.282688 0.082 Uiso 1 1 calc R U . . .
C00C C 0.9548(2) 0.34239(9) 0.4683(2) 0.0727(6) Uani 1 1 d . . . . .
C00D C 0.6968(2) 0.44108(8) 0.1348(2) 0.0729(6) Uani 1 1 d . . . . .
C00E C 0.5059(2) 0.47498(8) 0.2022(2) 0.0704(5) Uani 1 1 d . . . . .
C00F C 0.9626(2) 0.30975(10) 0.6976(2) 0.0773(6) Uani 1 1 d . . . . .
C00G C 0.8520(3) 0.43988(9) 0.1596(3) 0.0814(6) Uani 1 1 d . . . . .
C00H C 0.5260(2) 0.66092(10) 0.6014(3) 0.0847(7) Uani 1 1 d . . . . .
H00H H 0.466152 0.644498 0.647384 0.102 Uiso 1 1 calc R U . . .
C00I C 0.6046(3) 0.41055(10) 0.0360(3) 0.0918(8) Uani 1 1 d . . . . .
H00I H 0.635996 0.388721 -0.020705 0.110 Uiso 1 1 calc R U . . .
C00J C 0.6640(2) 0.61420(10) 0.4672(3) 0.0874(7) Uani 1 1 d . . . . .
H00J H 0.741201 0.635938 0.497569 0.105 Uiso 1 1 calc R U . . .
C00K C 0.4172(3) 0.44349(10) 0.1025(3) 0.0881(7) Uani 1 1 d . . . . .
H00K H 0.324107 0.443729 0.091465 0.106 Uiso 1 1 calc R U . . .
C00L C 0.2775(2) 0.53209(12) 0.3733(3) 0.0934(8) Uani 1 1 d . . . . .
H00L H 0.189927 0.523566 0.374117 0.112 Uiso 1 1 calc R U . . .
C00M C 0.8648(3) 0.36715(13) 0.3380(3) 0.0718(7) Uani 0.8 1 d . U P A 1
H00A H 0.852862 0.341531 0.264746 0.086 Uiso 0.8 1 calc R U P A 1
H00C H 0.775531 0.374842 0.346393 0.086 Uiso 0.8 1 calc R U P A 1
C00N C 0.4670(3) 0.41216(12) 0.0208(3) 0.1040(9) Uani 1 1 d . . . . .
H00N H 0.406798 0.391502 -0.046539 0.125 Uiso 1 1 calc R U . . .
C00O C 0.9262(3) 0.41868(13) 0.3050(3) 0.0721(7) Uani 0.8 1 d . U P A 1
H00D H 1.021616 0.412346 0.314354 0.087 Uiso 0.8 1 calc R U P A 1
H00E H 0.922424 0.446275 0.369881 0.087 Uiso 0.8 1 calc R U P A 1
C00P C 0.9923(4) 0.25199(11) 0.6682(3) 0.1088(9) Uani 1 1 d . . . . .
H00F H 0.908338 0.234052 0.621017 0.163 Uiso 1 1 calc R U . . .
H00G H 1.035729 0.233521 0.751738 0.163 Uiso 1 1 calc R U . . .
H00M H 1.051741 0.251758 0.613351 0.163 Uiso 1 1 calc R U . . .
C00Q C 0.9077(3) 0.49701(11) 0.1593(4) 0.1086(9) Uani 1 1 d . . . . .
H00O H 0.864466 0.513592 0.073170 0.163 Uiso 1 1 calc R U . . .
H00P H 1.004569 0.495439 0.175409 0.163 Uiso 1 1 calc R U . . .
H00Q H 0.889108 0.517915 0.229183 0.163 Uiso 1 1 calc R U . . .
C00R C 1.0920(3) 0.33753(15) 0.7817(3) 0.1220(11) Uani 1 1 d . . . . .
H00R H 1.156439 0.338523 0.732237 0.183 Uiso 1 1 calc R U . . .
H00S H 1.130668 0.317969 0.864537 0.183 Uiso 1 1 calc R U . . .
H00T H 1.071150 0.373741 0.801824 0.183 Uiso 1 1 calc R U . . .
C00S C 0.6514(3) 0.68019(13) 0.7049(3) 0.1070(9) Uani 1 1 d . . . . .
H00U H 0.713786 0.695359 0.661495 0.128 Uiso 1 1 calc R U . . .
H00V H 0.696767 0.650260 0.761370 0.128 Uiso 1 1 calc R U . . .
C00T C 0.6120(4) 0.72356(16) 0.7921(3) 0.1172(10) Uani 1 1 d . . . . .
H00W H 0.559103 0.707226 0.844203 0.141 Uiso 1 1 calc R U . . .
H00X H 0.693920 0.739088 0.854725 0.141 Uiso 1 1 calc R U . . .
C00U C 0.4139(4) 0.74450(14) 0.5977(4) 0.1260(12) Uani 1 1 d . . . . .
H00Y H 0.350905 0.728656 0.639474 0.151 Uiso 1 1 calc R U . . .
H H 0.366153 0.773253 0.538294 0.151 Uiso 1 1 calc R U . . .
C00V C 0.8539(4) 0.30916(17) 0.7681(3) 0.1234(12) Uani 1 1 d . . . . .
H00Z H 0.837677 0.345377 0.792284 0.185 Uiso 1 1 calc R U . . .
HA H 0.884662 0.287390 0.848264 0.185 Uiso 1 1 calc R U . . .
HB H 0.770839 0.294330 0.708368 0.185 Uiso 1 1 calc R U . . .
C00W C 0.8920(4) 0.40766(16) 0.0533(4) 0.1266(12) Uani 1 1 d . . . . .
H00 H 0.863548 0.370795 0.054667 0.190 Uiso 1 1 calc R U . . .
HC H 0.989311 0.408986 0.072537 0.190 Uiso 1 1 calc R U . . .
HD H 0.848300 0.422898 -0.034431 0.190 Uiso 1 1 calc R U . . .
C00X C 0.5291(4) 0.76724(14) 0.7022(4) 0.1215(11) Uani 1 1 d . . . . .
H1 H 0.496292 0.792412 0.756414 0.146 Uiso 1 1 calc R U . . .
HE H 0.586691 0.787031 0.660623 0.146 Uiso 1 1 calc R U . . .
C1 C 0.8999(12) 0.4011(5) 0.3948(11) 0.068(2) Uani 0.2 1 d . U P A 2
H1A H 0.809662 0.409766 0.399363 0.082 Uiso 0.2 1 calc R U P A 2
H1B H 0.962399 0.430166 0.435081 0.082 Uiso 0.2 1 calc R U P A 2
C2 C 0.8970(13) 0.3897(5) 0.2486(13) 0.072(3) Uani 0.2 1 d . U P A 2
H2A H 0.987288 0.378798 0.248332 0.086 Uiso 0.2 1 calc R U P A 2
H2B H 0.834380 0.360239 0.211753 0.086 Uiso 0.2 1 calc R U P A 2


_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
O001 C00C 1.221(2) . ?
O002 C00H 1.422(3) . ?
O002 C00U 1.441(4) . ?
N003 C00A 1.361(3) . ?
N003 C00H 1.454(3) . ?
N003 C00J 1.373(3) . ?
N004 H004 0.8600 . ?
N004 C00C 1.336(3) . ?
N004 C00F 1.467(3) . ?
N005 C00A 1.330(3) . ?
N005 C00L 1.339(3) . ?
N006 C008 1.391(3) . ?
N006 C00J 1.306(3) . ?
N007 C009 1.349(3) . ?
N007 C00L 1.330(4) . ?
C008 C009 1.389(3) . ?
C008 C00A 1.397(3) . ?
C009 C00E 1.483(3) . ?
C00B H00B 0.9300 . ?
C00B C00D 1.394(3) . ?
C00B C00E 1.386(3) . ?
C00C C00M 1.513(4) . ?
C00C C1 1.656(11) . ?
C00D C00G 1.539(3) . ?
C00D C00I 1.386(3) . ?
C00E C00K 1.388(3) . ?
C00F C00P 1.513(4) . ?
C00F C00R 1.513(4) . ?
C00F C00V 1.520(4) . ?
C00G C00O 1.558(4) . ?
C00G C00Q 1.526(4) . ?
C00G C00W 1.522(4) . ?
C00G C2 1.532(12) . ?
C00H H00H 0.9800 . ?
C00H C00S 1.479(4) . ?
C00I H00I 0.9300 . ?
C00I C00N 1.378(4) . ?
C00J H00J 0.9300 . ?
C00K H00K 0.9300 . ?
C00K C00N 1.365(4) . ?
C00L H00L 0.9300 . ?
C00M H00A 0.9700 . ?
C00M H00C 0.9700 . ?
C00M C00O 1.511(4) . ?
C00N H00N 0.9300 . ?
C00O H00D 0.9700 . ?
C00O H00E 0.9700 . ?
C00P H00F 0.9600 . ?
C00P H00G 0.9600 . ?
C00P H00M 0.9600 . ?
C00Q H00O 0.9600 . ?
C00Q H00P 0.9600 . ?
C00Q H00Q 0.9600 . ?
C00R H00R 0.9600 . ?
C00R H00S 0.9600 . ?
C00R H00T 0.9600 . ?
C00S H00U 0.9700 . ?
C00S H00V 0.9700 . ?
C00S C00T 1.541(4) . ?
C00T H00W 0.9700 . ?
C00T H00X 0.9700 . ?
C00T C00X 1.508(5) . ?
C00U H00Y 0.9700 . ?
C00U H 0.9700 . ?
C00U C00X 1.450(5) . ?
C00V H00Z 0.9600 . ?
C00V HA 0.9600 . ?
C00V HB 0.9600 . ?
C00W H00 0.9600 . ?
C00W HC 0.9600 . ?
C00W HD 0.9600 . ?
C00X H1 0.9700 . ?
C00X HE 0.9700 . ?
C1 H1A 0.9700 . ?
C1 H1B 0.9700 . ?
C1 C2 1.540(17) . ?
C2 H2A 0.9700 . ?
C2 H2B 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
C00H O002 C00U 111.3(2) . . ?
C00A N003 C00H 125.11(19) . . ?
C00A N003 C00J 105.01(19) . . ?
C00J N003 C00H 129.87(19) . . ?
C00C N004 H004 117.0 . . ?
C00C N004 C00F 126.01(18) . . ?
C00F N004 H004 117.0 . . ?
C00A N005 C00L 110.6(2) . . ?
C00J N006 C008 103.39(19) . . ?
C00L N007 C009 119.1(2) . . ?
N006 C008 C00A 109.93(19) . . ?
C009 C008 N006 132.9(2) . . ?
C009 C008 C00A 117.1(2) . . ?
N007 C009 C008 117.6(2) . . ?
N007 C009 C00E 117.9(2) . . ?
C008 C009 C00E 124.6(2) . . ?
N003 C00A C008 106.62(18) . . ?
N005 C00A N003 126.7(2) . . ?
N005 C00A C008 126.7(2) . . ?
C00D C00B H00B 118.8 . . ?
C00E C00B H00B 118.8 . . ?
C00E C00B C00D 122.4(2) . . ?
O001 C00C N004 124.0(2) . . ?
O001 C00C C00M 119.0(2) . . ?
O001 C00C C1 122.2(4) . . ?
N004 C00C C00M 116.73(19) . . ?
N004 C00C C1 105.1(4) . . ?
C00B C00D C00G 119.5(2) . . ?
C00I C00D C00B 117.2(2) . . ?
C00I C00D C00G 123.3(2) . . ?
C00B C00E C009 120.72(19) . . ?
C00B C00E C00K 118.5(2) . . ?
C00K C00E C009 120.8(2) . . ?
N004 C00F C00P 109.5(2) . . ?
N004 C00F C00R 110.6(2) . . ?
N004 C00F C00V 105.9(2) . . ?
C00P C00F C00V 108.4(3) . . ?
C00R C00F C00P 110.4(2) . . ?
C00R C00F C00V 112.0(3) . . ?
C00D C00G C00O 109.72(19) . . ?
C00Q C00G C00D 110.7(2) . . ?
C00Q C00G C00O 104.1(2) . . ?
C00Q C00G C2 135.2(6) . . ?
C00W C00G C00D 113.1(2) . . ?
C00W C00G C00O 111.6(2) . . ?
C00W C00G C00Q 107.2(2) . . ?
C00W C00G C2 85.2(5) . . ?
C2 C00G C00D 102.6(5) . . ?
O002 C00H N003 105.4(2) . . ?
O002 C00H H00H 108.5 . . ?
O002 C00H C00S 111.8(2) . . ?
N003 C00H H00H 108.5 . . ?
N003 C00H C00S 113.9(2) . . ?
C00S C00H H00H 108.5 . . ?
C00D C00I H00I 119.6 . . ?
C00N C00I C00D 120.8(3) . . ?
C00N C00I H00I 119.6 . . ?
N003 C00J H00J 122.5 . . ?
N006 C00J N003 115.0(2) . . ?
N006 C00J H00J 122.5 . . ?
C00E C00K H00K 120.1 . . ?
C00N C00K C00E 119.8(3) . . ?
C00N C00K H00K 120.1 . . ?
N005 C00L H00L 115.6 . . ?
N007 C00L N005 128.9(2) . . ?
N007 C00L H00L 115.6 . . ?
C00C C00M H00A 109.4 . . ?
C00C C00M H00C 109.4 . . ?
H00A C00M H00C 108.0 . . ?
C00O C00M C00C 111.3(2) . . ?
C00O C00M H00A 109.4 . . ?
C00O C00M H00C 109.4 . . ?
C00I C00N H00N 119.4 . . ?
C00K C00N C00I 121.3(3) . . ?
C00K C00N H00N 119.4 . . ?
C00G C00O H00D 109.0 . . ?
C00G C00O H00E 109.0 . . ?
C00M C00O C00G 113.1(3) . . ?
C00M C00O H00D 109.0 . . ?
C00M C00O H00E 109.0 . . ?
H00D C00O H00E 107.8 . . ?
C00F C00P H00F 109.5 . . ?
C00F C00P H00G 109.5 . . ?
C00F C00P H00M 109.5 . . ?
H00F C00P H00G 109.5 . . ?
H00F C00P H00M 109.5 . . ?
H00G C00P H00M 109.5 . . ?
C00G C00Q H00O 109.5 . . ?
C00G C00Q H00P 109.5 . . ?
C00G C00Q H00Q 109.5 . . ?
H00O C00Q H00P 109.5 . . ?
H00O C00Q H00Q 109.5 . . ?
H00P C00Q H00Q 109.5 . . ?
C00F C00R H00R 109.5 . . ?
C00F C00R H00S 109.5 . . ?
C00F C00R H00T 109.5 . . ?
H00R C00R H00S 109.5 . . ?
H00R C00R H00T 109.5 . . ?
H00S C00R H00T 109.5 . . ?
C00H C00S H00U 109.9 . . ?
C00H C00S H00V 109.9 . . ?
C00H C00S C00T 108.8(3) . . ?
H00U C00S H00V 108.3 . . ?
C00T C00S H00U 109.9 . . ?
C00T C00S H00V 109.9 . . ?
C00S C00T H00W 109.7 . . ?
C00S C00T H00X 109.7 . . ?
H00W C00T H00X 108.2 . . ?
C00X C00T C00S 109.7(3) . . ?
C00X C00T H00W 109.7 . . ?
C00X C00T H00X 109.7 . . ?
O002 C00U H00Y 109.1 . . ?
O002 C00U H 109.1 . . ?
O002 C00U C00X 112.7(3) . . ?
H00Y C00U H 107.8 . . ?
C00X C00U H00Y 109.1 . . ?
C00X C00U H 109.1 . . ?
C00F C00V H00Z 109.5 . . ?
C00F C00V HA 109.5 . . ?
C00F C00V HB 109.5 . . ?
H00Z C00V HA 109.5 . . ?
H00Z C00V HB 109.5 . . ?
HA C00V HB 109.5 . . ?
C00G C00W H00 109.5 . . ?
C00G C00W HC 109.5 . . ?
C00G C00W HD 109.5 . . ?
H00 C00W HC 109.5 . . ?
H00 C00W HD 109.5 . . ?
HC C00W HD 109.5 . . ?
C00T C00X H1 109.4 . . ?
C00T C00X HE 109.4 . . ?
C00U C00X C00T 111.0(3) . . ?
C00U C00X H1 109.4 . . ?
C00U C00X HE 109.4 . . ?
H1 C00X HE 108.0 . . ?
C00C C1 H1A 111.5 . . ?
C00C C1 H1B 111.5 . . ?
H1A C1 H1B 109.3 . . ?
C2 C1 C00C 101.2(8) . . ?
C2 C1 H1A 111.5 . . ?
C2 C1 H1B 111.5 . . ?
C00G C2 C1 111.0(9) . . ?
C00G C2 H2A 109.4 . . ?
C00G C2 H2B 109.4 . . ?
C1 C2 H2A 109.4 . . ?
C1 C2 H2B 109.4 . . ?
H2A C2 H2B 108.0 . . ?

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
O001 C00C C00M C00O -68.9(3) . . . . ?
O001 C00C C1 C2 59.6(10) . . . . ?
O002 C00H C00S C00T 57.9(3) . . . . ?
O002 C00U C00X C00T -55.1(5) . . . . ?
N003 C00H C00S C00T 177.2(2) . . . . ?
N004 C00C C00M C00O 117.1(3) . . . . ?
N004 C00C C1 C2 -151.6(7) . . . . ?
N006 C008 C009 N007 -179.8(2) . . . . ?
N006 C008 C009 C00E -0.1(4) . . . . ?
N006 C008 C00A N003 -1.0(3) . . . . ?
N006 C008 C00A N005 179.3(2) . . . . ?
N007 C009 C00E C00B -163.5(2) . . . . ?
N007 C009 C00E C00K 17.8(3) . . . . ?
C008 N006 C00J N003 -0.2(3) . . . . ?
C008 C009 C00E C00B 16.9(3) . . . . ?
C008 C009 C00E C00K -161.9(2) . . . . ?
C009 N007 C00L N005 0.1(4) . . . . ?
C009 C008 C00A N003 179.12(19) . . . . ?
C009 C008 C00A N005 -0.6(3) . . . . ?
C009 C00E C00K C00N 178.4(2) . . . . ?
C00A N003 C00H O002 -84.6(3) . . . . ?
C00A N003 C00H C00S 152.5(3) . . . . ?
C00A N003 C00J N006 -0.4(3) . . . . ?
C00A N005 C00L N007 -0.4(4) . . . . ?
C00A C008 C009 N007 0.1(3) . . . . ?
C00A C008 C009 C00E 179.77(18) . . . . ?
C00B C00D C00G C00O 60.9(3) . . . . ?
C00B C00D C00G C00Q -53.5(3) . . . . ?
C00B C00D C00G C00W -173.8(2) . . . . ?
C00B C00D C00G C2 96.1(6) . . . . ?
C00B C00D C00I C00N -0.4(3) . . . . ?
C00B C00E C00K C00N -0.4(3) . . . . ?
C00C N004 C00F C00P -53.9(3) . . . . ?
C00C N004 C00F C00R 68.0(3) . . . . ?
C00C N004 C00F C00V -170.5(3) . . . . ?
C00C C00M C00O C00G 169.2(2) . . . . ?
C00C C1 C2 C00G -178.4(7) . . . . ?
C00D C00B C00E C009 -179.16(18) . . . . ?
C00D C00B C00E C00K -0.3(3) . . . . ?
C00D C00G C00O C00M 49.2(3) . . . . ?
C00D C00G C2 C1 -76.1(10) . . . . ?
C00D C00I C00N C00K -0.4(4) . . . . ?
C00E C00B C00D C00G -177.95(19) . . . . ?
C00E C00B C00D C00I 0.8(3) . . . . ?
C00E C00K C00N C00I 0.8(4) . . . . ?
C00F N004 C00C O001 -2.5(4) . . . . ?
C00F N004 C00C C00M 171.2(2) . . . . ?
C00F N004 C00C C1 -150.6(5) . . . . ?
C00G C00D C00I C00N 178.2(2) . . . . ?
C00H O002 C00U C00X 58.1(4) . . . . ?
C00H N003 C00A N005 0.6(4) . . . . ?
C00H N003 C00A C008 -179.1(2) . . . . ?
C00H N003 C00J N006 179.5(2) . . . . ?
C00H C00S C00T C00X -53.9(4) . . . . ?
C00I C00D C00G C00O -117.8(3) . . . . ?
C00I C00D C00G C00Q 127.9(3) . . . . ?
C00I C00D C00G C00W 7.6(3) . . . . ?
C00I C00D C00G C2 -82.6(6) . . . . ?
C00J N003 C00A N005 -179.5(2) . . . . ?
C00J N003 C00A C008 0.8(2) . . . . ?
C00J N003 C00H O002 95.6(3) . . . . ?
C00J N003 C00H C00S -27.4(4) . . . . ?
C00J N006 C008 C009 -179.4(3) . . . . ?
C00J N006 C008 C00A 0.7(3) . . . . ?
C00L N005 C00A N003 -179.0(2) . . . . ?
C00L N005 C00A C008 0.7(3) . . . . ?
C00L N007 C009 C008 0.1(3) . . . . ?
C00L N007 C009 C00E -179.6(2) . . . . ?
C00Q C00G C00O C00M 167.7(2) . . . . ?
C00Q C00G C2 C1 61.6(12) . . . . ?
C00S C00T C00X C00U 53.0(4) . . . . ?
C00U O002 C00H N003 176.0(2) . . . . ?
C00U O002 C00H C00S -59.8(3) . . . . ?
C00W C00G C00O C00M -77.0(3) . . . . ?
C00W C00G C2 C1 171.3(9) . . . . ?

_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 2.047
_oxdiff_exptl_absorpt_empirical_full_min 0.636
####################################################################### 
# 
# 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_liuhch_0824_auto
_database_code_depnum_ccdc_archive 'CCDC 2105563'
loop_
_audit_author_name
_audit_author_address
'hong-chao liu'
;lanzhou uniiversity
China
;
_audit_update_record             
;
2021-08-26 deposited with the CCDC.	2022-04-12 downloaded from the CCDC.
;
_audit_creation_date             2021-08-24
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6032)
;
_shelx_SHELXL_version_number     2018/1
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C20 H26 Br N3 O'
_chemical_formula_sum            'C20 H26 Br N3 O'
_chemical_formula_weight         404.35
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.6763 1.2805 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      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_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   6.36816(5)
_cell_length_b                   31.0073(3)
_cell_length_c                   10.01092(9)
_cell_angle_alpha                90
_cell_angle_beta                 97.3165(8)
_cell_angle_gamma                90
_cell_volume                     1960.65(3)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    10668
_cell_measurement_temperature    149.99(10)
_cell_measurement_theta_max      76.1290
_cell_measurement_theta_min      4.6600
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    2.946
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.53016
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.41.105a (Rigaku Oxford Diffraction, 2021)
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    1.370
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             840
_exptl_crystal_size_max          0.09
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.03
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0243
_diffrn_reflns_av_unetI/netI     0.0222
_diffrn_reflns_Laue_measured_fraction_full 0.986
_diffrn_reflns_Laue_measured_fraction_max 0.948
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       37
_diffrn_reflns_limit_k_min       -38
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            12690
_diffrn_reflns_point_group_measured_fraction_full 0.986
_diffrn_reflns_point_group_measured_fraction_max 0.948
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         76.447
_diffrn_reflns_theta_min         4.676
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      149.99(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.986
_diffrn_measured_fraction_theta_max 0.948
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     54.00  79.00   0.50    0.05    --   46.32  61.00 -91.00   50
  2  ω    104.00 164.00   0.50    0.05    --  104.25  61.00-180.00  120
  3  ω     88.00 174.00   0.50    0.05    --  104.25  61.00 -91.00  172
  4  ω     97.00 152.00   0.50    0.05    --  104.25  45.00 -30.00  110
  5  ω     32.00 102.00   0.50    0.05    --  104.25 -77.00 -90.00  140
  6  ω     32.00  59.00   0.50    0.05    --  104.25 -61.00-150.00   54
  7  ω     40.00  73.00   0.50    0.05    --  104.25 -61.00 -30.00   66
  8  ω     32.00  57.00   0.50    0.05    --  104.25 -61.00 129.00   50
  9  ω    -25.00  48.00   0.50    0.05    --   46.32 -61.00 129.00  146
 10  ω    -63.00  25.00   0.50    0.05    --  -46.32  61.00 -91.00  176
 11  ω    -68.00 -32.00   0.50    0.05    -- -102.00  61.00-120.00   72
 12  ω    -63.00 -38.00   0.50    0.05    -- -102.00  61.00 -91.00   50
 13  ω    -68.00 -38.00   0.50    0.05    -- -102.00  61.00  30.00   60
 14  ω    -91.00 -30.00   0.50    0.05    -- -102.00 125.00 120.00  122
 15  ω     33.00 111.00   0.50    0.05    --  104.25-125.00 120.00  156
 16  ω   -154.00-129.00   0.50    0.05    -- -102.00 -61.00 129.00   50
 17  ω   -175.00-137.00   0.50    0.05    -- -102.00 -94.00  60.00   76
 18  ω   -129.00 -87.00   0.50    0.05    -- -102.00 -94.00  60.00   84
 19  ω   -106.00 -56.00   0.50    0.05    --  -46.32 -61.00 129.00  100
 20  ω    -84.00 -74.00   0.50    0.05    --  -46.32-125.00 -90.00   20
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy R, DW system, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.1724598000
_diffrn_orient_matrix_UB_12      -0.0338315000
_diffrn_orient_matrix_UB_13      0.0154983000
_diffrn_orient_matrix_UB_21      -0.0105282000
_diffrn_orient_matrix_UB_22      -0.0113671000
_diffrn_orient_matrix_UB_23      -0.1505002000
_diffrn_orient_matrix_UB_31      0.1721716000
_diffrn_orient_matrix_UB_32      -0.0345656000
_diffrn_orient_matrix_UB_33      0.0343199000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'Rigaku (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3729
_reflns_number_total             3894
_reflns_odcompleteness_completeness 98.44
_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.
 
 _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 1.171.41.105a (Rigaku OD, 2021)'
_computing_data_collection       'CrysAlisPro 1.171.41.105a (Rigaku OD, 2021)'
_computing_data_reduction        'CrysAlisPro 1.171.41.105a (Rigaku OD, 2021)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/1 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT  (Sheldrick, 2015)'
_refine_diff_density_max         0.318
_refine_diff_density_min         -0.352
_refine_diff_density_rms         0.052
_refine_ls_extinction_coef       0.00261(14)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/1 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.067
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     232
_refine_ls_number_reflns         3894
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0283
_refine_ls_R_factor_gt           0.0272
_refine_ls_restrained_S_all      1.067
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0261P)²+1.1912P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0656
_refine_ls_wR_factor_ref         0.0663
_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
2.a Secondary CH2 refined with riding coordinates:
 C14(H14A,H14B), C15(H15A,H15B)
2.b Aromatic/amide H refined with riding coordinates:
 N3(H3), C2(H2), C4(H4), C6(H6), C7(H7), C8(H8), C10(H10)
2.c Idealised Me refined as rotating group:
 C12(H12A,H12B,H12C), C13(H13A,H13B,H13C), C18(H18A,H18B,H18C), C19(H19A,H19B,
 H19C), C20(H20A,H20B,H20C)
;
_atom_sites_solution_hydrogens   geom
_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 -0.25472(3) 0.48498(2) 0.10377(2) 0.03008(9) Uani 1 1 d . . . . .
O1 O 0.5999(2) 0.25367(4) 1.08107(12) 0.0317(3) Uani 1 1 d . . . . .
N1 N 0.2497(2) 0.45675(5) 0.38902(13) 0.0215(3) Uani 1 1 d . . . . .
N2 N -0.0646(2) 0.44127(4) 0.48706(14) 0.0223(3) Uani 1 1 d . . . . .
N3 N 0.6582(2) 0.23015(5) 0.87544(14) 0.0275(3) Uani 1 1 d . . . . .
H3 H 0.633630 0.235069 0.788280 0.033 Uiso 1 1 calc R U . . .
C1 C 0.1468(2) 0.44297(5) 0.49036(16) 0.0182(3) Uani 1 1 d . . . . .
C2 C 0.1308(3) 0.46936(5) 0.27669(17) 0.0225(3) Uani 1 1 d . . . . .
H2 H 0.197938 0.479518 0.203258 0.027 Uiso 1 1 calc R U . . .
C3 C -0.0875(3) 0.46807(5) 0.26423(16) 0.0208(3) Uani 1 1 d . . . . .
C4 C -0.1810(3) 0.45370(6) 0.37338(16) 0.0232(3) Uani 1 1 d . . . . .
H4 H -0.331007 0.452668 0.367253 0.028 Uiso 1 1 calc R U . . .
C5 C 0.2767(2) 0.42870(5) 0.61619(15) 0.0180(3) Uani 1 1 d . . . . .
C6 C 0.4857(2) 0.44237(5) 0.64543(17) 0.0207(3) Uani 1 1 d . . . . .
H6 H 0.547061 0.460504 0.584433 0.025 Uiso 1 1 calc R U . . .
C7 C 0.6032(2) 0.42923(5) 0.76454(17) 0.0224(3) Uani 1 1 d . . . . .
H7 H 0.745894 0.438444 0.785268 0.027 Uiso 1 1 calc R U . . .
C8 C 0.5142(3) 0.40278(5) 0.85353(17) 0.0216(3) Uani 1 1 d . . . . .
H8 H 0.596613 0.394511 0.935344 0.026 Uiso 1 1 calc R U . . .
C9 C 0.3059(2) 0.38794(5) 0.82585(16) 0.0185(3) Uani 1 1 d . . . . .
C10 C 0.1888(2) 0.40162(5) 0.70638(16) 0.0185(3) Uani 1 1 d . . . . .
H10 H 0.046189 0.392376 0.685571 0.022 Uiso 1 1 calc R U . . .
C11 C 0.2108(3) 0.36013(5) 0.92990(17) 0.0218(3) Uani 1 1 d . . . . .
C12 C 0.0011(3) 0.33896(6) 0.8724(2) 0.0292(4) Uani 1 1 d . . . . .
H12A H -0.103641 0.361385 0.844053 0.044 Uiso 1 1 calc R U . . .
H12B H -0.050488 0.320906 0.941689 0.044 Uiso 1 1 calc R U . . .
H12C H 0.023280 0.321074 0.794732 0.044 Uiso 1 1 calc R U . . .
C13 C 0.1699(3) 0.39023(6) 1.04608(19) 0.0331(4) Uani 1 1 d . . . . .
H13A H 0.303481 0.403490 1.085049 0.050 Uiso 1 1 calc R U . . .
H13B H 0.110479 0.373540 1.115465 0.050 Uiso 1 1 calc R U . . .
H13C H 0.069688 0.412814 1.011689 0.050 Uiso 1 1 calc R U . . .
C14 C 0.3660(3) 0.32469(5) 0.98876(16) 0.0220(3) Uani 1 1 d . . . . .
H14A H 0.494372 0.338822 1.035339 0.026 Uiso 1 1 calc R U . . .
H14B H 0.299189 0.308506 1.057416 0.026 Uiso 1 1 calc R U . . .
C15 C 0.4341(3) 0.29263(5) 0.88765(16) 0.0224(3) Uani 1 1 d . . . . .
H15A H 0.513706 0.307961 0.823388 0.027 Uiso 1 1 calc R U . . .
H15B H 0.306913 0.279598 0.835944 0.027 Uiso 1 1 calc R U . . .
C16 C 0.5725(3) 0.25707(5) 0.95762(16) 0.0215(3) Uani 1 1 d . . . . .
C17 C 0.7918(3) 0.19258(6) 0.92137(18) 0.0301(4) Uani 1 1 d . . . . .
C18 C 0.8507(5) 0.17049(9) 0.7953(2) 0.0647(9) Uani 1 1 d . . . . .
H18A H 0.722552 0.159113 0.742409 0.097 Uiso 1 1 calc R U . . .
H18B H 0.949024 0.146746 0.821335 0.097 Uiso 1 1 calc R U . . .
H18C H 0.918342 0.191395 0.741034 0.097 Uiso 1 1 calc R U . . .
C19 C 0.9936(3) 0.20807(7) 1.0075(3) 0.0454(5) Uani 1 1 d . . . . .
H19A H 1.071334 0.227552 0.954374 0.068 Uiso 1 1 calc R U . . .
H19B H 1.082678 0.183191 1.036686 0.068 Uiso 1 1 calc R U . . .
H19C H 0.955808 0.223401 1.086706 0.068 Uiso 1 1 calc R U . . .
C20 C 0.6681(3) 0.16146(6) 0.9993(2) 0.0368(4) Uani 1 1 d . . . . .
H20A H 0.632192 0.175650 1.080855 0.055 Uiso 1 1 calc R U . . .
H20B H 0.754563 0.135877 1.024305 0.055 Uiso 1 1 calc R U . . .
H20C H 0.537767 0.152824 0.942795 0.055 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
Br1 C3 1.8851(16) . ?
O1 C16 1.230(2) . ?
N1 C1 1.345(2) . ?
N1 C2 1.332(2) . ?
N2 C1 1.344(2) . ?
N2 C4 1.333(2) . ?
N3 H3 0.8800 . ?
N3 C16 1.336(2) . ?
N3 C17 1.481(2) . ?
C1 C5 1.484(2) . ?
C2 H2 0.9500 . ?
C2 C3 1.380(2) . ?
C3 C4 1.383(2) . ?
C4 H4 0.9500 . ?
C5 C6 1.392(2) . ?
C5 C10 1.401(2) . ?
C6 H6 0.9500 . ?
C6 C7 1.386(2) . ?
C7 H7 0.9500 . ?
C7 C8 1.384(2) . ?
C8 H8 0.9500 . ?
C8 C9 1.398(2) . ?
C9 C10 1.392(2) . ?
C9 C11 1.535(2) . ?
C10 H10 0.9500 . ?
C11 C12 1.533(2) . ?
C11 C13 1.539(2) . ?
C11 C14 1.544(2) . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12C 0.9800 . ?
C13 H13A 0.9800 . ?
C13 H13B 0.9800 . ?
C13 H13C 0.9800 . ?
C14 H14A 0.9900 . ?
C14 H14B 0.9900 . ?
C14 C15 1.521(2) . ?
C15 H15A 0.9900 . ?
C15 H15B 0.9900 . ?
C15 C16 1.525(2) . ?
C17 C18 1.524(3) . ?
C17 C19 1.531(3) . ?
C17 C20 1.522(3) . ?
C18 H18A 0.9800 . ?
C18 H18B 0.9800 . ?
C18 H18C 0.9800 . ?
C19 H19A 0.9800 . ?
C19 H19B 0.9800 . ?
C19 H19C 0.9800 . ?
C20 H20A 0.9800 . ?
C20 H20B 0.9800 . ?
C20 H20C 0.9800 . ?

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 N1 C1 116.78(14) . . ?
C4 N2 C1 117.12(14) . . ?
C16 N3 H3 117.8 . . ?
C16 N3 C17 124.32(14) . . ?
C17 N3 H3 117.8 . . ?
N1 C1 C5 117.55(13) . . ?
N2 C1 N1 125.22(14) . . ?
N2 C1 C5 117.23(13) . . ?
N1 C2 H2 119.1 . . ?
N1 C2 C3 121.71(15) . . ?
C3 C2 H2 119.1 . . ?
C2 C3 Br1 121.47(12) . . ?
C2 C3 C4 117.90(15) . . ?
C4 C3 Br1 120.63(12) . . ?
N2 C4 C3 121.26(15) . . ?
N2 C4 H4 119.4 . . ?
C3 C4 H4 119.4 . . ?
C6 C5 C1 120.15(14) . . ?
C6 C5 C10 119.78(14) . . ?
C10 C5 C1 120.07(14) . . ?
C5 C6 H6 120.4 . . ?
C7 C6 C5 119.24(15) . . ?
C7 C6 H6 120.4 . . ?
C6 C7 H7 119.8 . . ?
C8 C7 C6 120.50(15) . . ?
C8 C7 H7 119.8 . . ?
C7 C8 H8 119.2 . . ?
C7 C8 C9 121.56(15) . . ?
C9 C8 H8 119.2 . . ?
C8 C9 C11 119.77(14) . . ?
C10 C9 C8 117.42(14) . . ?
C10 C9 C11 122.69(14) . . ?
C5 C10 H10 119.3 . . ?
C9 C10 C5 121.49(14) . . ?
C9 C10 H10 119.3 . . ?
C9 C11 C13 106.95(13) . . ?
C9 C11 C14 111.74(13) . . ?
C12 C11 C9 112.68(14) . . ?
C12 C11 C13 108.66(15) . . ?
C12 C11 C14 108.88(14) . . ?
C13 C11 C14 107.76(14) . . ?
C11 C12 H12A 109.5 . . ?
C11 C12 H12B 109.5 . . ?
C11 C12 H12C 109.5 . . ?
H12A C12 H12B 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C11 C13 H13A 109.5 . . ?
C11 C13 H13B 109.5 . . ?
C11 C13 H13C 109.5 . . ?
H13A C13 H13B 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
C11 C14 H14A 108.3 . . ?
C11 C14 H14B 108.3 . . ?
H14A C14 H14B 107.4 . . ?
C15 C14 C11 115.73(13) . . ?
C15 C14 H14A 108.3 . . ?
C15 C14 H14B 108.3 . . ?
C14 C15 H15A 109.4 . . ?
C14 C15 H15B 109.4 . . ?
C14 C15 C16 111.34(13) . . ?
H15A C15 H15B 108.0 . . ?
C16 C15 H15A 109.4 . . ?
C16 C15 H15B 109.4 . . ?
O1 C16 N3 123.23(15) . . ?
O1 C16 C15 121.53(14) . . ?
N3 C16 C15 115.24(14) . . ?
N3 C17 C18 106.78(15) . . ?
N3 C17 C19 109.63(16) . . ?
N3 C17 C20 110.07(15) . . ?
C18 C17 C19 109.3(2) . . ?
C20 C17 C18 109.7(2) . . ?
C20 C17 C19 111.25(16) . . ?
C17 C18 H18A 109.5 . . ?
C17 C18 H18B 109.5 . . ?
C17 C18 H18C 109.5 . . ?
H18A C18 H18B 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
C17 C19 H19A 109.5 . . ?
C17 C19 H19B 109.5 . . ?
C17 C19 H19C 109.5 . . ?
H19A C19 H19B 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
C17 C20 H20A 109.5 . . ?
C17 C20 H20B 109.5 . . ?
C17 C20 H20C 109.5 . . ?
H20A C20 H20B 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 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
Br1 C3 C4 N2 179.39(12) . . . . ?
N1 C1 C5 C6 21.2(2) . . . . ?
N1 C1 C5 C10 -159.23(14) . . . . ?
N1 C2 C3 Br1 -178.82(12) . . . . ?
N1 C2 C3 C4 0.9(2) . . . . ?
N2 C1 C5 C6 -158.54(15) . . . . ?
N2 C1 C5 C10 21.1(2) . . . . ?
C1 N1 C2 C3 -0.5(2) . . . . ?
C1 N2 C4 C3 -0.6(2) . . . . ?
C1 C5 C6 C7 178.96(14) . . . . ?
C1 C5 C10 C9 -179.45(14) . . . . ?
C2 N1 C1 N2 -0.4(2) . . . . ?
C2 N1 C1 C5 179.87(14) . . . . ?
C2 C3 C4 N2 -0.3(2) . . . . ?
C4 N2 C1 N1 1.0(2) . . . . ?
C4 N2 C1 C5 -179.33(14) . . . . ?
C5 C6 C7 C8 0.1(2) . . . . ?
C6 C5 C10 C9 0.1(2) . . . . ?
C6 C7 C8 C9 1.0(2) . . . . ?
C7 C8 C9 C10 -1.5(2) . . . . ?
C7 C8 C9 C11 -177.60(15) . . . . ?
C8 C9 C10 C5 0.9(2) . . . . ?
C8 C9 C11 C12 -167.92(14) . . . . ?
C8 C9 C11 C13 72.74(18) . . . . ?
C8 C9 C11 C14 -45.0(2) . . . . ?
C9 C11 C14 C15 -60.22(19) . . . . ?
C10 C5 C6 C7 -0.6(2) . . . . ?
C10 C9 C11 C12 16.2(2) . . . . ?
C10 C9 C11 C13 -103.16(18) . . . . ?
C10 C9 C11 C14 139.14(15) . . . . ?
C11 C9 C10 C5 176.89(14) . . . . ?
C11 C14 C15 C16 -175.41(14) . . . . ?
C12 C11 C14 C15 64.89(18) . . . . ?
C13 C11 C14 C15 -177.43(15) . . . . ?
C14 C15 C16 O1 7.6(2) . . . . ?
C14 C15 C16 N3 -173.04(15) . . . . ?
C16 N3 C17 C18 178.7(2) . . . . ?
C16 N3 C17 C19 -63.0(2) . . . . ?
C16 N3 C17 C20 59.7(2) . . . . ?
C17 N3 C16 O1 1.4(3) . . . . ?
C17 N3 C16 C15 -177.92(16) . . . . ?

_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 1.687
_oxdiff_exptl_absorpt_empirical_full_min 0.567
####################################################################### 
# 
# 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_liuhongchao_0830-1_auto
_database_code_depnum_ccdc_archive 'CCDC 2106363'
loop_
_audit_author_name
_audit_author_address
liuhch
;lanzhou university
China
;
_audit_update_record             
;
2021-08-30 deposited with the CCDC.	2022-04-12 downloaded from the CCDC.
;
_audit_creation_date             2021-08-30
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6032)
;
_shelx_SHELXL_version_number     2018/1
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C22 H30 N2 O2'
_chemical_formula_sum            'C22 H30 N2 O2'
_chemical_formula_weight         354.48
_chemical_melting_point          ?
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/c 1'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   19.4831(8)
_cell_length_b                   10.8800(4)
_cell_length_c                   9.8987(3)
_cell_angle_alpha                90
_cell_angle_beta                 99.028(3)
_cell_angle_gamma                90
_cell_volume                     2072.29(13)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    5882
_cell_measurement_temperature    302.58(10)
_cell_measurement_theta_max      73.8040
_cell_measurement_theta_min      2.3050
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.570
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.68015
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.41.105a (Rigaku Oxford Diffraction, 2021)
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    1.136
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             768
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.07
_exptl_crystal_size_min          0.05
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  ?
_diffrn_reflns_av_unetI/netI     0.0834
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.955
_diffrn_reflns_limit_h_max       24
_diffrn_reflns_limit_h_min       -24
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_number            15890
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.955
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         76.210
_diffrn_reflns_theta_min         2.296
_diffrn_ambient_environment      air
_diffrn_ambient_temperature      302.58(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.955
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     39.00  71.00   0.50    1.20    --  104.25 -61.00  30.00   64
  2  ω     93.00 168.00   0.50    1.20    --  104.25  45.00 -90.00  150
  3  ω    101.00 165.00   0.50    1.20    --  104.25  45.00-150.00  128
  4  ω    -24.00  26.00   0.50    0.50    --   46.32 -19.00-180.00  100
  5  ω     40.00  65.00   0.50    1.20    --  104.25 -77.00-180.00   50
  6  ω     70.00 106.00   0.50    1.20    --  104.25 -77.00-180.00   72
  7  ω     29.00  63.00   0.50    0.50    --   46.32-137.00-147.00   68
  8  ω     32.00 115.00   0.50    1.20    --  104.25-131.00  28.00  166
  9  ω     37.00 111.00   0.50    1.20    --  104.25-125.00  60.00  148
 10  ω     41.00  88.00   0.50    1.20    --  104.25 -94.00  90.00   94
 11  ω     25.00  96.00   0.50    0.50    --   46.32-131.00  28.00  142
 12  ω     52.00  77.00   0.50    1.20    --  104.25-137.00-147.00   50
 13  ω    -25.00  28.00   0.50    0.50    --  -46.32  19.00-120.00  106
 14  ω    -85.00 -60.00   0.50    0.50    --  -46.32 137.00 -85.00   50
 15  ω    -69.00 -31.00   0.50    1.20    -- -102.00  61.00-150.00   76
 16  ω    -81.00 -56.00   0.50    0.50    --  -46.32 131.00  98.00   50
 17  ω   -113.00 -37.00   0.50    1.20    -- -102.00 131.00  98.00  152
 18  ω    -55.00 -30.00   0.50    1.20    -- -102.00  61.00  30.00   50
 19  ω   -127.00 -86.00   0.50    1.20    -- -102.00 -61.00 -60.00   82
 20  ω   -115.00 -90.00   0.50    0.50    --  -46.32-125.00 -90.00   50
 21  ω   -114.00 -88.00   0.50    0.50    --  -46.32-137.00-147.00   52
 22  ω   -100.00 -74.00   0.50    0.50    --  -46.32-131.00  28.00   52
 23  ω   -118.00 -75.00   0.50    0.50    --  -46.32-125.00  60.00   86
 24  ω   -119.00 -74.00   0.50    0.50    --  -46.32-125.00 150.00   90
 25  ω   -173.00-140.00   0.50    1.20    -- -102.00 -61.00 -60.00   66
 26  ω   -147.00-122.00   0.50    1.20    -- -102.00-131.00  28.00   50
 27  ω   -101.00 -68.00   0.50    1.20    -- -102.00-137.00-147.00   66
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy R, DW system, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0712729000
_diffrn_orient_matrix_UB_12      -0.0644394000
_diffrn_orient_matrix_UB_13      -0.0247382000
_diffrn_orient_matrix_UB_21      0.0364326000
_diffrn_orient_matrix_UB_22      -0.1260290000
_diffrn_orient_matrix_UB_23      0.0168213000
_diffrn_orient_matrix_UB_31      -0.0025268000
_diffrn_orient_matrix_UB_32      0.0033556000
_diffrn_orient_matrix_UB_33      0.1546971000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'Rigaku (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                11742
_reflns_number_total             15890
_reflns_odcompleteness_completeness 99.97
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_reflns_special_details          
;
 _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 1.171.41.105a (Rigaku OD, 2021)'
_computing_data_collection       'CrysAlisPro 1.171.41.105a (Rigaku OD, 2021)'
_computing_data_reduction        'CrysAlisPro 1.171.41.105a (Rigaku OD, 2021)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/1 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT  (Sheldrick, 2015)'
_refine_diff_density_max         0.312
_refine_diff_density_min         -0.249
_refine_diff_density_rms         0.057
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.085
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     242
_refine_ls_number_reflns         15890
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0976
_refine_ls_R_factor_gt           0.0771
_refine_ls_restrained_S_all      1.085
_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)+(0.1262P)²+0.6353P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2360
_refine_ls_wR_factor_ref         0.2523
_refine_special_details          
;
 Refined as a 2-component twin.
;
_olex2_refinement_description    
;
1. Twinned data refinement
 Scales: 0.768(6)
 0.232(6)
2. 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
3.a Secondary CH2 refined with riding coordinates:
 C17(H17A,H17B), C18(H18A,H18B)
3.b Aromatic/amide H refined with riding coordinates:
 N3(H3), C2(H2), C3(H3A), C4(H4), C5(H5), C8(H8), C10(H10), C12(H12)
3.c Idealised Me refined as rotating group:
 C13(H13A,H13B,H13C), C15(H15A,H15B,H15C), C16(H16A,H16B,H16C), C20(H20A,H20B,
 H20C), C22(H22A,H22B,H22C), C23(H23A,H23B,H23C)
;
_atom_sites_solution_hydrogens   geom
_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
O1 O 0.29314(16) 0.5802(3) 0.3521(2) 0.0819(9) Uani 1 1 d . . . . .
O2 O 0.15089(15) 0.7430(2) 0.5959(2) 0.0756(8) Uani 1 1 d . . . . .
N3 N 0.12000(14) 0.7997(2) 0.7957(2) 0.0511(7) Uani 1 1 d . . . . .
H3 H 0.126377 0.785396 0.882177 0.061 Uiso 1 1 calc R U . . .
C1 C 0.44829(17) 0.2661(3) 0.5940(3) 0.0553(8) Uani 1 1 d . . . . .
C2 C 0.5050(2) 0.2945(4) 0.5316(5) 0.0828(12) Uani 1 1 d . . . . .
H2 H 0.505724 0.366093 0.480410 0.099 Uiso 1 1 calc R U . . .
C3 C 0.5615(3) 0.2123(6) 0.5474(6) 0.1085(17) Uani 1 1 d . . . . .
H3A H 0.600062 0.228314 0.505611 0.130 Uiso 1 1 calc R U . . .
C4 C 0.5591(3) 0.1090(5) 0.6247(6) 0.1018(15) Uani 1 1 d . . . . .
H4 H 0.596199 0.054102 0.638116 0.122 Uiso 1 1 calc R U . . .
C5 C 0.5019(3) 0.0890(5) 0.6806(5) 0.1004(15) Uani 1 1 d . . . . .
H5 H 0.500391 0.017874 0.732154 0.120 Uiso 1 1 calc R U . . .
N6 N 0.44687(19) 0.1634(3) 0.6680(4) 0.0820(10) Uani 1 1 d . . . . .
C7 C 0.38708(16) 0.3484(3) 0.5814(3) 0.0497(7) Uani 1 1 d . . . . .
C8 C 0.37132(18) 0.4267(3) 0.4685(3) 0.0562(8) Uani 1 1 d . . . . .
H8 H 0.399869 0.429013 0.401552 0.067 Uiso 1 1 calc R U . . .
C9 C 0.31318(19) 0.5003(3) 0.4575(3) 0.0564(8) Uani 1 1 d . . . . .
C10 C 0.26978(18) 0.4972(3) 0.5555(3) 0.0542(8) Uani 1 1 d . . . . .
H10 H 0.230977 0.548099 0.546390 0.065 Uiso 1 1 calc R U . . .
C11 C 0.28351(16) 0.4189(2) 0.6673(3) 0.0457(7) Uani 1 1 d . . . . .
C12 C 0.34278(16) 0.3450(3) 0.6778(3) 0.0488(7) Uani 1 1 d . . . . .
H12 H 0.352790 0.291928 0.751926 0.059 Uiso 1 1 calc R U . . .
C13 C 0.3267(3) 0.5739(5) 0.2355(4) 0.0936(14) Uani 1 1 d . . . . .
H13A H 0.301841 0.623333 0.163604 0.140 Uiso 1 1 calc R U . . .
H13B H 0.327622 0.490148 0.205339 0.140 Uiso 1 1 calc R U . . .
H13C H 0.373403 0.603967 0.258354 0.140 Uiso 1 1 calc R U . . .
C14 C 0.23325(17) 0.4061(3) 0.7721(3) 0.0513(7) Uani 1 1 d . . . . .
C15 C 0.2728(2) 0.4051(4) 0.9174(3) 0.0689(10) Uani 1 1 d . . . . .
H15A H 0.302970 0.334872 0.929509 0.103 Uiso 1 1 calc R U . . .
H15B H 0.240372 0.400840 0.981011 0.103 Uiso 1 1 calc R U . . .
H15C H 0.299889 0.478789 0.933393 0.103 Uiso 1 1 calc R U . . .
C16 C 0.1948(2) 0.2835(3) 0.7430(5) 0.0825(12) Uani 1 1 d . . . . .
H16A H 0.168522 0.285032 0.652432 0.124 Uiso 1 1 calc R U . . .
H16B H 0.163928 0.271241 0.808405 0.124 Uiso 1 1 calc R U . . .
H16C H 0.227917 0.217581 0.749868 0.124 Uiso 1 1 calc R U . . .
C17 C 0.17827(16) 0.5085(3) 0.7581(3) 0.0519(8) Uani 1 1 d . . . . .
H17A H 0.154454 0.509050 0.664407 0.062 Uiso 1 1 calc R U . . .
H17B H 0.144170 0.487956 0.816151 0.062 Uiso 1 1 calc R U . . .
C18 C 0.20502(17) 0.6386(3) 0.7945(3) 0.0510(7) Uani 1 1 d . . . . .
H18A H 0.208759 0.651191 0.892390 0.061 Uiso 1 1 calc R U . . .
H18B H 0.250913 0.648378 0.769574 0.061 Uiso 1 1 calc R U . . .
C19 C 0.15649(17) 0.7326(3) 0.7203(3) 0.0482(7) Uani 1 1 d . . . . .
C20 C 0.0102(3) 0.8418(5) 0.6447(6) 0.1043(16) Uani 1 1 d . . . . .
H20A H 0.028025 0.807285 0.567887 0.156 Uiso 1 1 calc R U . . .
H20B H -0.022542 0.905546 0.613547 0.156 Uiso 1 1 calc R U . . .
H20C H -0.012392 0.778760 0.689294 0.156 Uiso 1 1 calc R U . . .
C21 C 0.06993(19) 0.8956(3) 0.7450(3) 0.0577(9) Uani 1 1 d . . . . .
C22 C 0.1050(3) 0.9946(4) 0.6737(6) 0.1052(16) Uani 1 1 d . . . . .
H22A H 0.140794 1.032618 0.737932 0.158 Uiso 1 1 calc R U . . .
H22B H 0.071390 1.055270 0.637373 0.158 Uiso 1 1 calc R U . . .
H22C H 0.125266 0.958746 0.600554 0.158 Uiso 1 1 calc R U . . .
C23 C 0.0425(4) 0.9481(7) 0.8674(5) 0.143(3) Uani 1 1 d . . . . .
H23A H 0.021016 0.883914 0.912489 0.215 Uiso 1 1 calc R U . . .
H23B H 0.008905 1.010861 0.837626 0.215 Uiso 1 1 calc R U . . .
H23C H 0.080238 0.982862 0.929710 0.215 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 C9 1.368(4) . ?
O1 C13 1.415(5) . ?
O2 C19 1.224(3) . ?
N3 H3 0.8600 . ?
N3 C19 1.327(4) . ?
N3 C21 1.463(4) . ?
C1 C2 1.383(5) . ?
C1 N6 1.338(5) . ?
C1 C7 1.481(5) . ?
C2 H2 0.9300 . ?
C2 C3 1.408(7) . ?
C3 H3A 0.9300 . ?
C3 C4 1.365(7) . ?
C4 H4 0.9300 . ?
C4 C5 1.338(7) . ?
C5 H5 0.9300 . ?
C5 N6 1.333(5) . ?
C7 C8 1.400(4) . ?
C7 C12 1.384(4) . ?
C8 H8 0.9300 . ?
C8 C9 1.377(5) . ?
C9 C10 1.384(5) . ?
C10 H10 0.9300 . ?
C10 C11 1.389(4) . ?
C11 C12 1.397(4) . ?
C11 C14 1.540(4) . ?
C12 H12 0.9300 . ?
C13 H13A 0.9600 . ?
C13 H13B 0.9600 . ?
C13 H13C 0.9600 . ?
C14 C15 1.522(5) . ?
C14 C16 1.535(5) . ?
C14 C17 1.536(4) . ?
C15 H15A 0.9600 . ?
C15 H15B 0.9600 . ?
C15 H15C 0.9600 . ?
C16 H16A 0.9600 . ?
C16 H16B 0.9600 . ?
C16 H16C 0.9600 . ?
C17 H17A 0.9700 . ?
C17 H17B 0.9700 . ?
C17 C18 1.532(4) . ?
C18 H18A 0.9700 . ?
C18 H18B 0.9700 . ?
C18 C19 1.504(4) . ?
C20 H20A 0.9600 . ?
C20 H20B 0.9600 . ?
C20 H20C 0.9600 . ?
C20 C21 1.523(6) . ?
C21 C22 1.509(6) . ?
C21 C23 1.510(5) . ?
C22 H22A 0.9600 . ?
C22 H22B 0.9600 . ?
C22 H22C 0.9600 . ?
C23 H23A 0.9600 . ?
C23 H23B 0.9600 . ?
C23 H23C 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
C9 O1 C13 118.6(3) . . ?
C19 N3 H3 117.0 . . ?
C19 N3 C21 126.0(2) . . ?
C21 N3 H3 117.0 . . ?
C2 C1 C7 121.0(3) . . ?
N6 C1 C2 121.2(3) . . ?
N6 C1 C7 117.8(3) . . ?
C1 C2 H2 120.9 . . ?
C1 C2 C3 118.2(4) . . ?
C3 C2 H2 120.9 . . ?
C2 C3 H3A 120.3 . . ?
C4 C3 C2 119.5(4) . . ?
C4 C3 H3A 120.3 . . ?
C3 C4 H4 121.0 . . ?
C5 C4 C3 117.9(4) . . ?
C5 C4 H4 121.0 . . ?
C4 C5 H5 117.5 . . ?
N6 C5 C4 125.0(5) . . ?
N6 C5 H5 117.5 . . ?
C5 N6 C1 118.2(4) . . ?
C8 C7 C1 120.5(3) . . ?
C12 C7 C1 120.4(3) . . ?
C12 C7 C8 119.0(3) . . ?
C7 C8 H8 120.3 . . ?
C9 C8 C7 119.4(3) . . ?
C9 C8 H8 120.3 . . ?
O1 C9 C8 124.3(3) . . ?
O1 C9 C10 114.7(3) . . ?
C8 C9 C10 121.0(3) . . ?
C9 C10 H10 119.6 . . ?
C9 C10 C11 120.7(3) . . ?
C11 C10 H10 119.6 . . ?
C10 C11 C12 117.7(3) . . ?
C10 C11 C14 121.9(3) . . ?
C12 C11 C14 120.2(3) . . ?
C7 C12 C11 122.1(3) . . ?
C7 C12 H12 119.0 . . ?
C11 C12 H12 119.0 . . ?
O1 C13 H13A 109.5 . . ?
O1 C13 H13B 109.5 . . ?
O1 C13 H13C 109.5 . . ?
H13A C13 H13B 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
C15 C14 C11 110.9(3) . . ?
C15 C14 C16 109.3(3) . . ?
C15 C14 C17 109.4(2) . . ?
C16 C14 C11 107.2(2) . . ?
C16 C14 C17 107.5(3) . . ?
C17 C14 C11 112.5(2) . . ?
C14 C15 H15A 109.5 . . ?
C14 C15 H15B 109.5 . . ?
C14 C15 H15C 109.5 . . ?
H15A C15 H15B 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
C14 C16 H16A 109.5 . . ?
C14 C16 H16B 109.5 . . ?
C14 C16 H16C 109.5 . . ?
H16A C16 H16B 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
C14 C17 H17A 108.2 . . ?
C14 C17 H17B 108.2 . . ?
H17A C17 H17B 107.4 . . ?
C18 C17 C14 116.2(3) . . ?
C18 C17 H17A 108.2 . . ?
C18 C17 H17B 108.2 . . ?
C17 C18 H18A 109.6 . . ?
C17 C18 H18B 109.6 . . ?
H18A C18 H18B 108.1 . . ?
C19 C18 C17 110.4(3) . . ?
C19 C18 H18A 109.6 . . ?
C19 C18 H18B 109.6 . . ?
O2 C19 N3 122.9(3) . . ?
O2 C19 C18 120.3(3) . . ?
N3 C19 C18 116.8(2) . . ?
H20A C20 H20B 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
C21 C20 H20A 109.5 . . ?
C21 C20 H20B 109.5 . . ?
C21 C20 H20C 109.5 . . ?
N3 C21 C20 110.4(3) . . ?
N3 C21 C22 110.0(3) . . ?
N3 C21 C23 107.2(3) . . ?
C22 C21 C20 109.0(4) . . ?
C22 C21 C23 110.4(4) . . ?
C23 C21 C20 109.8(5) . . ?
C21 C22 H22A 109.5 . . ?
C21 C22 H22B 109.5 . . ?
C21 C22 H22C 109.5 . . ?
H22A C22 H22B 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
C21 C23 H23A 109.5 . . ?
C21 C23 H23B 109.5 . . ?
C21 C23 H23C 109.5 . . ?
H23A C23 H23B 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 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
O1 C9 C10 C11 179.2(3) . . . . ?
C1 C2 C3 C4 -0.9(8) . . . . ?
C1 C7 C8 C9 178.5(3) . . . . ?
C1 C7 C12 C11 -178.2(3) . . . . ?
C2 C1 N6 C5 0.3(6) . . . . ?
C2 C1 C7 C8 25.7(5) . . . . ?
C2 C1 C7 C12 -157.3(3) . . . . ?
C2 C3 C4 C5 1.2(9) . . . . ?
C3 C4 C5 N6 -0.8(9) . . . . ?
C4 C5 N6 C1 0.0(8) . . . . ?
N6 C1 C2 C3 0.1(6) . . . . ?
N6 C1 C7 C8 -154.3(3) . . . . ?
N6 C1 C7 C12 22.7(4) . . . . ?
C7 C1 C2 C3 -179.9(4) . . . . ?
C7 C1 N6 C5 -179.6(4) . . . . ?
C7 C8 C9 O1 179.7(3) . . . . ?
C7 C8 C9 C10 -0.6(5) . . . . ?
C8 C7 C12 C11 -1.2(4) . . . . ?
C8 C9 C10 C11 -0.5(5) . . . . ?
C9 C10 C11 C12 0.7(4) . . . . ?
C9 C10 C11 C14 -175.2(3) . . . . ?
C10 C11 C12 C7 0.1(4) . . . . ?
C10 C11 C14 C15 -136.5(3) . . . . ?
C10 C11 C14 C16 104.3(3) . . . . ?
C10 C11 C14 C17 -13.6(4) . . . . ?
C11 C14 C17 C18 -67.1(3) . . . . ?
C12 C7 C8 C9 1.4(4) . . . . ?
C12 C11 C14 C15 47.7(4) . . . . ?
C12 C11 C14 C16 -71.6(4) . . . . ?
C12 C11 C14 C17 170.5(3) . . . . ?
C13 O1 C9 C8 10.9(5) . . . . ?
C13 O1 C9 C10 -168.7(4) . . . . ?
C14 C11 C12 C7 176.1(3) . . . . ?
C14 C17 C18 C19 154.5(3) . . . . ?
C15 C14 C17 C18 56.6(4) . . . . ?
C16 C14 C17 C18 175.2(3) . . . . ?
C17 C18 C19 O2 -68.2(4) . . . . ?
C17 C18 C19 N3 110.3(3) . . . . ?
C19 N3 C21 C20 61.5(5) . . . . ?
C19 N3 C21 C22 -58.8(4) . . . . ?
C19 N3 C21 C23 -178.9(5) . . . . ?
C21 N3 C19 O2 -1.4(5) . . . . ?
C21 N3 C19 C18 -179.9(3) . . . . ?

_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 2.311
_oxdiff_exptl_absorpt_empirical_full_min 0.350
loop_
_twin_individual_id
_twin_individual_mass_fraction_refined
1 0.768(6)
2 0.232(6)

