# Electronic Supplementary Material (ESI) for Chemical Science.
# This journal is © The Royal Society of Chemistry 2019

####################################################################### 
# 
# 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_jg-g135-c1-f4-polarminorproductscaled
_audit_block_doi                 10.5517/ccdc.csd.cc22jzf1
_database_code_depnum_ccdc_archive 'CCDC 1922943'
loop_
_citation_id
_citation_doi
_citation_year
1 10.1039/C9SC03976G 2019
loop_
_audit_author_name
_audit_author_address
'Michael Gardiner'
;Australian National University
Australia
;
_audit_update_record             
;
2019-06-14 deposited with the CCDC.	2019-09-19 downloaded from the CCDC.
;
_audit_creation_date             2019-05-22
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2016/6
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C25 H24 N2 O4'
_chemical_formula_sum            'C25 H24 N2 O4'
_chemical_formula_weight         416.46
_chemical_absolute_configuration ad
_chemical_melting_point          ?
_chemical_oxdiff_formula         C25H24N2O4
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      tetragonal
_space_group_IT_number           82
_space_group_name_H-M_alt        'I -4'
_space_group_name_Hall           'I -4'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, z'
'y, -x, -z'
'-y, x, -z'
'x+1/2, y+1/2, z+1/2'
'-x+1/2, -y+1/2, z+1/2'
'y+1/2, -x+1/2, -z+1/2'
'-y+1/2, x+1/2, -z+1/2'

_cell_length_a                   18.1165(5)
_cell_length_b                   18.1165(5)
_cell_length_c                   12.8619(11)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     4221.4(4)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    2954
_cell_measurement_temperature    150.00(10)
_cell_measurement_theta_max      73.3340
_cell_measurement_theta_min      4.2010
_shelx_estimated_absorpt_T_max   0.976
_shelx_estimated_absorpt_T_min   0.817
_exptl_absorpt_coefficient_mu    0.725
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.83634
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.36a (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    1.311
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             1760
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
-1 -12 0 0.0185
1 12 0 0.0185
0 2 -8 0.1361
0 -2 8 0.1361
-11 2 -1 0.0167
11 -2 1 0.0167

_exptl_crystal_size_max          0.29
_exptl_crystal_size_mid          0.037
_exptl_crystal_size_min          0.033
loop_
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
-1.0014 -11.9998 0.0150 -1.0226 0.0207 0.0376
1.0014 11.9998 -0.0150 1.0226 -0.0207 -0.0376
0.0144 1.9862 -7.9999 0.2050 -0.0337 0.9508
-0.0144 -1.9862 7.9999 -0.2050 0.0337 -0.9508
-11.0031 1.9954 -0.9949 0.0760 -0.9504 0.0992
11.0031 -1.9954 0.9949 -0.0760 0.9504 -0.0992

_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0488
_diffrn_reflns_av_unetI/netI     0.0580
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            12779
_diffrn_reflns_point_group_measured_fraction_full 0.966
_diffrn_reflns_point_group_measured_fraction_max 0.966
_diffrn_reflns_theta_full        66.589
_diffrn_reflns_theta_max         66.589
_diffrn_reflns_theta_min         6.457
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      150.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 8.1297
_diffrn_detector_type            EosS2
_diffrn_measured_fraction_theta_full 0.996
_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   -103.00 -72.00   1.00    3.00    --  -36.95 -57.00 150.00   31
  2  ω    -45.00 -20.00   1.00    3.00    --  -36.95 -46.00 -84.64   25
  3  ω     81.00 107.00   1.00    3.00    --   36.95  19.00-120.00   26
  4  ω     31.00  65.00   1.00    3.00    --   36.95  57.00  30.00   34
  5  ω      4.00  29.00   1.00    3.00    --   36.95  88.00  41.48   25
  6  ω      2.00  55.00   1.00    3.00    --   36.95 -38.00-150.00   53
  7  ω     32.00  57.00   1.00    3.00    --   36.95  19.00-120.00   25
  8  ω     14.00 103.00   1.00    3.00    --   36.95  19.00  60.00   89
  9  ω     26.00  51.00   1.00    3.00    --   36.95  38.00   0.00   25
 10  ω      6.00  53.00   1.00    3.00    --   36.95 -99.00 150.00   47
 11  ω     33.00  83.00   1.00    3.00    --   36.95-125.00 -60.00   50
 12  ω      5.00  30.00   1.00    3.00    --   36.95  89.00-101.73   25
 13  ω     83.00 110.00   1.00   12.00    --  111.00 -25.00-150.00   27
 14  ω    138.00 165.00   1.00   12.00    --  111.00  50.00 -60.00   27
 15  ω     95.00 120.00   1.00   12.00    --  111.00  50.00 -60.00   25
 16  ω    129.00 156.00   1.00   12.00    --  111.00  64.00 -60.00   27
 17  ω     43.00  72.00   1.00   12.00    --  111.00 -92.00 150.00   29
 18  ω     73.00 109.00   1.00   12.00    --  111.00-111.00   0.00   36
 19  ω     92.00 119.00   1.00   12.00    --  111.00  38.00  30.00   27
 20  ω     90.00 117.00   1.00   12.00    --  111.00  25.00   0.00   27
 21  ω    145.00 177.00   1.00   12.00    --  111.00  25.00   0.00   32
 22  ω     45.00  77.00   1.00   12.00    --  111.00 -25.00-150.00   32
 23  ω     94.00 120.00   1.00   12.00    --  111.00  50.00 -30.00   26
 24  ω     91.00 117.00   1.00   12.00    --  111.00  64.00 -30.00   26
 25  ω    101.00 177.00   1.00   12.00    --  111.00  38.00 150.00   76
 26  ω     88.00 120.00   1.00   12.00    --  111.00  25.00 -60.00   32
 27  ω     92.00 118.00   1.00   12.00    --  111.00  38.00 -30.00   26
 28  ω    141.00 168.00   1.00   12.00    --  111.00  64.00   0.00   27
 29  ω     91.00 117.00   1.00   12.00    --  111.00  64.00 -60.00   26
 30  ω     86.00 113.00   1.00   12.00    --  111.00 -77.00-120.00   27
 31  ω     42.00  67.00   1.00   12.00    --  111.00-111.00  60.00   25
 32  ω     45.00  85.00   1.00   12.00    --  111.00 -77.00-120.00   40
 33  ω     46.00 102.00   1.00   12.00    --  111.00 -25.00-120.00   56
 34  ω     88.00 115.00   1.00   12.00    --  111.00  25.00 -30.00   27
 35  ω     94.00 121.00   1.00   12.00    --  111.00  64.00   0.00   27
 36  ω     92.00 119.00   1.00   12.00    --  111.00  38.00 -60.00   27
 37  ω     95.00 120.00   1.00   12.00    --  111.00  50.00 -90.00   25
 38  ω     95.00 122.00   1.00   12.00    --  111.00  50.00  30.00   27
 39  ω    108.00 133.00   1.00   12.00    --  111.00 178.00 -60.00   25
 40  ω     91.00 118.00   1.00   12.00    --  111.00  64.00 -90.00   27
 41  ω    100.00 127.00   1.00   12.00    --  111.00  64.00  30.00   27
 42  ω     66.00  91.00   1.00   12.00    --  111.00 178.00 -60.00   25
 43  ω     94.00 119.00   1.00   12.00    --  111.00  38.00   0.00   25
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, EosS2'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0088338000
_diffrn_orient_matrix_UB_12      0.0844777000
_diffrn_orient_matrix_UB_13      -0.0046358000
_diffrn_orient_matrix_UB_21      0.0845877000
_diffrn_orient_matrix_UB_22      -0.0087829000
_diffrn_orient_matrix_UB_23      0.0021793000
_diffrn_orient_matrix_UB_31      0.0011925000
_diffrn_orient_matrix_UB_32      -0.0033809000
_diffrn_orient_matrix_UB_33      -0.1196834000
_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         0.845
_reflns_Friedel_fraction_full    0.932
_reflns_Friedel_fraction_max     0.932
_reflns_number_gt                3074
_reflns_number_total             3605
_reflns_odcompleteness_completeness 98.36
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     74.33
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 Structure factors included contributions from the .fab file.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.40.36a (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.40.36a (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.40.36a (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 (Sheldrick, 2015)'
_refine_diff_density_max         0.134
_refine_diff_density_min         -0.179
_refine_diff_density_rms         0.037
_refine_ls_abs_structure_details 
;
 Flack x determined using 1176 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.19(18)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.014
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     283
_refine_ls_number_reflns         3605
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0516
_refine_ls_R_factor_gt           0.0405
_refine_ls_restrained_S_all      1.014
_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)+(0.0366P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0816
_refine_ls_wR_factor_ref         0.0871
_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:
 C3(H3), C5(H5), C6(H6), C10(H10), C15(H15), C24(H24)
2.b Secondary CH2 refined with riding coordinates:
 C4(H4A,H4B), C11(H11A,H11B)
2.c Aromatic/amide H refined with riding coordinates:
 C19(H19), C20(H20), C21(H21), C22(H22), C23(H23)
2.d Idealised Me refined as rotating group:
 C1(H1A,H1B,H1C), C8(H8A,H8B,H8C), C13(H13A,H13B,H13C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.22703(17) 0.89268(14) 0.3054(2) 0.0445(7) Uani 1 1 d . . . . .
O2 O 0.39980(18) 0.89160(17) 0.0496(3) 0.0672(11) Uani 1 1 d . . . . .
O3 O 0.43997(13) 0.60559(13) 0.1169(2) 0.0404(7) Uani 1 1 d . . . . .
O4 O 0.26071(13) 0.43434(13) 0.1688(2) 0.0363(6) Uani 1 1 d . . . . .
N1 N 0.31955(16) 0.90638(15) 0.1850(3) 0.0337(7) Uani 1 1 d . . . . .
N2 N 0.35985(15) 0.51165(14) 0.1574(3) 0.0292(6) Uani 1 1 d . . . . .
C1 C 0.3534(2) 0.9720(2) 0.2322(4) 0.0463(11) Uani 1 1 d . . . . .
H1A H 0.318194 1.011629 0.233152 0.069 Uiso 1 1 calc GR . . . .
H1B H 0.395739 0.986469 0.192287 0.069 Uiso 1 1 calc GR . . . .
H1C H 0.368303 0.960820 0.302093 0.069 Uiso 1 1 calc GR . . . .
C2 C 0.34562(19) 0.87260(19) 0.0970(4) 0.0373(9) Uani 1 1 d . . . . .
C3 C 0.29458(18) 0.80858(17) 0.0708(3) 0.0295(7) Uani 1 1 d . . . . .
H3 H 0.268268 0.820224 0.006309 0.035 Uiso 1 1 calc R . . . .
C4 C 0.33801(18) 0.73651(17) 0.0549(3) 0.0312(8) Uani 1 1 d . . . . .
H4A H 0.365568 0.738736 -0.009672 0.037 Uiso 1 1 calc R . . . .
H4B H 0.372675 0.729525 0.111536 0.037 Uiso 1 1 calc R . . . .
C5 C 0.28354(17) 0.67275(17) 0.0516(3) 0.0285(7) Uani 1 1 d . . . . .
H5 H 0.251135 0.682540 -0.007799 0.034 Uiso 1 1 calc R . . . .
C6 C 0.32002(18) 0.59663(17) 0.0296(3) 0.0289(7) Uani 1 1 d . . . . .
H6 H 0.339961 0.596762 -0.041187 0.035 Uiso 1 1 calc R . . . .
C7 C 0.38129(17) 0.57547(17) 0.1050(3) 0.0295(7) Uani 1 1 d . . . . .
C8 C 0.40650(18) 0.47265(19) 0.2313(3) 0.0365(8) Uani 1 1 d . . . . .
H8A H 0.379596 0.431976 0.260529 0.055 Uiso 1 1 calc GR . . . .
H8B H 0.421029 0.505782 0.285881 0.055 Uiso 1 1 calc GR . . . .
H8C H 0.449657 0.454475 0.196396 0.055 Uiso 1 1 calc GR . . . .
C9 C 0.29137(18) 0.48675(17) 0.1279(3) 0.0299(8) Uani 1 1 d . . . . .
C10 C 0.26308(18) 0.53350(17) 0.0394(3) 0.0307(8) Uani 1 1 d . . . . .
H10 H 0.262993 0.504289 -0.024693 0.037 Uiso 1 1 calc R . . . .
C11 C 0.18413(18) 0.55944(18) 0.0633(4) 0.0370(9) Uani 1 1 d . . . . .
H11A H 0.162947 0.582034 0.001832 0.044 Uiso 1 1 calc R . . . .
H11B H 0.153905 0.517265 0.081959 0.044 Uiso 1 1 calc R . . . .
C12 C 0.18407(17) 0.61450(17) 0.1516(3) 0.0306(8) Uani 1 1 d . . . . .
C13 C 0.12792(18) 0.60232(19) 0.2355(4) 0.0435(11) Uani 1 1 d . . . . .
H13A H 0.137532 0.556155 0.269541 0.065 Uiso 1 1 calc GR . . . .
H13B H 0.079447 0.601319 0.205389 0.065 Uiso 1 1 calc GR . . . .
H13C H 0.130830 0.641701 0.285281 0.065 Uiso 1 1 calc GR . . . .
C14 C 0.23334(17) 0.66939(17) 0.1462(3) 0.0267(7) Uani 1 1 d . . . . .
C15 C 0.23920(16) 0.73306(16) 0.2230(3) 0.0245(7) Uani 1 1 d . . . . .
H15 H 0.195569 0.732221 0.268018 0.029 Uiso 1 1 calc R . . . .
C16 C 0.30562(17) 0.72648(16) 0.2891(3) 0.0259(7) Uani 1 1 d . . . . .
C17 C 0.35950(17) 0.72097(16) 0.3425(3) 0.0274(7) Uani 1 1 d . . . . .
C18 C 0.42229(16) 0.71174(16) 0.4097(3) 0.0263(7) Uani 1 1 d . . . . .
C19 C 0.42744(18) 0.75172(19) 0.5013(3) 0.0331(8) Uani 1 1 d . . . . .
H19 H 0.391399 0.786364 0.517699 0.040 Uiso 1 1 calc R . . . .
C20 C 0.4865(2) 0.7402(2) 0.5689(3) 0.0413(9) Uani 1 1 d . . . . .
H20 H 0.489794 0.767323 0.630031 0.050 Uiso 1 1 calc R . . . .
C21 C 0.54004(18) 0.6886(2) 0.5454(3) 0.0365(8) Uani 1 1 d . . . . .
H21 H 0.579050 0.680699 0.591046 0.044 Uiso 1 1 calc R . . . .
C22 C 0.53564(18) 0.64868(18) 0.4539(3) 0.0342(8) Uani 1 1 d . . . . .
H22 H 0.571724 0.613928 0.438101 0.041 Uiso 1 1 calc R . . . .
C23 C 0.47750(17) 0.66042(18) 0.3857(3) 0.0316(8) Uani 1 1 d . . . . .
H23 H 0.475179 0.634063 0.323745 0.038 Uiso 1 1 calc R . . . .
C24 C 0.23866(16) 0.80641(16) 0.1602(3) 0.0264(7) Uani 1 1 d . . . . .
H24 H 0.189098 0.813962 0.131519 0.032 Uiso 1 1 calc R . . . .
C25 C 0.25836(18) 0.87219(17) 0.2274(3) 0.0303(7) Uani 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C25 1.211(5) . ?
O2 C2 1.205(5) . ?
O3 C7 1.205(4) . ?
O4 C9 1.219(4) . ?
N1 C1 1.469(4) . ?
N1 C2 1.372(5) . ?
N1 C25 1.381(5) . ?
N2 C7 1.393(4) . ?
N2 C8 1.455(4) . ?
N2 C9 1.373(4) . ?
C1 H1A 0.9600 . ?
C1 H1B 0.9600 . ?
C1 H1C 0.9600 . ?
C2 C3 1.521(4) . ?
C3 H3 0.9800 . ?
C3 C4 1.538(4) . ?
C3 C24 1.532(5) . ?
C4 H4A 0.9700 . ?
C4 H4B 0.9700 . ?
C4 C5 1.520(4) . ?
C5 H5 0.9800 . ?
C5 C6 1.555(4) . ?
C5 C14 1.520(5) . ?
C6 H6 0.9800 . ?
C6 C7 1.523(5) . ?
C6 C10 1.545(4) . ?
C8 H8A 0.9600 . ?
C8 H8B 0.9600 . ?
C8 H8C 0.9600 . ?
C9 C10 1.508(5) . ?
C10 H10 0.9800 . ?
C10 C11 1.537(4) . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C11 C12 1.512(5) . ?
C12 C13 1.499(5) . ?
C12 C14 1.338(5) . ?
C13 H13A 0.9600 . ?
C13 H13B 0.9600 . ?
C13 H13C 0.9600 . ?
C14 C15 1.522(5) . ?
C15 H15 0.9800 . ?
C15 C16 1.478(4) . ?
C15 C24 1.555(4) . ?
C16 C17 1.197(5) . ?
C17 C18 1.439(5) . ?
C18 C19 1.386(5) . ?
C18 C23 1.400(5) . ?
C19 H19 0.9300 . ?
C19 C20 1.394(5) . ?
C20 H20 0.9300 . ?
C20 C21 1.380(5) . ?
C21 H21 0.9300 . ?
C21 C22 1.383(6) . ?
C22 H22 0.9300 . ?
C22 C23 1.387(5) . ?
C23 H23 0.9300 . ?
C24 H24 0.9800 . ?
C24 C25 1.515(5) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 N1 C1 124.0(3) . . ?
C2 N1 C25 113.7(3) . . ?
C25 N1 C1 122.3(3) . . ?
C7 N2 C8 123.8(3) . . ?
C9 N2 C7 113.0(3) . . ?
C9 N2 C8 123.1(3) . . ?
N1 C1 H1A 109.5 . . ?
N1 C1 H1B 109.5 . . ?
N1 C1 H1C 109.5 . . ?
H1A C1 H1B 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
O2 C2 N1 124.8(4) . . ?
O2 C2 C3 127.0(4) . . ?
N1 C2 C3 108.3(3) . . ?
C2 C3 H3 108.6 . . ?
C2 C3 C4 111.5(3) . . ?
C2 C3 C24 104.8(3) . . ?
C4 C3 H3 108.6 . . ?
C24 C3 H3 108.6 . . ?
C24 C3 C4 114.6(3) . . ?
C3 C4 H4A 110.0 . . ?
C3 C4 H4B 110.0 . . ?
H4A C4 H4B 108.4 . . ?
C5 C4 C3 108.5(3) . . ?
C5 C4 H4A 110.0 . . ?
C5 C4 H4B 110.0 . . ?
C4 C5 H5 105.8 . . ?
C4 C5 C6 113.8(3) . . ?
C4 C5 C14 113.4(3) . . ?
C6 C5 H5 105.8 . . ?
C14 C5 H5 105.8 . . ?
C14 C5 C6 111.4(3) . . ?
C5 C6 H6 108.9 . . ?
C7 C6 C5 114.7(3) . . ?
C7 C6 H6 108.9 . . ?
C7 C6 C10 104.4(3) . . ?
C10 C6 C5 111.0(3) . . ?
C10 C6 H6 108.9 . . ?
O3 C7 N2 124.1(3) . . ?
O3 C7 C6 127.6(3) . . ?
N2 C7 C6 108.3(3) . . ?
N2 C8 H8A 109.5 . . ?
N2 C8 H8B 109.5 . . ?
N2 C8 H8C 109.5 . . ?
H8A C8 H8B 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
O4 C9 N2 123.3(3) . . ?
O4 C9 C10 127.4(3) . . ?
N2 C9 C10 109.3(3) . . ?
C6 C10 H10 109.4 . . ?
C9 C10 C6 104.5(3) . . ?
C9 C10 H10 109.4 . . ?
C9 C10 C11 109.7(3) . . ?
C11 C10 C6 114.3(3) . . ?
C11 C10 H10 109.4 . . ?
C10 C11 H11A 109.5 . . ?
C10 C11 H11B 109.5 . . ?
H11A C11 H11B 108.1 . . ?
C12 C11 C10 110.7(3) . . ?
C12 C11 H11A 109.5 . . ?
C12 C11 H11B 109.5 . . ?
C13 C12 C11 116.4(3) . . ?
C14 C12 C11 116.8(3) . . ?
C14 C12 C13 126.8(4) . . ?
C12 C13 H13A 109.5 . . ?
C12 C13 H13B 109.5 . . ?
C12 C13 H13C 109.5 . . ?
H13A C13 H13B 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
C5 C14 C15 116.6(3) . . ?
C12 C14 C5 118.1(3) . . ?
C12 C14 C15 125.2(3) . . ?
C14 C15 H15 108.4 . . ?
C14 C15 C24 108.0(3) . . ?
C16 C15 C14 111.7(3) . . ?
C16 C15 H15 108.4 . . ?
C16 C15 C24 111.9(2) . . ?
C24 C15 H15 108.4 . . ?
C17 C16 C15 179.8(4) . . ?
C16 C17 C18 177.2(4) . . ?
C19 C18 C17 120.2(3) . . ?
C19 C18 C23 119.1(3) . . ?
C23 C18 C17 120.6(3) . . ?
C18 C19 H19 119.9 . . ?
C18 C19 C20 120.2(3) . . ?
C20 C19 H19 119.9 . . ?
C19 C20 H20 119.8 . . ?
C21 C20 C19 120.3(4) . . ?
C21 C20 H20 119.8 . . ?
C20 C21 H21 120.0 . . ?
C20 C21 C22 120.0(4) . . ?
C22 C21 H21 120.0 . . ?
C21 C22 H22 120.0 . . ?
C21 C22 C23 120.1(3) . . ?
C23 C22 H22 120.0 . . ?
C18 C23 H23 119.8 . . ?
C22 C23 C18 120.3(4) . . ?
C22 C23 H23 119.8 . . ?
C3 C24 C15 114.0(2) . . ?
C3 C24 H24 108.7 . . ?
C15 C24 H24 108.7 . . ?
C25 C24 C3 104.6(3) . . ?
C25 C24 C15 112.0(3) . . ?
C25 C24 H24 108.7 . . ?
O1 C25 N1 124.4(3) . . ?
O1 C25 C24 127.1(3) . . ?
N1 C25 C24 108.5(3) . . ?


_ins_header                      
;
TITL JG-G135-C1-F4-Polar minor productscaled in I4(1) 
REM I4(1) (#80 in standard setting)
CELL 1.54184  18.116510  18.116510  12.861925  90.0000  90.0000  90.0000
ZERR    8.00   0.000497   0.000497   0.001136   0.0000   0.0000   0.0000
LATT -2
SYMM -x+1/2,-y+1/2, z+1/2 
SYMM -y, x+1/2, z+1/4 
SYMM  y+1/2,-x, z+3/4 
SFAC C H N O
UNIT 200.00 192.00 16.00 32.00
TREF
HKLF 4
END
;
_olex2_date_sample_data_collection 2019-05-20
_olex2_date_sample_submission    2019-05-16
_olex2_exptl_crystal_mounting_method 
'The crystal was mounted on a MITIGEN holder with oil'
_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 1.386
_oxdiff_exptl_absorpt_empirical_full_min 0.764
####################################################################### 
# 
# 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_jg-g136scaled
_audit_block_doi                 10.5517/ccdc.csd.cc22jzh3
_database_code_depnum_ccdc_archive 'CCDC 1922945'
loop_
_citation_id
_citation_doi
_citation_year
1 10.1039/C9SC03976G 2019
loop_
_audit_author_name
_audit_author_address
'Michael Gardiner'
;Australian National University
Australia
;
_audit_update_record             
;
2019-06-14 deposited with the CCDC.	2019-09-19 downloaded from the CCDC.
;
_audit_creation_date             2019-05-16
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2016/6
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C25 H24 N2 O4, H0.34 O0.17'
_chemical_formula_sum            'C25 H24.34 N2 O4.17'
_chemical_formula_weight         419.53
_chemical_absolute_configuration .
_chemical_melting_point          ?
_chemical_oxdiff_formula         C25H24N2O4
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           5
_space_group_name_H-M_alt        'C 1 2 1'
_space_group_name_Hall           'C 2y'
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                   22.1402(8)
_cell_length_b                   6.8047(2)
_cell_length_c                   14.2360(5)
_cell_angle_alpha                90
_cell_angle_beta                 100.710(4)
_cell_angle_gamma                90
_cell_volume                     2107.40(13)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    12495
_cell_measurement_temperature    150.01(10)
_cell_measurement_theta_max      29.5140
_cell_measurement_theta_min      4.1840
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.091
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.94839
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.36a (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    1.322
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             887
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
30 -2 -1 0.0425
-31 0 1 0.0918
-6 -9 -3 0.3129
-8 9 3 0.2923
-5 -1 20 0.1007
7 -1 -20 0.1420
-3 8 -9 0.2457
8 -4 -18 0.1674
6 -9 1 0.2847

_exptl_crystal_size_max          0.664
_exptl_crystal_size_mid          0.285
_exptl_crystal_size_min          0.191
loop_
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
29.9902 -2.0011 -1.0051 0.3621 -0.8286 0.4061
-30.9911 0.0022 1.0043 -0.3600 0.9106 -0.2118
-6.0062 -8.9945 -3.0013 -0.1581 0.3818 0.8839
-7.9902 8.9955 3.0035 -0.0268 0.0248 -0.9766
-4.9830 -1.0019 19.9879 0.9258 0.3780 -0.0615
6.9813 -0.9972 -19.9891 -0.8842 -0.3831 0.2757
-3.0019 7.9973 -8.9902 -0.5436 -0.2177 -0.7657
7.9809 -3.9960 -17.9919 -0.7496 -0.3120 0.5709
5.9939 -8.9959 0.9943 0.1972 0.0745 0.9376

_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0222
_diffrn_reflns_av_unetI/netI     0.0217
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.908
_diffrn_reflns_limit_h_max       30
_diffrn_reflns_limit_h_min       -30
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            18911
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.860
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.931
_diffrn_reflns_theta_min         3.385
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      150.01(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.1872
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.908
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -44.00  42.00   1.00   47.50    --  -11.22  77.00 -60.00   86
  2  ω    -21.00  42.00   1.00   47.50    --   11.61  77.00 -60.00   63
  3  ω    -13.00  86.00   1.00   47.50    --   11.61  37.00-150.00   99
  4  ω    -42.00  44.00   1.00   47.50    --   11.61 -77.00  90.00   86
  5  ω    -15.00  53.00   1.00   47.50    --   11.61 -99.00-150.00   68
  6  ω    -44.00  14.00   1.00   47.50    --  -11.22  77.00  30.00   58
  7  ω    -21.00  42.00   1.00   47.50    --   11.61  77.00 120.00   63
  8  ω    -13.00  86.00   1.00   47.50    --   11.61  37.00  60.00   99
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'New Xcalibur, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0132119000
_diffrn_orient_matrix_UB_12      -0.0076759000
_diffrn_orient_matrix_UB_13      0.0492295000
_diffrn_orient_matrix_UB_21      -0.0290490000
_diffrn_orient_matrix_UB_22      -0.0264955000
_diffrn_orient_matrix_UB_23      0.0103402000
_diffrn_orient_matrix_UB_31      0.0066168000
_diffrn_orient_matrix_UB_32      -0.1005344000
_diffrn_orient_matrix_UB_33      -0.0064665000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_reflns_Friedel_coverage         0.758
_reflns_Friedel_fraction_full    0.999
_reflns_Friedel_fraction_max     0.805
_reflns_number_gt                4930
_reflns_number_total             5250
_reflns_odcompleteness_completeness 99.70
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.40.36a (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.40.36a (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.40.36a (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 (Sheldrick, 2015)'
_refine_diff_density_max         0.205
_refine_diff_density_min         -0.174
_refine_diff_density_rms         0.035
_refine_ls_abs_structure_details 
;
 Flack x determined using 2015 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.1(3)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.058
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     293
_refine_ls_number_reflns         5250
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0385
_refine_ls_R_factor_gt           0.0355
_refine_ls_restrained_S_all      1.058
_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)+(0.0473P)²+0.6368P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0878
_refine_ls_wR_factor_ref         0.0904
_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. Others
 Sof(O5)=FVAR(1)
 Sof(H5A)=2*FVAR(2)
3.a Ternary CH refined with riding coordinates:
 C3(H3), C7(H7), C16(H16), C20(H20), C24(H24)
3.b Secondary CH2 refined with riding coordinates:
 C4(H4A,H4B), C21(H21A,H21B)
3.c Aromatic/amide H refined with riding coordinates:
 C5(H5), C11(H11), C12(H12), C13(H13), C14(H14), C15(H15)
3.d Idealised Me refined as rotating group:
 C1(H1A,H1B,H1C), C18(H18A,H18B,H18C), C23(H23A,H23B,H23C)
;
_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
O1 O 0.39856(9) 0.5675(3) 0.36894(13) 0.0583(6) Uani 1 1 d . . . . .
O2 O 0.34854(7) 1.0864(2) 0.17187(11) 0.0369(3) Uani 1 1 d . . . . .
O3 O 0.57940(10) 0.1997(3) 0.43974(15) 0.0674(6) Uani 1 1 d . . . . .
O4 O 0.67425(7) 0.7811(3) 0.41242(11) 0.0490(4) Uani 1 1 d . . . . .
N1 N 0.37284(9) 0.8516(3) 0.28674(12) 0.0378(4) Uani 1 1 d . . . . .
N2 N 0.63785(8) 0.4760(3) 0.43956(12) 0.0379(4) Uani 1 1 d . . . . .
C1 C 0.36074(19) 0.9698(5) 0.3666(2) 0.0745(11) Uani 1 1 d . . . . .
H1A H 0.398478 0.991445 0.410889 0.112 Uiso 1 1 calc GR . . . .
H1B H 0.332223 0.901887 0.398298 0.112 Uiso 1 1 calc GR . . . .
H1C H 0.343549 1.093860 0.343205 0.112 Uiso 1 1 calc GR . . . .
C2 C 0.36426(8) 0.9199(3) 0.19506(13) 0.0274(4) Uani 1 1 d . . . . .
C3 C 0.37665(8) 0.7552(3) 0.12970(13) 0.0242(3) Uani 1 1 d . . . . .
H3 H 0.337643 0.714813 0.089897 0.029 Uiso 1 1 calc R . . . .
C4 C 0.41953(8) 0.8310(3) 0.06447(12) 0.0246(3) Uani 1 1 d . . . . .
H4A H 0.417226 0.744707 0.009698 0.029 Uiso 1 1 calc R . . . .
H4B H 0.406618 0.961275 0.041304 0.029 Uiso 1 1 calc R . . . .
C5 C 0.48435(8) 0.8387(2) 0.11860(12) 0.0219(3) Uani 1 1 d . . . . .
H5 H 0.509321 0.944174 0.109398 0.026 Uiso 1 1 calc R . . . .
C6 C 0.50668(7) 0.6975(2) 0.17938(12) 0.0194(3) Uani 1 1 d . . . . .
C7 C 0.57164(7) 0.7057(3) 0.23656(12) 0.0213(3) Uani 1 1 d . . . . .
H7 H 0.589610 0.833573 0.225886 0.026 Uiso 1 1 calc R . . . .
C8 C 0.61038(8) 0.5495(3) 0.20709(12) 0.0230(3) Uani 1 1 d . . . . .
C9 C 0.64089(8) 0.4160(3) 0.18830(12) 0.0245(3) Uani 1 1 d . . . . .
C10 C 0.67562(8) 0.2472(3) 0.16868(13) 0.0233(3) Uani 1 1 d . . . . .
C11 C 0.68902(8) 0.2158(3) 0.07807(12) 0.0241(3) Uani 1 1 d . . . . .
H11 H 0.676550 0.306806 0.029592 0.029 Uiso 1 1 calc R . . . .
C12 C 0.72096(8) 0.0490(3) 0.06016(14) 0.0271(4) Uani 1 1 d . . . . .
H12 H 0.729590 0.027910 -0.000529 0.033 Uiso 1 1 calc R . . . .
C13 C 0.74004(8) -0.0861(3) 0.13183(14) 0.0291(4) Uani 1 1 d . . . . .
H13 H 0.761827 -0.197100 0.119567 0.035 Uiso 1 1 calc R . . . .
C14 C 0.72674(10) -0.0564(3) 0.22185(15) 0.0343(4) Uani 1 1 d . . . . .
H14 H 0.739257 -0.148276 0.269876 0.041 Uiso 1 1 calc R . . . .
C15 C 0.69487(9) 0.1096(3) 0.24091(14) 0.0316(4) Uani 1 1 d . . . . .
H15 H 0.686295 0.129425 0.301725 0.038 Uiso 1 1 calc R . . . .
C16 C 0.56867(8) 0.6865(3) 0.34368(13) 0.0263(4) Uani 1 1 d . . . . .
H16 H 0.549152 0.803343 0.365033 0.032 Uiso 1 1 calc R . . . .
C17 C 0.63305(9) 0.6624(3) 0.40226(13) 0.0344(5) Uani 1 1 d . . . . .
C18 C 0.69501(11) 0.3969(5) 0.49436(16) 0.0562(7) Uani 1 1 d . . . . .
H18A H 0.728945 0.439580 0.466191 0.084 Uiso 1 1 calc GR . . . .
H18B H 0.693215 0.255963 0.493840 0.084 Uiso 1 1 calc GR . . . .
H18C H 0.700444 0.443278 0.559080 0.084 Uiso 1 1 calc GR . . . .
C19 C 0.58403(10) 0.3698(4) 0.41903(15) 0.0401(5) Uani 1 1 d . . . . .
C20 C 0.53411(9) 0.5013(3) 0.36517(13) 0.0295(4) Uani 1 1 d . . . . .
H20 H 0.505973 0.536937 0.408025 0.035 Uiso 1 1 calc R . . . .
C21 C 0.49781(8) 0.3916(3) 0.27907(13) 0.0268(4) Uani 1 1 d . . . . .
H21A H 0.465600 0.316915 0.300500 0.032 Uiso 1 1 calc R . . . .
H21B H 0.525201 0.298130 0.257116 0.032 Uiso 1 1 calc R . . . .
C22 C 0.46786(8) 0.5186(2) 0.19267(12) 0.0223(3) Uani 1 1 d . . . . .
C23 C 0.46252(9) 0.3851(3) 0.10405(14) 0.0310(4) Uani 1 1 d . . . . .
H23A H 0.440380 0.452897 0.049138 0.046 Uiso 1 1 calc GR . . . .
H23B H 0.440946 0.267012 0.114348 0.046 Uiso 1 1 calc GR . . . .
H23C H 0.502891 0.352318 0.093477 0.046 Uiso 1 1 calc GR . . . .
C24 C 0.40105(8) 0.5849(3) 0.19822(14) 0.0270(4) Uani 1 1 d . . . . .
H24 H 0.373818 0.471840 0.181160 0.032 Uiso 1 1 calc R . . . .
C25 C 0.39214(9) 0.6580(3) 0.29531(16) 0.0348(5) Uani 1 1 d . . . . .
O5 O 0.500000 0.9442(14) 0.500000 0.080(5) Uani 0.342(16) 2 d S T P . .
H5A H 0.478(5) 1.032(17) 0.530(8) 0.08(3) Uiso 0.342(16) 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C25 1.201(3) . ?
O2 C2 1.213(2) . ?
O3 C19 1.204(3) . ?
O4 C17 1.207(3) . ?
N1 C1 1.458(3) . ?
N1 C2 1.365(2) . ?
N1 C25 1.383(3) . ?
N2 C17 1.372(3) . ?
N2 C18 1.460(3) . ?
N2 C19 1.377(3) . ?
C1 H1A 0.9600 . ?
C1 H1B 0.9600 . ?
C1 H1C 0.9600 . ?
C2 C3 1.514(3) . ?
C3 H3 0.9800 . ?
C3 C4 1.535(3) . ?
C3 C24 1.546(2) . ?
C4 H4A 0.9700 . ?
C4 H4B 0.9700 . ?
C4 C5 1.498(2) . ?
C5 H5 0.9300 . ?
C5 C6 1.326(2) . ?
C6 C7 1.516(2) . ?
C6 C22 1.522(2) . ?
C7 H7 0.9800 . ?
C7 C8 1.475(2) . ?
C7 C16 1.544(2) . ?
C8 C9 1.192(2) . ?
C9 C10 1.438(2) . ?
C10 C11 1.393(2) . ?
C10 C15 1.398(3) . ?
C11 H11 0.9300 . ?
C11 C12 1.386(2) . ?
C12 H12 0.9300 . ?
C12 C13 1.380(3) . ?
C13 H13 0.9300 . ?
C13 C14 1.382(3) . ?
C14 H14 0.9300 . ?
C14 C15 1.385(3) . ?
C15 H15 0.9300 . ?
C16 H16 0.9800 . ?
C16 C17 1.520(2) . ?
C16 C20 1.534(3) . ?
C18 H18A 0.9600 . ?
C18 H18B 0.9600 . ?
C18 H18C 0.9600 . ?
C19 C20 1.515(3) . ?
C20 H20 0.9800 . ?
C20 C21 1.529(3) . ?
C21 H21A 0.9700 . ?
C21 H21B 0.9700 . ?
C21 C22 1.548(2) . ?
C22 C23 1.541(2) . ?
C22 C24 1.563(2) . ?
C23 H23A 0.9600 . ?
C23 H23B 0.9600 . ?
C23 H23C 0.9600 . ?
C24 H24 0.9800 . ?
C24 C25 1.516(3) . ?
O5 H5A 0.92(13) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 N1 C1 122.99(19) . . ?
C2 N1 C25 113.24(17) . . ?
C25 N1 C1 123.7(2) . . ?
C17 N2 C18 123.0(2) . . ?
C17 N2 C19 113.63(17) . . ?
C19 N2 C18 123.4(2) . . ?
N1 C1 H1A 109.5 . . ?
N1 C1 H1B 109.5 . . ?
N1 C1 H1C 109.5 . . ?
H1A C1 H1B 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
O2 C2 N1 124.09(19) . . ?
O2 C2 C3 126.86(18) . . ?
N1 C2 C3 109.05(16) . . ?
C2 C3 H3 108.8 . . ?
C2 C3 C4 109.01(15) . . ?
C2 C3 C24 104.42(15) . . ?
C4 C3 H3 108.8 . . ?
C4 C3 C24 116.79(14) . . ?
C24 C3 H3 108.8 . . ?
C3 C4 H4A 109.7 . . ?
C3 C4 H4B 109.7 . . ?
H4A C4 H4B 108.2 . . ?
C5 C4 C3 109.97(14) . . ?
C5 C4 H4A 109.7 . . ?
C5 C4 H4B 109.7 . . ?
C4 C5 H5 119.5 . . ?
C6 C5 C4 121.06(15) . . ?
C6 C5 H5 119.5 . . ?
C5 C6 C7 121.68(15) . . ?
C5 C6 C22 120.67(15) . . ?
C7 C6 C22 117.65(14) . . ?
C6 C7 H7 108.8 . . ?
C6 C7 C16 108.46(13) . . ?
C8 C7 C6 111.37(14) . . ?
C8 C7 H7 108.8 . . ?
C8 C7 C16 110.70(14) . . ?
C16 C7 H7 108.8 . . ?
C9 C8 C7 175.61(18) . . ?
C8 C9 C10 176.55(19) . . ?
C11 C10 C9 121.06(16) . . ?
C11 C10 C15 119.37(16) . . ?
C15 C10 C9 119.55(16) . . ?
C10 C11 H11 120.0 . . ?
C12 C11 C10 119.97(17) . . ?
C12 C11 H11 120.0 . . ?
C11 C12 H12 119.8 . . ?
C13 C12 C11 120.41(17) . . ?
C13 C12 H12 119.8 . . ?
C12 C13 H13 120.0 . . ?
C12 C13 C14 119.96(17) . . ?
C14 C13 H13 120.0 . . ?
C13 C14 H14 119.8 . . ?
C13 C14 C15 120.34(18) . . ?
C15 C14 H14 119.8 . . ?
C10 C15 H15 120.0 . . ?
C14 C15 C10 119.94(17) . . ?
C14 C15 H15 120.0 . . ?
C7 C16 H16 109.9 . . ?
C17 C16 C7 110.07(14) . . ?
C17 C16 H16 109.9 . . ?
C17 C16 C20 104.69(16) . . ?
C20 C16 C7 112.40(15) . . ?
C20 C16 H16 109.9 . . ?
O4 C17 N2 124.75(19) . . ?
O4 C17 C16 127.2(2) . . ?
N2 C17 C16 108.01(18) . . ?
N2 C18 H18A 109.5 . . ?
N2 C18 H18B 109.5 . . ?
N2 C18 H18C 109.5 . . ?
H18A C18 H18B 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
O3 C19 N2 124.2(2) . . ?
O3 C19 C20 127.2(2) . . ?
N2 C19 C20 108.59(19) . . ?
C16 C20 H20 108.6 . . ?
C19 C20 C16 104.01(16) . . ?
C19 C20 H20 108.6 . . ?
C19 C20 C21 110.05(17) . . ?
C21 C20 C16 116.63(15) . . ?
C21 C20 H20 108.6 . . ?
C20 C21 H21A 108.1 . . ?
C20 C21 H21B 108.1 . . ?
C20 C21 C22 116.62(15) . . ?
H21A C21 H21B 107.3 . . ?
C22 C21 H21A 108.1 . . ?
C22 C21 H21B 108.1 . . ?
C6 C22 C21 112.14(14) . . ?
C6 C22 C23 109.21(14) . . ?
C6 C22 C24 109.71(13) . . ?
C21 C22 C24 112.99(14) . . ?
C23 C22 C21 106.12(14) . . ?
C23 C22 C24 106.39(14) . . ?
C22 C23 H23A 109.5 . . ?
C22 C23 H23B 109.5 . . ?
C22 C23 H23C 109.5 . . ?
H23A C23 H23B 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 109.5 . . ?
C3 C24 C22 114.05(14) . . ?
C3 C24 H24 107.8 . . ?
C22 C24 H24 107.8 . . ?
C25 C24 C3 103.89(15) . . ?
C25 C24 C22 115.20(15) . . ?
C25 C24 H24 107.8 . . ?
O1 C25 N1 123.4(2) . . ?
O1 C25 C24 127.8(2) . . ?
N1 C25 C24 108.82(16) . . ?


_ins_header                      
;
TITL JG-G136scaled in C2 
REM C2 (#5 in standard setting)
CELL 0.71073  22.140197   6.804719  14.236007  90.0000 100.7095  90.0000
ZERR    4.00   0.000847   0.000203   0.000540   0.0000   0.0036   0.0000
LATT -7
SYMM -x, y,-z 
SFAC C H N O
UNIT 100.00 96.00 8.00 16.00
TREF
HKLF 4
END
;
_olex2_date_sample_data_collection 2019-05-13
_olex2_date_sample_submission    2019-05-10
_olex2_exptl_crystal_mounting_method 
'The crystal was mounted on a MITIGEN holder with oil'
_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 1.071
_oxdiff_exptl_absorpt_empirical_full_min 0.932
####################################################################### 
# 
# 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_jg-g135-c1-f3-major-nonpolarscaled
_audit_block_doi                 10.5517/ccdc.csd.cc22jzg2
_database_code_depnum_ccdc_archive 'CCDC 1922944'
loop_
_citation_id
_citation_doi
_citation_year
1 10.1039/C9SC03976G 2019
loop_
_audit_author_name
_audit_author_address
'Michael Gardiner'
;Australian National University
Australia
;
_audit_update_record             
;
2019-06-14 deposited with the CCDC.	2019-09-19 downloaded from the CCDC.
;
_audit_creation_date             2019-05-23
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2016/6
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C25 H24 N2 O4'
_chemical_formula_sum            'C25 H24 N2 O4'
_chemical_formula_weight         416.46
_chemical_melting_point          ?
_chemical_oxdiff_formula         c25h24n2o5
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_H-M_alt        'C 1 2/c 1'
_space_group_name_Hall           '-C 2yc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z-1/2'

_cell_length_a                   21.8655(7)
_cell_length_b                   6.7309(2)
_cell_length_c                   29.0129(8)
_cell_angle_alpha                90
_cell_angle_beta                 100.540(3)
_cell_angle_gamma                90
_cell_volume                     4197.9(2)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    14908
_cell_measurement_temperature    150.00(10)
_cell_measurement_theta_max      29.7050
_cell_measurement_theta_min      4.1120
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.090
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.98033
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.36a (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    1.318
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       prism
_exptl_crystal_F_000             1760
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
-27 0 26 0.1029
27 0 -26 0.1029
-3 -9 -4 0.2025
3 9 4 0.2025
-10 0 40 0.1330
10 0 -40 0.1330
22 0 23 0.1451
-22 0 -23 0.1451
20 -7 -2 0.1743

_exptl_crystal_size_max          0.452
_exptl_crystal_size_mid          0.323
_exptl_crystal_size_min          0.206
loop_
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
-26.9771 -0.0027 26.0031 -0.8718 0.4326 0.2307
26.9771 0.0027 -26.0031 0.8718 -0.4326 -0.2307
-2.9983 -8.9934 -3.9977 -0.3410 -0.1504 -0.8844
2.9983 8.9934 3.9977 0.3410 0.1504 0.8844
-9.9838 -0.0020 39.9803 -0.8437 -0.2422 0.4549
9.9838 0.0020 -39.9803 0.8437 0.2422 -0.4549
21.9926 0.0008 22.9671 -0.0474 -0.9379 0.3495
-21.9926 -0.0008 -22.9671 0.0474 0.9379 -0.3495
19.9881 -6.9934 -2.0163 0.0680 -0.7745 -0.6036

_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0213
_diffrn_reflns_av_unetI/netI     0.0154
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.896
_diffrn_reflns_limit_h_max       30
_diffrn_reflns_limit_h_min       -27
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       40
_diffrn_reflns_limit_l_min       -40
_diffrn_reflns_number            36549
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.896
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         30.077
_diffrn_reflns_theta_min         3.289
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      150.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.3744
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.896
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -15.00  30.00   1.00   43.84    --  -11.22 -99.00  30.00   45
  2  ω    -21.00  42.00   1.00   43.84    --   11.46  77.00 -60.00   63
  3  ω    -42.00  44.00   1.00   43.84    --   11.46 -77.00  30.00   86
  4  ω    -77.00 100.00   1.00   43.84    --   11.46   0.00  60.00  177
  5  ω    -98.00 -37.00   1.00   43.84    --  -11.22 178.00-180.00   61
  6  ω    -42.00  21.00   1.00   43.84    --  -11.22 -77.00   0.00   63
  7  ω    -15.00  10.00   1.00   43.84    --   11.46 -99.00-120.00   25
  8  ω    -17.00  84.00   1.00   43.84    --   11.46  57.00-180.00  101
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'New Xcalibur, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0157679000
_diffrn_orient_matrix_UB_12      0.0402939000
_diffrn_orient_matrix_UB_13      -0.0171626000
_diffrn_orient_matrix_UB_21      -0.0288102000
_diffrn_orient_matrix_UB_22      0.0322174000
_diffrn_orient_matrix_UB_23      -0.0132499000
_diffrn_orient_matrix_UB_31      0.0031734000
_diffrn_orient_matrix_UB_32      0.0918711000
_diffrn_orient_matrix_UB_33      0.0121746000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                4780
_reflns_number_total             5529
_reflns_odcompleteness_completeness 99.70
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 Structure factors included contributions from the .fab file.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.40.36a (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.40.36a (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.40.36a (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 (Sheldrick, 2015)'
_refine_diff_density_max         0.303
_refine_diff_density_min         -0.219
_refine_diff_density_rms         0.042
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.052
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     283
_refine_ls_number_reflns         5529
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0530
_refine_ls_R_factor_gt           0.0446
_refine_ls_restrained_S_all      1.052
_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)+(0.0489P)²+3.7901P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1104
_refine_ls_wR_factor_ref         0.1174
_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:
 C3(H3), C5(H5), C6(H6), C10(H10), C15(H15), C24(H24)
2.b Secondary CH2 refined with riding coordinates:
 C4(H4A,H4B), C11(H11A,H11B)
2.c Aromatic/amide H refined with riding coordinates:
 C19(H19), C20(H20), C21(H21), C22(H22), C23(H23)
2.d Idealised Me refined as rotating group:
 C1(H1A,H1B,H1C), C8(H8A,H8B,H8C), C13(H13A,H13B,H13C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.69081(5) 0.2701(2) 0.28883(4) 0.0496(3) Uani 1 1 d . . . . .
O2 O 0.59224(8) 0.8653(2) 0.28027(5) 0.0681(4) Uani 1 1 d . . . . .
O3 O 0.42668(5) 0.45277(18) 0.31434(4) 0.0514(3) Uani 1 1 d . . . . .
O4 O 0.43894(5) -0.04805(14) 0.42011(4) 0.0390(2) Uani 1 1 d . . . . .
N1 N 0.64959(5) 0.5829(2) 0.27792(4) 0.0338(3) Uani 1 1 d . . . . .
N2 N 0.42676(5) 0.17490(16) 0.35959(4) 0.0313(2) Uani 1 1 d . . . . .
C1 C 0.69471(8) 0.6622(3) 0.25160(5) 0.0507(4) Uani 1 1 d . . . . .
H1A H 0.735787 0.621683 0.266236 0.076 Uiso 1 1 calc GR . . . .
H1B H 0.692343 0.804587 0.251141 0.076 Uiso 1 1 calc GR . . . .
H1C H 0.685783 0.612499 0.220069 0.076 Uiso 1 1 calc GR . . . .
C2 C 0.60125(7) 0.6916(2) 0.28945(5) 0.0372(3) Uani 1 1 d . . . . .
C3 C 0.56355(6) 0.55860(19) 0.31559(4) 0.0268(3) Uani 1 1 d . . . . .
H3 H 0.523925 0.528207 0.294982 0.032 Uiso 1 1 calc R . . . .
C4 C 0.55001(6) 0.66434(17) 0.35950(4) 0.0253(2) Uani 1 1 d . . . . .
H4A H 0.513227 0.746109 0.350555 0.030 Uiso 1 1 calc R . . . .
H4B H 0.584511 0.752316 0.371179 0.030 Uiso 1 1 calc R . . . .
C5 C 0.53976(5) 0.52628(16) 0.39951(4) 0.0214(2) Uani 1 1 d . . . . .
H5 H 0.550873 0.605687 0.428132 0.026 Uiso 1 1 calc R . . . .
C6 C 0.47103(5) 0.46306(17) 0.39794(5) 0.0262(2) Uani 1 1 d . . . . .
H6 H 0.447080 0.579375 0.404524 0.031 Uiso 1 1 calc R . . . .
C7 C 0.43983(6) 0.3723(2) 0.35202(5) 0.0312(3) Uani 1 1 d . . . . .
C8 C 0.39708(10) 0.0425(3) 0.32249(6) 0.0580(5) Uani 1 1 d . . . . .
H8A H 0.424155 0.023012 0.300301 0.087 Uiso 1 1 calc GR . . . .
H8B H 0.358673 0.100208 0.306925 0.087 Uiso 1 1 calc GR . . . .
H8C H 0.388847 -0.083147 0.335790 0.087 Uiso 1 1 calc GR . . . .
C9 C 0.44321(6) 0.11962(18) 0.40575(4) 0.0268(2) Uani 1 1 d . . . . .
C10 C 0.46617(6) 0.30124(17) 0.43457(4) 0.0255(2) Uani 1 1 d . . . . .
H10 H 0.434738 0.340984 0.452901 0.031 Uiso 1 1 calc R . . . .
C11 C 0.52693(6) 0.25674(18) 0.46792(4) 0.0262(2) Uani 1 1 d . . . . .
H11A H 0.537917 0.368193 0.489004 0.031 Uiso 1 1 calc R . . . .
H11B H 0.521681 0.140674 0.486630 0.031 Uiso 1 1 calc R . . . .
C12 C 0.57838(5) 0.21967(16) 0.44075(4) 0.0215(2) Uani 1 1 d . . . . .
C13 C 0.62011(6) 0.04518(19) 0.45554(4) 0.0302(3) Uani 1 1 d . . . . .
H13A H 0.650405 0.035048 0.435515 0.045 Uiso 1 1 calc GR . . . .
H13B H 0.595701 -0.074169 0.453169 0.045 Uiso 1 1 calc GR . . . .
H13C H 0.640925 0.063074 0.487388 0.045 Uiso 1 1 calc GR . . . .
C14 C 0.58329(5) 0.34885(16) 0.40658(4) 0.0196(2) Uani 1 1 d . . . . .
C15 C 0.63271(5) 0.33822(17) 0.37613(4) 0.0215(2) Uani 1 1 d . . . . .
H15 H 0.652450 0.207053 0.379881 0.026 Uiso 1 1 calc R . . . .
C16 C 0.68054(5) 0.49142(18) 0.39040(4) 0.0237(2) Uani 1 1 d . . . . .
C17 C 0.71686(5) 0.62447(18) 0.39963(4) 0.0253(2) Uani 1 1 d . . . . .
C18 C 0.75649(5) 0.79499(18) 0.41026(4) 0.0236(2) Uani 1 1 d . . . . .
C19 C 0.79112(5) 0.8221(2) 0.45521(4) 0.0284(3) Uani 1 1 d . . . . .
H19 H 0.791564 0.723774 0.477788 0.034 Uiso 1 1 calc R . . . .
C20 C 0.82484(6) 0.9951(2) 0.46627(5) 0.0352(3) Uani 1 1 d . . . . .
H20 H 0.846988 1.014146 0.496501 0.042 Uiso 1 1 calc R . . . .
C21 C 0.82574(7) 1.1400(2) 0.43253(5) 0.0369(3) Uani 1 1 d . . . . .
H21 H 0.848707 1.255626 0.440013 0.044 Uiso 1 1 calc R . . . .
C22 C 0.79245(7) 1.1124(2) 0.38772(5) 0.0353(3) Uani 1 1 d . . . . .
H22 H 0.793420 1.209304 0.365004 0.042 Uiso 1 1 calc R . . . .
C23 C 0.75764(6) 0.9417(2) 0.37637(5) 0.0300(3) Uani 1 1 d . . . . .
H23 H 0.735049 0.924673 0.346211 0.036 Uiso 1 1 calc R . . . .
C24 C 0.60203(6) 0.36683(18) 0.32413(4) 0.0245(2) Uani 1 1 d . . . . .
H24 H 0.575949 0.251772 0.313103 0.029 Uiso 1 1 calc R . . . .
C25 C 0.65240(6) 0.3915(2) 0.29489(4) 0.0320(3) Uani 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C25 1.2075(18) . ?
O2 C2 1.2078(19) . ?
O3 C7 1.2067(16) . ?
O4 C9 1.2124(15) . ?
N1 C1 1.4547(17) . ?
N1 C2 1.376(2) . ?
N1 C25 1.3766(19) . ?
N2 C7 1.3847(16) . ?
N2 C8 1.4554(18) . ?
N2 C9 1.3731(17) . ?
C1 H1A 0.9600 . ?
C1 H1B 0.9600 . ?
C1 H1C 0.9600 . ?
C2 C3 1.5114(18) . ?
C3 H3 0.9800 . ?
C3 C4 1.5348(17) . ?
C3 C24 1.5359(18) . ?
C4 H4A 0.9700 . ?
C4 H4B 0.9700 . ?
C4 C5 1.5350(16) . ?
C5 H5 0.9800 . ?
C5 C6 1.5545(16) . ?
C5 C14 1.5175(15) . ?
C6 H6 0.9800 . ?
C6 C7 1.5105(19) . ?
C6 C10 1.5389(17) . ?
C8 H8A 0.9600 . ?
C8 H8B 0.9600 . ?
C8 H8C 0.9600 . ?
C9 C10 1.5139(17) . ?
C10 H10 0.9800 . ?
C10 C11 1.5234(18) . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C11 C12 1.5079(17) . ?
C12 C13 1.5009(17) . ?
C12 C14 1.3378(16) . ?
C13 H13A 0.9600 . ?
C13 H13B 0.9600 . ?
C13 H13C 0.9600 . ?
C14 C15 1.5173(15) . ?
C15 H15 0.9800 . ?
C15 C16 1.4730(16) . ?
C15 C24 1.5471(16) . ?
C16 C17 1.1945(17) . ?
C17 C18 1.4372(16) . ?
C18 C19 1.3950(17) . ?
C18 C23 1.3970(18) . ?
C19 H19 0.9300 . ?
C19 C20 1.3843(19) . ?
C20 H20 0.9300 . ?
C20 C21 1.384(2) . ?
C21 H21 0.9300 . ?
C21 C22 1.381(2) . ?
C22 H22 0.9300 . ?
C22 C23 1.3844(19) . ?
C23 H23 0.9300 . ?
C24 H24 0.9800 . ?
C24 C25 1.5173(17) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 N1 C1 123.91(14) . . ?
C2 N1 C25 113.34(11) . . ?
C25 N1 C1 122.73(14) . . ?
C7 N2 C8 123.18(12) . . ?
C9 N2 C7 112.94(11) . . ?
C9 N2 C8 123.86(12) . . ?
N1 C1 H1A 109.5 . . ?
N1 C1 H1B 109.5 . . ?
N1 C1 H1C 109.5 . . ?
H1A C1 H1B 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
O2 C2 N1 124.23(14) . . ?
O2 C2 C3 127.03(15) . . ?
N1 C2 C3 108.74(12) . . ?
C2 C3 H3 108.7 . . ?
C2 C3 C4 110.34(11) . . ?
C2 C3 C24 104.22(11) . . ?
C4 C3 H3 108.7 . . ?
C4 C3 C24 116.04(10) . . ?
C24 C3 H3 108.7 . . ?
C3 C4 H4A 108.5 . . ?
C3 C4 H4B 108.5 . . ?
C3 C4 C5 115.09(10) . . ?
H4A C4 H4B 107.5 . . ?
C5 C4 H4A 108.5 . . ?
C5 C4 H4B 108.5 . . ?
C4 C5 H5 105.2 . . ?
C4 C5 C6 114.68(10) . . ?
C6 C5 H5 105.2 . . ?
C14 C5 C4 113.82(9) . . ?
C14 C5 H5 105.2 . . ?
C14 C5 C6 111.57(9) . . ?
C5 C6 H6 108.9 . . ?
C7 C6 C5 114.52(10) . . ?
C7 C6 H6 108.9 . . ?
C7 C6 C10 104.22(10) . . ?
C10 C6 C5 111.23(10) . . ?
C10 C6 H6 108.9 . . ?
O3 C7 N2 123.55(13) . . ?
O3 C7 C6 127.70(12) . . ?
N2 C7 C6 108.74(11) . . ?
N2 C8 H8A 109.5 . . ?
N2 C8 H8B 109.5 . . ?
N2 C8 H8C 109.5 . . ?
H8A C8 H8B 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
O4 C9 N2 124.36(12) . . ?
O4 C9 C10 126.91(12) . . ?
N2 C9 C10 108.73(10) . . ?
C6 C10 H10 109.0 . . ?
C9 C10 C6 104.36(10) . . ?
C9 C10 H10 109.0 . . ?
C9 C10 C11 110.77(10) . . ?
C11 C10 C6 114.54(10) . . ?
C11 C10 H10 109.0 . . ?
C10 C11 H11A 109.6 . . ?
C10 C11 H11B 109.6 . . ?
H11A C11 H11B 108.1 . . ?
C12 C11 C10 110.36(10) . . ?
C12 C11 H11A 109.6 . . ?
C12 C11 H11B 109.6 . . ?
C13 C12 C11 116.92(10) . . ?
C14 C12 C11 116.66(11) . . ?
C14 C12 C13 126.40(11) . . ?
C12 C13 H13A 109.5 . . ?
C12 C13 H13B 109.5 . . ?
C12 C13 H13C 109.5 . . ?
H13A C13 H13B 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
C12 C14 C5 118.57(10) . . ?
C12 C14 C15 124.27(10) . . ?
C15 C14 C5 117.02(9) . . ?
C14 C15 H15 108.9 . . ?
C14 C15 C24 109.50(9) . . ?
C16 C15 C14 110.36(9) . . ?
C16 C15 H15 108.9 . . ?
C16 C15 C24 110.24(9) . . ?
C24 C15 H15 108.9 . . ?
C17 C16 C15 175.27(13) . . ?
C16 C17 C18 175.52(13) . . ?
C19 C18 C17 120.54(11) . . ?
C19 C18 C23 119.26(11) . . ?
C23 C18 C17 120.08(11) . . ?
C18 C19 H19 119.9 . . ?
C20 C19 C18 120.11(12) . . ?
C20 C19 H19 119.9 . . ?
C19 C20 H20 119.8 . . ?
C19 C20 C21 120.31(13) . . ?
C21 C20 H20 119.8 . . ?
C20 C21 H21 120.1 . . ?
C22 C21 C20 119.84(12) . . ?
C22 C21 H21 120.1 . . ?
C21 C22 H22 119.8 . . ?
C21 C22 C23 120.49(13) . . ?
C23 C22 H22 119.8 . . ?
C18 C23 H23 120.0 . . ?
C22 C23 C18 119.96(12) . . ?
C22 C23 H23 120.0 . . ?
C3 C24 C15 112.89(9) . . ?
C3 C24 H24 110.0 . . ?
C15 C24 H24 110.0 . . ?
C25 C24 C3 104.47(10) . . ?
C25 C24 C15 109.22(10) . . ?
C25 C24 H24 110.0 . . ?
O1 C25 N1 124.60(13) . . ?
O1 C25 C24 127.06(13) . . ?
N1 C25 C24 108.25(12) . . ?

_smtbx_masks_special_details     ?
loop_
_smtbx_masks_void_nr
_smtbx_masks_void_average_x
_smtbx_masks_void_average_y
_smtbx_masks_void_average_z
_smtbx_masks_void_volume
_smtbx_masks_void_count_electrons
_smtbx_masks_void_content
1 0.000 0.338 0.750 10.6 1.7 H1O0.5
2 0.000 0.663 0.250 10.6 1.7 H1O0.5
3 0.500 0.163 0.250 10.6 1.7 H1O0.5
4 0.500 0.838 0.750 10.6 1.7 H1O0.5


_ins_header                      
;
TITL JG-G135-C1-F3-Major-Nonpolarscaled in C2/c 
REM C2/c (#15 in standard setting)
CELL 0.71073  21.865503   6.730941  29.012927  90.0000 100.5400  90.0000
ZERR    7.00   0.000650   0.000159   0.000760   0.0000   0.0027   0.0000
LATT  7
SYMM -x, y,-z+1/2 
SFAC C H N O
UNIT 175.00 168.00 14.00 35.00
TREF
HKLF 4
END
;
_olex2_date_sample_data_collection 2019-05-22
_olex2_date_sample_submission    2019-05-20
_olex2_exptl_crystal_mounting_method 
'The crystal was mounted on a MITIGEN holder with oil'
_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 1.066
_oxdiff_exptl_absorpt_empirical_full_min 0.956
