# Electronic Supplementary Material (ESI) for Chemical Science.
# This journal is © The Royal Society of Chemistry 2020

####################################################################### 
# 
# 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_rs4
_database_code_depnum_ccdc_archive 'CCDC 1944266'
loop_
_audit_author_name
_audit_author_address
'Guy Clarkson'
;University of Warwick
United Kingdom
;
_audit_update_record             
;
2019-07-30 deposited with the CCDC.	2019-12-26 downloaded from the CCDC.
;
_audit_creation_date             2018-04-06
_audit_creation_method           
;
Olex2 1.2
(compiled 2017.08.10 svn.r3458 for OlexSys, GUI svn.r5381)
;
_shelx_SHELXL_version_number     2018/3
__publ_contact_author_name       'Professor Michael Shipman'
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C23 H24 N2 O5 S'
_chemical_formula_sum            'C23 H24 N2 O5 S'
_chemical_formula_weight         440.50
_chemical_absolute_configuration ad
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C20 H20 N2 O2 S'
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'
S S 0.3331 0.5567 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      orthorhombic
_space_group_IT_number           18
_space_group_name_H-M_alt        'P 21 21 2'
_space_group_name_Hall           'P 2 2ab'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, z'
'-x+1/2, y+1/2, -z'
'x+1/2, -y+1/2, -z'

_cell_length_a                   30.4605(6)
_cell_length_b                   11.6596(2)
_cell_length_c                   6.11590(10)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2172.11(7)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    10459
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      73.0630
_cell_measurement_theta_min      4.0070
_shelx_estimated_absorpt_T_max   0.984
_shelx_estimated_absorpt_T_min   0.684
_exptl_absorpt_coefficient_mu    1.643
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.63206
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.46 (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.347
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             928
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.02
_exptl_crystal_size_min          0.01
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0524
_diffrn_reflns_av_unetI/netI     0.0377
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       37
_diffrn_reflns_limit_h_min       -37
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       6
_diffrn_reflns_limit_l_min       -7
_diffrn_reflns_number            21406
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         73.432
_diffrn_reflns_theta_min         2.901
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      150(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.3046
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω   -112.00 -15.00   1.00    2.50    --  -41.80 -57.00-150.00   97
  2  ω    -68.00  28.00   1.00    2.50    --  -41.80  57.00-180.00   96
  3  ω      1.00  82.00   1.00    2.50    --   41.80 -99.00  90.00   81
  4  ω     32.00 137.00   1.00   25.00    --  106.00 -77.00-180.00  105
  5  ω     82.00 177.00   1.00   25.00    --  106.00  45.00 150.00   95
  6  ω     34.00 121.00   1.00   25.00    --  106.00-125.00-180.00   87
  7  ω     25.00 109.00   1.00   25.00    --  106.00 -94.00-180.00   84
  8  ω     82.00 177.00   1.00   25.00    --  106.00  45.00 -90.00   95
  9  ω     31.00 130.00   1.00   25.00    --  106.00 -30.00 150.00   99
 10  ω   -112.00 -15.00   1.00    2.50    --  -41.80 -57.00 120.00   97
 11  ω   -116.00 -10.00   1.00    2.50    --  -41.80 -77.00  60.00  106
 12  ω     36.00 134.00   1.00   25.00    --  106.00 -61.00 -60.00   98
 13  ω     78.00 176.00   1.00   25.00    --  106.00  61.00-150.00   98
 14  ω     82.00 177.00   1.00   25.00    --  106.00  45.00  90.00   95
 15  ω     78.00 176.00   1.00   25.00    --  106.00  61.00  30.00   98
 16  ω     78.00 109.00   1.00   25.00    --  106.00  61.00 -60.00   31
 17  ω     82.00 171.00   1.00   25.00    --  106.00  30.00   0.00   89
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, AtlasS2'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0504117000
_diffrn_orient_matrix_UB_12      -0.0093220000
_diffrn_orient_matrix_UB_13      -0.0115894000
_diffrn_orient_matrix_UB_21      -0.0039409000
_diffrn_orient_matrix_UB_22      0.1294558000
_diffrn_orient_matrix_UB_23      0.0468306000
_diffrn_orient_matrix_UB_31      0.0015990000
_diffrn_orient_matrix_UB_32      0.0249301000
_diffrn_orient_matrix_UB_33      -0.2470887000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\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         0.711
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     0.986
_reflns_number_gt                4140
_reflns_number_total             4351
_reflns_odcompleteness_completeness 99.92
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     71.98
_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 1.171.38.46 (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.238
_refine_diff_density_min         -0.272
_refine_diff_density_rms         0.040
_refine_ls_abs_structure_details 
;
 Flack x determined using 1629 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
Flack x: 0.004(13) Shelx2018
Hooft y: 0.005(10) Olex2
;
_refine_ls_abs_structure_Flack   0.004(13)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.073
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     341
_refine_ls_number_reflns         4351
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0386
_refine_ls_R_factor_gt           0.0362
_refine_ls_restrained_S_all      1.073
_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)+(0.0359P)²+0.5447P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0887
_refine_ls_wR_factor_ref         0.0904
_refine_special_details          ?
_olex2_refinement_description    
;
The NH and OH were located in a difference map. The OH was placed at a calculate position for the refinement 
but the hydrogen of the NH was given a Ueqiv 1.5 time the Uanis of N10 and refined with a DFIX restraint 
(as there is no suitable geometric restraint for this type of hydrogen to ride on the parent nitrogen). 
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All C(H,H,H,H) groups, All O(H) groups
2. Restrained distances
 N10-H10
 0.9 with sigma of 0.02
3. Others
 Sof(C17A)=Sof(H17A)=Sof(C16A)=Sof(H16A)=Sof(C14A)=Sof(H14A)=Sof(C13A)=
 Sof(H13A)=Sof(C15A)=Sof(C18A)=Sof(H18D)=Sof(H18E)=Sof(H18F)=1-FVAR(1)
 Sof(C15)=Sof(C13)=Sof(H13)=Sof(C14)=Sof(H14)=Sof(C18)=Sof(H18A)=Sof(H18B)=
 Sof(H18C)=Sof(C17)=Sof(H17)=Sof(C16)=Sof(H16)=FVAR(1)
4.a Ternary CH refined with riding coordinates:
 C7(H7A)
4.b Secondary CH2 refined with riding coordinates:
 C8(H8A,H8B), C21(H21A,H21B)
4.c Aromatic/amide H refined with riding coordinates:
 C5(H5), C27(H27), C23(H23), C1(H1), C4(H4), C25(H25), C2(H2), C3(H3),
 C26(H26), C24(H24), C13(H13), C14(H14), C17(H17), C16(H16), C17A(H17A),
 C16A(H16A), C14A(H14A), C13A(H13A)
4.d Idealised Me refined as rotating group:
 C18(H18A,H18B,H18C), C18A(H18D,H18E,H18F)
4.e Idealised tetrahedral OH refined as rotating group:
 O7(H7)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
S11 S 0.50736(2) 0.25424(5) 0.09701(12) 0.03478(16) Uani 1 1 d . . . . .
O7 O 0.55426(7) -0.01080(17) 0.7802(4) 0.0391(5) Uani 1 1 d . . . . .
H7 H 0.544315 -0.076720 0.804946 0.059 Uiso 1 1 calc GR . . . .
O19 O 0.62164(7) 0.18570(18) 0.0043(3) 0.0374(4) Uani 1 1 d . . . . .
O20 O 0.64443(6) 0.19153(18) 0.3574(3) 0.0376(4) Uani 1 1 d . . . . .
O11A O 0.48996(7) 0.28616(17) 0.3051(4) 0.0451(5) Uani 1 1 d . . . . .
N9 N 0.57363(7) 0.16078(19) 0.2871(4) 0.0332(5) Uani 1 1 d . . . . .
O11B O 0.47841(8) 0.21730(18) -0.0746(5) 0.0583(7) Uani 1 1 d . . . . .
N10 N 0.53902(7) 0.14095(19) 0.1394(4) 0.0340(5) Uani 1 1 d D . . . .
C12 C 0.53922(9) 0.3689(2) -0.0011(4) 0.0308(5) Uani 1 1 d . . . . .
C19 C 0.61422(9) 0.1794(2) 0.1977(5) 0.0321(6) Uani 1 1 d . . . . .
C6 C 0.61015(9) -0.0542(2) 0.5063(5) 0.0334(6) Uani 1 1 d . . . . .
C22 C 0.69687(9) 0.3336(2) 0.2255(5) 0.0358(6) Uani 1 1 d . . . . .
C5 C 0.64392(10) -0.0462(2) 0.6594(5) 0.0391(6) Uani 1 1 d . . . . .
H5 H 0.638623 -0.010836 0.796837 0.047 Uiso 1 1 calc R . . . .
C7 C 0.56584(9) -0.0014(2) 0.5542(5) 0.0346(6) Uani 1 1 d . . . . .
H7A H 0.542872 -0.039342 0.462516 0.042 Uiso 1 1 calc R . . . .
C27 C 0.69012(10) 0.4183(3) 0.3809(6) 0.0438(7) Uani 1 1 d . . . . .
H27 H 0.679390 0.398173 0.521633 0.053 Uiso 1 1 calc R . . . .
C8 C 0.56523(9) 0.1282(2) 0.5130(5) 0.0344(6) Uani 1 1 d . . . . .
H8A H 0.536198 0.158666 0.556790 0.041 Uiso 1 1 calc R . . . .
H8B H 0.587608 0.164756 0.607431 0.041 Uiso 1 1 calc R . . . .
C21 C 0.68876(9) 0.2092(3) 0.2811(6) 0.0412(7) Uani 1 1 d . . . . .
H21A H 0.693956 0.161375 0.149807 0.049 Uiso 1 1 calc R . . . .
H21B H 0.709679 0.184602 0.395793 0.049 Uiso 1 1 calc R . . . .
C23 C 0.71209(10) 0.3644(3) 0.0200(5) 0.0412(6) Uani 1 1 d . . . . .
H23 H 0.716254 0.307144 -0.088576 0.049 Uiso 1 1 calc R . . . .
C1 C 0.61833(10) -0.1055(3) 0.3062(6) 0.0427(7) Uani 1 1 d . . . . .
H1 H 0.595395 -0.112068 0.201710 0.051 Uiso 1 1 calc R . . . .
C4 C 0.68518(10) -0.0895(3) 0.6118(7) 0.0453(7) Uani 1 1 d . . . . .
H4 H 0.708038 -0.084235 0.716983 0.054 Uiso 1 1 calc R . . . .
C25 C 0.71482(10) 0.5619(3) 0.1279(6) 0.0465(7) Uani 1 1 d . . . . .
H25 H 0.721253 0.639724 0.095201 0.056 Uiso 1 1 calc R . . . .
C15 C 0.5928(5) 0.5555(15) -0.120(2) 0.030(3) Uani 0.498(13) 1 d . . P A 1
C2 C 0.66006(11) -0.1476(3) 0.2571(6) 0.0512(8) Uani 1 1 d . . . . .
H2 H 0.665718 -0.181217 0.118385 0.061 Uiso 1 1 calc R . . . .
C3 C 0.69314(10) -0.1403(3) 0.4113(7) 0.0476(7) Uani 1 1 d . . . . .
H3 H 0.721431 -0.170196 0.379441 0.057 Uiso 1 1 calc R . . . .
C26 C 0.69892(11) 0.5323(3) 0.3325(6) 0.0476(8) Uani 1 1 d . . . . .
H26 H 0.694053 0.589961 0.439504 0.057 Uiso 1 1 calc R . . . .
C24 C 0.72131(11) 0.4784(3) -0.0282(6) 0.0468(7) Uani 1 1 d . . . . .
H24 H 0.732071 0.498766 -0.168751 0.056 Uiso 1 1 calc R . . . .
C13 C 0.5536(4) 0.4504(9) 0.1531(17) 0.034(2) Uani 0.498(13) 1 d . . P A 1
H13 H 0.545305 0.442301 0.302034 0.040 Uiso 0.498(13) 1 calc R . P A 1
C14 C 0.5796(4) 0.5422(9) 0.0906(17) 0.034(2) Uani 0.498(13) 1 d . . P A 1
H14 H 0.588406 0.596860 0.197195 0.041 Uiso 0.498(13) 1 calc R . P A 1
C18 C 0.6196(4) 0.6595(11) -0.1921(18) 0.041(2) Uani 0.498(13) 1 d . . P A 1
H18A H 0.609807 0.727491 -0.111379 0.062 Uiso 0.498(13) 1 calc GR . P A 1
H18B H 0.615389 0.672088 -0.349163 0.062 Uiso 0.498(13) 1 calc GR . P A 1
H18C H 0.650746 0.645710 -0.162261 0.062 Uiso 0.498(13) 1 calc GR . P A 1
C17 C 0.5537(4) 0.3845(6) -0.2198(10) 0.0357(19) Uani 0.498(13) 1 d . . P A 1
H17 H 0.544791 0.331330 -0.328717 0.043 Uiso 0.498(13) 1 calc R . P A 1
C16 C 0.5804(3) 0.4751(6) -0.2778(10) 0.036(2) Uani 0.498(13) 1 d . . P A 1
H16 H 0.590311 0.482788 -0.424287 0.043 Uiso 0.498(13) 1 calc R . P A 1
C17A C 0.5281(4) 0.4003(5) -0.2106(10) 0.0344(17) Uani 0.502(13) 1 d . . P A 2
H17A H 0.506110 0.361155 -0.291553 0.041 Uiso 0.502(13) 1 calc R . P A 2
C16A C 0.5511(4) 0.4936(6) -0.2969(10) 0.045(2) Uani 0.502(13) 1 d . . P A 2
H16A H 0.544576 0.517921 -0.441460 0.053 Uiso 0.502(13) 1 calc R . P A 2
C14A C 0.5909(3) 0.5160(9) 0.036(2) 0.039(2) Uani 0.502(13) 1 d . . P A 2
H14A H 0.612432 0.554681 0.120628 0.047 Uiso 0.502(13) 1 calc R . P A 2
C13A C 0.5676(4) 0.4250(9) 0.1283(19) 0.032(2) Uani 0.502(13) 1 d . . P A 2
H13A H 0.571738 0.403682 0.276796 0.039 Uiso 0.502(13) 1 calc R . P A 2
C15A C 0.5831(5) 0.5519(15) -0.181(2) 0.040(3) Uani 0.502(13) 1 d . . P A 2
C18A C 0.6075(5) 0.6512(12) -0.271(3) 0.066(4) Uani 0.502(13) 1 d . . P A 2
H18D H 0.638865 0.633234 -0.276435 0.100 Uiso 0.502(13) 1 calc GR . P A 2
H18E H 0.602703 0.718414 -0.178148 0.100 Uiso 0.502(13) 1 calc GR . P A 2
H18F H 0.596916 0.667719 -0.419599 0.100 Uiso 0.502(13) 1 calc GR . P A 2
H10 H 0.5481(18) 0.104(5) 0.021(7) 0.100 Uiso 1 1 d DR . . . .


_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
S11 O11A 1.428(2) . ?
S11 O11B 1.437(2) . ?
S11 N10 1.656(2) . ?
S11 C12 1.757(3) . ?
O7 H7 0.8400 . ?
O7 C7 1.430(3) . ?
O19 C19 1.206(4) . ?
O20 C19 1.349(4) . ?
O20 C21 1.443(3) . ?
N9 N10 1.407(3) . ?
N9 C19 1.369(4) . ?
N9 C8 1.456(4) . ?
N10 H10 0.88(3) . ?
C12 C13 1.408(11) . ?
C12 C17 1.420(7) . ?
C12 C17A 1.375(7) . ?
C12 C13A 1.343(11) . ?
C6 C5 1.394(4) . ?
C6 C7 1.512(4) . ?
C6 C1 1.385(5) . ?
C22 C27 1.386(5) . ?
C22 C21 1.511(4) . ?
C22 C23 1.387(4) . ?
C5 H5 0.9500 . ?
C5 C4 1.385(4) . ?
C7 H7A 1.0000 . ?
C7 C8 1.532(4) . ?
C27 H27 0.9500 . ?
C27 C26 1.388(5) . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C21 H21A 0.9900 . ?
C21 H21B 0.9900 . ?
C23 H23 0.9500 . ?
C23 C24 1.391(5) . ?
C1 H1 0.9500 . ?
C1 C2 1.395(5) . ?
C4 H4 0.9500 . ?
C4 C3 1.383(5) . ?
C25 H25 0.9500 . ?
C25 C26 1.386(5) . ?
C25 C24 1.377(5) . ?
C15 C14 1.356(17) . ?
C15 C18 1.53(2) . ?
C15 C16 1.399(14) . ?
C2 H2 0.9500 . ?
C2 C3 1.383(5) . ?
C3 H3 0.9500 . ?
C26 H26 0.9500 . ?
C24 H24 0.9500 . ?
C13 H13 0.9500 . ?
C13 C14 1.386(15) . ?
C14 H14 0.9500 . ?
C18 H18A 0.9800 . ?
C18 H18B 0.9800 . ?
C18 H18C 0.9800 . ?
C17 H17 0.9500 . ?
C17 C16 1.379(9) . ?
C16 H16 0.9500 . ?
C17A H17A 0.9500 . ?
C17A C16A 1.398(10) . ?
C16A H16A 0.9500 . ?
C16A C15A 1.381(16) . ?
C14A H14A 0.9500 . ?
C14A C13A 1.395(14) . ?
C14A C15A 1.411(16) . ?
C13A H13A 0.9500 . ?
C15A C18A 1.48(2) . ?
C18A H18D 0.9800 . ?
C18A H18E 0.9800 . ?
C18A H18F 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
O11A S11 O11B 120.10(16) . . ?
O11A S11 N10 106.52(13) . . ?
O11A S11 C12 108.12(13) . . ?
O11B S11 N10 103.45(12) . . ?
O11B S11 C12 108.52(15) . . ?
N10 S11 C12 109.79(12) . . ?
C7 O7 H7 109.5 . . ?
C19 O20 C21 114.7(2) . . ?
N10 N9 C8 115.8(2) . . ?
C19 N9 N10 116.5(2) . . ?
C19 N9 C8 125.4(2) . . ?
S11 N10 H10 116(4) . . ?
N9 N10 S11 113.94(17) . . ?
N9 N10 H10 112(4) . . ?
C13 C12 S11 117.2(5) . . ?
C13 C12 C17 116.6(5) . . ?
C17 C12 S11 126.2(3) . . ?
C17A C12 S11 112.6(4) . . ?
C13A C12 S11 121.7(5) . . ?
C13A C12 C17A 125.3(6) . . ?
O19 C19 O20 125.1(3) . . ?
O19 C19 N9 124.8(3) . . ?
O20 C19 N9 110.1(2) . . ?
C5 C6 C7 120.1(3) . . ?
C1 C6 C5 119.3(3) . . ?
C1 C6 C7 120.5(3) . . ?
C27 C22 C21 120.4(3) . . ?
C27 C22 C23 119.2(3) . . ?
C23 C22 C21 120.5(3) . . ?
C6 C5 H5 119.9 . . ?
C4 C5 C6 120.3(3) . . ?
C4 C5 H5 119.9 . . ?
O7 C7 C6 112.1(2) . . ?
O7 C7 H7A 109.6 . . ?
O7 C7 C8 103.4(2) . . ?
C6 C7 H7A 109.6 . . ?
C6 C7 C8 112.4(2) . . ?
C8 C7 H7A 109.6 . . ?
C22 C27 H27 119.8 . . ?
C22 C27 C26 120.5(3) . . ?
C26 C27 H27 119.8 . . ?
N9 C8 C7 114.3(2) . . ?
N9 C8 H8A 108.7 . . ?
N9 C8 H8B 108.7 . . ?
C7 C8 H8A 108.7 . . ?
C7 C8 H8B 108.7 . . ?
H8A C8 H8B 107.6 . . ?
O20 C21 C22 111.2(2) . . ?
O20 C21 H21A 109.4 . . ?
O20 C21 H21B 109.4 . . ?
C22 C21 H21A 109.4 . . ?
C22 C21 H21B 109.4 . . ?
H21A C21 H21B 108.0 . . ?
C22 C23 H23 119.8 . . ?
C22 C23 C24 120.5(3) . . ?
C24 C23 H23 119.8 . . ?
C6 C1 H1 119.8 . . ?
C6 C1 C2 120.4(3) . . ?
C2 C1 H1 119.8 . . ?
C5 C4 H4 120.0 . . ?
C3 C4 C5 120.1(3) . . ?
C3 C4 H4 120.0 . . ?
C26 C25 H25 120.0 . . ?
C24 C25 H25 120.0 . . ?
C24 C25 C26 120.0(3) . . ?
C14 C15 C18 121.6(12) . . ?
C14 C15 C16 120.0(13) . . ?
C16 C15 C18 118.4(11) . . ?
C1 C2 H2 120.2 . . ?
C3 C2 C1 119.7(3) . . ?
C3 C2 H2 120.2 . . ?
C4 C3 H3 119.9 . . ?
C2 C3 C4 120.2(3) . . ?
C2 C3 H3 119.9 . . ?
C27 C26 H26 120.0 . . ?
C25 C26 C27 119.9(3) . . ?
C25 C26 H26 120.0 . . ?
C23 C24 H24 120.0 . . ?
C25 C24 C23 120.0(3) . . ?
C25 C24 H24 120.0 . . ?
C12 C13 H13 119.5 . . ?
C14 C13 C12 121.0(8) . . ?
C14 C13 H13 119.5 . . ?
C15 C14 C13 121.2(10) . . ?
C15 C14 H14 119.4 . . ?
C13 C14 H14 119.4 . . ?
C15 C18 H18A 109.5 . . ?
C15 C18 H18B 109.5 . . ?
C15 C18 H18C 109.5 . . ?
H18A C18 H18B 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
C12 C17 H17 119.2 . . ?
C16 C17 C12 121.6(5) . . ?
C16 C17 H17 119.2 . . ?
C15 C16 H16 120.2 . . ?
C17 C16 C15 119.6(9) . . ?
C17 C16 H16 120.2 . . ?
C12 C17A H17A 122.1 . . ?
C12 C17A C16A 115.8(6) . . ?
C16A C17A H17A 122.1 . . ?
C17A C16A H16A 118.6 . . ?
C15A C16A C17A 122.9(9) . . ?
C15A C16A H16A 118.6 . . ?
C13A C14A H14A 119.3 . . ?
C13A C14A C15A 121.3(11) . . ?
C15A C14A H14A 119.3 . . ?
C12 C13A C14A 117.3(10) . . ?
C12 C13A H13A 121.3 . . ?
C14A C13A H13A 121.3 . . ?
C16A C15A C14A 117.1(13) . . ?
C16A C15A C18A 123.1(12) . . ?
C14A C15A C18A 119.8(12) . . ?
C15A C18A H18D 109.5 . . ?
C15A C18A H18E 109.5 . . ?
C15A C18A H18F 109.5 . . ?
H18D C18A H18E 109.5 . . ?
H18D C18A H18F 109.5 . . ?
H18E C18A H18F 109.5 . . ?

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
O7 H7 O11B 0.84 1.93 2.753(3) 167.8 2_656 yes
N10 H10 O7 0.88(3) 2.00(3) 2.859(3) 163(6) 1_554 yes

_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 1.509
_oxdiff_exptl_absorpt_empirical_full_min 0.490
####################################################################### 
# 
# 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_cd8
_database_code_depnum_ccdc_archive 'CCDC 1944270'
loop_
_audit_author_name
_audit_author_address
'Guy Clarkson'
;University of Warwick
United Kingdom
;
_audit_update_record             
;
2019-07-30 deposited with the CCDC.	2019-12-26 downloaded from the CCDC.
;
_audit_creation_date             2019-07-01
_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        ?
_chemical_formula_moiety         'C20 H23 N3 O3'
_chemical_formula_sum            'C20 H23 N3 O3'
_chemical_formula_weight         353.41
_chemical_absolute_configuration .
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C20 H20 N2 O2'
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      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'

_cell_length_a                   7.19100(10)
_cell_length_b                   13.50450(10)
_cell_length_c                   18.6644(2)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1812.52(3)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    7023
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      73.4330
_cell_measurement_theta_min      3.9980
_shelx_estimated_absorpt_T_max   0.945
_shelx_estimated_absorpt_T_min   0.814
_exptl_absorpt_coefficient_mu    0.716
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.67671
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.57a (Rigaku Oxford Diffraction, 2019)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.295
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             752
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.08
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0227
_diffrn_reflns_av_unetI/netI     0.0229
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.989
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            10496
_diffrn_reflns_point_group_measured_fraction_full 0.989
_diffrn_reflns_point_group_measured_fraction_max 0.964
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         73.587
_diffrn_reflns_theta_min         4.041
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      150(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.3046
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.989
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω   -116.00 -17.00   1.00    1.00    --  -41.82 -37.00 150.00   99
  2  ω    -30.00  70.00   1.00    1.00    --   41.82 -57.00 -60.00  100
  3  ω     34.00 133.00   1.00    4.00    --  107.00 -45.00  90.00   99
  4  ω     81.00 178.00   1.00    4.00    --  107.00  45.00 -90.00   97
  5  ω     97.00 178.00   1.00    4.00    --  107.00 125.00-120.00   81
  6  ω    103.00 178.00   1.00    4.00    --  107.00  77.00-150.00   75
  7  ω     34.00 112.00   1.00    4.00    --  107.00-125.00 -90.00   78
  8  ω   -114.00 -14.00   1.00    1.00    --  -41.82 -57.00   0.00  100
  9  ω   -114.00 -14.00   1.00    1.00    --  -41.82 -57.00 -90.00  100
 10  ω     81.00 178.00   1.00    4.00    --  107.00  45.00  90.00   97
 11  ω    103.00 134.00   1.00    4.00    --  107.00  77.00 150.00   31
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, AtlasS2'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0062113000
_diffrn_orient_matrix_UB_12      -0.0620429000
_diffrn_orient_matrix_UB_13      0.0692104000
_diffrn_orient_matrix_UB_21      -0.0054221000
_diffrn_orient_matrix_UB_22      0.0956151000
_diffrn_orient_matrix_UB_23      0.0449680000
_diffrn_orient_matrix_UB_31      -0.2141083000
_diffrn_orient_matrix_UB_32      -0.0042433000
_diffrn_orient_matrix_UB_33      0.0009029000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\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         0.689
_reflns_Friedel_fraction_full    0.974
_reflns_Friedel_fraction_max     0.929
_reflns_number_gt                3409
_reflns_number_total             3514
_reflns_odcompleteness_completeness 99.29
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     72.42
_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. Completness statistics refer to single and
 composite reflections containing twin component 1 only.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.40.57a (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.40.57a (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.57a (Rigaku OD, 2019)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.137
_refine_diff_density_min         -0.237
_refine_diff_density_rms         0.041
_refine_ls_abs_structure_details 
;
 Refined as an inversion twin with TWIN and BASF.
 BASF 0.19(26) Shelx 2018
 Hooft y 0.28(9) Olex2

;
_refine_ls_abs_structure_Flack   0.2(3)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.948
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     238
_refine_ls_number_reflns         3514
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0336
_refine_ls_R_factor_gt           0.0325
_refine_ls_restrained_S_all      0.948
_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)+(0.1000P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1052
_refine_ls_wR_factor_ref         0.1083
_refine_special_details          
;
 Refined as a 2-component inversion twin.
;
_olex2_refinement_description    
;
1. Twinned data refinement
 Scales: 0.8(3)
 0.2(3)
2. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
3.a Ternary CH refined with riding coordinates:
 C20(H20), C7(H7)
3.b Secondary CH2 refined with riding coordinates:
 C8(H8A,H8B), C19(H19A,H19B), C9(H9A,H9B)
3.c Aromatic/amide H refined with riding coordinates:
 C14(H14), C18(H18), C1(H1), C5(H5), C17(H17), C15(H15), C3(H3), C4(H4), C2(H2)
3.d Idealised Me refined as rotating group:
 C21(H21A,H21B,H21C), C22(H22A,H22B,H22C)
;
_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
O12 O 0.6361(2) 0.75859(9) 0.54680(7) 0.0294(3) Uani 1 1 d . . . . .
N10 N 0.6513(2) 0.50009(10) 0.57967(7) 0.0220(3) Uani 1 1 d . . . . .
N11 N 0.6645(2) 0.59228(10) 0.54284(7) 0.0224(3) Uani 1 1 d . . . . .
O16B O -0.0428(3) 0.66460(15) 0.80750(10) 0.0572(5) Uani 1 1 d . . . . .
N16 N 0.1247(3) 0.65591(14) 0.81747(10) 0.0446(5) Uani 1 1 d . . . . .
O16A O 0.1966(3) 0.6451(2) 0.87647(10) 0.0741(7) Uani 1 1 d . . . . .
C12 C 0.6029(2) 0.67675(12) 0.57291(9) 0.0221(3) Uani 1 1 d . . . . .
C6 C 0.7070(2) 0.58916(12) 0.41056(9) 0.0240(4) Uani 1 1 d . . . . .
C8 C 0.9162(2) 0.49778(13) 0.50076(10) 0.0289(4) Uani 1 1 d . . . . .
H8A H 0.895540 0.445257 0.464623 0.035 Uiso 1 1 calc R . . . .
H8B H 1.050423 0.514008 0.502360 0.035 Uiso 1 1 calc R . . . .
C13 C 0.4801(3) 0.66577(11) 0.63781(8) 0.0230(3) Uani 1 1 d . . . . .
C19 C 0.5192(2) 0.43331(11) 0.54224(9) 0.0233(3) Uani 1 1 d . . . . .
H19A H 0.579846 0.405035 0.499235 0.028 Uiso 1 1 calc R . . . .
H19B H 0.409307 0.471602 0.526381 0.028 Uiso 1 1 calc R . . . .
C14 C 0.5559(3) 0.65619(14) 0.70608(9) 0.0300(4) Uani 1 1 d . . . . .
H14 H 0.686957 0.652749 0.712102 0.036 Uiso 1 1 calc R . . . .
C18 C 0.2884(3) 0.67117(13) 0.62852(10) 0.0275(4) Uani 1 1 d . . . . .
H18 H 0.237767 0.678016 0.581777 0.033 Uiso 1 1 calc R . . . .
C1 C 0.5192(3) 0.60988(13) 0.40130(9) 0.0270(4) Uani 1 1 d . . . . .
H1 H 0.443864 0.624441 0.441763 0.032 Uiso 1 1 calc R . . . .
C20 C 0.4570(3) 0.34948(12) 0.59186(9) 0.0257(4) Uani 1 1 d . . . . .
H20 H 0.569482 0.315350 0.611471 0.031 Uiso 1 1 calc R . . . .
C7 C 0.7988(2) 0.59080(12) 0.48360(9) 0.0226(4) Uani 1 1 d . . . . .
H7 H 0.880008 0.650713 0.487061 0.027 Uiso 1 1 calc R . . . .
C5 C 0.8155(3) 0.57019(14) 0.34978(11) 0.0327(4) Uani 1 1 d . . . . .
H5 H 0.944621 0.557187 0.355101 0.039 Uiso 1 1 calc R . . . .
C17 C 0.1714(3) 0.66658(13) 0.68735(10) 0.0298(4) Uani 1 1 d . . . . .
H17 H 0.040255 0.669854 0.681579 0.036 Uiso 1 1 calc R . . . .
C16 C 0.2495(3) 0.65716(14) 0.75450(10) 0.0306(4) Uani 1 1 d . . . . .
C15 C 0.4398(3) 0.65167(14) 0.76522(10) 0.0337(4) Uani 1 1 d . . . . .
H15 H 0.489679 0.644960 0.812108 0.040 Uiso 1 1 calc R . . . .
C9 C 0.8453(2) 0.46523(12) 0.57503(10) 0.0265(4) Uani 1 1 d . . . . .
H9A H 0.850879 0.392281 0.579781 0.032 Uiso 1 1 calc R . . . .
H9B H 0.921595 0.495299 0.613443 0.032 Uiso 1 1 calc R . . . .
C3 C 0.5494(3) 0.58949(17) 0.27362(11) 0.0395(5) Uani 1 1 d . . . . .
H3 H 0.495373 0.589087 0.227181 0.047 Uiso 1 1 calc R . . . .
C4 C 0.7371(4) 0.57014(17) 0.28209(11) 0.0404(5) Uani 1 1 d . . . . .
H4 H 0.812214 0.556794 0.241353 0.048 Uiso 1 1 calc R . . . .
C21 C 0.3419(3) 0.38970(14) 0.65379(10) 0.0331(4) Uani 1 1 d . . . . .
H21A H 0.413696 0.440167 0.679467 0.050 Uiso 1 1 calc GR . . . .
H21B H 0.310752 0.335571 0.686632 0.050 Uiso 1 1 calc GR . . . .
H21C H 0.227280 0.419259 0.635144 0.050 Uiso 1 1 calc GR . . . .
C2 C 0.4409(3) 0.60943(14) 0.33307(10) 0.0339(4) Uani 1 1 d . . . . .
H2 H 0.312060 0.622899 0.327324 0.041 Uiso 1 1 calc R . . . .
C22 C 0.3420(4) 0.27514(14) 0.54917(11) 0.0412(5) Uani 1 1 d . . . . .
H22A H 0.238850 0.309547 0.525571 0.062 Uiso 1 1 calc GR . . . .
H22B H 0.292556 0.224515 0.581593 0.062 Uiso 1 1 calc GR . . . .
H22C H 0.420824 0.243615 0.512901 0.062 Uiso 1 1 calc GR . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O12 C12 1.231(2) . ?
N10 N11 1.4253(18) . ?
N10 C19 1.484(2) . ?
N10 C9 1.475(2) . ?
N11 C12 1.346(2) . ?
N11 C7 1.468(2) . ?
O16B N16 1.225(3) . ?
N16 O16A 1.225(3) . ?
N16 C16 1.479(2) . ?
C12 C13 1.506(2) . ?
C6 C1 1.390(3) . ?
C6 C7 1.515(2) . ?
C6 C5 1.401(2) . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C8 C7 1.547(2) . ?
C8 C9 1.541(2) . ?
C13 C14 1.392(2) . ?
C13 C18 1.391(3) . ?
C19 H19A 0.9900 . ?
C19 H19B 0.9900 . ?
C19 C20 1.529(2) . ?
C14 H14 0.9500 . ?
C14 C15 1.385(3) . ?
C18 H18 0.9500 . ?
C18 C17 1.385(3) . ?
C1 H1 0.9500 . ?
C1 C2 1.393(3) . ?
C20 H20 1.0000 . ?
C20 C21 1.522(3) . ?
C20 C22 1.525(3) . ?
C7 H7 1.0000 . ?
C5 H5 0.9500 . ?
C5 C4 1.384(3) . ?
C17 H17 0.9500 . ?
C17 C16 1.379(3) . ?
C16 C15 1.386(3) . ?
C15 H15 0.9500 . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C3 H3 0.9500 . ?
C3 C4 1.384(3) . ?
C3 C2 1.383(3) . ?
C4 H4 0.9500 . ?
C21 H21A 0.9800 . ?
C21 H21B 0.9800 . ?
C21 H21C 0.9800 . ?
C2 H2 0.9500 . ?
C22 H22A 0.9800 . ?
C22 H22B 0.9800 . ?
C22 H22C 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
N11 N10 C19 110.26(13) . . ?
N11 N10 C9 100.82(13) . . ?
C9 N10 C19 112.56(13) . . ?
N10 N11 C7 113.27(12) . . ?
C12 N11 N10 121.15(14) . . ?
C12 N11 C7 122.81(13) . . ?
O16B N16 O16A 124.3(2) . . ?
O16B N16 C16 118.4(2) . . ?
O16A N16 C16 117.4(2) . . ?
O12 C12 N11 122.13(15) . . ?
O12 C12 C13 121.35(14) . . ?
N11 C12 C13 116.40(14) . . ?
C1 C6 C7 122.16(16) . . ?
C1 C6 C5 118.53(17) . . ?
C5 C6 C7 119.26(15) . . ?
H8A C8 H8B 109.0 . . ?
C7 C8 H8A 111.0 . . ?
C7 C8 H8B 111.0 . . ?
C9 C8 H8A 111.0 . . ?
C9 C8 H8B 111.0 . . ?
C9 C8 C7 103.71(14) . . ?
C14 C13 C12 121.03(16) . . ?
C18 C13 C12 118.40(15) . . ?
C18 C13 C14 120.47(17) . . ?
N10 C19 H19A 109.5 . . ?
N10 C19 H19B 109.5 . . ?
N10 C19 C20 110.60(14) . . ?
H19A C19 H19B 108.1 . . ?
C20 C19 H19A 109.5 . . ?
C20 C19 H19B 109.5 . . ?
C13 C14 H14 120.1 . . ?
C15 C14 C13 119.82(18) . . ?
C15 C14 H14 120.1 . . ?
C13 C18 H18 120.0 . . ?
C17 C18 C13 120.07(17) . . ?
C17 C18 H18 120.0 . . ?
C6 C1 H1 119.8 . . ?
C6 C1 C2 120.39(17) . . ?
C2 C1 H1 119.8 . . ?
C19 C20 H20 109.0 . . ?
C21 C20 C19 110.78(14) . . ?
C21 C20 H20 109.0 . . ?
C21 C20 C22 109.68(17) . . ?
C22 C20 C19 109.23(14) . . ?
C22 C20 H20 109.0 . . ?
N11 C7 C6 113.04(14) . . ?
N11 C7 C8 102.37(13) . . ?
N11 C7 H7 108.9 . . ?
C6 C7 C8 114.35(14) . . ?
C6 C7 H7 108.9 . . ?
C8 C7 H7 108.9 . . ?
C6 C5 H5 119.6 . . ?
C4 C5 C6 120.83(18) . . ?
C4 C5 H5 119.6 . . ?
C18 C17 H17 120.8 . . ?
C16 C17 C18 118.50(17) . . ?
C16 C17 H17 120.8 . . ?
C17 C16 N16 118.45(18) . . ?
C17 C16 C15 122.57(18) . . ?
C15 C16 N16 118.96(18) . . ?
C14 C15 C16 118.56(18) . . ?
C14 C15 H15 120.7 . . ?
C16 C15 H15 120.7 . . ?
N10 C9 C8 105.96(14) . . ?
N10 C9 H9A 110.5 . . ?
N10 C9 H9B 110.5 . . ?
C8 C9 H9A 110.5 . . ?
C8 C9 H9B 110.5 . . ?
H9A C9 H9B 108.7 . . ?
C4 C3 H3 120.1 . . ?
C2 C3 H3 120.1 . . ?
C2 C3 C4 119.71(18) . . ?
C5 C4 H4 119.9 . . ?
C3 C4 C5 120.12(18) . . ?
C3 C4 H4 119.9 . . ?
C20 C21 H21A 109.5 . . ?
C20 C21 H21B 109.5 . . ?
C20 C21 H21C 109.5 . . ?
H21A C21 H21B 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
C1 C2 H2 119.8 . . ?
C3 C2 C1 120.41(18) . . ?
C3 C2 H2 119.8 . . ?
C20 C22 H22A 109.5 . . ?
C20 C22 H22B 109.5 . . ?
C20 C22 H22C 109.5 . . ?
H22A C22 H22B 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.395
_oxdiff_exptl_absorpt_empirical_full_min 0.682
loop_
_twin_individual_id
_twin_individual_mass_fraction_refined
1 0.8(3)
2 0.2(3)
####################################################################### 
# 
# 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_sr3
_database_code_depnum_ccdc_archive 'CCDC 1944273'
loop_
_audit_author_name
_audit_author_address
'Guy Clarkson'
;University of Warwick
United Kingdom
;
_audit_update_record             
;
2019-07-30 deposited with the CCDC.	2019-12-26 downloaded from the CCDC.
;
_audit_creation_date             2019-06-27
_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        ?
_chemical_formula_moiety         'C20 H25 N3 O2'
_chemical_formula_sum            'C20 H25 N3 O2'
_chemical_formula_weight         339.43
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C20 H20 N2 O2'
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                   6.81180(10)
_cell_length_b                   17.54950(10)
_cell_length_c                   15.11130(10)
_cell_angle_alpha                90
_cell_angle_beta                 91.4270(10)
_cell_angle_gamma                90
_cell_volume                     1805.90(3)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    10563
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      73.4580
_cell_measurement_theta_min      2.4840
_shelx_estimated_absorpt_T_max   0.903
_shelx_estimated_absorpt_T_min   0.870
_exptl_absorpt_coefficient_mu    0.652
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.32614
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.57a (Rigaku Oxford Diffraction, 2019)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.248
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             728
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.16
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0208
_diffrn_reflns_av_unetI/netI     0.0152
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.984
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            15714
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.984
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         73.609
_diffrn_reflns_theta_min         3.861
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      150(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.3046
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.984
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -66.00  33.00   1.00    1.00    --  -41.82  37.00  90.00   99
  2  ω    -66.00  33.00   1.00    1.00    --  -41.82  37.00-150.00   99
  3  ω     27.00  98.00   1.00    1.00    --   41.82-125.00 120.00   71
  4  ω     24.00 107.00   1.00    4.00    --  107.00 -94.00 120.00   83
  5  ω     34.00 112.00   1.00    4.00    --  107.00-125.00  60.00   78
  6  ω     34.00 112.00   1.00    4.00    --  107.00-125.00-120.00   78
  7  ω     97.00 178.00   1.00    4.00    --  107.00 125.00 150.00   81
  8  ω     81.00 178.00   1.00    4.00    --  107.00  45.00 -30.00   97
  9  ω     34.00 112.00   1.00    4.00    --  107.00-125.00 -30.00   78
 10  ω     78.00 178.00   1.00    4.00    --  107.00  61.00-120.00  100
 11  ω   -114.00 -14.00   1.00    1.00    --  -41.82 -57.00-120.00  100
 12  ω    -66.00  33.00   1.00    1.00    --  -41.82  37.00 -30.00   99
 13  ω   -114.00 -14.00   1.00    1.00    --  -41.82 -57.00  90.00  100
 14  ω   -116.00 -17.00   1.00    1.00    --  -41.82 -37.00 -30.00   99
 15  ω     78.00 178.00   1.00    4.00    --  107.00  61.00 150.00  100
 16  ω     78.00 178.00   1.00    4.00    --  107.00  61.00-180.00  100
 17  ω     78.00 153.00   1.00    4.00    --  107.00  61.00  30.00   75
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, AtlasS2'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0436299000
_diffrn_orient_matrix_UB_12      0.0280316000
_diffrn_orient_matrix_UB_13      -0.0940947000
_diffrn_orient_matrix_UB_21      0.0752039000
_diffrn_orient_matrix_UB_22      -0.0799479000
_diffrn_orient_matrix_UB_23      -0.0241024000
_diffrn_orient_matrix_UB_31      -0.2088828000
_diffrn_orient_matrix_UB_32      -0.0229530000
_diffrn_orient_matrix_UB_33      -0.0310713000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\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                3380
_reflns_number_total             3594
_reflns_odcompleteness_completeness 99.33
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     71.98
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.40.57a (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.40.57a (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.57a (Rigaku OD, 2019)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.208
_refine_diff_density_min         -0.199
_refine_diff_density_rms         0.033
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.038
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     229
_refine_ls_number_reflns         3594
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0348
_refine_ls_R_factor_gt           0.0330
_refine_ls_restrained_S_all      1.038
_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)+(0.0409P)²+0.4735P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0833
_refine_ls_wR_factor_ref         0.0846
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C11(H11)
2.b Secondary CH2 refined with riding coordinates:
 C8(H8A,H8B), C9(H9A,H9B), C10(H10A,H10B)
2.c Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C4(H4), C5(H5), C20(H20), C21(H21), C22(H22), C23(H23),
 C24(H24)
2.d Idealised Me refined as rotating group:
 C16(H16A,H16B,H16C), C17(H17A,H17B,H17C), C18(H18A,H18B,H18C)
;
_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
N1 N 0.25863(14) 0.17276(5) 0.66975(6) 0.0291(2) Uani 1 1 d . . . . .
C2 C 0.3230(2) 0.10094(7) 0.66055(8) 0.0374(3) Uani 1 1 d . . . . .
H2 H 0.230469 0.060877 0.666550 0.045 Uiso 1 1 calc R . . . .
C3 C 0.5135(2) 0.08140(7) 0.64304(8) 0.0425(3) Uani 1 1 d . . . . .
H3 H 0.551426 0.029642 0.636581 0.051 Uiso 1 1 calc R . . . .
C4 C 0.64870(19) 0.14025(7) 0.63512(7) 0.0366(3) Uani 1 1 d . . . . .
H4 H 0.781793 0.129102 0.622921 0.044 Uiso 1 1 calc R . . . .
C5 C 0.58937(16) 0.21464(6) 0.64499(7) 0.0277(2) Uani 1 1 d . . . . .
H5 H 0.680245 0.255424 0.640413 0.033 Uiso 1 1 calc R . . . .
C6 C 0.39039(15) 0.22869(6) 0.66206(6) 0.0221(2) Uani 1 1 d . . . . .
N7 N 0.31802(11) 0.30185(5) 0.66912(5) 0.02129(18) Uani 1 1 d . . . . .
C8 C 0.12487(14) 0.32025(6) 0.70313(7) 0.0269(2) Uani 1 1 d . . . . .
H8A H 0.137037 0.334250 0.766496 0.032 Uiso 1 1 calc R . . . .
H8B H 0.037306 0.275390 0.697626 0.032 Uiso 1 1 calc R . . . .
C9 C 0.03868(15) 0.38671(7) 0.65006(7) 0.0295(2) Uani 1 1 d . . . . .
H9A H -0.083523 0.404279 0.677726 0.035 Uiso 1 1 calc R . . . .
H9B H 0.005002 0.369507 0.589163 0.035 Uiso 1 1 calc R . . . .
C10 C 0.18422(15) 0.45269(6) 0.64636(7) 0.0268(2) Uani 1 1 d . . . . .
H10A H 0.199166 0.475713 0.705953 0.032 Uiso 1 1 calc R . . . .
H10B H 0.131379 0.492256 0.605600 0.032 Uiso 1 1 calc R . . . .
C11 C 0.38625(14) 0.42700(6) 0.61495(6) 0.0215(2) Uani 1 1 d . . . . .
H11 H 0.479663 0.470150 0.625784 0.026 Uiso 1 1 calc R . . . .
N12 N 0.45214(11) 0.36266(5) 0.67211(5) 0.01949(18) Uani 1 1 d . . . . .
C13 C 0.53434(14) 0.38347(6) 0.75467(6) 0.0207(2) Uani 1 1 d . . . . .
O13 O 0.62189(11) 0.44275(4) 0.76557(5) 0.02795(17) Uani 1 1 d . . . . .
O14 O 0.50930(10) 0.32875(4) 0.81480(4) 0.02340(16) Uani 1 1 d . . . . .
C15 C 0.58853(15) 0.33978(6) 0.90642(6) 0.0230(2) Uani 1 1 d . . . . .
C16 C 0.50939(19) 0.27081(7) 0.95431(7) 0.0334(3) Uani 1 1 d . . . . .
H16A H 0.365551 0.272597 0.953185 0.050 Uiso 1 1 calc GR . . . .
H16B H 0.558418 0.270990 1.015833 0.050 Uiso 1 1 calc GR . . . .
H16C H 0.553034 0.224254 0.924869 0.050 Uiso 1 1 calc GR . . . .
C17 C 0.81119(16) 0.33865(7) 0.90582(7) 0.0327(3) Uani 1 1 d . . . . .
H17A H 0.855633 0.291756 0.877368 0.049 Uiso 1 1 calc GR . . . .
H17B H 0.863392 0.340619 0.966802 0.049 Uiso 1 1 calc GR . . . .
H17C H 0.858383 0.382858 0.872916 0.049 Uiso 1 1 calc GR . . . .
C18 C 0.50761(18) 0.41234(6) 0.94605(7) 0.0321(2) Uani 1 1 d . . . . .
H18A H 0.564751 0.456568 0.916607 0.048 Uiso 1 1 calc GR . . . .
H18B H 0.541293 0.414070 1.009445 0.048 Uiso 1 1 calc GR . . . .
H18C H 0.364497 0.413280 0.937695 0.048 Uiso 1 1 calc GR . . . .
C19 C 0.39691(14) 0.40570(6) 0.51753(6) 0.0212(2) Uani 1 1 d . . . . .
C20 C 0.24722(15) 0.42358(6) 0.45657(7) 0.0256(2) Uani 1 1 d . . . . .
H20 H 0.130160 0.446620 0.476556 0.031 Uiso 1 1 calc R . . . .
C21 C 0.26643(16) 0.40825(6) 0.36690(7) 0.0286(2) Uani 1 1 d . . . . .
H21 H 0.162320 0.420477 0.326366 0.034 Uiso 1 1 calc R . . . .
C22 C 0.43598(17) 0.37537(6) 0.33653(7) 0.0284(2) Uani 1 1 d . . . . .
H22 H 0.448944 0.364780 0.275301 0.034 Uiso 1 1 calc R . . . .
C23 C 0.58702(17) 0.35795(6) 0.39611(7) 0.0302(2) Uani 1 1 d . . . . .
H23 H 0.704660 0.335731 0.375613 0.036 Uiso 1 1 calc R . . . .
C24 C 0.56733(15) 0.37282(6) 0.48575(7) 0.0271(2) Uani 1 1 d . . . . .
H24 H 0.671785 0.360359 0.526000 0.032 Uiso 1 1 calc R . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
N1 C2 1.3430(15) . ?
N1 C6 1.3371(14) . ?
C2 H2 0.9500 . ?
C2 C3 1.374(2) . ?
C3 H3 0.9500 . ?
C3 C4 1.3910(19) . ?
C4 H4 0.9500 . ?
C4 C5 1.3757(16) . ?
C5 H5 0.9500 . ?
C5 C6 1.4078(14) . ?
C6 N7 1.3804(13) . ?
N7 C8 1.4605(12) . ?
N7 N12 1.4047(11) . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C8 C9 1.5247(15) . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C9 C10 1.5262(16) . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C10 C11 1.5346(13) . ?
C11 H11 1.0000 . ?
C11 N12 1.4844(12) . ?
C11 C19 1.5223(13) . ?
N12 C13 1.4031(12) . ?
C13 O13 1.2084(12) . ?
C13 O14 1.3359(12) . ?
O14 C15 1.4860(11) . ?
C15 C16 1.5162(14) . ?
C15 C17 1.5171(15) . ?
C15 C18 1.5168(14) . ?
C16 H16A 0.9800 . ?
C16 H16B 0.9800 . ?
C16 H16C 0.9800 . ?
C17 H17A 0.9800 . ?
C17 H17B 0.9800 . ?
C17 H17C 0.9800 . ?
C18 H18A 0.9800 . ?
C18 H18B 0.9800 . ?
C18 H18C 0.9800 . ?
C19 C20 1.3928(14) . ?
C19 C24 1.3925(14) . ?
C20 H20 0.9500 . ?
C20 C21 1.3909(14) . ?
C21 H21 0.9500 . ?
C21 C22 1.3798(16) . ?
C22 H22 0.9500 . ?
C22 C23 1.3844(16) . ?
C23 H23 0.9500 . ?
C23 C24 1.3892(15) . ?
C24 H24 0.9500 . ?

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
C6 N1 C2 117.29(10) . . ?
N1 C2 H2 117.8 . . ?
N1 C2 C3 124.50(12) . . ?
C3 C2 H2 117.8 . . ?
C2 C3 H3 121.3 . . ?
C2 C3 C4 117.50(11) . . ?
C4 C3 H3 121.3 . . ?
C3 C4 H4 120.1 . . ?
C5 C4 C3 119.89(12) . . ?
C5 C4 H4 120.1 . . ?
C4 C5 H5 120.9 . . ?
C4 C5 C6 118.23(11) . . ?
C6 C5 H5 120.9 . . ?
N1 C6 C5 122.59(10) . . ?
N1 C6 N7 115.74(9) . . ?
N7 C6 C5 121.63(9) . . ?
C6 N7 C8 124.02(8) . . ?
C6 N7 N12 118.41(8) . . ?
N12 N7 C8 114.31(8) . . ?
N7 C8 H8A 109.9 . . ?
N7 C8 H8B 109.9 . . ?
N7 C8 C9 108.81(8) . . ?
H8A C8 H8B 108.3 . . ?
C9 C8 H8A 109.9 . . ?
C9 C8 H8B 109.9 . . ?
C8 C9 H9A 109.4 . . ?
C8 C9 H9B 109.4 . . ?
C8 C9 C10 110.95(8) . . ?
H9A C9 H9B 108.0 . . ?
C10 C9 H9A 109.4 . . ?
C10 C9 H9B 109.4 . . ?
C9 C10 H10A 109.2 . . ?
C9 C10 H10B 109.2 . . ?
C9 C10 C11 112.14(8) . . ?
H10A C10 H10B 107.9 . . ?
C11 C10 H10A 109.2 . . ?
C11 C10 H10B 109.2 . . ?
C10 C11 H11 107.4 . . ?
N12 C11 C10 107.70(8) . . ?
N12 C11 H11 107.4 . . ?
N12 C11 C19 110.79(8) . . ?
C19 C11 C10 115.85(8) . . ?
C19 C11 H11 107.4 . . ?
N7 N12 C11 111.85(7) . . ?
C13 N12 N7 118.11(7) . . ?
C13 N12 C11 115.32(8) . . ?
O13 C13 N12 122.00(9) . . ?
O13 C13 O14 126.66(9) . . ?
O14 C13 N12 111.28(8) . . ?
C13 O14 C15 119.38(7) . . ?
O14 C15 C16 102.45(8) . . ?
O14 C15 C17 109.43(8) . . ?
O14 C15 C18 110.49(8) . . ?
C16 C15 C17 111.09(9) . . ?
C16 C15 C18 110.17(9) . . ?
C18 C15 C17 112.74(9) . . ?
C15 C16 H16A 109.5 . . ?
C15 C16 H16B 109.5 . . ?
C15 C16 H16C 109.5 . . ?
H16A C16 H16B 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
C15 C17 H17A 109.5 . . ?
C15 C17 H17B 109.5 . . ?
C15 C17 H17C 109.5 . . ?
H17A C17 H17B 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
C15 C18 H18A 109.5 . . ?
C15 C18 H18B 109.5 . . ?
C15 C18 H18C 109.5 . . ?
H18A C18 H18B 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
C20 C19 C11 122.17(9) . . ?
C24 C19 C11 119.71(9) . . ?
C24 C19 C20 117.91(9) . . ?
C19 C20 H20 119.5 . . ?
C21 C20 C19 121.04(10) . . ?
C21 C20 H20 119.5 . . ?
C20 C21 H21 119.8 . . ?
C22 C21 C20 120.31(10) . . ?
C22 C21 H21 119.8 . . ?
C21 C22 H22 120.3 . . ?
C21 C22 C23 119.39(10) . . ?
C23 C22 H22 120.3 . . ?
C22 C23 H23 119.9 . . ?
C22 C23 C24 120.29(10) . . ?
C24 C23 H23 119.9 . . ?
C19 C24 H24 119.5 . . ?
C23 C24 C19 121.05(9) . . ?
C23 C24 H24 119.5 . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 2.480
_oxdiff_exptl_absorpt_empirical_full_min 0.671
####################################################################### 
# 
# 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_cd7
_database_code_depnum_ccdc_archive 'CCDC 1944269'
loop_
_audit_author_name
_audit_author_address
'Guy Clarkson'
;University of Warwick
United Kingdom
;
_audit_update_record             
;
2019-07-30 deposited with the CCDC.	2019-12-26 downloaded from the CCDC.
;
_audit_creation_date             2019-02-26
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3510 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         '2(C22 H21 N3 O2), 0.25(H2 O)'
_chemical_formula_sum            'C44 H42.50 N6 O4.25'
_chemical_formula_weight         723.34
_chemical_absolute_configuration rmad
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C20 H20 N2 O2'
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           4
_space_group_name_H-M_alt        'P 1 21 1'
_space_group_name_Hall           'P 2yb'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z'

_cell_length_a                   10.18405(5)
_cell_length_b                   9.71457(5)
_cell_length_c                   18.82762(9)
_cell_angle_alpha                90
_cell_angle_beta                 93.0169(4)
_cell_angle_gamma                90
_cell_volume                     1860.102(16)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    29109
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      73.3780
_cell_measurement_theta_min      4.3180
_shelx_estimated_absorpt_T_max   0.948
_shelx_estimated_absorpt_T_min   0.854
_exptl_absorpt_coefficient_mu    0.679
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.37742
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'CrysAlisPro 1.171.40.40a (Rigaku Oxford Diffraction, 2019) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm.'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.291
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             765
_exptl_crystal_size_max          0.24
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.08
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0176
_diffrn_reflns_av_unetI/netI     0.0104
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            35330
_diffrn_reflns_point_group_measured_fraction_full 0.992
_diffrn_reflns_point_group_measured_fraction_max 0.984
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         73.526
_diffrn_reflns_theta_min         4.347
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      150(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.3046
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_details      
'List of Runs (angles in degrees, time in seconds): # Type Start End Width tₑₓₚ ω θ κ φ Frames -------------------------------------------------------------------------- 1 ω -68.00 31.00 1.00 4.00 -- -41.82 45.00 110.00 99 2 ω -114.00 -14.00 1.00 4.00 -- -41.82 -57.00 150.00 100 3 ω 57.00 131.00 1.00 4.00 -- 41.82 178.00 60.00 74 4 ω 57.00 131.00 1.00 4.00 -- 41.82 178.00 -90.00 74 5 ω 17.00 116.00 1.00 4.00 -- 41.82 37.00 -30.00 99 6 ω 17.00 116.00 1.00 4.00 -- 41.82 37.00-120.00 99 7 ω 74.00 178.00 1.00 16.00 -- 107.00 77.00 120.00 104 8 ω 24.00 110.00 1.00 16.00 -- 107.00 -94.00 -30.00 86 9 ω 74.00 178.00 1.00 16.00 -- 107.00 77.00 150.00 104 10 ω 78.00 178.00 1.00 16.00 -- 107.00 61.00-120.00 100 11 ω 78.00 178.00 1.00 16.00 -- 107.00 61.00-150.00 100 12 ω 34.00 118.00 1.00 16.00 -- 107.00-125.00 -30.00 84 13 ω 94.00 178.00 1.00 16.00 -- 107.00 125.00 0.00 84 14 ω 74.00 178.00 1.00 16.00 -- 107.00 77.00-120.00 104 15 ω 74.00 178.00 1.00 16.00 -- 107.00 77.00-150.00 104 16 ω 78.00 178.00 1.00 16.00 -- 107.00 61.00-180.00 100 17 ω 35.00 136.00 1.00 16.00 -- 107.00 -61.00 -30.00 101 18 ω 74.00 178.00 1.00 16.00 -- 107.00 77.00-180.00 104 19 ω 94.00 178.00 1.00 16.00 -- 107.00 125.00 30.00 84 20 ω 81.00 178.00 1.00 16.00 -- 107.00 45.00 110.00 97 21 ω -114.00 -14.00 1.00 4.00 -- -41.82 -57.00 30.00 100 22 ω -118.00 -9.00 1.00 4.00 -- -41.82 -77.00 -30.00 109 23 ω -66.00 33.00 1.00 4.00 -- -41.82 37.00-120.00 99 24 ω -118.00 -9.00 1.00 4.00 -- -41.82 -77.00-150.00 109 25 ω -118.00 -9.00 1.00 4.00 -- -41.82 -77.00 90.00 109 26 ω 9.00 118.00 1.00 4.00 -- 41.82 77.00 -30.00 109 27 ω 81.00 178.00 1.00 16.00 -- 107.00 45.00 -30.00 97 28 ω 78.00 178.00 1.00 16.00 -- 107.00 61.00 60.00 100 29 ω 74.00 178.00 1.00 16.00 -- 107.00 77.00 -90.00 104 30 ω 74.00 178.00 1.00 16.00 -- 107.00 77.00 -30.00 104 31 ω 78.00 178.00 1.00 16.00 -- 107.00 61.00 30.00 100 32 ω 94.00 178.00 1.00 16.00 -- 107.00 125.00 -90.00 84'
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, AtlasS2'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0544785000
_diffrn_orient_matrix_UB_12      0.0722652000
_diffrn_orient_matrix_UB_13      0.0650689000
_diffrn_orient_matrix_UB_21      -0.1190733000
_diffrn_orient_matrix_UB_22      0.0511032000
_diffrn_orient_matrix_UB_23      -0.0465648000
_diffrn_orient_matrix_UB_31      -0.0761721000
_diffrn_orient_matrix_UB_32      -0.1315775000
_diffrn_orient_matrix_UB_33      0.0176563000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\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         0.859
_reflns_Friedel_fraction_full    0.983
_reflns_Friedel_fraction_max     0.969
_reflns_number_gt                7318
_reflns_number_total             7385
_reflns_odcompleteness_completeness 99.97
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     69.95
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.40.40a (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.40.40a (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.40a (Rigaku OD, 2019)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.135
_refine_diff_density_min         -0.195
_refine_diff_density_rms         0.035
_refine_ls_abs_structure_details 
;
 Flack x determined using 3337 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
Flack x: -0.05(3) Shelx
Hooft y: -0.04(2) Olex2
This is OK as the structure contains no heavy atoms in it, additionally the assignment of stereochemistry has 
been made by reference to an unchanging chiral centre in the synthetic procedure.
;
_refine_ls_abs_structure_Flack   -0.05(3)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.044
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     496
_refine_ls_number_reflns         7385
_refine_ls_number_restraints     37
_refine_ls_R_factor_all          0.0259
_refine_ls_R_factor_gt           0.0257
_refine_ls_restrained_S_all      1.053
_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)+(0.0408P)²+0.2075P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0679
_refine_ls_wR_factor_ref         0.0682
_refine_special_details          ?
_olex2_refinement_description    
;
A small amount of electron density was modelled as a partially occupied 
water 25% occupancy and is the source of the fractional formula. 
A RIGU restraint was used to give some of the atoms of one of the phenyl rings 
less extreme elliptical thermal parameters.

1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H,H) groups
2. Rigid body (RIGU) restrains
 C211, C212, C213, C214, C215, C216
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.001
3. Others
 Fixed Sof: O1(0.25) H1A(0.25) H1B(0.25)
4.a Free rotating group:
 O1(H1A,H1B)
4.b Ternary CH refined with riding coordinates:
 C110(H110), C210(H210)
4.c Secondary CH2 refined with riding coordinates:
 C109(H10A,H10B), C209(H20A,H20B), C208(H20C,H20D), C108(H10C,H10D)
4.d Aromatic/amide H refined with riding coordinates:
 C120(H120), C119(H119), C223(H223), C116(H116), C222(H222), C204(H204),
 C123(H123), C104(H104), C219(H219), C203(H203), C114(H114), C212(H212),
 C115(H115), C205(H205), C103(H103), C105(H105), C220(H220), C122(H122),
 C202(H202), C113(H113), C213(H213), C112(H112), C102(H102), C214(H214),
 C216(H216), C215(H215)
4.e Idealised Me refined as rotating group:
 C124(H12A,H12B,H12C), C224(H22A,H22B,H22C)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     ?
_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
O117 O 0.41260(11) 0.77152(12) 0.46571(6) 0.0331(3) Uani 1 1 d . . . . .
O217 O 0.23596(10) 0.30761(12) 0.03688(6) 0.0310(2) Uani 1 1 d . . . . .
O221 O -0.17916(11) -0.08596(13) 0.17113(6) 0.0361(3) Uani 1 1 d . . . . .
O121 O 0.83897(11) 0.39759(12) 0.32839(6) 0.0332(3) Uani 1 1 d . . . . .
N211 N 0.37638(11) 0.20520(12) 0.11693(6) 0.0234(2) Uani 1 1 d . . . . .
N110 N 0.28107(11) 0.69285(12) 0.37487(6) 0.0237(2) Uani 1 1 d . . . . .
N207 N 0.40053(11) 0.08383(12) 0.15796(6) 0.0242(2) Uani 1 1 d . . . . .
N201 N 0.50124(13) 0.00105(14) 0.26277(7) 0.0298(3) Uani 1 1 d . . . . .
N107 N 0.25730(12) 0.57855(12) 0.32830(7) 0.0257(3) Uani 1 1 d . . . . .
N101 N 0.16201(13) 0.51593(14) 0.21847(7) 0.0319(3) Uani 1 1 d . . . . .
C217 C 0.25149(14) 0.22658(15) 0.08641(7) 0.0246(3) Uani 1 1 d . . . . .
C218 C 0.13865(13) 0.15006(15) 0.11501(8) 0.0248(3) Uani 1 1 d . . . . .
C206 C 0.44800(13) 0.10996(15) 0.22922(7) 0.0238(3) Uani 1 1 d . . . . .
C120 C 0.64975(14) 0.53806(16) 0.29186(7) 0.0258(3) Uani 1 1 d . . . . .
H120 H 0.666194 0.529397 0.242855 0.031 Uiso 1 1 calc R . . . .
C117 C 0.40238(14) 0.70155(15) 0.41152(8) 0.0253(3) Uani 1 1 d . . . . .
C119 C 0.54158(14) 0.61189(16) 0.31274(8) 0.0256(3) Uani 1 1 d . . . . .
H119 H 0.483391 0.652432 0.277606 0.031 Uiso 1 1 calc R . . . .
C223 C 0.12264(14) 0.12165(16) 0.18629(8) 0.0266(3) Uani 1 1 d . . . . .
H223 H 0.185311 0.155253 0.221235 0.032 Uiso 1 1 calc R . . . .
C106 C 0.21728(13) 0.61742(15) 0.25741(8) 0.0251(3) Uani 1 1 d . . . . .
C116 C 0.18944(16) 0.97524(17) 0.39383(8) 0.0293(3) Uani 1 1 d . . . . .
H116 H 0.279410 0.959381 0.385561 0.035 Uiso 1 1 calc R . . . .
C222 C 0.01653(14) 0.04495(17) 0.20726(8) 0.0271(3) Uani 1 1 d . . . . .
H222 H 0.005927 0.027398 0.256262 0.033 Uiso 1 1 calc R . . . .
C110 C 0.16245(14) 0.71993(15) 0.41662(8) 0.0259(3) Uani 1 1 d . . . . .
H110 H 0.188286 0.705682 0.468071 0.031 Uiso 1 1 calc R . . . .
C221 C -0.07445(14) -0.00621(16) 0.15600(8) 0.0272(3) Uani 1 1 d . . . . .
C111 C 0.10848(14) 0.86455(16) 0.40819(7) 0.0258(3) Uani 1 1 d . . . . .
C204 C 0.47261(15) 0.25001(18) 0.33295(8) 0.0317(3) Uani 1 1 d . . . . .
H204 H 0.462265 0.334862 0.357108 0.038 Uiso 1 1 calc R . . . .
C121 C 0.73404(14) 0.47673(15) 0.34333(8) 0.0249(3) Uani 1 1 d . . . . .
C123 C 0.60615(15) 0.56984(18) 0.43523(8) 0.0308(3) Uani 1 1 d . . . . .
H123 H 0.592756 0.582694 0.484345 0.037 Uiso 1 1 calc R . . . .
C104 C 0.20660(16) 0.77308(18) 0.15966(8) 0.0336(3) Uani 1 1 d . . . . .
H104 H 0.221905 0.860929 0.139521 0.040 Uiso 1 1 calc R . . . .
C118 C 0.51710(14) 0.62742(15) 0.38417(8) 0.0247(3) Uani 1 1 d . . . . .
C219 C 0.04302(14) 0.10254(18) 0.06476(8) 0.0311(3) Uani 1 1 d . . . . .
H219 H 0.050276 0.125159 0.016031 0.037 Uiso 1 1 calc R . . . .
C210 C 0.49073(14) 0.23384(17) 0.07198(7) 0.0276(3) Uani 1 1 d . . . . .
H210 H 0.457839 0.232148 0.020998 0.033 Uiso 1 1 calc R . . . .
C211 C 0.55372(15) 0.37283(19) 0.08668(8) 0.0311(3) Uani 1 1 d . U . . .
C203 C 0.53026(16) 0.13841(19) 0.36838(8) 0.0347(4) Uani 1 1 d . . . . .
H203 H 0.560793 0.145257 0.416807 0.042 Uiso 1 1 calc R . . . .
C114 C 0.00944(19) 1.13379(19) 0.40327(9) 0.0418(4) Uani 1 1 d . . . . .
H114 H -0.024028 1.225083 0.401855 0.050 Uiso 1 1 calc R . . . .
C212 C 0.47941(17) 0.48557(18) 0.10614(8) 0.0345(3) Uani 1 1 d . U . . .
H212 H 0.388673 0.473609 0.113840 0.041 Uiso 1 1 calc R . . . .
C115 C 0.14041(19) 1.10901(18) 0.39139(8) 0.0364(4) Uani 1 1 d . . . . .
H115 H 0.196999 1.183585 0.381552 0.044 Uiso 1 1 calc R . . . .
C205 C 0.43017(15) 0.23706(16) 0.26207(8) 0.0278(3) Uani 1 1 d . . . . .
H205 H 0.390344 0.312040 0.236718 0.033 Uiso 1 1 calc R . . . .
C103 C 0.14825(17) 0.6693(2) 0.11829(9) 0.0381(4) Uani 1 1 d . . . . .
H103 H 0.122895 0.684303 0.069629 0.046 Uiso 1 1 calc R . . . .
C105 C 0.24231(15) 0.74782(16) 0.23038(8) 0.0283(3) Uani 1 1 d . . . . .
H105 H 0.282646 0.817226 0.259616 0.034 Uiso 1 1 calc R . . . .
C220 C -0.06119(15) 0.02379(19) 0.08446(8) 0.0330(3) Uani 1 1 d . . . . .
H220 H -0.123727 -0.009904 0.049476 0.040 Uiso 1 1 calc R . . . .
C109 C 0.06830(15) 0.60305(17) 0.39308(9) 0.0331(3) Uani 1 1 d . . . . .
H10A H 0.020508 0.567250 0.433639 0.040 Uiso 1 1 calc R . . . .
H10B H 0.003848 0.634178 0.355261 0.040 Uiso 1 1 calc R . . . .
C122 C 0.71240(15) 0.49517(18) 0.41510(8) 0.0314(3) Uani 1 1 d . . . . .
H122 H 0.771378 0.455929 0.450268 0.038 Uiso 1 1 calc R . . . .
C202 C 0.54181(16) 0.01763(19) 0.33124(9) 0.0341(3) Uani 1 1 d . . . . .
H202 H 0.580970 -0.058944 0.355536 0.041 Uiso 1 1 calc R . . . .
C209 C 0.57952(15) 0.10774(19) 0.08522(9) 0.0340(3) Uani 1 1 d . . . . .
H20A H 0.616196 0.075519 0.040482 0.041 Uiso 1 1 calc R . . . .
H20B H 0.652789 0.128858 0.120172 0.041 Uiso 1 1 calc R . . . .
C113 C -0.07210(17) 1.0243(2) 0.41720(10) 0.0425(4) Uani 1 1 d . . . . .
H113 H -0.162223 1.040808 0.424851 0.051 Uiso 1 1 calc R . . . .
C208 C 0.48732(16) 0.00101(17) 0.11438(9) 0.0324(3) Uani 1 1 d . . . . .
H20C H 0.436394 -0.046570 0.075447 0.039 Uiso 1 1 calc R . . . .
H20D H 0.536571 -0.068193 0.143754 0.039 Uiso 1 1 calc R . . . .
C213 C 0.5355(2) 0.6154(2) 0.11452(9) 0.0457(4) Uani 1 1 d . U . . .
H213 H 0.482865 0.690972 0.127807 0.055 Uiso 1 1 calc R . . . .
C112 C -0.02373(16) 0.89034(19) 0.42016(9) 0.0350(4) Uani 1 1 d . . . . .
H112 H -0.080605 0.816211 0.430337 0.042 Uiso 1 1 calc R . . . .
C102 C 0.12833(16) 0.54400(19) 0.14996(9) 0.0370(4) Uani 1 1 d . . . . .
H102 H 0.088335 0.472917 0.121725 0.044 Uiso 1 1 calc R . . . .
C108 C 0.16079(16) 0.49500(16) 0.36523(9) 0.0328(3) Uani 1 1 d . . . . .
H10C H 0.203928 0.441550 0.404684 0.039 Uiso 1 1 calc R . . . .
H10D H 0.113426 0.430992 0.331952 0.039 Uiso 1 1 calc R . . . .
C214 C 0.6670(2) 0.6354(3) 0.10369(10) 0.0556(5) Uani 1 1 d . U . . .
H214 H 0.705198 0.724281 0.108808 0.067 Uiso 1 1 calc R . . . .
C124 C 0.85482(18) 0.3639(2) 0.25556(10) 0.0445(4) Uani 1 1 d . . . . .
H12A H 0.867734 0.448553 0.228457 0.067 Uiso 1 1 calc GR . . . .
H12B H 0.776045 0.316194 0.236239 0.067 Uiso 1 1 calc GR . . . .
H12C H 0.931568 0.303974 0.251975 0.067 Uiso 1 1 calc GR . . . .
C216 C 0.68717(17) 0.3928(2) 0.07624(10) 0.0450(4) Uani 1 1 d . U . . .
H216 H 0.740368 0.317688 0.063052 0.054 Uiso 1 1 calc R . . . .
C215 C 0.7421(2) 0.5240(3) 0.08530(11) 0.0576(5) Uani 1 1 d . U . . .
H215 H 0.833121 0.536752 0.078646 0.069 Uiso 1 1 calc R . . . .
C224 C -0.18746(18) -0.1320(2) 0.24257(10) 0.0455(5) Uani 1 1 d . . . . .
H22A H -0.265344 -0.190397 0.246041 0.068 Uiso 1 1 calc GR . . . .
H22B H -0.194256 -0.052355 0.274087 0.068 Uiso 1 1 calc GR . . . .
H22C H -0.108491 -0.185032 0.256725 0.068 Uiso 1 1 calc GR . . . .
O1 O 0.6605(6) 0.8797(6) 0.4956(3) 0.0488(12) Uiso 0.25 1 d . . P . .
H1A H 0.708082 0.809388 0.489208 0.073 Uiso 0.25 1 d G . P . .
H1B H 0.579893 0.856611 0.492217 0.073 Uiso 0.25 1 d G . P . .


_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
O117 C117 1.2258(18) . ?
O217 C217 1.2243(18) . ?
O221 C221 1.3603(19) . ?
O221 C224 1.424(2) . ?
O121 C121 1.3579(18) . ?
O121 C124 1.427(2) . ?
N211 N207 1.4238(17) . ?
N211 C217 1.3835(18) . ?
N211 C210 1.5012(17) . ?
N110 N107 1.4275(16) . ?
N110 C117 1.3857(18) . ?
N110 C110 1.4988(18) . ?
N207 C206 1.4249(18) . ?
N207 C208 1.4758(19) . ?
N201 C206 1.3328(19) . ?
N201 C202 1.343(2) . ?
N107 C106 1.4258(19) . ?
N107 C108 1.476(2) . ?
N101 C106 1.3353(19) . ?
N101 C102 1.345(2) . ?
C217 C218 1.493(2) . ?
C218 C223 1.388(2) . ?
C218 C219 1.400(2) . ?
C206 C205 1.397(2) . ?
C120 C119 1.389(2) . ?
C120 C121 1.394(2) . ?
C117 C118 1.487(2) . ?
C119 C118 1.389(2) . ?
C223 C222 1.387(2) . ?
C106 C105 1.394(2) . ?
C116 C111 1.390(2) . ?
C116 C115 1.392(2) . ?
C222 C221 1.394(2) . ?
C110 C111 1.514(2) . ?
C110 C109 1.536(2) . ?
C221 C220 1.392(2) . ?
C111 C112 1.399(2) . ?
C204 C203 1.387(3) . ?
C204 C205 1.387(2) . ?
C121 C122 1.392(2) . ?
C123 C118 1.403(2) . ?
C123 C122 1.373(2) . ?
C104 C103 1.389(2) . ?
C104 C105 1.384(2) . ?
C219 C220 1.375(2) . ?
C210 C211 1.514(2) . ?
C210 C209 1.535(2) . ?
C211 C212 1.391(3) . ?
C211 C216 1.397(2) . ?
C203 C202 1.374(3) . ?
C114 C115 1.385(3) . ?
C114 C113 1.383(3) . ?
C212 C213 1.391(2) . ?
C103 C102 1.375(3) . ?
C109 C108 1.522(2) . ?
C209 C208 1.521(2) . ?
C113 C112 1.392(3) . ?
C213 C214 1.379(3) . ?
C214 C215 1.379(4) . ?
C216 C215 1.399(3) . ?

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
C221 O221 C224 117.57(13) . . ?
C121 O121 C124 117.31(12) . . ?
N207 N211 C210 110.02(11) . . ?
C217 N211 N207 118.58(11) . . ?
C217 N211 C210 117.48(11) . . ?
N107 N110 C110 110.08(11) . . ?
C117 N110 N107 118.12(11) . . ?
C117 N110 C110 116.76(11) . . ?
N211 N207 C206 113.81(11) . . ?
N211 N207 C208 103.96(11) . . ?
C206 N207 C208 115.92(11) . . ?
C206 N201 C202 117.18(14) . . ?
N110 N107 C108 103.53(11) . . ?
C106 N107 N110 113.56(11) . . ?
C106 N107 C108 114.95(12) . . ?
C106 N101 C102 117.11(15) . . ?
O217 C217 N211 119.47(13) . . ?
O217 C217 C218 121.60(13) . . ?
N211 C217 C218 118.93(12) . . ?
C223 C218 C217 125.42(13) . . ?
C223 C218 C219 118.36(13) . . ?
C219 C218 C217 116.22(13) . . ?
N201 C206 N207 114.47(13) . . ?
N201 C206 C205 123.43(13) . . ?
C205 C206 N207 121.92(13) . . ?
C119 C120 C121 119.51(13) . . ?
O117 C117 N110 118.87(13) . . ?
O117 C117 C118 121.52(13) . . ?
N110 C117 C118 119.61(12) . . ?
C120 C119 C118 121.05(13) . . ?
C222 C223 C218 120.99(13) . . ?
N101 C106 N107 114.20(13) . . ?
N101 C106 C105 123.40(14) . . ?
C105 C106 N107 122.26(13) . . ?
C111 C116 C115 120.87(15) . . ?
C223 C222 C221 119.61(13) . . ?
N110 C110 C111 113.96(12) . . ?
N110 C110 C109 103.12(12) . . ?
C111 C110 C109 115.98(12) . . ?
O221 C221 C222 123.92(14) . . ?
O221 C221 C220 116.04(13) . . ?
C220 C221 C222 120.04(14) . . ?
C116 C111 C110 121.50(13) . . ?
C116 C111 C112 118.58(15) . . ?
C112 C111 C110 119.76(14) . . ?
C205 C204 C203 119.64(15) . . ?
O121 C121 C120 124.09(13) . . ?
O121 C121 C122 116.13(13) . . ?
C122 C121 C120 119.78(13) . . ?
C122 C123 C118 120.81(14) . . ?
C105 C104 C103 119.60(16) . . ?
C119 C118 C117 124.90(13) . . ?
C119 C118 C123 118.54(13) . . ?
C123 C118 C117 116.56(13) . . ?
C220 C219 C218 121.36(14) . . ?
N211 C210 C211 113.33(12) . . ?
N211 C210 C209 103.20(12) . . ?
C211 C210 C209 116.21(12) . . ?
C212 C211 C210 121.27(14) . . ?
C212 C211 C216 118.31(17) . . ?
C216 C211 C210 120.29(17) . . ?
C202 C203 C204 117.91(14) . . ?
C113 C114 C115 119.35(16) . . ?
C213 C212 C211 121.21(17) . . ?
C114 C115 C116 120.25(17) . . ?
C204 C205 C206 117.71(15) . . ?
C102 C103 C104 117.92(15) . . ?
C104 C105 C106 117.95(14) . . ?
C219 C220 C221 119.56(14) . . ?
C108 C109 C110 102.76(12) . . ?
C123 C122 C121 120.22(13) . . ?
N201 C202 C203 124.12(15) . . ?
C208 C209 C210 103.48(12) . . ?
C114 C113 C112 120.79(16) . . ?
N207 C208 C209 103.20(12) . . ?
C214 C213 C212 120.5(2) . . ?
C113 C112 C111 120.16(17) . . ?
N101 C102 C103 124.01(15) . . ?
N107 C108 C109 102.86(12) . . ?
C213 C214 C215 118.86(19) . . ?
C211 C216 C215 119.7(2) . . ?
C214 C215 C216 121.44(18) . . ?

_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 2.001
_oxdiff_exptl_absorpt_empirical_full_min 0.695
####################################################################### 
# 
# 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_cd5
_database_code_depnum_ccdc_archive 'CCDC 1944267'
loop_
_audit_author_name
_audit_author_address
'Guy Clarkson'
;University of Warwick
United Kingdom
;
_audit_update_record             
;
2019-07-30 deposited with the CCDC.	2019-12-26 downloaded from the CCDC.
;
_audit_creation_date             2018-04-04
_audit_creation_method           
;
Olex2 1.2
(compiled 2017.08.10 svn.r3458 for OlexSys, GUI svn.r5381)
;
_shelx_SHELXL_version_number     2018/3
__publ_contact_author_name       'Professor Michael Shipman'
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C24 H21 F3 N2 O4 S'
_chemical_formula_sum            'C24 H21 F3 N2 O4 S'
_chemical_formula_weight         490.49
_chemical_absolute_configuration ad
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C20 H20 N2 O3 S F3'
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'
F F 0.0727 0.0534 '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'
S S 0.3331 0.5567 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'

_cell_length_a                   32.8358(3)
_cell_length_b                   11.60538(10)
_cell_length_c                   5.85758(7)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2232.16(4)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    42722
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      73.2910
_cell_measurement_theta_min      3.9570
_shelx_estimated_absorpt_T_max   0.964
_shelx_estimated_absorpt_T_min   0.610
_exptl_absorpt_coefficient_mu    1.827
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.24902
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.46 (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.460
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1016
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.02
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0917
_diffrn_reflns_av_unetI/netI     0.0256
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       40
_diffrn_reflns_limit_h_min       -40
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       7
_diffrn_reflns_limit_l_min       -6
_diffrn_reflns_number            72297
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         73.525
_diffrn_reflns_theta_min         4.040
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      150(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.3046
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -64.00  31.00   1.00    3.00    --  -41.61  37.00  30.00   95
  2  ω   -127.00 -34.00   1.00    3.00    --  -41.61 178.00  90.00   93
  3  ω   -112.00 -15.00   1.00    3.00    --  -41.61 -57.00  60.00   97
  4  ω   -115.00 -19.00   1.00    3.00    --  -41.61 -37.00-150.00   96
  5  ω     25.00 109.00   1.00   12.00    --  106.00 -94.00  60.00   84
  6  ω     82.00 178.00   1.00   12.00    --  106.00  30.00   0.00   96
  7  ω     82.00 177.00   1.00   12.00    --  106.00  45.00-180.00   95
  8  ω     78.00 176.00   1.00   12.00    --  106.00  61.00  90.00   98
  9  ω     34.00 121.00   1.00   12.00    --  106.00-125.00 -30.00   87
 10  ω     31.00 116.00   1.00   12.00    --  106.00-112.00-148.00   85
 11  ω     34.00 121.00   1.00   12.00    --  106.00-125.00   0.00   87
 12  ω     75.00 178.00   1.00   12.00    --  106.00  77.00-120.00  103
 13  ω     82.00 177.00   1.00   12.00    --  106.00  45.00  30.00   95
 14  ω     32.00 137.00   1.00   12.00    --  106.00 -77.00 120.00  105
 15  ω     35.00 130.00   1.00   12.00    --  106.00 -45.00 150.00   95
 16  ω     32.00 137.00   1.00   12.00    --  106.00 -77.00 -30.00  105
 17  ω   -112.00 -15.00   1.00    3.00    --  -41.61 -57.00 -30.00   97
 18  ω   -112.00 -15.00   1.00    3.00    --  -41.61 -57.00 150.00   97
 19  ω   -115.00 -10.00   1.00    3.00    --  -41.61 -77.00 -90.00  105
 20  ω    -68.00  29.00   1.00    3.00    --  -41.61  57.00 120.00   97
 21  ω     75.00 178.00   1.00   12.00    --  106.00  77.00-150.00  103
 22  ω     78.00 176.00   1.00   12.00    --  106.00  61.00-150.00   98
 23  ω     75.00 178.00   1.00   12.00    --  106.00  77.00 120.00  103
 24  ω     75.00 178.00   1.00   12.00    --  106.00  77.00 -60.00  103
 25  ω     82.00 177.00   1.00   12.00    --  106.00  45.00 -60.00   95
 26  ω     78.00 176.00   1.00   12.00    --  106.00  61.00  30.00   98
 27  ω     75.00 178.00   1.00   12.00    --  106.00  77.00 -30.00  103
 28  ω     78.00 176.00   1.00   12.00    --  106.00  61.00-180.00   98
 29  ω     78.00 176.00   1.00   12.00    --  106.00  61.00 120.00   98
 30  ω     78.00 176.00   1.00   12.00    --  106.00  61.00 150.00   98
 31  ω     75.00 178.00   1.00   12.00    --  106.00  77.00 -90.00  103
 32  ω     78.00 176.00   1.00   12.00    --  106.00  61.00  60.00   98
 33  ω   -112.00 -62.00   1.00    3.00    --  -41.61-143.00 140.00   50
 34  ω   -115.00 -10.00   1.00    3.00    --  -41.61 -77.00  60.00  105
 35  ω   -115.00 -10.00   1.00    3.00    --  -41.61 -77.00   0.00  105
 36  ω   -115.00 -10.00   1.00    3.00    --  -41.61 -77.00-180.00  105
 37  ω     75.00 178.00   1.00   12.00    --  106.00  77.00  90.00  103
 38  ω     75.00 178.00   1.00   12.00    --  106.00  77.00-180.00  103
 39  ω     78.00 176.00   1.00   12.00    --  106.00  61.00   0.00   98
 40  ω     78.00 176.00   1.00   12.00    --  106.00  61.00 -90.00   98
 41  ω     75.00 178.00   1.00   12.00    --  106.00  77.00  30.00  103
 42  ω     78.00 176.00   1.00   12.00    --  106.00  61.00 -60.00   98
 43  ω     78.00 176.00   1.00   12.00    --  106.00  61.00-120.00   98
 44  ω     35.00 130.00   1.00   12.00    --  106.00 -45.00 -30.00   95
 45  ω     78.00 176.00   1.00   12.00    --  106.00  61.00 -30.00   98
 46  ω     35.00 122.00   1.00   12.00    --  106.00-127.00 -49.00   87
 47  ω     75.00 178.00   1.00   12.00    --  106.00  77.00   0.00  103
 48  ω     75.00 178.00   1.00   12.00    --  106.00  77.00  60.00  103
 49  ω   -115.00 -10.00   1.00    3.00    --  -41.61 -77.00 150.00  105
 50  ω   -115.00 -19.00   1.00    3.00    --  -41.61 -37.00   0.00   96
 51  ω   -115.00 -10.00   1.00    3.00    --  -41.61 -77.00-150.00  105
 52  ω     57.00 128.00   1.00    3.00    --   41.61 178.00 -30.00   71
 53  ω     75.00 169.00   1.00   12.00    --  106.00  77.00 150.00   94
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, AtlasS2'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0458786000
_diffrn_orient_matrix_UB_12      -0.0277282000
_diffrn_orient_matrix_UB_13      0.0031571000
_diffrn_orient_matrix_UB_21      0.0094991000
_diffrn_orient_matrix_UB_22      -0.1272232000
_diffrn_orient_matrix_UB_23      -0.0528252000
_diffrn_orient_matrix_UB_31      0.0025203000
_diffrn_orient_matrix_UB_32      -0.0257326000
_diffrn_orient_matrix_UB_33      0.2576446000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\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         0.713
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     0.996
_reflns_number_gt                4477
_reflns_number_total             4499
_reflns_odcompleteness_completeness 99.92
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     72.42
_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 1.171.38.46 (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         1.096
_refine_diff_density_min         -0.510
_refine_diff_density_rms         0.082
_refine_ls_abs_structure_details 
;
 Flack x determined using 1810 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).

Flack x: 0.015(9) Shelx2018
Hooft y: 0.009(5) Olex2
;
_refine_ls_abs_structure_Flack   0.015(9)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.093
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     308
_refine_ls_number_reflns         4499
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0618
_refine_ls_R_factor_gt           0.0616
_refine_ls_restrained_S_all      1.093
_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)+(0.0243P)²+7.3814P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1477
_refine_ls_wR_factor_ref         0.1478
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C12(H12)
2.b Secondary CH2 refined with riding coordinates:
 C11(H11A,H11B), C7(H7A,H7B)
2.c Aromatic/amide H refined with riding coordinates:
 C22(H22), C26(H26), C14(H14), C18(H18), C17(H17), C15(H15), C5(H5), C23(H23),
 C25(H25), C1(H1), C4(H4), C2(H2), C3(H3)
2.d Idealised Me refined as rotating group:
 C27(H27A,H27B,H27C)
;
_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
S20 S 0.46863(4) 0.60292(11) 0.2908(2) 0.0206(3) Uani 1 1 d . . . . .
O8 O 0.43038(11) 0.8653(3) 0.1862(6) 0.0222(8) Uani 1 1 d . . . . .
O20A O 0.49369(11) 0.5146(3) 0.3889(7) 0.0280(9) Uani 1 1 d . . . . .
O20B O 0.46694(12) 0.6136(3) 0.0481(6) 0.0295(8) Uani 1 1 d . . . . .
O9 O 0.43038(13) 0.9824(3) 0.4973(7) 0.0304(9) Uani 1 1 d . . . . .
N10 N 0.45890(13) 0.8059(4) 0.5137(7) 0.0201(9) Uani 1 1 d . . . . .
N12 N 0.48734(13) 0.7297(4) 0.3906(7) 0.0195(9) Uani 1 1 d . . . . .
F19C F 0.69375(13) 0.7409(6) 0.1826(10) 0.0775(17) Uani 1 1 d . . . . .
F19B F 0.70956(12) 0.7156(5) 0.5278(11) 0.0822(19) Uani 1 1 d . . . . .
F19A F 0.69803(12) 0.8839(4) 0.3990(11) 0.0762(18) Uani 1 1 d . . . . .
C12 C 0.51453(16) 0.7280(4) 0.5966(8) 0.0196(10) Uani 1 1 d . . . . .
H12 H 0.509872 0.656906 0.689351 0.023 Uiso 1 1 calc R . . . .
C13 C 0.55871(16) 0.7439(4) 0.5468(9) 0.0186(10) Uani 1 1 d . . . . .
C11 C 0.48965(15) 0.8305(4) 0.6922(9) 0.0216(10) Uani 1 1 d . . . . .
H11A H 0.479692 0.818865 0.850031 0.026 Uiso 1 1 calc R . . . .
H11B H 0.503237 0.906155 0.675372 0.026 Uiso 1 1 calc R . . . .
C21 C 0.41825(15) 0.5902(4) 0.3928(9) 0.0223(11) Uani 1 1 d . . . . .
C22 C 0.41085(17) 0.5418(5) 0.6036(10) 0.0264(12) Uani 1 1 d . . . . .
H22 H 0.432771 0.517676 0.697970 0.032 Uiso 1 1 calc R . . . .
C26 C 0.38681(16) 0.6266(5) 0.2550(10) 0.0273(12) Uani 1 1 d . . . . .
H26 H 0.392409 0.660580 0.110870 0.033 Uiso 1 1 calc R . . . .
C7 C 0.40686(17) 0.9509(5) 0.0589(9) 0.0262(12) Uani 1 1 d . . . . .
H7A H 0.416628 0.953387 -0.100951 0.031 Uiso 1 1 calc R . . . .
H7B H 0.411209 1.027909 0.127181 0.031 Uiso 1 1 calc R . . . .
C16 C 0.64136(16) 0.7649(5) 0.4518(11) 0.0280(12) Uani 1 1 d . . . . .
C9 C 0.43957(15) 0.8949(5) 0.3996(9) 0.0207(10) Uani 1 1 d . . . . .
C14 C 0.58768(16) 0.7076(4) 0.7054(10) 0.0237(11) Uani 1 1 d . . . . .
H14 H 0.579040 0.675790 0.846757 0.028 Uiso 1 1 calc R . . . .
C18 C 0.57155(16) 0.7940(4) 0.3430(9) 0.0238(11) Uani 1 1 d . . . . .
H18 H 0.552092 0.821317 0.235917 0.029 Uiso 1 1 calc R . . . .
C17 C 0.61273(16) 0.8037(5) 0.2971(11) 0.0280(12) Uani 1 1 d . . . . .
H17 H 0.621415 0.837532 0.157638 0.034 Uiso 1 1 calc R . . . .
C6 C 0.36253(18) 0.9233(5) 0.0612(9) 0.0270(12) Uani 1 1 d . . . . .
C15 C 0.62878(17) 0.7175(5) 0.6594(10) 0.0277(12) Uani 1 1 d . . . . .
H15 H 0.648332 0.692206 0.767929 0.033 Uiso 1 1 calc R . . . .
C5 C 0.33796(18) 0.9505(6) 0.2495(11) 0.0362(14) Uani 1 1 d . . . . .
H5 H 0.349612 0.988432 0.377468 0.043 Uiso 1 1 calc R . . . .
C23 C 0.37114(18) 0.5290(5) 0.6752(12) 0.0329(13) Uani 1 1 d . . . . .
H23 H 0.365795 0.496095 0.820690 0.039 Uiso 1 1 calc R . . . .
C25 C 0.34696(17) 0.6134(5) 0.3281(12) 0.0363(14) Uani 1 1 d . . . . .
H25 H 0.325216 0.638636 0.233559 0.044 Uiso 1 1 calc R . . . .
C24 C 0.33857(17) 0.5636(5) 0.5376(13) 0.0359(15) Uani 1 1 d . . . . .
C1 C 0.3447(2) 0.8650(6) -0.1203(10) 0.0384(15) Uani 1 1 d . . . . .
H1 H 0.360864 0.842679 -0.247168 0.046 Uiso 1 1 calc R . . . .
C19 C 0.68557(19) 0.7757(6) 0.3942(13) 0.0381(15) Uani 1 1 d . . . . .
C4 C 0.2971(2) 0.9227(7) 0.2513(13) 0.0471(18) Uani 1 1 d . . . . .
H4 H 0.280733 0.942170 0.379460 0.057 Uiso 1 1 calc R . . . .
C2 C 0.3037(2) 0.8391(7) -0.1184(13) 0.052(2) Uani 1 1 d . . . . .
H2 H 0.291703 0.801859 -0.246268 0.062 Uiso 1 1 calc R . . . .
C27 C 0.2952(2) 0.5441(8) 0.6141(16) 0.057(2) Uani 1 1 d . . . . .
H27A H 0.287782 0.463248 0.589225 0.086 Uiso 1 1 calc GR . . . .
H27B H 0.276887 0.593797 0.525887 0.086 Uiso 1 1 calc GR . . . .
H27C H 0.292720 0.562552 0.776752 0.086 Uiso 1 1 calc GR . . . .
C3 C 0.2800(2) 0.8669(7) 0.0672(14) 0.0487(19) Uani 1 1 d . . . . .
H3 H 0.251878 0.847639 0.068517 0.058 Uiso 1 1 calc R . . . .


_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
S20 O20A 1.435(4) . ?
S20 O20B 1.428(4) . ?
S20 N12 1.698(4) . ?
S20 C21 1.765(5) . ?
O8 C7 1.462(6) . ?
O8 C9 1.331(6) . ?
O9 C9 1.204(6) . ?
N10 N12 1.475(6) . ?
N10 C11 1.481(7) . ?
N10 C9 1.384(7) . ?
N12 C12 1.501(6) . ?
F19C C19 1.331(9) . ?
F19B C19 1.311(8) . ?
F19A C19 1.320(8) . ?
C12 H12 1.0000 . ?
C12 C13 1.491(7) . ?
C12 C11 1.547(7) . ?
C13 C14 1.394(7) . ?
C13 C18 1.393(7) . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
C21 C22 1.378(8) . ?
C21 C26 1.377(7) . ?
C22 H22 0.9500 . ?
C22 C23 1.378(8) . ?
C26 H26 0.9500 . ?
C26 C25 1.385(8) . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C7 C6 1.491(8) . ?
C16 C17 1.381(8) . ?
C16 C15 1.397(9) . ?
C16 C19 1.496(8) . ?
C14 H14 0.9500 . ?
C14 C15 1.381(8) . ?
C18 H18 0.9500 . ?
C18 C17 1.383(8) . ?
C17 H17 0.9500 . ?
C6 C5 1.402(8) . ?
C6 C1 1.390(8) . ?
C15 H15 0.9500 . ?
C5 H5 0.9500 . ?
C5 C4 1.381(9) . ?
C23 H23 0.9500 . ?
C23 C24 1.398(9) . ?
C25 H25 0.9500 . ?
C25 C24 1.384(10) . ?
C24 C27 1.511(8) . ?
C1 H1 0.9500 . ?
C1 C2 1.379(10) . ?
C4 H4 0.9500 . ?
C4 C3 1.377(11) . ?
C2 H2 0.9500 . ?
C2 C3 1.375(11) . ?
C27 H27A 0.9800 . ?
C27 H27B 0.9800 . ?
C27 H27C 0.9800 . ?
C3 H3 0.9500 . ?

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
O20A S20 N12 105.9(2) . . ?
O20A S20 C21 110.0(3) . . ?
O20B S20 O20A 118.9(3) . . ?
O20B S20 N12 106.4(2) . . ?
O20B S20 C21 107.9(3) . . ?
N12 S20 C21 107.2(2) . . ?
C9 O8 C7 115.0(4) . . ?
N12 N10 C11 91.7(3) . . ?
C9 N10 N12 120.1(4) . . ?
C9 N10 C11 120.7(4) . . ?
N10 N12 S20 117.3(3) . . ?
N10 N12 C12 89.5(3) . . ?
C12 N12 S20 118.7(3) . . ?
N12 C12 H12 110.9 . . ?
N12 C12 C11 88.1(4) . . ?
C13 C12 N12 114.8(4) . . ?
C13 C12 H12 110.9 . . ?
C13 C12 C11 119.3(4) . . ?
C11 C12 H12 110.9 . . ?
C14 C13 C12 119.8(5) . . ?
C18 C13 C12 120.9(5) . . ?
C18 C13 C14 119.4(5) . . ?
N10 C11 C12 87.5(4) . . ?
N10 C11 H11A 114.1 . . ?
N10 C11 H11B 114.1 . . ?
C12 C11 H11A 114.1 . . ?
C12 C11 H11B 114.1 . . ?
H11A C11 H11B 111.2 . . ?
C22 C21 S20 120.2(4) . . ?
C26 C21 S20 118.6(4) . . ?
C26 C21 C22 121.2(5) . . ?
C21 C22 H22 120.5 . . ?
C21 C22 C23 119.0(5) . . ?
C23 C22 H22 120.5 . . ?
C21 C26 H26 120.2 . . ?
C21 C26 C25 119.5(6) . . ?
C25 C26 H26 120.2 . . ?
O8 C7 H7A 109.3 . . ?
O8 C7 H7B 109.3 . . ?
O8 C7 C6 111.4(4) . . ?
H7A C7 H7B 108.0 . . ?
C6 C7 H7A 109.3 . . ?
C6 C7 H7B 109.3 . . ?
C17 C16 C15 119.9(5) . . ?
C17 C16 C19 119.0(6) . . ?
C15 C16 C19 121.1(5) . . ?
O8 C9 N10 111.4(4) . . ?
O9 C9 O8 127.4(5) . . ?
O9 C9 N10 121.0(5) . . ?
C13 C14 H14 119.6 . . ?
C15 C14 C13 120.8(5) . . ?
C15 C14 H14 119.6 . . ?
C13 C18 H18 120.1 . . ?
C17 C18 C13 119.8(5) . . ?
C17 C18 H18 120.1 . . ?
C16 C17 C18 120.7(6) . . ?
C16 C17 H17 119.6 . . ?
C18 C17 H17 119.6 . . ?
C5 C6 C7 121.4(5) . . ?
C1 C6 C7 120.7(5) . . ?
C1 C6 C5 117.9(6) . . ?
C16 C15 H15 120.3 . . ?
C14 C15 C16 119.4(5) . . ?
C14 C15 H15 120.3 . . ?
C6 C5 H5 119.6 . . ?
C4 C5 C6 120.9(6) . . ?
C4 C5 H5 119.6 . . ?
C22 C23 H23 119.4 . . ?
C22 C23 C24 121.1(6) . . ?
C24 C23 H23 119.4 . . ?
C26 C25 H25 119.7 . . ?
C24 C25 C26 120.5(6) . . ?
C24 C25 H25 119.7 . . ?
C23 C24 C27 120.5(7) . . ?
C25 C24 C23 118.6(5) . . ?
C25 C24 C27 120.9(6) . . ?
C6 C1 H1 119.6 . . ?
C2 C1 C6 120.8(6) . . ?
C2 C1 H1 119.6 . . ?
F19C C19 C16 112.3(6) . . ?
F19B C19 F19C 105.8(6) . . ?
F19B C19 F19A 107.9(6) . . ?
F19B C19 C16 113.8(6) . . ?
F19A C19 F19C 104.2(6) . . ?
F19A C19 C16 112.1(5) . . ?
C5 C4 H4 120.0 . . ?
C3 C4 C5 120.0(7) . . ?
C3 C4 H4 120.0 . . ?
C1 C2 H2 119.8 . . ?
C3 C2 C1 120.5(7) . . ?
C3 C2 H2 119.8 . . ?
C24 C27 H27A 109.5 . . ?
C24 C27 H27B 109.5 . . ?
C24 C27 H27C 109.5 . . ?
H27A C27 H27B 109.5 . . ?
H27A C27 H27C 109.5 . . ?
H27B C27 H27C 109.5 . . ?
C4 C3 H3 120.0 . . ?
C2 C3 C4 119.9(7) . . ?
C2 C3 H3 120.0 . . ?

_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 2.144
_oxdiff_exptl_absorpt_empirical_full_min 0.372
####################################################################### 
# 
# 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_sr2
_database_code_depnum_ccdc_archive 'CCDC 1944271'
loop_
_audit_author_name
_audit_author_address
'Guy Clarkson'
;University of Warwick
United Kingdom
;
_audit_update_record             
;
2019-07-30 deposited with the CCDC.	2019-12-26 downloaded from the CCDC.
;
_audit_creation_date             2019-06-26
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3510 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C22 H25 N3 O2'
_chemical_formula_sum            'C22 H25 N3 O2'
_chemical_formula_weight         363.45
_chemical_absolute_configuration rmad
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C20 H20 N2 O2'
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           4
_space_group_name_H-M_alt        'P 1 21 1'
_space_group_name_Hall           'P 2yb'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z'

_cell_length_a                   12.47130(5)
_cell_length_b                   9.02632(4)
_cell_length_c                   17.84198(7)
_cell_angle_alpha                90
_cell_angle_beta                 92.8702(4)
_cell_angle_gamma                90
_cell_volume                     2005.951(14)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    44954
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      73.3790
_cell_measurement_theta_min      3.5120
_shelx_estimated_absorpt_T_max   0.907
_shelx_estimated_absorpt_T_min   0.826
_exptl_absorpt_coefficient_mu    0.622
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.39377
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.57a (Rigaku Oxford Diffraction, 2019)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.203
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             776
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.16
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0352
_diffrn_reflns_av_unetI/netI     0.0200
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            60499
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         73.631
_diffrn_reflns_theta_min         3.548
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      150(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.3046
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω   -114.00 -14.00   1.00    1.00    --  -41.94 -57.00-180.00  100
  2  ω    -33.00  66.00   1.00    1.00    --   41.94 -37.00  30.00   99
  3  ω      6.00  83.00   1.00    1.00    --   41.94 -99.00   0.00   77
  4  ω      7.00  33.00   1.00    1.00    --   41.94  84.00 -18.18   26
  5  ω      6.00  83.00   1.00    1.00    --   41.94 -99.00-150.00   77
  6  ω      9.00  42.00   1.00    1.00    --   41.94  78.00 -60.66   33
  7  ω     77.00 178.00   1.00    4.00    --  107.00  64.00 102.43  101
  8  ω     78.00 178.00   1.00    4.00    --  107.00  61.00-150.00  100
  9  ω     78.00 178.00   1.00    4.00    --  107.00  62.00-179.28  100
 10  ω     78.00 178.00   1.00    4.00    --  107.00  61.00 -90.00  100
 11  ω     24.00 107.00   1.00    4.00    --  107.00 -94.00  30.00   83
 12  ω     78.00 178.00   1.00    4.00    --  107.00  61.00-120.00  100
 13  ω     80.00 178.00   1.00    4.00    --  107.00  49.00 155.49   98
 14  ω     76.00 178.00   1.00    4.00    --  107.00  72.00 -45.94  102
 15  ω     35.00 136.00   1.00    4.00    --  107.00 -61.00   0.00  101
 16  ω     97.00 178.00   1.00    4.00    --  107.00 125.00  60.00   81
 17  ω     34.00 112.00   1.00    4.00    --  107.00-125.00  30.00   78
 18  ω     75.00 178.00   1.00    4.00    --  107.00  73.00 -67.64  103
 19  ω   -114.00 -14.00   1.00    1.00    --  -41.94 -57.00  30.00  100
 20  ω    -33.00  66.00   1.00    1.00    --   41.94 -37.00-120.00   99
 21  ω      9.00  42.00   1.00    1.00    --   41.94  80.00 164.04   33
 22  ω      8.00  42.00   1.00    1.00    --   41.94  82.00   9.19   34
 23  ω     24.00 107.00   1.00    4.00    --  107.00 -94.00 -90.00   83
 24  ω     78.00 178.00   1.00    4.00    --  107.00  61.00  60.00  100
 25  ω     34.00 112.00   1.00    4.00    --  107.00-125.00 -90.00   78
 26  ω     78.00 178.00   1.00    4.00    --  107.00  61.00  90.00  100
 27  ω     78.00 178.00   1.00    4.00    --  107.00  61.00  30.00  100
 28  ω     78.00 178.00   1.00    4.00    --  107.00  61.00 120.00  100
 29  ω     34.00 112.00   1.00    4.00    --  107.00-125.00-150.00   78
 30  ω     77.00 178.00   1.00    4.00    --  107.00  68.00 150.45  101
 31  ω     34.00 112.00   1.00    4.00    --  107.00-125.00-180.00   78
 32  ω    103.00 178.00   1.00    4.00    --  107.00  77.00 -30.00   75
 33  ω     76.00 178.00   1.00    4.00    --  107.00  69.00  41.07  102
 34  ω     78.00 178.00   1.00    4.00    --  107.00  61.00   0.00  100
 35  ω   -116.00 -18.00   1.00    1.00    --  -41.94 -37.00 -60.00   98
 36  ω      8.00  42.00   1.00    1.00    --   41.94  82.00-104.87   34
 37  ω      7.00  33.00   1.00    1.00    --   41.94  84.00 119.63   26
 38  ω      9.00  42.00   1.00    1.00    --   41.94  79.00-161.42   33
 39  ω     78.00 178.00   1.00    4.00    --  107.00  61.00 150.00  100
 40  ω     79.00 178.00   1.00    4.00    --  107.00  55.00  76.38   99
 41  ω     76.00 178.00   1.00    4.00    --  107.00  72.00-137.31  102
 42  ω     81.00 178.00   1.00    4.00    --  107.00  45.00  30.00   97
 43  ω     81.00 178.00   1.00    4.00    --  107.00  45.00   0.00   97
 44  ω     24.00 107.00   1.00    4.00    --  107.00 -94.00  90.00   83
 45  ω     81.00 178.00   1.00    4.00    --  107.00  45.00 -60.00   97
 46  ω     80.00 178.00   1.00    4.00    --  107.00  51.00 142.90   98
 47  ω     76.00 178.00   1.00    4.00    --  107.00  71.00 163.91  102
 48  ω     24.00 107.00   1.00    4.00    --  107.00 -94.00-150.00   83
 49  ω     35.00 136.00   1.00    4.00    --  107.00 -61.00-150.00  101
 50  ω     81.00 178.00   1.00    4.00    --  107.00  45.00 -90.00   97
 51  ω   -116.00 -18.00   1.00    1.00    --  -41.94 -37.00  90.00   98
 52  ω    -87.00  -6.00   1.00    1.00    --  -41.94 125.00 120.00   81
 53  ω      7.00  33.00   1.00    1.00    --   41.94  84.00  57.18   26
 54  ω      8.00  34.00   1.00    1.00    --   41.94  83.00 147.98   26
 55  ω     81.00 169.00   1.00    4.00    --  107.00  45.00-120.00   88
 56  ω     78.00 178.00   1.00    4.00    --  107.00  61.00 -60.00  100
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, AtlasS2'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.1034655000
_diffrn_orient_matrix_UB_12      0.0376667000
_diffrn_orient_matrix_UB_13      0.0397019000
_diffrn_orient_matrix_UB_21      -0.0318233000
_diffrn_orient_matrix_UB_22      -0.1109690000
_diffrn_orient_matrix_UB_23      0.0628279000
_diffrn_orient_matrix_UB_31      -0.0598644000
_diffrn_orient_matrix_UB_32      0.1240424000
_diffrn_orient_matrix_UB_33      -0.0441730000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\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         0.869
_reflns_Friedel_fraction_full    0.998
_reflns_Friedel_fraction_max     0.992
_reflns_number_gt                7973
_reflns_number_total             8067
_reflns_odcompleteness_completeness 99.98
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     71.98
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.40.57a (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.40.57a (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.57a (Rigaku OD, 2019)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.108
_refine_diff_density_min         -0.162
_refine_diff_density_rms         0.031
_refine_ls_abs_structure_details 
;
 Flack x determined using 3649 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
 Flack x: 0.01(6) Shelx 2018
 Hooft y: 0.01(3) Olex2
 Synthesised from a known chiral starting material
;
_refine_ls_abs_structure_Flack   0.01(6)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.038
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     493
_refine_ls_number_reflns         8067
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0283
_refine_ls_R_factor_gt           0.0280
_refine_ls_restrained_S_all      1.038
_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)+(0.0444P)²+0.2036P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0739
_refine_ls_wR_factor_ref         0.0743
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C113(H113), C213(H213)
2.b Secondary CH2 refined with riding coordinates:
 C110(H11A,H11B), C111(H11C,H11D), C112(H11E,H11F), C210(H21A,H21B), C211(H21C,
 H21D), C212(H21E,H21F)
2.c Aromatic/amide H refined with riding coordinates:
 C104(H104), C105(H105), C107(H107), C108(H108), C122(H122), C123(H123),
 C124(H124), C125(H125), C126(H126), C204(H204), C205(H205), C207(H207),
 C208(H208), C222(H222), C223(H223), C224(H224), C225(H225), C226(H226)
2.d Idealised Me refined as rotating group:
 C118(H11G,H11H,H11I), C119(H11J,H11K,H11L), C120(H12A,H12B,H12C), C218(H21G,
 H21H,H21I), C219(H21J,H21K,H21L), C220(H22A,H22B,H22C)
;
_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
N101 N 0.59403(13) 0.1581(2) 0.69250(9) 0.0474(4) Uani 1 1 d . . . . .
C102 C 0.62978(13) 0.2006(2) 0.74880(10) 0.0350(4) Uani 1 1 d . . . . .
C103 C 0.67364(12) 0.25649(18) 0.81937(9) 0.0294(3) Uani 1 1 d . . . . .
C104 C 0.78355(13) 0.28582(19) 0.82990(9) 0.0312(3) Uani 1 1 d . . . . .
H104 H 0.830180 0.265371 0.790684 0.037 Uiso 1 1 calc R . . . .
C105 C 0.82470(11) 0.34410(19) 0.89668(9) 0.0295(3) Uani 1 1 d . . . . .
H105 H 0.899450 0.363544 0.903186 0.035 Uiso 1 1 calc R . . . .
C106 C 0.75664(11) 0.37503(16) 0.95535(9) 0.0257(3) Uani 1 1 d . . . . .
C107 C 0.64654(11) 0.34509(18) 0.94432(9) 0.0283(3) Uani 1 1 d . . . . .
H107 H 0.599653 0.365619 0.983363 0.034 Uiso 1 1 calc R . . . .
C108 C 0.60564(12) 0.28641(18) 0.87772(9) 0.0298(3) Uani 1 1 d . . . . .
H108 H 0.531014 0.266083 0.871251 0.036 Uiso 1 1 calc R . . . .
N109 N 0.79807(10) 0.42948(15) 1.02314(8) 0.0276(3) Uani 1 1 d . . . . .
C110 C 0.91166(12) 0.4665(2) 1.03592(10) 0.0336(3) Uani 1 1 d . . . . .
H11A H 0.931277 0.548233 1.002267 0.040 Uiso 1 1 calc R . . . .
H11B H 0.956638 0.379347 1.025203 0.040 Uiso 1 1 calc R . . . .
C111 C 0.93062(14) 0.5133(2) 1.11778(11) 0.0394(4) Uani 1 1 d . . . . .
H11C H 1.006925 0.497758 1.133859 0.047 Uiso 1 1 calc R . . . .
H11D H 0.913956 0.619879 1.123156 0.047 Uiso 1 1 calc R . . . .
C112 C 0.85897(14) 0.4217(2) 1.16700(10) 0.0390(4) Uani 1 1 d . . . . .
H11E H 0.878075 0.441498 1.220587 0.047 Uiso 1 1 calc R . . . .
H11F H 0.869942 0.314890 1.157455 0.047 Uiso 1 1 calc R . . . .
C113 C 0.74032(13) 0.46292(19) 1.14909(9) 0.0296(3) Uani 1 1 d . . . . .
H113 H 0.724779 0.553063 1.179268 0.036 Uiso 1 1 calc R . . . .
N114 N 0.72838(10) 0.50585(15) 1.06889(7) 0.0267(3) Uani 1 1 d . . . . .
C115 C 0.70553(11) 0.65371(17) 1.05304(9) 0.0266(3) Uani 1 1 d . . . . .
O115 O 0.66083(9) 0.73362(13) 1.09655(7) 0.0326(2) Uani 1 1 d . . . . .
O116 O 0.73590(9) 0.68907(13) 0.98500(6) 0.0301(2) Uani 1 1 d . . . . .
C117 C 0.72318(13) 0.84216(19) 0.95627(10) 0.0320(3) Uani 1 1 d . . . . .
C118 C 0.76459(17) 0.8277(2) 0.87803(11) 0.0456(4) Uani 1 1 d . . . . .
H11G H 0.838806 0.791649 0.881555 0.068 Uiso 1 1 calc GR . . . .
H11H H 0.762121 0.924588 0.853257 0.068 Uiso 1 1 calc GR . . . .
H11I H 0.719587 0.757393 0.848781 0.068 Uiso 1 1 calc GR . . . .
C119 C 0.79384(15) 0.9444(2) 1.00459(13) 0.0439(4) Uani 1 1 d . . . . .
H11J H 0.767880 0.947143 1.055511 0.066 Uiso 1 1 calc GR . . . .
H11K H 0.791458 1.044361 0.983157 0.066 Uiso 1 1 calc GR . . . .
H11L H 0.867903 0.907759 1.006359 0.066 Uiso 1 1 calc GR . . . .
C120 C 0.60597(14) 0.8880(2) 0.95332(11) 0.0399(4) Uani 1 1 d . . . . .
H12A H 0.561952 0.808475 0.930449 0.060 Uiso 1 1 calc GR . . . .
H12B H 0.596657 0.978374 0.923275 0.060 Uiso 1 1 calc GR . . . .
H12C H 0.583594 0.906675 1.004343 0.060 Uiso 1 1 calc GR . . . .
C121 C 0.66018(12) 0.34542(18) 1.16927(8) 0.0285(3) Uani 1 1 d . . . . .
C122 C 0.57786(13) 0.3811(2) 1.21594(9) 0.0326(3) Uani 1 1 d . . . . .
H122 H 0.572075 0.479346 1.234385 0.039 Uiso 1 1 calc R . . . .
C123 C 0.50415(15) 0.2747(2) 1.23584(10) 0.0413(4) Uani 1 1 d . . . . .
H123 H 0.448955 0.299970 1.268370 0.050 Uiso 1 1 calc R . . . .
C124 C 0.51107(18) 0.1320(2) 1.20831(10) 0.0457(4) Uani 1 1 d . . . . .
H124 H 0.460087 0.059383 1.221339 0.055 Uiso 1 1 calc R . . . .
C125 C 0.59269(18) 0.0951(2) 1.16159(11) 0.0444(4) Uani 1 1 d . . . . .
H125 H 0.597661 -0.002968 1.142708 0.053 Uiso 1 1 calc R . . . .
C126 C 0.66702(16) 0.2012(2) 1.14244(10) 0.0371(4) Uani 1 1 d . . . . .
H126 H 0.723043 0.175113 1.110758 0.044 Uiso 1 1 calc R . . . .
N201 N 0.94566(15) 0.9012(2) 0.19709(10) 0.0519(4) Uani 1 1 d . . . . .
C202 C 0.90151(14) 0.8424(2) 0.24358(10) 0.0390(4) Uani 1 1 d . . . . .
C203 C 0.84640(13) 0.76914(19) 0.30186(9) 0.0319(3) Uani 1 1 d . . . . .
C204 C 0.90305(13) 0.71744(19) 0.36644(10) 0.0335(3) Uani 1 1 d . . . . .
H204 H 0.978512 0.731550 0.371995 0.040 Uiso 1 1 calc R . . . .
C205 C 0.85003(12) 0.64638(19) 0.42181(9) 0.0315(3) Uani 1 1 d . . . . .
H205 H 0.889239 0.612801 0.465577 0.038 Uiso 1 1 calc R . . . .
C206 C 0.73852(12) 0.62274(17) 0.41455(8) 0.0262(3) Uani 1 1 d . . . . .
C207 C 0.68171(12) 0.67584(18) 0.35011(9) 0.0287(3) Uani 1 1 d . . . . .
H207 H 0.606252 0.661769 0.344453 0.034 Uiso 1 1 calc R . . . .
C208 C 0.73515(13) 0.74854(19) 0.29482(9) 0.0306(3) Uani 1 1 d . . . . .
H208 H 0.695924 0.784832 0.251635 0.037 Uiso 1 1 calc R . . . .
N209 N 0.68449(10) 0.55179(15) 0.46999(7) 0.0275(3) Uani 1 1 d . . . . .
C210 C 0.57615(12) 0.49046(19) 0.45660(10) 0.0318(3) Uani 1 1 d . . . . .
H21A H 0.576646 0.412124 0.417788 0.038 Uiso 1 1 calc R . . . .
H21B H 0.525761 0.569269 0.438968 0.038 Uiso 1 1 calc R . . . .
C211 C 0.54121(14) 0.4259(2) 0.53073(10) 0.0362(4) Uani 1 1 d . . . . .
H21C H 0.571471 0.325242 0.538052 0.043 Uiso 1 1 calc R . . . .
H21D H 0.461951 0.418565 0.529932 0.043 Uiso 1 1 calc R . . . .
C212 C 0.58148(14) 0.5272(2) 0.59495(10) 0.0385(4) Uani 1 1 d . . . . .
H21E H 0.549339 0.496974 0.642220 0.046 Uiso 1 1 calc R . . . .
H21F H 0.560311 0.630912 0.583902 0.046 Uiso 1 1 calc R . . . .
C213 C 0.70471(13) 0.51505(19) 0.60341(9) 0.0317(3) Uani 1 1 d . . . . .
H213 H 0.721915 0.427302 0.636050 0.038 Uiso 1 1 calc R . . . .
N214 N 0.74553(10) 0.48288(15) 0.52833(7) 0.0282(3) Uani 1 1 d . . . . .
C215 C 0.78836(11) 0.34345(18) 0.51659(9) 0.0274(3) Uani 1 1 d . . . . .
O215 O 0.82529(10) 0.26674(14) 0.56717(7) 0.0355(3) Uani 1 1 d . . . . .
O216 O 0.78621(9) 0.31393(12) 0.44325(6) 0.0306(2) Uani 1 1 d . . . . .
C217 C 0.81560(13) 0.16598(18) 0.41533(9) 0.0294(3) Uani 1 1 d . . . . .
C218 C 0.80671(17) 0.1889(2) 0.33135(10) 0.0415(4) Uani 1 1 d . . . . .
H21G H 0.733361 0.219305 0.316185 0.062 Uiso 1 1 calc GR . . . .
H21H H 0.823790 0.096143 0.306025 0.062 Uiso 1 1 calc GR . . . .
H21I H 0.857196 0.266152 0.317387 0.062 Uiso 1 1 calc GR . . . .
C219 C 0.92871(14) 0.1235(2) 0.44164(11) 0.0416(4) Uani 1 1 d . . . . .
H21J H 0.977289 0.206641 0.433532 0.062 Uiso 1 1 calc GR . . . .
H21K H 0.951708 0.037188 0.413218 0.062 Uiso 1 1 calc GR . . . .
H21L H 0.930377 0.099027 0.495203 0.062 Uiso 1 1 calc GR . . . .
C220 C 0.73197(16) 0.0568(2) 0.43973(11) 0.0412(4) Uani 1 1 d . . . . .
H22A H 0.732681 0.053767 0.494654 0.062 Uiso 1 1 calc GR . . . .
H22B H 0.748297 -0.041991 0.420505 0.062 Uiso 1 1 calc GR . . . .
H22C H 0.660841 0.087808 0.419798 0.062 Uiso 1 1 calc GR . . . .
C221 C 0.76317(13) 0.64686(19) 0.63844(9) 0.0312(3) Uani 1 1 d . . . . .
C222 C 0.74436(17) 0.7911(2) 0.61436(10) 0.0415(4) Uani 1 1 d . . . . .
H222 H 0.689530 0.810125 0.576702 0.050 Uiso 1 1 calc R . . . .
C223 C 0.80465(18) 0.9081(2) 0.64460(11) 0.0459(4) Uani 1 1 d . . . . .
H223 H 0.790801 1.006404 0.627692 0.055 Uiso 1 1 calc R . . . .
C224 C 0.88493(16) 0.8814(2) 0.69939(10) 0.0423(4) Uani 1 1 d . . . . .
H224 H 0.926935 0.961082 0.719620 0.051 Uiso 1 1 calc R . . . .
C225 C 0.90369(15) 0.7386(2) 0.72452(10) 0.0401(4) Uani 1 1 d . . . . .
H225 H 0.958056 0.720230 0.762590 0.048 Uiso 1 1 calc R . . . .
C226 C 0.84355(13) 0.6222(2) 0.69440(9) 0.0341(3) Uani 1 1 d . . . . .
H226 H 0.857098 0.524283 0.711999 0.041 Uiso 1 1 calc R . . . .


_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
N101 C102 1.145(2) . ?
C102 C103 1.439(2) . ?
C103 C104 1.399(2) . ?
C103 C108 1.402(2) . ?
C104 H104 0.9500 . ?
C104 C105 1.378(2) . ?
C105 H105 0.9500 . ?
C105 C106 1.408(2) . ?
C106 C107 1.404(2) . ?
C106 N109 1.382(2) . ?
C107 H107 0.9500 . ?
C107 C108 1.375(2) . ?
C108 H108 0.9500 . ?
N109 C110 1.4622(19) . ?
N109 N114 1.4029(18) . ?
C110 H11A 0.9900 . ?
C110 H11B 0.9900 . ?
C110 C111 1.527(3) . ?
C111 H11C 0.9900 . ?
C111 H11D 0.9900 . ?
C111 C112 1.527(3) . ?
C112 H11E 0.9900 . ?
C112 H11F 0.9900 . ?
C112 C113 1.543(2) . ?
C113 H113 1.0000 . ?
C113 N114 1.483(2) . ?
C113 C121 1.513(2) . ?
N114 C115 1.391(2) . ?
C115 O115 1.2153(19) . ?
C115 O116 1.3286(19) . ?
O116 C117 1.4797(19) . ?
C117 C118 1.518(2) . ?
C117 C119 1.515(3) . ?
C117 C120 1.518(2) . ?
C118 H11G 0.9800 . ?
C118 H11H 0.9800 . ?
C118 H11I 0.9800 . ?
C119 H11J 0.9800 . ?
C119 H11K 0.9800 . ?
C119 H11L 0.9800 . ?
C120 H12A 0.9800 . ?
C120 H12B 0.9800 . ?
C120 H12C 0.9800 . ?
C121 C122 1.392(2) . ?
C121 C126 1.391(2) . ?
C122 H122 0.9500 . ?
C122 C123 1.388(3) . ?
C123 H123 0.9500 . ?
C123 C124 1.383(3) . ?
C124 H124 0.9500 . ?
C124 C125 1.388(3) . ?
C125 H125 0.9500 . ?
C125 C126 1.387(3) . ?
C126 H126 0.9500 . ?
N201 C202 1.148(3) . ?
C202 C203 1.436(3) . ?
C203 C204 1.401(2) . ?
C203 C208 1.399(2) . ?
C204 H204 0.9500 . ?
C204 C205 1.375(3) . ?
C205 H205 0.9500 . ?
C205 C206 1.406(2) . ?
C206 C207 1.404(2) . ?
C206 N209 1.382(2) . ?
C207 H207 0.9500 . ?
C207 C208 1.383(2) . ?
C208 H208 0.9500 . ?
N209 C210 1.4686(19) . ?
N209 N214 1.4037(18) . ?
C210 H21A 0.9900 . ?
C210 H21B 0.9900 . ?
C210 C211 1.529(2) . ?
C211 H21C 0.9900 . ?
C211 H21D 0.9900 . ?
C211 C212 1.531(2) . ?
C212 H21E 0.9900 . ?
C212 H21F 0.9900 . ?
C212 C213 1.541(2) . ?
C213 H213 1.0000 . ?
C213 N214 1.485(2) . ?
C213 C221 1.514(2) . ?
N214 C215 1.387(2) . ?
C215 O215 1.210(2) . ?
C215 O216 1.3345(19) . ?
O216 C217 1.4778(18) . ?
C217 C218 1.511(2) . ?
C217 C219 1.514(2) . ?
C217 C220 1.515(3) . ?
C218 H21G 0.9800 . ?
C218 H21H 0.9800 . ?
C218 H21I 0.9800 . ?
C219 H21J 0.9800 . ?
C219 H21K 0.9800 . ?
C219 H21L 0.9800 . ?
C220 H22A 0.9800 . ?
C220 H22B 0.9800 . ?
C220 H22C 0.9800 . ?
C221 C222 1.387(3) . ?
C221 C226 1.397(2) . ?
C222 H222 0.9500 . ?
C222 C223 1.390(3) . ?
C223 H223 0.9500 . ?
C223 C224 1.385(3) . ?
C224 H224 0.9500 . ?
C224 C225 1.381(3) . ?
C225 H225 0.9500 . ?
C225 C226 1.384(3) . ?
C226 H226 0.9500 . ?

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
N101 C102 C103 178.9(2) . . ?
C104 C103 C102 120.72(14) . . ?
C104 C103 C108 119.26(15) . . ?
C108 C103 C102 119.99(14) . . ?
C103 C104 H104 119.7 . . ?
C105 C104 C103 120.54(14) . . ?
C105 C104 H104 119.7 . . ?
C104 C105 H105 119.8 . . ?
C104 C105 C106 120.42(14) . . ?
C106 C105 H105 119.8 . . ?
C107 C106 C105 118.64(14) . . ?
N109 C106 C105 120.55(13) . . ?
N109 C106 C107 120.77(13) . . ?
C106 C107 H107 119.6 . . ?
C108 C107 C106 120.88(14) . . ?
C108 C107 H107 119.6 . . ?
C103 C108 H108 119.9 . . ?
C107 C108 C103 120.26(14) . . ?
C107 C108 H108 119.9 . . ?
C106 N109 C110 122.33(13) . . ?
C106 N109 N114 117.95(12) . . ?
N114 N109 C110 114.88(13) . . ?
N109 C110 H11A 110.0 . . ?
N109 C110 H11B 110.0 . . ?
N109 C110 C111 108.35(13) . . ?
H11A C110 H11B 108.4 . . ?
C111 C110 H11A 110.0 . . ?
C111 C110 H11B 110.0 . . ?
C110 C111 H11C 109.8 . . ?
C110 C111 H11D 109.8 . . ?
H11C C111 H11D 108.2 . . ?
C112 C111 C110 109.45(15) . . ?
C112 C111 H11C 109.8 . . ?
C112 C111 H11D 109.8 . . ?
C111 C112 H11E 109.8 . . ?
C111 C112 H11F 109.8 . . ?
C111 C112 C113 109.47(14) . . ?
H11E C112 H11F 108.2 . . ?
C113 C112 H11E 109.8 . . ?
C113 C112 H11F 109.8 . . ?
C112 C113 H113 107.1 . . ?
N114 C113 C112 108.15(13) . . ?
N114 C113 H113 107.1 . . ?
N114 C113 C121 112.16(13) . . ?
C121 C113 C112 114.82(14) . . ?
C121 C113 H113 107.1 . . ?
N109 N114 C113 113.45(12) . . ?
C115 N114 N109 118.68(12) . . ?
C115 N114 C113 117.17(13) . . ?
O115 C115 N114 122.38(14) . . ?
O115 C115 O116 127.01(15) . . ?
O116 C115 N114 110.57(13) . . ?
C115 O116 C117 120.69(12) . . ?
O116 C117 C118 101.69(14) . . ?
O116 C117 C119 108.81(14) . . ?
O116 C117 C120 110.66(14) . . ?
C119 C117 C118 111.15(15) . . ?
C119 C117 C120 112.68(15) . . ?
C120 C117 C118 111.29(15) . . ?
C117 C118 H11G 109.5 . . ?
C117 C118 H11H 109.5 . . ?
C117 C118 H11I 109.5 . . ?
H11G C118 H11H 109.5 . . ?
H11G C118 H11I 109.5 . . ?
H11H C118 H11I 109.5 . . ?
C117 C119 H11J 109.5 . . ?
C117 C119 H11K 109.5 . . ?
C117 C119 H11L 109.5 . . ?
H11J C119 H11K 109.5 . . ?
H11J C119 H11L 109.5 . . ?
H11K C119 H11L 109.5 . . ?
C117 C120 H12A 109.5 . . ?
C117 C120 H12B 109.5 . . ?
C117 C120 H12C 109.5 . . ?
H12A C120 H12B 109.5 . . ?
H12A C120 H12C 109.5 . . ?
H12B C120 H12C 109.5 . . ?
C122 C121 C113 119.74(15) . . ?
C126 C121 C113 121.43(15) . . ?
C126 C121 C122 118.83(16) . . ?
C121 C122 H122 119.6 . . ?
C123 C122 C121 120.74(16) . . ?
C123 C122 H122 119.6 . . ?
C122 C123 H123 120.0 . . ?
C124 C123 C122 119.98(17) . . ?
C124 C123 H123 120.0 . . ?
C123 C124 H124 120.1 . . ?
C123 C124 C125 119.83(18) . . ?
C125 C124 H124 120.1 . . ?
C124 C125 H125 120.0 . . ?
C126 C125 C124 120.08(18) . . ?
C126 C125 H125 120.0 . . ?
C121 C126 H126 119.7 . . ?
C125 C126 C121 120.53(17) . . ?
C125 C126 H126 119.7 . . ?
N201 C202 C203 179.8(2) . . ?
C204 C203 C202 120.60(15) . . ?
C208 C203 C202 120.29(16) . . ?
C208 C203 C204 119.11(15) . . ?
C203 C204 H204 119.8 . . ?
C205 C204 C203 120.37(15) . . ?
C205 C204 H204 119.8 . . ?
C204 C205 H205 119.6 . . ?
C204 C205 C206 120.90(14) . . ?
C206 C205 H205 119.6 . . ?
C207 C206 C205 118.65(15) . . ?
N209 C206 C205 121.32(13) . . ?
N209 C206 C207 120.01(13) . . ?
C206 C207 H207 119.9 . . ?
C208 C207 C206 120.30(14) . . ?
C208 C207 H207 119.9 . . ?
C203 C208 H208 119.7 . . ?
C207 C208 C203 120.66(15) . . ?
C207 C208 H208 119.7 . . ?
C206 N209 C210 122.41(13) . . ?
C206 N209 N214 118.05(12) . . ?
N214 N209 C210 114.45(13) . . ?
N209 C210 H21A 110.2 . . ?
N209 C210 H21B 110.2 . . ?
N209 C210 C211 107.63(13) . . ?
H21A C210 H21B 108.5 . . ?
C211 C210 H21A 110.2 . . ?
C211 C210 H21B 110.2 . . ?
C210 C211 H21C 109.9 . . ?
C210 C211 H21D 109.9 . . ?
C210 C211 C212 108.84(14) . . ?
H21C C211 H21D 108.3 . . ?
C212 C211 H21C 109.9 . . ?
C212 C211 H21D 109.9 . . ?
C211 C212 H21E 110.0 . . ?
C211 C212 H21F 110.0 . . ?
C211 C212 C213 108.61(14) . . ?
H21E C212 H21F 108.3 . . ?
C213 C212 H21E 110.0 . . ?
C213 C212 H21F 110.0 . . ?
C212 C213 H213 107.3 . . ?
N214 C213 C212 108.11(13) . . ?
N214 C213 H213 107.3 . . ?
N214 C213 C221 110.26(13) . . ?
C221 C213 C212 116.23(14) . . ?
C221 C213 H213 107.3 . . ?
N209 N214 C213 112.61(12) . . ?
C215 N214 N209 119.26(13) . . ?
C215 N214 C213 117.74(13) . . ?
O215 C215 N214 122.80(15) . . ?
O215 C215 O216 127.25(15) . . ?
O216 C215 N214 109.89(13) . . ?
C215 O216 C217 121.18(12) . . ?
O216 C217 C218 101.73(13) . . ?
O216 C217 C219 111.57(14) . . ?
O216 C217 C220 107.78(13) . . ?
C218 C217 C219 111.30(15) . . ?
C218 C217 C220 110.89(15) . . ?
C219 C217 C220 112.97(15) . . ?
C217 C218 H21G 109.5 . . ?
C217 C218 H21H 109.5 . . ?
C217 C218 H21I 109.5 . . ?
H21G C218 H21H 109.5 . . ?
H21G C218 H21I 109.5 . . ?
H21H C218 H21I 109.5 . . ?
C217 C219 H21J 109.5 . . ?
C217 C219 H21K 109.5 . . ?
C217 C219 H21L 109.5 . . ?
H21J C219 H21K 109.5 . . ?
H21J C219 H21L 109.5 . . ?
H21K C219 H21L 109.5 . . ?
C217 C220 H22A 109.5 . . ?
C217 C220 H22B 109.5 . . ?
C217 C220 H22C 109.5 . . ?
H22A C220 H22B 109.5 . . ?
H22A C220 H22C 109.5 . . ?
H22B C220 H22C 109.5 . . ?
C222 C221 C213 122.63(15) . . ?
C222 C221 C226 118.38(16) . . ?
C226 C221 C213 118.90(16) . . ?
C221 C222 H222 119.6 . . ?
C221 C222 C223 120.88(17) . . ?
C223 C222 H222 119.6 . . ?
C222 C223 H223 120.0 . . ?
C224 C223 C222 119.98(19) . . ?
C224 C223 H223 120.0 . . ?
C223 C224 H224 120.1 . . ?
C225 C224 C223 119.75(18) . . ?
C225 C224 H224 120.1 . . ?
C224 C225 H225 119.9 . . ?
C224 C225 C226 120.21(17) . . ?
C226 C225 H225 119.9 . . ?
C221 C226 H226 119.6 . . ?
C225 C226 C221 120.79(17) . . ?
C225 C226 H226 119.6 . . ?

_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 1.941
_oxdiff_exptl_absorpt_empirical_full_min 0.688
####################################################################### 
# 
# 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_sr1
_database_code_depnum_ccdc_archive 'CCDC 1944272'
loop_
_audit_author_name
_audit_author_address
'Guy Clarkson'
;University of Warwick
United Kingdom
;
_audit_update_record             
;
2019-07-30 deposited with the CCDC.	2019-12-26 downloaded from the CCDC.
;
_audit_creation_date             2019-06-02
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3510 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C20 H19 N3 O'
_chemical_formula_sum            'C20 H19 N3 O'
_chemical_formula_weight         317.38
_chemical_absolute_configuration rmad
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C20 H20 N2 O2'
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           4
_space_group_name_H-M_alt        'P 1 21 1'
_space_group_name_Hall           'P 2yb'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z'

_cell_length_a                   10.10659(11)
_cell_length_b                   5.94958(5)
_cell_length_c                   13.62038(10)
_cell_angle_alpha                90
_cell_angle_beta                 99.5974(8)
_cell_angle_gamma                90
_cell_volume                     807.530(13)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    9966
_cell_measurement_temperature    150.00(10)
_cell_measurement_theta_max      73.3540
_cell_measurement_theta_min      3.2700
_shelx_estimated_absorpt_T_max   0.974
_shelx_estimated_absorpt_T_min   0.881
_exptl_absorpt_coefficient_mu    0.652
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.02824
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'CrysAlisPro 1.171.40.53a (Rigaku Oxford Diffraction, 2019) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm.'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.305
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             336
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.04
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0310
_diffrn_reflns_av_unetI/netI     0.0200
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            15974
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.989
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         73.522
_diffrn_reflns_theta_min         3.291
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      150.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.3046
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_details      
'List of Runs (angles in degrees, time in seconds): # Type Start End Width tₑₓₚ ω θ κ φ Frames -------------------------------------------------------------------------- 1 ω -116.00 -17.00 1.00 2.00 -- -41.82 -37.00-180.00 99 2 ω -129.00 -34.00 1.00 2.00 -- -41.82 178.00 90.00 95 3 ω -116.00 -17.00 1.00 2.00 -- -41.82 -37.00 -90.00 99 4 ω 57.00 131.00 1.00 2.00 -- 41.82 178.00-150.00 74 5 ω 17.00 116.00 1.00 2.00 -- 41.82 37.00 90.00 99 6 ω 24.00 110.00 1.00 8.00 -- 107.00 -94.00 150.00 86 7 ω 34.00 118.00 1.00 8.00 -- 107.00-125.00 150.00 84 8 ω 78.00 178.00 1.00 8.00 -- 107.00 61.00 -90.00 100 9 ω 24.00 110.00 1.00 8.00 -- 107.00 -94.00 -60.00 86 10 ω 74.00 178.00 1.00 8.00 -- 107.00 77.00-120.00 104 11 ω 94.00 178.00 1.00 8.00 -- 107.00 125.00 -60.00 84 12 ω 94.00 178.00 1.00 8.00 -- 107.00 125.00 150.00 84 13 ω 74.00 178.00 1.00 8.00 -- 107.00 77.00-150.00 104 14 ω 78.00 178.00 1.00 8.00 -- 107.00 61.00 -60.00 100 15 ω 94.00 178.00 1.00 8.00 -- 107.00 125.00 30.00 84 16 ω 81.00 178.00 1.00 8.00 -- 107.00 45.00 0.00 97 17 ω 35.00 136.00 1.00 8.00 -- 107.00 -61.00 0.00 101 18 ω 34.00 118.00 1.00 8.00 -- 107.00-125.00 0.00 84 19 ω -114.00 -13.00 1.00 2.00 -- -41.82 -59.00 11.00 101 20 ω -118.00 -9.00 1.00 2.00 -- -41.82 -77.00 -60.00 109 21 ω -118.00 -9.00 1.00 2.00 -- -41.82 -77.00 150.00 109 22 ω 57.00 131.00 1.00 2.00 -- 41.82 178.00 60.00 74 23 ω 78.00 178.00 1.00 8.00 -- 107.00 61.00 -30.00 100 24 ω 78.00 178.00 1.00 8.00 -- 107.00 59.00 152.00 100 25 ω 74.00 178.00 1.00 8.00 -- 107.00 77.00 30.00 104 26 ω 74.00 178.00 1.00 8.00 -- 107.00 77.00 0.00 104 27 ω 81.00 178.00 1.00 8.00 -- 107.00 45.00 120.00 97 28 ω 74.00 178.00 1.00 8.00 -- 107.00 77.00 120.00 104 29 ω 78.00 178.00 1.00 8.00 -- 107.00 61.00-180.00 100 30 ω 34.00 118.00 1.00 8.00 -- 107.00-125.00 -90.00 84 31 ω 78.00 178.00 1.00 8.00 -- 107.00 61.00-150.00 100 32 ω 76.00 178.00 1.00 8.00 -- 107.00 69.00 87.85 102 33 ω 74.00 178.00 1.00 8.00 -- 107.00 77.00 60.00 104'
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, AtlasS2'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0929279000
_diffrn_orient_matrix_UB_12      0.0254897000
_diffrn_orient_matrix_UB_13      -0.0781592000
_diffrn_orient_matrix_UB_21      0.0824052000
_diffrn_orient_matrix_UB_22      0.1786576000
_diffrn_orient_matrix_UB_23      0.0655727000
_diffrn_orient_matrix_UB_31      0.0919859000
_diffrn_orient_matrix_UB_32      -0.1856442000
_diffrn_orient_matrix_UB_33      0.0524339000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\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         0.799
_reflns_Friedel_fraction_full    0.996
_reflns_Friedel_fraction_max     0.976
_reflns_number_gt                3150
_reflns_number_total             3240
_reflns_odcompleteness_completeness 100.00
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     71.98
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.40.53a (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.40.53a (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.53a (Rigaku OD, 2019)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.143
_refine_diff_density_min         -0.174
_refine_diff_density_rms         0.030
_refine_ls_abs_structure_details 
;
 Flack x determined using 1364 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
Flack x: 0.00(8)  Shelxl 2018
Hooft y: 0.04(8)  Olex2
Absolute configuration established by the structure determination of the compound containing a chiral reference molecule 
of known absolute configuration and confirmed by anomalous-dispersion effects with diffraction measurements on the crystal.
;
_refine_ls_abs_structure_Flack   0.00(8)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.046
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     220
_refine_ls_number_reflns         3240
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0282
_refine_ls_R_factor_gt           0.0274
_refine_ls_restrained_S_all      1.046
_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)+(0.0402P)²+0.0804P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0699
_refine_ls_wR_factor_ref         0.0705
_refine_special_details          ?
_olex2_refinement_description    
;
The NH was located in a difference map but refined with thermal parameters 1.2 times the equivalent isotropic displacement 
parameter of the nitrogen atom to which it is attached
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
2.a Ternary CH refined with riding coordinates:
 C16(H16A)
2.b Secondary CH2 refined with riding coordinates:
 C15(H15A,H15B), C14(H14A,H14B), C13(H13A,H13B)
2.c Aromatic/amide H refined with riding coordinates:
 C3(H3), C8(H8), C22(H22), C9(H9), C4(H4), C5(H5), C6(H6), C18(H18), C20(H20),
 C19(H19), C21(H21)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     ?
_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
O11 O 0.36096(12) 0.7702(2) 0.65251(9) 0.0357(3) Uani 1 1 d . . . . .
N1 N 0.03889(13) 0.6128(2) 0.67753(9) 0.0246(3) Uani 1 1 d . . . . .
N16 N 0.45242(13) 0.5403(3) 0.81477(11) 0.0310(3) Uani 1 1 d . . . . .
H16 H 0.491(2) 0.602(4) 0.7643(16) 0.037 Uiso 1 1 d R . . . .
N12 N 0.31303(13) 0.5903(3) 0.78677(10) 0.0325(3) Uani 1 1 d . . . . .
C11 C 0.27684(16) 0.7077(3) 0.70266(12) 0.0273(3) Uani 1 1 d . . . . .
C10 C 0.13113(15) 0.7637(3) 0.66754(11) 0.0257(3) Uani 1 1 d . . . . .
C3 C -0.19199(16) 0.5017(3) 0.64777(11) 0.0271(3) Uani 1 1 d . . . . .
H3 H -0.168252 0.364180 0.681622 0.032 Uiso 1 1 calc R . . . .
C2 C -0.09165(15) 0.6611(3) 0.63714(10) 0.0239(3) Uani 1 1 d . . . . .
C17 C 0.61839(16) 0.2404(3) 0.83906(11) 0.0266(3) Uani 1 1 d . . . . .
C16 C 0.47078(15) 0.2950(3) 0.81844(11) 0.0282(3) Uani 1 1 d . . . . .
H16A H 0.430051 0.228934 0.752838 0.034 Uiso 1 1 calc R . . . .
C8 C -0.02563(17) 1.0232(3) 0.57899(11) 0.0282(3) Uani 1 1 d . . . . .
H8 H -0.046705 1.163160 0.546560 0.034 Uiso 1 1 calc R . . . .
C7 C -0.12851(16) 0.8666(3) 0.58662(11) 0.0258(3) Uani 1 1 d . . . . .
C22 C 0.71327(16) 0.3873(3) 0.89003(12) 0.0296(3) Uani 1 1 d . . . . .
H22 H 0.685478 0.528386 0.912116 0.036 Uiso 1 1 calc R . . . .
C9 C 0.10404(17) 0.9728(3) 0.61835(12) 0.0281(3) Uani 1 1 d . . . . .
H9 H 0.174509 1.075385 0.612935 0.034 Uiso 1 1 calc R . . . .
C4 C -0.32352(16) 0.5455(3) 0.60923(12) 0.0319(4) Uani 1 1 d . . . . .
H4 H -0.390612 0.438098 0.616836 0.038 Uiso 1 1 calc R . . . .
C5 C -0.36044(17) 0.7488(3) 0.55830(12) 0.0345(4) Uani 1 1 d . . . . .
H5 H -0.452035 0.776706 0.531953 0.041 Uiso 1 1 calc R . . . .
C6 C -0.26557(17) 0.9054(3) 0.54665(12) 0.0319(4) Uani 1 1 d . . . . .
H6 H -0.291325 1.040852 0.511681 0.038 Uiso 1 1 calc R . . . .
C15 C 0.39776(17) 0.2026(3) 0.89983(13) 0.0363(4) Uani 1 1 d . . . . .
H15A H 0.441957 0.258648 0.965606 0.044 Uiso 1 1 calc R . . . .
H15B H 0.403165 0.036401 0.900661 0.044 Uiso 1 1 calc R . . . .
C18 C 0.66173(19) 0.0350(3) 0.80744(14) 0.0356(4) Uani 1 1 d . . . . .
H18 H 0.598535 -0.065106 0.771072 0.043 Uiso 1 1 calc R . . . .
C20 C 0.88933(18) 0.1211(4) 0.87872(13) 0.0383(4) Uani 1 1 d . . . . .
H20 H 0.981342 0.079726 0.892734 0.046 Uiso 1 1 calc R . . . .
C19 C 0.7957(2) -0.0256(3) 0.82826(15) 0.0407(4) Uani 1 1 d . . . . .
H19 H 0.823469 -0.168303 0.807833 0.049 Uiso 1 1 calc R . . . .
C14 C 0.25016(17) 0.2754(4) 0.88118(13) 0.0406(4) Uani 1 1 d . . . . .
H14A H 0.202097 0.195979 0.821907 0.049 Uiso 1 1 calc R . . . .
H14B H 0.207972 0.232670 0.939065 0.049 Uiso 1 1 calc R . . . .
C21 C 0.84839(18) 0.3286(3) 0.90878(12) 0.0356(4) Uani 1 1 d . . . . .
H21 H 0.912685 0.431008 0.942242 0.043 Uiso 1 1 calc R . . . .
C13 C 0.23699(17) 0.5264(4) 0.86481(12) 0.0375(4) Uani 1 1 d . . . . .
H13A H 0.141364 0.567232 0.844626 0.045 Uiso 1 1 calc R . . . .
H13B H 0.272262 0.606962 0.927293 0.045 Uiso 1 1 calc R . . . .


_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
O11 C11 1.233(2) . ?
N1 C10 1.318(2) . ?
N1 C2 1.3726(19) . ?
N16 H16 0.92(2) . ?
N16 N12 1.4279(19) . ?
N16 C16 1.471(2) . ?
N12 C11 1.340(2) . ?
N12 C13 1.462(2) . ?
C11 C10 1.508(2) . ?
C10 C9 1.418(2) . ?
C3 H3 0.9500 . ?
C3 C2 1.414(2) . ?
C3 C4 1.370(2) . ?
C2 C7 1.422(2) . ?
C17 C16 1.507(2) . ?
C17 C22 1.394(2) . ?
C17 C18 1.391(2) . ?
C16 H16A 1.0000 . ?
C16 C15 1.533(2) . ?
C8 H8 0.9500 . ?
C8 C7 1.413(2) . ?
C8 C9 1.364(2) . ?
C7 C6 1.420(2) . ?
C22 H22 0.9500 . ?
C22 C21 1.391(2) . ?
C9 H9 0.9500 . ?
C4 H4 0.9500 . ?
C4 C5 1.413(3) . ?
C5 H5 0.9500 . ?
C5 C6 1.365(3) . ?
C6 H6 0.9500 . ?
C15 H15A 0.9900 . ?
C15 H15B 0.9900 . ?
C15 C14 1.533(2) . ?
C18 H18 0.9500 . ?
C18 C19 1.385(3) . ?
C20 H20 0.9500 . ?
C20 C19 1.383(3) . ?
C20 C21 1.386(3) . ?
C19 H19 0.9500 . ?
C14 H14A 0.9900 . ?
C14 H14B 0.9900 . ?
C14 C13 1.512(3) . ?
C21 H21 0.9500 . ?
C13 H13A 0.9900 . ?
C13 H13B 0.9900 . ?

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
C10 N1 C2 117.72(13) . . ?
N12 N16 H16 104.0(13) . . ?
N12 N16 C16 109.20(13) . . ?
C16 N16 H16 110.8(15) . . ?
N16 N12 C13 111.50(12) . . ?
C11 N12 N16 116.97(13) . . ?
C11 N12 C13 130.97(14) . . ?
O11 C11 N12 121.04(15) . . ?
O11 C11 C10 118.98(14) . . ?
N12 C11 C10 119.97(13) . . ?
N1 C10 C11 119.14(14) . . ?
N1 C10 C9 124.23(14) . . ?
C9 C10 C11 116.44(14) . . ?
C2 C3 H3 120.0 . . ?
C4 C3 H3 120.0 . . ?
C4 C3 C2 119.97(15) . . ?
N1 C2 C3 118.44(14) . . ?
N1 C2 C7 122.07(14) . . ?
C3 C2 C7 119.48(14) . . ?
C22 C17 C16 122.35(15) . . ?
C18 C17 C16 119.02(15) . . ?
C18 C17 C22 118.62(16) . . ?
N16 C16 C17 109.62(13) . . ?
N16 C16 H16A 109.2 . . ?
N16 C16 C15 107.91(14) . . ?
C17 C16 H16A 109.2 . . ?
C17 C16 C15 111.65(13) . . ?
C15 C16 H16A 109.2 . . ?
C7 C8 H8 120.1 . . ?
C9 C8 H8 120.1 . . ?
C9 C8 C7 119.80(14) . . ?
C8 C7 C2 117.77(14) . . ?
C8 C7 C6 123.19(15) . . ?
C6 C7 C2 119.04(15) . . ?
C17 C22 H22 119.8 . . ?
C21 C22 C17 120.45(17) . . ?
C21 C22 H22 119.8 . . ?
C10 C9 H9 120.8 . . ?
C8 C9 C10 118.40(15) . . ?
C8 C9 H9 120.8 . . ?
C3 C4 H4 119.6 . . ?
C3 C4 C5 120.72(16) . . ?
C5 C4 H4 119.6 . . ?
C4 C5 H5 119.7 . . ?
C6 C5 C4 120.54(15) . . ?
C6 C5 H5 119.7 . . ?
C7 C6 H6 119.9 . . ?
C5 C6 C7 120.23(16) . . ?
C5 C6 H6 119.9 . . ?
C16 C15 H15A 109.5 . . ?
C16 C15 H15B 109.5 . . ?
C16 C15 C14 110.56(14) . . ?
H15A C15 H15B 108.1 . . ?
C14 C15 H15A 109.5 . . ?
C14 C15 H15B 109.5 . . ?
C17 C18 H18 119.6 . . ?
C19 C18 C17 120.89(17) . . ?
C19 C18 H18 119.6 . . ?
C19 C20 H20 120.1 . . ?
C19 C20 C21 119.74(17) . . ?
C21 C20 H20 120.1 . . ?
C18 C19 H19 119.9 . . ?
C20 C19 C18 120.14(18) . . ?
C20 C19 H19 119.9 . . ?
C15 C14 H14A 109.4 . . ?
C15 C14 H14B 109.4 . . ?
H14A C14 H14B 108.0 . . ?
C13 C14 C15 111.27(15) . . ?
C13 C14 H14A 109.4 . . ?
C13 C14 H14B 109.4 . . ?
C22 C21 H21 119.9 . . ?
C20 C21 C22 120.11(16) . . ?
C20 C21 H21 119.9 . . ?
N12 C13 C14 108.65(16) . . ?
N12 C13 H13A 110.0 . . ?
N12 C13 H13B 110.0 . . ?
C14 C13 H13A 110.0 . . ?
C14 C13 H13B 110.0 . . ?
H13A C13 H13B 108.3 . . ?

_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 23.590
_oxdiff_exptl_absorpt_empirical_full_min 0.548
####################################################################### 
# 
# 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_sr5
_database_code_depnum_ccdc_archive 'CCDC 1955341'
loop_
_audit_author_name
_audit_author_address
'Guy Clarkson'
;University of Warwick
United Kingdom
;
_audit_update_record             
;
2019-09-23 deposited with the CCDC.	2019-12-26 downloaded from the CCDC.
;
_audit_creation_date             2019-08-20
_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        ?
_chemical_formula_moiety         'C28 H30 N2 O2'
_chemical_formula_sum            'C28 H30 N2 O2'
_chemical_formula_weight         426.54
_chemical_absolute_configuration rmad
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C20 H20 N2 O2'
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      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'

_cell_length_a                   8.33247(2)
_cell_length_b                   15.71709(6)
_cell_length_c                   17.93381(5)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2348.651(13)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    54333
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      73.5390
_cell_measurement_theta_min      2.7790
_shelx_estimated_absorpt_T_max   0.890
_shelx_estimated_absorpt_T_min   0.890
_exptl_absorpt_coefficient_mu    0.595
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.30258
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.57a (Rigaku Oxford Diffraction, 2019)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.206
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             912
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.2
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0275
_diffrn_reflns_av_unetI/netI     0.0106
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            70707
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         73.664
_diffrn_reflns_theta_min         3.740
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      150(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.3046
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω   -116.00 -17.00   1.00    1.00    --  -41.82 -37.00 -30.00   99
  2  ω    -66.00  33.00   1.00    1.00    --  -41.82  37.00 150.00   99
  3  ω    -74.00  34.00   1.00    1.00    --  -41.82  77.00-120.00  108
  4  ω      8.00  34.00   1.00    1.00    --   41.82  83.00 -29.61   26
  5  ω     81.00 178.00   1.00    4.00    --  107.00  45.00-180.00   97
  6  ω     78.00 178.00   1.00    4.00    --  107.00  61.00 120.00  100
  7  ω     35.00 136.00   1.00    4.00    --  107.00 -61.00-180.00  101
  8  ω     34.00 112.00   1.00    4.00    --  107.00-125.00 120.00   78
  9  ω     81.00 178.00   1.00    4.00    --  107.00  45.00 -90.00   97
 10  ω     97.00 178.00   1.00    4.00    --  107.00 125.00-150.00   81
 11  ω     24.00 107.00   1.00    4.00    --  107.00 -94.00 -30.00   83
 12  ω     24.00 107.00   1.00    4.00    --  107.00 -94.00 120.00   83
 13  ω     78.00 178.00   1.00    4.00    --  107.00  61.00   0.00  100
 14  ω     35.00 136.00   1.00    4.00    --  107.00 -61.00  60.00  101
 15  ω     34.00 115.00   1.00    4.00    --  107.00-128.00-102.00   81
 16  ω     97.00 178.00   1.00    4.00    --  107.00 125.00-180.00   81
 17  ω     35.00 125.00   1.00    4.00    --  107.00-141.00  85.00   90
 18  ω     37.00 127.00   1.00    4.00    --  107.00-144.00   9.58   90
 19  ω   -114.00 -14.00   1.00    1.00    --  -41.82 -57.00 120.00  100
 20  ω      8.00  42.00   1.00    1.00    --   41.82  81.00 -77.48   34
 21  ω      8.00  42.00   1.00    1.00    --   41.82  81.00 171.92   34
 22  ω      7.00  33.00   1.00    1.00    --   41.82  84.00 109.34   26
 23  ω      8.00  42.00   1.00    1.00    --   41.82  81.00-117.99   34
 24  ω     78.00 178.00   1.00    4.00    --  107.00  61.00 -60.00  100
 25  ω     78.00 178.00   1.00    4.00    --  107.00  60.00 144.03  100
 26  ω     78.00 178.00   1.00    4.00    --  107.00  61.00  60.00  100
 27  ω     78.00 178.00   1.00    4.00    --  107.00  61.00  90.00  100
 28  ω     97.00 178.00   1.00    4.00    --  107.00 125.00 120.00   81
 29  ω     78.00 178.00   1.00    4.00    --  107.00  61.00 -30.00  100
 30  ω     78.00 178.00   1.00    4.00    --  107.00  61.00-120.00  100
 31  ω     78.00 178.00   1.00    4.00    --  107.00  61.00 -90.00  100
 32  ω     78.00 178.00   1.00    4.00    --  107.00  61.00-180.00  100
 33  ω     78.00 178.00   1.00    4.00    --  107.00  61.00 107.82  100
 34  ω     78.00 178.00   1.00    4.00    --  107.00  61.00  30.00  100
 35  ω     78.00 178.00   1.00    4.00    --  107.00  62.00  74.48  100
 36  ω     75.00 178.00   1.00    4.00    --  107.00  74.00-152.84  103
 37  ω     76.00 178.00   1.00    4.00    --  107.00  72.00  33.79  102
 38  ω     78.00 178.00   1.00    4.00    --  107.00  61.00-150.00  100
 39  ω    -66.00  33.00   1.00    1.00    --  -41.82  37.00  60.00   99
 40  ω   -114.00 -14.00   1.00    1.00    --  -41.82 -57.00-120.00  100
 41  ω      8.00  42.00   1.00    1.00    --   41.82  81.00  13.45   34
 42  ω      8.00  34.00   1.00    1.00    --   41.82  83.00  78.36   26
 43  ω      7.00  33.00   1.00    1.00    --   41.82  84.00 126.66   26
 44  ω     79.00 178.00   1.00    4.00    --  107.00  56.00 -32.60   99
 45  ω     81.00 178.00   1.00    4.00    --  107.00  45.00 -60.00   97
 46  ω     78.00 178.00   1.00    4.00    --  107.00  59.00-155.30  100
 47  ω     29.00 108.00   1.00    4.00    --  107.00-106.00 176.81   79
 48  ω     77.00 178.00   1.00    4.00    --  107.00  67.00 -12.31  101
 49  ω     78.00 178.00   1.00    4.00    --  107.00  63.00 158.14  100
 50  ω     78.00 178.00   1.00    4.00    --  107.00  61.00 150.00  100
 51  ω     34.00 112.00   1.00    4.00    --  107.00-125.00 -60.00   78
 52  ω     76.00 178.00   1.00    4.00    --  107.00  72.00  87.25  102
 53  ω     81.00 130.00   1.00    4.00    --  107.00  45.00 -30.00   49
 54  ω     81.00 178.00   1.00    4.00    --  107.00  45.00  30.00   97
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, AtlasS2'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.1682378000
_diffrn_orient_matrix_UB_12      -0.0009115000
_diffrn_orient_matrix_UB_13      0.0356225000
_diffrn_orient_matrix_UB_21      0.0764893000
_diffrn_orient_matrix_UB_22      -0.0053588000
_diffrn_orient_matrix_UB_23      -0.0780653000
_diffrn_orient_matrix_UB_31      0.0057363000
_diffrn_orient_matrix_UB_32      0.0978653000
_diffrn_orient_matrix_UB_33      -0.0039339000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\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         0.754
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     0.995
_reflns_number_gt                4709
_reflns_number_total             4736
_reflns_odcompleteness_completeness 99.85
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     72.42
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.40.57a (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.40.57a (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.57a (Rigaku OD, 2019)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.156
_refine_diff_density_min         -0.186
_refine_diff_density_rms         0.033
_refine_ls_abs_structure_details 
;
 Flack x determined using 2014 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
 Flack x: 0.01(3) Shelx 2018
 Hooft y: 0.02(3) Olex2
;
_refine_ls_abs_structure_Flack   0.01(3)
_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     290
_refine_ls_number_reflns         4736
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0279
_refine_ls_R_factor_gt           0.0277
_refine_ls_restrained_S_all      1.085
_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)+(0.0385P)²+0.3008P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0703
_refine_ls_wR_factor_ref         0.0705
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C11(H11)
2.b Secondary CH2 refined with riding coordinates:
 C12(H12A,H12B), C13(H13A,H13B), C14(H14A,H14B), C15(H15A,H15B), C17(H17A,H17B)
2.c Aromatic/amide H refined with riding coordinates:
 C4(H4), C5(H5), C7(H7), C8(H8), C18(H18), C19(H19), C21(H21), C22(H22),
 C23(H23), C24(H24), C25(H25), C27(H27), C28(H28), C29(H29), C30(H30), C31(H31)
2.d Idealised Me refined as rotating group:
 C1(H1A,H1B,H1C)
;
_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
O2 O 0.79942(18) 0.73278(7) 0.97320(6) 0.0424(3) Uani 1 1 d . . . . .
O9 O 0.65082(16) 0.73483(7) 0.63330(6) 0.0379(3) Uani 1 1 d . . . . .
N10 N 0.75978(13) 0.60264(7) 0.62889(6) 0.0220(2) Uani 1 1 d . . . . .
N16 N 0.71480(14) 0.59110(8) 0.55294(6) 0.0251(2) Uani 1 1 d . . . . .
C1 C 0.8630(3) 0.81230(12) 0.99836(10) 0.0508(5) Uani 1 1 d . . . . .
H1A H 0.805298 0.859048 0.974087 0.076 Uiso 1 1 calc GR . . . .
H1B H 0.977227 0.815639 0.985685 0.076 Uiso 1 1 calc GR . . . .
H1C H 0.850009 0.816691 1.052531 0.076 Uiso 1 1 calc GR . . . .
C3 C 0.79361(19) 0.71990(9) 0.89782(8) 0.0299(3) Uani 1 1 d . . . . .
C4 C 0.71198(18) 0.64718(9) 0.87474(8) 0.0295(3) Uani 1 1 d . . . . .
H4 H 0.667371 0.609605 0.910691 0.035 Uiso 1 1 calc R . . . .
C5 C 0.69582(17) 0.62961(9) 0.79952(8) 0.0269(3) Uani 1 1 d . . . . .
H5 H 0.640663 0.579749 0.784036 0.032 Uiso 1 1 calc R . . . .
C6 C 0.75991(16) 0.68457(9) 0.74631(8) 0.0247(3) Uani 1 1 d . . . . .
C7 C 0.84314(18) 0.75619(9) 0.76998(8) 0.0277(3) Uani 1 1 d . . . . .
H7 H 0.887565 0.793805 0.734017 0.033 Uiso 1 1 calc R . . . .
C8 C 0.86256(19) 0.77377(9) 0.84541(9) 0.0306(3) Uani 1 1 d . . . . .
H8 H 0.922318 0.822096 0.860949 0.037 Uiso 1 1 calc R . . . .
C9 C 0.72096(18) 0.67631(9) 0.66470(8) 0.0263(3) Uani 1 1 d . . . . .
C11 C 0.87033(16) 0.53718(8) 0.65818(7) 0.0231(3) Uani 1 1 d . . . . .
H11 H 0.921878 0.561187 0.703931 0.028 Uiso 1 1 calc R . . . .
C12 C 1.00461(18) 0.51903(10) 0.60190(9) 0.0312(3) Uani 1 1 d . . . . .
H12A H 1.094547 0.490985 0.628304 0.037 Uiso 1 1 calc R . . . .
H12B H 0.963812 0.478639 0.564024 0.037 Uiso 1 1 calc R . . . .
C13 C 1.06882(19) 0.59806(12) 0.56205(10) 0.0396(4) Uani 1 1 d . . . . .
H13A H 1.183234 0.589011 0.549469 0.048 Uiso 1 1 calc R . . . .
H13B H 1.062377 0.647350 0.596298 0.048 Uiso 1 1 calc R . . . .
C14 C 0.9758(2) 0.61861(13) 0.49055(9) 0.0410(4) Uani 1 1 d . . . . .
H14A H 1.034632 0.663230 0.462792 0.049 Uiso 1 1 calc R . . . .
H14B H 0.973125 0.567066 0.458843 0.049 Uiso 1 1 calc R . . . .
C15 C 0.8044(2) 0.64875(11) 0.50314(8) 0.0341(3) Uani 1 1 d . . . . .
H15A H 0.806319 0.706482 0.525199 0.041 Uiso 1 1 calc R . . . .
H15B H 0.748385 0.652316 0.454549 0.041 Uiso 1 1 calc R . . . .
C17 C 0.53928(17) 0.59355(10) 0.54243(8) 0.0291(3) Uani 1 1 d . . . . .
H17A H 0.504190 0.653089 0.534742 0.035 Uiso 1 1 calc R . . . .
H17B H 0.485442 0.571513 0.587692 0.035 Uiso 1 1 calc R . . . .
C18 C 0.49186(18) 0.54063(10) 0.47618(8) 0.0293(3) Uani 1 1 d . . . . .
H18 H 0.538843 0.485842 0.471228 0.035 Uiso 1 1 calc R . . . .
C19 C 0.38863(17) 0.56541(9) 0.42411(8) 0.0277(3) Uani 1 1 d . . . . .
H19 H 0.351420 0.622449 0.426924 0.033 Uiso 1 1 calc R . . . .
C20 C 0.32605(16) 0.51303(9) 0.36232(8) 0.0244(3) Uani 1 1 d . . . . .
C21 C 0.37148(18) 0.42824(10) 0.35162(8) 0.0293(3) Uani 1 1 d . . . . .
H21 H 0.444630 0.402391 0.385351 0.035 Uiso 1 1 calc R . . . .
C22 C 0.31109(18) 0.38147(10) 0.29241(9) 0.0311(3) Uani 1 1 d . . . . .
H22 H 0.343262 0.323981 0.285789 0.037 Uiso 1 1 calc R . . . .
C23 C 0.20380(18) 0.41827(10) 0.24275(8) 0.0314(3) Uani 1 1 d . . . . .
H23 H 0.162998 0.386271 0.202002 0.038 Uiso 1 1 calc R . . . .
C24 C 0.15673(18) 0.50181(10) 0.25301(8) 0.0309(3) Uani 1 1 d . . . . .
H24 H 0.083322 0.527266 0.219168 0.037 Uiso 1 1 calc R . . . .
C25 C 0.21617(17) 0.54867(9) 0.31250(8) 0.0268(3) Uani 1 1 d . . . . .
H25 H 0.181675 0.605740 0.319423 0.032 Uiso 1 1 calc R . . . .
C26 C 0.78287(16) 0.45659(8) 0.68129(7) 0.0235(3) Uani 1 1 d . . . . .
C27 C 0.7923(2) 0.42701(10) 0.75415(8) 0.0323(3) Uani 1 1 d . . . . .
H27 H 0.858000 0.455930 0.789249 0.039 Uiso 1 1 calc R . . . .
C28 C 0.7064(3) 0.35540(10) 0.77616(9) 0.0419(4) Uani 1 1 d . . . . .
H28 H 0.714164 0.335685 0.826104 0.050 Uiso 1 1 calc R . . . .
C29 C 0.6096(2) 0.31265(10) 0.72583(11) 0.0404(4) Uani 1 1 d . . . . .
H29 H 0.547936 0.265059 0.741456 0.048 Uiso 1 1 calc R . . . .
C30 C 0.6038(2) 0.33993(10) 0.65260(11) 0.0371(4) Uani 1 1 d . . . . .
H30 H 0.539880 0.309991 0.617427 0.044 Uiso 1 1 calc R . . . .
C31 C 0.69055(18) 0.41075(9) 0.63017(8) 0.0295(3) Uani 1 1 d . . . . .
H31 H 0.687180 0.428273 0.579495 0.035 Uiso 1 1 calc R . . . .


_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
O2 C1 1.431(2) . ?
O2 C3 1.3678(18) . ?
O9 C9 1.2266(18) . ?
N10 N16 1.4242(15) . ?
N10 C9 1.3630(17) . ?
N10 C11 1.4775(17) . ?
N16 C15 1.4751(19) . ?
N16 C17 1.4751(18) . ?
C1 H1A 0.9800 . ?
C1 H1B 0.9800 . ?
C1 H1C 0.9800 . ?
C3 C4 1.393(2) . ?
C3 C8 1.389(2) . ?
C4 H4 0.9500 . ?
C4 C5 1.384(2) . ?
C5 H5 0.9500 . ?
C5 C6 1.393(2) . ?
C6 C7 1.389(2) . ?
C6 C9 1.5048(19) . ?
C7 H7 0.9500 . ?
C7 C8 1.390(2) . ?
C8 H8 0.9500 . ?
C11 H11 1.0000 . ?
C11 C12 1.5336(19) . ?
C11 C26 1.5190(19) . ?
C12 H12A 0.9900 . ?
C12 H12B 0.9900 . ?
C12 C13 1.530(2) . ?
C13 H13A 0.9900 . ?
C13 H13B 0.9900 . ?
C13 C14 1.533(2) . ?
C14 H14A 0.9900 . ?
C14 H14B 0.9900 . ?
C14 C15 1.521(2) . ?
C15 H15A 0.9900 . ?
C15 H15B 0.9900 . ?
C17 H17A 0.9900 . ?
C17 H17B 0.9900 . ?
C17 C18 1.503(2) . ?
C18 H18 0.9500 . ?
C18 C19 1.328(2) . ?
C19 H19 0.9500 . ?
C19 C20 1.4758(19) . ?
C20 C21 1.399(2) . ?
C20 C25 1.397(2) . ?
C21 H21 0.9500 . ?
C21 C22 1.386(2) . ?
C22 H22 0.9500 . ?
C22 C23 1.388(2) . ?
C23 H23 0.9500 . ?
C23 C24 1.383(2) . ?
C24 H24 0.9500 . ?
C24 C25 1.388(2) . ?
C25 H25 0.9500 . ?
C26 C27 1.3891(19) . ?
C26 C31 1.397(2) . ?
C27 H27 0.9500 . ?
C27 C28 1.391(2) . ?
C28 H28 0.9500 . ?
C28 C29 1.384(3) . ?
C29 H29 0.9500 . ?
C29 C30 1.382(3) . ?
C30 H30 0.9500 . ?
C30 C31 1.387(2) . ?
C31 H31 0.9500 . ?

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
C3 O2 C1 117.01(14) . . ?
N16 N10 C11 114.55(10) . . ?
C9 N10 N16 119.76(11) . . ?
C9 N10 C11 124.88(11) . . ?
N10 N16 C15 111.57(11) . . ?
N10 N16 C17 112.32(10) . . ?
C15 N16 C17 114.09(12) . . ?
O2 C1 H1A 109.5 . . ?
O2 C1 H1B 109.5 . . ?
O2 C1 H1C 109.5 . . ?
H1A C1 H1B 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
O2 C3 C4 115.61(14) . . ?
O2 C3 C8 124.32(14) . . ?
C8 C3 C4 120.07(13) . . ?
C3 C4 H4 120.0 . . ?
C5 C4 C3 120.06(14) . . ?
C5 C4 H4 120.0 . . ?
C4 C5 H5 119.8 . . ?
C4 C5 C6 120.44(13) . . ?
C6 C5 H5 119.8 . . ?
C5 C6 C9 121.99(13) . . ?
C7 C6 C5 118.99(13) . . ?
C7 C6 C9 118.36(13) . . ?
C6 C7 H7 119.4 . . ?
C6 C7 C8 121.11(13) . . ?
C8 C7 H7 119.4 . . ?
C3 C8 C7 119.28(14) . . ?
C3 C8 H8 120.4 . . ?
C7 C8 H8 120.4 . . ?
O9 C9 N10 122.25(13) . . ?
O9 C9 C6 118.98(12) . . ?
N10 C9 C6 118.72(12) . . ?
N10 C11 H11 107.3 . . ?
N10 C11 C12 110.51(11) . . ?
N10 C11 C26 112.24(11) . . ?
C12 C11 H11 107.3 . . ?
C26 C11 H11 107.3 . . ?
C26 C11 C12 112.00(11) . . ?
C11 C12 H12A 108.7 . . ?
C11 C12 H12B 108.7 . . ?
H12A C12 H12B 107.6 . . ?
C13 C12 C11 114.31(13) . . ?
C13 C12 H12A 108.7 . . ?
C13 C12 H12B 108.7 . . ?
C12 C13 H13A 109.1 . . ?
C12 C13 H13B 109.1 . . ?
C12 C13 C14 112.64(14) . . ?
H13A C13 H13B 107.8 . . ?
C14 C13 H13A 109.1 . . ?
C14 C13 H13B 109.1 . . ?
C13 C14 H14A 108.6 . . ?
C13 C14 H14B 108.6 . . ?
H14A C14 H14B 107.6 . . ?
C15 C14 C13 114.59(13) . . ?
C15 C14 H14A 108.6 . . ?
C15 C14 H14B 108.6 . . ?
N16 C15 C14 111.94(13) . . ?
N16 C15 H15A 109.2 . . ?
N16 C15 H15B 109.2 . . ?
C14 C15 H15A 109.2 . . ?
C14 C15 H15B 109.2 . . ?
H15A C15 H15B 107.9 . . ?
N16 C17 H17A 109.6 . . ?
N16 C17 H17B 109.6 . . ?
N16 C17 C18 110.31(12) . . ?
H17A C17 H17B 108.1 . . ?
C18 C17 H17A 109.6 . . ?
C18 C17 H17B 109.6 . . ?
C17 C18 H18 117.8 . . ?
C19 C18 C17 124.31(14) . . ?
C19 C18 H18 117.8 . . ?
C18 C19 H19 116.8 . . ?
C18 C19 C20 126.39(14) . . ?
C20 C19 H19 116.8 . . ?
C21 C20 C19 122.61(13) . . ?
C25 C20 C19 119.23(12) . . ?
C25 C20 C21 118.16(13) . . ?
C20 C21 H21 119.6 . . ?
C22 C21 C20 120.81(13) . . ?
C22 C21 H21 119.6 . . ?
C21 C22 H22 119.9 . . ?
C21 C22 C23 120.29(14) . . ?
C23 C22 H22 119.9 . . ?
C22 C23 H23 120.2 . . ?
C24 C23 C22 119.53(14) . . ?
C24 C23 H23 120.2 . . ?
C23 C24 H24 119.8 . . ?
C23 C24 C25 120.33(14) . . ?
C25 C24 H24 119.8 . . ?
C20 C25 H25 119.6 . . ?
C24 C25 C20 120.86(13) . . ?
C24 C25 H25 119.6 . . ?
C27 C26 C11 120.57(13) . . ?
C27 C26 C31 118.42(13) . . ?
C31 C26 C11 121.01(12) . . ?
C26 C27 H27 119.7 . . ?
C26 C27 C28 120.57(15) . . ?
C28 C27 H27 119.7 . . ?
C27 C28 H28 119.8 . . ?
C29 C28 C27 120.49(15) . . ?
C29 C28 H28 119.8 . . ?
C28 C29 H29 120.3 . . ?
C30 C29 C28 119.32(15) . . ?
C30 C29 H29 120.3 . . ?
C29 C30 H30 119.8 . . ?
C29 C30 C31 120.39(16) . . ?
C31 C30 H30 119.8 . . ?
C26 C31 H31 119.6 . . ?
C30 C31 C26 120.71(14) . . ?
C30 C31 H31 119.6 . . ?

_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 2.335
_oxdiff_exptl_absorpt_empirical_full_min 0.738
####################################################################### 
# 
# 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_cd6
_database_code_depnum_ccdc_archive 'CCDC 1944268'
loop_
_audit_author_name
_audit_author_address
'Guy Clarkson'
;University of Warwick
United Kingdom
;
_audit_update_record             
;
2019-07-30 deposited with the CCDC.	2019-12-26 downloaded from the CCDC.
;
_audit_creation_date             2018-06-06
_audit_creation_method           
;
Olex2 1.2
(compiled Apr  3 2018 11:26:26 for OlexSys, GUI svn.r5486)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C24 H24 N2 O4 S'
_chemical_formula_sum            'C24 H24 N2 O4 S'
_chemical_formula_weight         436.51
_chemical_absolute_configuration ad
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C24 H24 N2 O4 S'
_chemical_oxdiff_usercomment     cd6
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'
S S 0.3331 0.5567 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'

_cell_length_a                   6.0985(4)
_cell_length_b                   11.5023(5)
_cell_length_c                   30.8387(15)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2163.2(2)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    5772
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      70.0300
_cell_measurement_theta_min      2.8950
_shelx_estimated_absorpt_T_max   0.984
_shelx_estimated_absorpt_T_min   0.760
_exptl_absorpt_coefficient_mu    1.610
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.69705
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'CrysAlisPro 1.171.39.46 (Rigaku Oxford Diffraction, 2018) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm.'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.340
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             920
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.01
_exptl_crystal_size_min          0.01
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.1033
_diffrn_reflns_av_unetI/netI     0.0835
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       32
_diffrn_reflns_limit_l_min       -37
_diffrn_reflns_number            17168
_diffrn_reflns_point_group_measured_fraction_full 0.990
_diffrn_reflns_point_group_measured_fraction_max 0.989
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         68.224
_diffrn_reflns_theta_min         2.866
_diffrn_ambient_temperature      100(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_details      
'List of Runs (angles in degrees, time in seconds): # Type Start End Width tₑₓₚ ω θ κ φ Frames -------------------------------------------------------------------------- 1 ω -63.00 22.00 0.50 4.00 -- 0.00 60.00-120.00 170 2 ω -53.00 81.00 0.50 4.00 -- 5.00 60.00 -60.00 268 3 ω -60.00 -33.00 0.50 20.00 -- -90.00 60.00 0.00 54 4 ω -99.00 -37.00 0.50 20.00 -- -90.00 60.00 120.00 124 5 ω -137.00 -84.00 0.50 20.00 -- -90.00 60.00-120.00 106 6 ω -36.00 -11.00 0.50 20.00 -- -90.00 60.00-120.00 50 7 ω -176.00 -46.00 0.50 20.00 -- -90.00 43.00 -30.00 260 8 ω -92.00 -66.00 0.50 20.00 -- -90.00 60.00 150.00 52 9 ω -178.00 -28.00 0.50 20.00 -- -90.00 60.00-180.00 300 10 ω -148.00 -4.00 0.50 20.00 -- -90.00 43.00 120.00 288 11 ω -179.00-105.00 0.50 20.00 -- -90.00 57.00 -30.00 148 12 ω -149.00 -1.00 0.50 20.00 -- -90.00 43.00 90.00 296'
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB AFC11 (RCD3): quarter-chi single'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.2207294000
_diffrn_orient_matrix_UB_12      0.0154348000
_diffrn_orient_matrix_UB_13      0.0236294000
_diffrn_orient_matrix_UB_21      -0.0150827000
_diffrn_orient_matrix_UB_22      0.1257332000
_diffrn_orient_matrix_UB_23      -0.0169530000
_diffrn_orient_matrix_UB_31      -0.1219265000
_diffrn_orient_matrix_UB_32      -0.0435685000
_diffrn_orient_matrix_UB_33      -0.0406060000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'Rigaku (Cu) X-ray Source'
_diffrn_special_details          ?
_reflns_Friedel_coverage         0.697
_reflns_Friedel_fraction_full    0.980
_reflns_Friedel_fraction_max     0.978
_reflns_number_gt                2982
_reflns_number_total             3915
_reflns_odcompleteness_completeness 99.53
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     68.13
_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 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.240
_refine_diff_density_min         -0.786
_refine_diff_density_rms         0.073
_refine_ls_abs_structure_details 
;
 Flack x determined using 961 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
Flack x: -0.03(3) Shelx2018
Hooft y: -0.05(2) Olex2

;
_refine_ls_abs_structure_Flack   -0.03(3)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.098
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     281
_refine_ls_number_reflns         3915
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0871
_refine_ls_R_factor_gt           0.0624
_refine_ls_restrained_S_all      1.098
_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)+(0.0967P)²+0.0730P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1550
_refine_ls_wR_factor_ref         0.1773
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C7(H7)
2.b Secondary CH2 refined with riding coordinates:
 C13(H13A,H13B), C9(H9A,H9B), C8(H8A,H8B)
2.c Aromatic/amide H refined with riding coordinates:
 C22(H22), C25(H25), C23(H23), C26(H26), C19(H19), C15(H15), C17(H17),
 C16(H16), C1(H1), C5(H5), C18(H18), C2(H2), C3(H3), C4(H4)
2.d Idealised Me refined as rotating group:
 C27(H27A,H27B,H27C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_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
S20 S 0.5755(3) 0.43651(11) 0.28463(4) 0.0379(4) Uani 1 1 d . . . . .
O12 O 0.6007(7) 0.6210(3) 0.37621(11) 0.0404(10) Uani 1 1 d . . . . .
O20B O 0.6941(7) 0.3298(3) 0.28211(12) 0.0418(10) Uani 1 1 d . . . . .
O20A O 0.6838(7) 0.5453(3) 0.27969(11) 0.0400(9) Uani 1 1 d . . . . .
O11 O 0.2488(8) 0.6786(4) 0.38811(12) 0.0494(11) Uani 1 1 d . . . . .
N10 N 0.3214(8) 0.5294(4) 0.34128(14) 0.0390(11) Uani 1 1 d . . . . .
N7 N 0.4744(8) 0.4368(4) 0.33458(14) 0.0376(11) Uani 1 1 d . . . . .
C14 C 0.6993(11) 0.6512(5) 0.45159(17) 0.0385(13) Uani 1 1 d . . . . .
C22 C 0.2553(10) 0.5388(5) 0.23675(17) 0.0391(14) Uani 1 1 d . . . . .
H22 H 0.306841 0.610273 0.248340 0.047 Uiso 1 1 calc R . . . .
C13 C 0.6763(12) 0.7064(5) 0.40787(17) 0.0430(15) Uani 1 1 d . . . . .
H13A H 0.570148 0.771332 0.409504 0.052 Uiso 1 1 calc R . . . .
H13B H 0.819504 0.738344 0.398580 0.052 Uiso 1 1 calc R . . . .
C11 C 0.3784(11) 0.6143(5) 0.37098(17) 0.0423(14) Uani 1 1 d . . . . .
C7 C 0.3694(10) 0.3253(5) 0.35145(18) 0.0406(14) Uani 1 1 d . . . . .
H7 H 0.346878 0.270455 0.326693 0.049 Uiso 1 1 calc R . . . .
C6 C 0.5181(10) 0.2695(5) 0.38430(18) 0.0402(14) Uani 1 1 d . . . . .
C25 C 0.1022(12) 0.3298(5) 0.20299(17) 0.0458(15) Uani 1 1 d . . . . .
H25 H 0.050503 0.258718 0.191102 0.055 Uiso 1 1 calc R . . . .
C21 C 0.3563(10) 0.4343(5) 0.24824(16) 0.0375(13) Uani 1 1 d . . . . .
C23 C 0.0800(12) 0.5375(5) 0.20842(17) 0.0465(15) Uani 1 1 d . . . . .
H23 H 0.013023 0.608858 0.200327 0.056 Uiso 1 1 calc R . . . .
C26 C 0.2785(12) 0.3285(5) 0.23145(18) 0.0444(15) Uani 1 1 d . . . . .
H26 H 0.345545 0.257107 0.239460 0.053 Uiso 1 1 calc R . . . .
C19 C 0.5352(12) 0.6562(5) 0.48231(18) 0.0434(15) Uani 1 1 d . . . . .
H19 H 0.401936 0.695051 0.475666 0.052 Uiso 1 1 calc R . . . .
C24 C -0.0006(11) 0.4341(6) 0.19151(17) 0.0474(15) Uani 1 1 d . . . . .
C15 C 0.8952(12) 0.5931(5) 0.46172(18) 0.0456(15) Uani 1 1 d . . . . .
H15 H 1.010629 0.589394 0.441069 0.055 Uiso 1 1 calc R . . . .
C17 C 0.7543(13) 0.5468(5) 0.53280(18) 0.0511(17) Uani 1 1 d . . . . .
H17 H 0.772183 0.511129 0.560355 0.061 Uiso 1 1 calc R . . . .
C9 C 0.1008(11) 0.4773(5) 0.34458(19) 0.0429(14) Uani 1 1 d . . . . .
H9A H 0.037397 0.462414 0.315551 0.052 Uiso 1 1 calc R . . . .
H9B H -0.000042 0.527720 0.361283 0.052 Uiso 1 1 calc R . . . .
C16 C 0.9194(13) 0.5410(5) 0.50224(19) 0.0499(15) Uani 1 1 d . . . . .
H16 H 1.051388 0.500940 0.508936 0.060 Uiso 1 1 calc R . . . .
C1 C 0.5756(13) 0.3253(5) 0.42308(18) 0.0495(16) Uani 1 1 d . . . . .
H1 H 0.517122 0.400071 0.429164 0.059 Uiso 1 1 calc R . . . .
C5 C 0.6101(12) 0.1613(5) 0.37642(18) 0.0468(16) Uani 1 1 d . . . . .
H5 H 0.575448 0.121953 0.350217 0.056 Uiso 1 1 calc R . . . .
C18 C 0.5618(13) 0.6054(5) 0.52281(19) 0.0489(16) Uani 1 1 d . . . . .
H18 H 0.447909 0.610638 0.543733 0.059 Uiso 1 1 calc R . . . .
C2 C 0.7149(13) 0.2739(5) 0.45255(19) 0.0506(17) Uani 1 1 d . . . . .
H2 H 0.750854 0.313078 0.478726 0.061 Uiso 1 1 calc R . . . .
C3 C 0.8031(13) 0.1648(5) 0.4440(2) 0.0508(17) Uani 1 1 d . . . . .
H3 H 0.898264 0.128951 0.464415 0.061 Uiso 1 1 calc R . . . .
C8 C 0.1472(11) 0.3648(6) 0.3684(2) 0.0496(16) Uani 1 1 d . . . . .
H8A H 0.032913 0.306085 0.362045 0.059 Uiso 1 1 calc R . . . .
H8B H 0.152592 0.377927 0.400118 0.059 Uiso 1 1 calc R . . . .
C4 C 0.7516(12) 0.1089(5) 0.4058(2) 0.0520(17) Uani 1 1 d . . . . .
H4 H 0.812726 0.034834 0.399579 0.062 Uiso 1 1 calc R . . . .
C27 C -0.1948(12) 0.4355(7) 0.1612(2) 0.0599(18) Uani 1 1 d . . . . .
H27A H -0.177534 0.374241 0.139356 0.090 Uiso 1 1 calc GR . . . .
H27B H -0.203576 0.511256 0.146758 0.090 Uiso 1 1 calc GR . . . .
H27C H -0.329558 0.421850 0.177746 0.090 Uiso 1 1 calc GR . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
S20 O20B 1.426(4) . ?
S20 O20A 1.424(4) . ?
S20 N7 1.659(5) . ?
S20 C21 1.746(6) . ?
O12 C13 1.459(6) . ?
O12 C11 1.367(8) . ?
O11 C11 1.204(7) . ?
N10 N7 1.432(6) . ?
N10 C11 1.383(7) . ?
N10 C9 1.476(8) . ?
N7 C7 1.524(7) . ?
C14 C13 1.497(8) . ?
C14 C19 1.379(8) . ?
C14 C15 1.404(9) . ?
C22 C21 1.396(8) . ?
C22 C23 1.381(9) . ?
C7 C6 1.504(8) . ?
C7 C8 1.522(9) . ?
C6 C1 1.401(8) . ?
C6 C5 1.387(8) . ?
C25 C26 1.388(9) . ?
C25 C24 1.399(9) . ?
C21 C26 1.405(8) . ?
C23 C24 1.389(9) . ?
C19 C18 1.388(9) . ?
C24 C27 1.509(9) . ?
C15 C16 1.394(8) . ?
C17 C16 1.381(9) . ?
C17 C18 1.388(10) . ?
C9 C8 1.515(8) . ?
C1 C2 1.378(9) . ?
C5 C4 1.388(9) . ?
C2 C3 1.390(9) . ?
C3 C4 1.379(9) . ?

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
O20B S20 N7 103.9(2) . . ?
O20B S20 C21 109.9(3) . . ?
O20A S20 O20B 121.0(3) . . ?
O20A S20 N7 105.7(2) . . ?
O20A S20 C21 107.4(3) . . ?
N7 S20 C21 108.2(2) . . ?
C11 O12 C13 115.5(5) . . ?
N7 N10 C9 107.5(4) . . ?
C11 N10 N7 117.2(5) . . ?
C11 N10 C9 118.0(5) . . ?
N10 N7 S20 112.2(3) . . ?
N10 N7 C7 107.7(4) . . ?
C7 N7 S20 118.1(4) . . ?
C19 C14 C13 122.2(6) . . ?
C19 C14 C15 119.0(5) . . ?
C15 C14 C13 118.8(6) . . ?
C23 C22 C21 119.5(5) . . ?
O12 C13 C14 110.3(4) . . ?
O12 C11 N10 111.5(5) . . ?
O11 C11 O12 124.4(6) . . ?
O11 C11 N10 124.0(6) . . ?
C6 C7 N7 109.6(5) . . ?
C6 C7 C8 115.6(5) . . ?
C8 C7 N7 103.9(4) . . ?
C1 C6 C7 122.0(5) . . ?
C5 C6 C7 120.6(5) . . ?
C5 C6 C1 117.3(6) . . ?
C26 C25 C24 121.1(5) . . ?
C22 C21 S20 119.2(4) . . ?
C22 C21 C26 120.2(5) . . ?
C26 C21 S20 120.5(5) . . ?
C22 C23 C24 121.4(6) . . ?
C25 C26 C21 119.0(6) . . ?
C14 C19 C18 121.0(6) . . ?
C25 C24 C27 121.2(6) . . ?
C23 C24 C25 118.7(6) . . ?
C23 C24 C27 120.1(6) . . ?
C16 C15 C14 119.6(6) . . ?
C16 C17 C18 119.3(6) . . ?
N10 C9 C8 102.1(5) . . ?
C17 C16 C15 120.9(7) . . ?
C2 C1 C6 121.4(6) . . ?
C6 C5 C4 121.8(6) . . ?
C17 C18 C19 120.2(6) . . ?
C1 C2 C3 120.1(6) . . ?
C4 C3 C2 119.6(6) . . ?
C9 C8 C7 104.7(5) . . ?
C3 C4 C5 119.8(6) . . ?

_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 2.790
_oxdiff_exptl_absorpt_empirical_full_min 0.402
