# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 2017

####################################################################### 
# 
# 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_anna_23082017_ypm30_3
_database_code_depnum_ccdc_archive 'CCDC 1571107'
_audit_update_record             
;
2017-08-26 deposited with the CCDC.
2017-09-11 downloaded from the CCDC.
;
_audit_creation_date             2017-08-27
_audit_creation_method           
;
Olex2 1.2
(compiled 2017.03.28 svn.r3405 for OlexSys, GUI svn.r5337)
;
_shelx_SHELXL_version_number     2016/6
_chemical_name_common            ?
_chemical_name_systematic        
((1R,2R)-2-(4-methoxyphenoxy)-1-phenylcyclopropyl)(pyrrolidin-1-yl)methanone
_chemical_formula_moiety         'C21 H23 N O3'
_chemical_formula_sum            'C21 H23 N O3'
_chemical_formula_weight         337.40
_chemical_melting_point          ?
_chemical_oxdiff_formula         C21H23NO3
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   11.9367(4)
_cell_length_b                   14.2449(4)
_cell_length_c                   11.4918(3)
_cell_angle_alpha                90
_cell_angle_beta                 112.287(4)
_cell_angle_gamma                90
_cell_volume                     1808.07(10)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    8142
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      75.8320
_cell_measurement_theta_min      5.0710
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.661
_exptl_absorpt_correction_T_max  0.884
_exptl_absorpt_correction_T_min  0.824
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.46 (Rigaku Oxford Diffraction, 2015)
Analytical numeric absorption correction using a multifaceted crystal
			model based on expressions derived by R.C. Clark & J.S. Reid.
(Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.239
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       irregular
_exptl_crystal_F_000             720
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
-4 3 -4 0.2028
0 1 -7 0.1896
-3 -4 -4 0.1774
1 9 2 0.1315
6 3 -6 0.1585
4 -3 4 0.2602
4 2 -7 0.1560
-8 -2 2 0.1154
7 2 -1 0.1280
-2 -2 7 0.2415
1 -1 7 0.2438
-7 2 4 0.1432
-1 9 0 0.1195
7 -5 -1 0.2023
-2 9 2 0.1099
1 -8 -3 0.1258
-2 -9 2 0.1603
-4 -6 -2 0.1384
3 8 -1 0.1123
1 -9 2 0.2097
-6 -2 6 0.1419
-6 5 4 0.1350
-2 9 1 0.1123
-3 9 1 0.1176
4 7 -5 0.1594
6 6 -1 0.1337
5 -2 -7 0.1281
-4 -3 -4 0.1758
4 -5 -6 0.1153
-2 -9 -1 0.1428
-6 -3 -2 0.1560
-2 8 -2 0.1576
0 4 6 0.2217

_exptl_crystal_preparation       ?
_exptl_crystal_recrystallization_method 
'Compound was crystallized from Hexane-EtOAc mixture'
_exptl_crystal_size_max          0.44
_exptl_crystal_size_mid          0.32
_exptl_crystal_size_min          0.23
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
-3.8351 3.1480 -4.1164 0.0283 -0.3845 0.9227
-0.2364 0.9014 -6.7823 0.4824 -0.0607 0.8738
-3.3422 -3.5160 -4.4333 -0.0245 0.3372 0.9411
0.6652 8.7688 1.8730 0.0753 -0.9332 -0.3514
6.2073 2.6467 -5.8926 0.9905 -0.1292 0.0464
3.8388 -3.1077 4.1258 -0.0279 0.3802 -0.9245
3.9126 2.1617 -7.1639 0.8804 -0.1138 0.4603
-7.5439 -1.6157 1.7472 -0.7874 0.0182 0.6162
7.2963 2.2746 -1.0777 0.7301 -0.0971 -0.6764
-1.7232 -1.5394 7.2614 -0.6926 0.0886 -0.7159
0.7716 -0.7152 6.5681 -0.4188 0.0523 -0.9066
-7.4422 1.8836 4.0052 -0.8794 -0.3662 0.3041
-1.0182 9.1451 -0.0643 0.0795 -0.9940 0.0750
6.6667 -4.5189 -1.4753 0.5866 0.6175 -0.5240
-1.6527 8.8330 2.0135 -0.1283 -0.9850 -0.1150
0.5686 -8.3975 -3.0568 0.1197 0.9241 0.3629
-2.0785 -8.7253 2.0974 -0.4781 0.8783 0.0073
-4.2808 -5.8245 -2.2143 -0.3030 0.5524 0.7766
3.0724 8.4747 -0.7210 0.4585 -0.8407 -0.2881
0.6142 -8.5269 2.3814 -0.2688 0.9068 -0.3248
-6.2105 -1.6888 6.1956 -0.9957 0.0253 -0.0888
-6.4204 4.6387 4.0410 -0.7478 -0.6407 0.1740
-2.2100 8.8267 1.3737 -0.1294 -0.9912 0.0266
-2.7714 8.6145 0.6289 -0.1268 -0.9749 0.1828
3.8327 6.5820 -4.8403 0.7846 -0.6002 0.1554
5.8138 5.9830 -1.1690 0.6772 -0.5202 -0.5204
4.6137 -2.1209 -6.9993 0.8524 0.3552 0.3837
-3.8723 -3.1893 -4.0765 -0.0889 0.2902 0.9528
3.8803 -5.4165 -5.8153 0.6481 0.6856 0.3316
-2.0132 -8.7034 -0.7663 -0.2668 0.8940 0.3599
-5.8707 -3.4855 -1.5402 -0.4438 0.2688 0.8548
-2.2722 8.1670 -1.6848 0.0732 -0.9041 0.4210
-0.1966 3.7056 6.3984 -0.4104 -0.4364 -0.8007

_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0411
_diffrn_reflns_av_unetI/netI     0.0263
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            11506
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         68.248
_diffrn_reflns_theta_min         4.002
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2529
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 0.999
_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    -38.00  28.00   1.00    2.00    --  -41.85  38.00  60.00   66
  2  ω    -67.00 -19.00   1.00    2.00    --  -41.85 -38.00 120.00   48
  3  ω    -32.00  65.00   1.00    2.00    --   41.85 -38.00-150.00   97
  4  ω     37.00 131.00   1.00    9.00    --  106.96 -45.00 -30.00   94
  5  ω     63.00  96.00   1.00    2.00    --   41.85-125.00   0.00   33
  6  ω     55.00  99.00   1.00    9.00    --  106.96 -95.00 -30.00   44
  7  ω     57.00 121.00   1.00    9.00    --  106.96-125.00 150.00   64
  8  ω     80.00 176.00   1.00    9.00    --  106.96  30.00 150.00   96
  9  ω    107.00 177.00   1.00    9.00    --  106.96 125.00 -60.00   70
 10  ω    125.00 156.00   1.00    9.00    --  106.96 125.00 -90.00   31
 11  ω     53.00  79.00   1.00    2.00    --   41.85-125.00-180.00   26
 12  ω     84.00 109.00   1.00    9.00    --  106.96 -95.00-180.00   25
 13  ω    106.00 132.00   1.00    9.00    --  106.96 -45.00 -30.00   26
 14  ω     30.00  56.00   1.00    9.00    --  106.96 -95.00-180.00   26
 15  ω     84.00 109.00   1.00    9.00    --  106.96 -95.00 -60.00   25
 16  ω     34.00  60.00   1.00    9.00    --  112.00 -95.00 150.00   26
 17  ω     68.00  94.00   1.00    9.00    --  112.00 -95.00 150.00   26
 18  ω     69.00 114.00   1.00    9.00    --  112.00 -61.00 -90.00   45
 19  ω    144.00 178.00   1.00    9.00    --  112.00  30.00-120.00   34
 20  ω     63.00 115.00   1.00    9.00    --  112.00-111.00 -60.00   52
 21  ω     45.00  80.00   1.00    9.00    --  112.00-111.00-150.00   35
 22  ω     90.00 116.00   1.00    9.00    --  112.00-111.00-150.00   26
 23  ω    113.00 139.00   1.00    9.00    --  112.00 111.00   0.00   26
 24  ω    143.00 168.00   1.00    9.00    --  112.00 111.00   0.00   25
 25  ω    111.00 137.00   1.00    9.00    --  112.00 111.00 -30.00   26
 26  ω    139.00 178.00   1.00    9.00    --  112.00 111.00  60.00   39
 27  ω     55.00  98.00   1.00    9.00    --  112.00 -30.00 -30.00   43
;
_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      0.0840080000
_diffrn_orient_matrix_UB_12      0.0175392000
_diffrn_orient_matrix_UB_13      -0.0717249000
_diffrn_orient_matrix_UB_21      0.0190583000
_diffrn_orient_matrix_UB_22      -0.1066126000
_diffrn_orient_matrix_UB_23      -0.0058798000
_diffrn_orient_matrix_UB_31      -0.1097319000
_diffrn_orient_matrix_UB_32      -0.0049041000
_diffrn_orient_matrix_UB_33      -0.1256668000
_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                2987
_reflns_number_total             3304
_reflns_odcompleteness_completeness 99.86
_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 1.171.38.46 (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         0.302
_refine_diff_density_min         -0.316
_refine_diff_density_rms         0.053
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.063
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     215
_refine_ls_number_reflns         3304
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0632
_refine_ls_R_factor_gt           0.0592
_refine_ls_restrained_S_all      1.063
_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)+(0.1068P)²+0.3423P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1653
_refine_ls_wR_factor_ref         0.1717
_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:
 C1(H1)
2.b Secondary CH2 refined with riding coordinates:
 C2(H2A,H2B), C5(H5A,H5B), C8(H8A,H8B), C6(H6A,H6B), C7(H7A,H7B)
2.c Aromatic/amide H refined with riding coordinates:
 C16(H16), C17(H17), C18(H18), C19(H19), C20(H20), C14(H14), C11(H11),
 C13(H13), C10(H10)
2.d Fitted hexagon refined as free rotating group:
 C15(C16,C17,C18,C19,C20)
2.e Idealised Me refined as rotating group:
 C21(H21A,H21B,H21C)
;
_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 0.52611(11) 0.42813(9) 0.71931(10) 0.0541(3) Uani 1 1 d . . . . .
O1 O 0.59330(12) 0.33400(9) 1.03840(12) 0.0578(3) Uani 1 1 d . . . . .
O3 O 0.12946(12) 0.46195(11) 0.27212(13) 0.0661(4) Uani 1 1 d . . . . .
N1 N 0.68631(13) 0.46060(10) 1.00228(12) 0.0491(4) Uani 1 1 d . . . . .
C4 C 0.64408(13) 0.37282(11) 0.97649(13) 0.0425(4) Uani 1 1 d . . . . .
C3 C 0.66803(14) 0.32021(11) 0.87339(14) 0.0426(4) Uani 1 1 d . . . . .
C9 C 0.42838(14) 0.43325(11) 0.60508(14) 0.0448(4) Uani 1 1 d . . . . .
C15 C 0.79509(8) 0.28029(8) 0.91240(10) 0.0452(4) Uani 1 1 d . . . . .
C16 C 0.82371(9) 0.22131(9) 0.83132(8) 0.0568(4) Uani 1 1 d G . . . .
H16 H 0.765937 0.208060 0.752031 0.068 Uiso 1 1 calc R . . . .
C17 C 0.93869(11) 0.18215(10) 0.86875(11) 0.0670(5) Uani 1 1 d G . . . .
H17 H 0.957839 0.142692 0.814495 0.080 Uiso 1 1 calc R . . . .
C18 C 1.02505(9) 0.20196(11) 0.98725(12) 0.0711(6) Uani 1 1 d G . . . .
H18 H 1.101973 0.175751 1.012293 0.085 Uiso 1 1 calc R . . . .
C19 C 0.99643(9) 0.26093(12) 1.06834(10) 0.0727(6) Uani 1 1 d G . . . .
H19 H 1.054207 0.274180 1.147627 0.087 Uiso 1 1 calc R . . . .
C20 C 0.88145(10) 0.30009(9) 1.03091(9) 0.0598(5) Uani 1 1 d G . . . .
H20 H 0.862305 0.339549 1.085165 0.072 Uiso 1 1 calc R . . . .
C1 C 0.59901(15) 0.34821(12) 0.73792(14) 0.0463(4) Uani 1 1 d . . . . .
H1 H 0.640491 0.339148 0.679713 0.056 Uiso 1 1 calc R . . . .
C12 C 0.22808(14) 0.45770(12) 0.38497(16) 0.0492(4) Uani 1 1 d . . . . .
C14 C 0.40175(16) 0.36679(12) 0.51097(16) 0.0517(4) Uani 1 1 d . . . . .
H14 H 0.450317 0.313927 0.521348 0.062 Uiso 1 1 calc R . . . .
C2 C 0.56235(15) 0.26245(12) 0.78666(16) 0.0513(4) Uani 1 1 d . . . . .
H2A H 0.580339 0.202373 0.757971 0.062 Uiso 1 1 calc R . . . .
H2B H 0.487240 0.264403 0.800755 0.062 Uiso 1 1 calc R . . . .
C5 C 0.67225(18) 0.51345(14) 1.10569(17) 0.0601(5) Uani 1 1 d . . . . .
H5A H 0.722382 0.487018 1.186504 0.072 Uiso 1 1 calc R . . . .
H5B H 0.588532 0.513315 1.098214 0.072 Uiso 1 1 calc R . . . .
C11 C 0.25522(17) 0.52399(13) 0.47840(18) 0.0578(5) Uani 1 1 d . . . . .
H11 H 0.206707 0.576901 0.467800 0.069 Uiso 1 1 calc R . . . .
C13 C 0.30150(17) 0.38007(13) 0.40073(17) 0.0557(4) Uani 1 1 d . . . . .
H13 H 0.283489 0.336001 0.336495 0.067 Uiso 1 1 calc R . . . .
C8 C 0.74137(18) 0.51860(14) 0.93278(18) 0.0587(5) Uani 1 1 d . . . . .
H8A H 0.707547 0.504298 0.843605 0.070 Uiso 1 1 calc R . . . .
H8B H 0.828493 0.510282 0.964556 0.070 Uiso 1 1 calc R . . . .
C10 C 0.35577(18) 0.51131(13) 0.58889(17) 0.0572(5) Uani 1 1 d . . . . .
H10 H 0.374281 0.555915 0.652542 0.069 Uiso 1 1 calc R . . . .
C6 C 0.7133(2) 0.61207(16) 1.0911(3) 0.0780(7) Uani 1 1 d . . . . .
H6A H 0.659869 0.658494 1.104263 0.094 Uiso 1 1 calc R . . . .
H6B H 0.795110 0.623247 1.150773 0.094 Uiso 1 1 calc R . . . .
C7 C 0.7081(2) 0.61630(16) 0.9582(3) 0.0832(7) Uani 1 1 d . . . . .
H7A H 0.627403 0.632802 0.900030 0.100 Uiso 1 1 calc R . . . .
H7B H 0.765239 0.661978 0.950664 0.100 Uiso 1 1 calc R . . . .
C21 C 0.0558(2) 0.5425(2) 0.2498(3) 0.0868(8) Uani 1 1 d . . . . .
H21A H -0.007110 0.538613 0.167593 0.130 Uiso 1 1 calc GR . . . .
H21B H 0.104027 0.597382 0.254883 0.130 Uiso 1 1 calc GR . . . .
H21C H 0.020149 0.546322 0.311867 0.130 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
O2 C9 1.3884(19) . ?
O2 C1 1.399(2) . ?
O1 C4 1.2273(19) . ?
O3 C12 1.383(2) . ?
O3 C21 1.409(3) . ?
N1 C4 1.339(2) . ?
N1 C5 1.469(2) . ?
N1 C8 1.466(2) . ?
C4 C3 1.518(2) . ?
C3 C15 1.5196(16) . ?
C3 C1 1.513(2) . ?
C3 C2 1.519(2) . ?
C9 C14 1.381(2) . ?
C9 C10 1.378(2) . ?
C15 C16 1.3900 . ?
C15 C20 1.3900 . ?
C16 H16 0.9300 . ?
C16 C17 1.3900 . ?
C17 H17 0.9300 . ?
C17 C18 1.3900 . ?
C18 H18 0.9300 . ?
C18 C19 1.3900 . ?
C19 H19 0.9300 . ?
C19 C20 1.3900 . ?
C20 H20 0.9300 . ?
C1 H1 0.9800 . ?
C1 C2 1.478(2) . ?
C12 C11 1.373(3) . ?
C12 C13 1.380(3) . ?
C14 H14 0.9300 . ?
C14 C13 1.387(2) . ?
C2 H2A 0.9700 . ?
C2 H2B 0.9700 . ?
C5 H5A 0.9700 . ?
C5 H5B 0.9700 . ?
C5 C6 1.518(3) . ?
C11 H11 0.9300 . ?
C11 C10 1.389(3) . ?
C13 H13 0.9300 . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C8 C7 1.506(3) . ?
C10 H10 0.9300 . ?
C6 H6A 0.9700 . ?
C6 H6B 0.9700 . ?
C6 C7 1.506(4) . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C21 H21A 0.9600 . ?
C21 H21B 0.9600 . ?
C21 H21C 0.9600 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C9 O2 C1 115.98(12) . . ?
C12 O3 C21 117.18(17) . . ?
C4 N1 C5 120.58(15) . . ?
C4 N1 C8 127.93(14) . . ?
C8 N1 C5 111.35(15) . . ?
O1 C4 N1 121.32(15) . . ?
O1 C4 C3 120.70(14) . . ?
N1 C4 C3 117.86(13) . . ?
C4 C3 C15 114.64(11) . . ?
C4 C3 C2 115.10(13) . . ?
C1 C3 C4 118.87(13) . . ?
C1 C3 C15 119.69(12) . . ?
C1 C3 C2 58.33(11) . . ?
C2 C3 C15 118.58(13) . . ?
C14 C9 O2 124.46(14) . . ?
C10 C9 O2 115.46(14) . . ?
C10 C9 C14 120.09(15) . . ?
C16 C15 C3 120.00(8) . . ?
C16 C15 C20 120.0 . . ?
C20 C15 C3 119.96(8) . . ?
C15 C16 H16 120.0 . . ?
C17 C16 C15 120.0 . . ?
C17 C16 H16 120.0 . . ?
C16 C17 H17 120.0 . . ?
C16 C17 C18 120.0 . . ?
C18 C17 H17 120.0 . . ?
C17 C18 H18 120.0 . . ?
C17 C18 C19 120.0 . . ?
C19 C18 H18 120.0 . . ?
C18 C19 H19 120.0 . . ?
C20 C19 C18 120.0 . . ?
C20 C19 H19 120.0 . . ?
C15 C20 H20 120.0 . . ?
C19 C20 C15 120.0 . . ?
C19 C20 H20 120.0 . . ?
O2 C1 C3 115.86(13) . . ?
O2 C1 H1 116.7 . . ?
O2 C1 C2 118.30(15) . . ?
C3 C1 H1 116.7 . . ?
C2 C1 C3 61.05(10) . . ?
C2 C1 H1 116.7 . . ?
C11 C12 O3 124.58(16) . . ?
C11 C12 C13 119.92(16) . . ?
C13 C12 O3 115.51(16) . . ?
C9 C14 H14 120.5 . . ?
C9 C14 C13 118.99(16) . . ?
C13 C14 H14 120.5 . . ?
C3 C2 H2A 117.7 . . ?
C3 C2 H2B 117.7 . . ?
C1 C2 C3 60.62(10) . . ?
C1 C2 H2A 117.7 . . ?
C1 C2 H2B 117.7 . . ?
H2A C2 H2B 114.8 . . ?
N1 C5 H5A 110.9 . . ?
N1 C5 H5B 110.9 . . ?
N1 C5 C6 104.12(17) . . ?
H5A C5 H5B 109.0 . . ?
C6 C5 H5A 110.9 . . ?
C6 C5 H5B 110.9 . . ?
C12 C11 H11 120.3 . . ?
C12 C11 C10 119.42(16) . . ?
C10 C11 H11 120.3 . . ?
C12 C13 C14 120.96(16) . . ?
C12 C13 H13 119.5 . . ?
C14 C13 H13 119.5 . . ?
N1 C8 H8A 111.3 . . ?
N1 C8 H8B 111.3 . . ?
N1 C8 C7 102.10(17) . . ?
H8A C8 H8B 109.2 . . ?
C7 C8 H8A 111.3 . . ?
C7 C8 H8B 111.3 . . ?
C9 C10 C11 120.62(16) . . ?
C9 C10 H10 119.7 . . ?
C11 C10 H10 119.7 . . ?
C5 C6 H6A 110.8 . . ?
C5 C6 H6B 110.8 . . ?
H6A C6 H6B 108.8 . . ?
C7 C6 C5 104.96(17) . . ?
C7 C6 H6A 110.8 . . ?
C7 C6 H6B 110.8 . . ?
C8 C7 C6 104.29(19) . . ?
C8 C7 H7A 110.9 . . ?
C8 C7 H7B 110.9 . . ?
C6 C7 H7A 110.9 . . ?
C6 C7 H7B 110.9 . . ?
H7A C7 H7B 108.9 . . ?
O3 C21 H21A 109.5 . . ?
O3 C21 H21B 109.5 . . ?
O3 C21 H21C 109.5 . . ?
H21A C21 H21B 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?

_olex2_date_sample_data_collection 2017-08-25
_olex2_exptl_crystal_mounting_method 
'Mounted on the glass stick by acrylic glue'
_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
- Detector area scaling
- B-factor correction
;
_oxdiff_exptl_absorpt_empirical_full_max 1.682
_oxdiff_exptl_absorpt_empirical_full_min 0.655
####################################################################### 
# 
# 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_anna_23082017_ypm29_1
_database_code_depnum_ccdc_archive 'CCDC 1570793'
_audit_update_record             
;
2017-08-24 deposited with the CCDC.
2017-09-11 downloaded from the CCDC.
;
_audit_creation_date             2017-08-25
_audit_creation_method           
;
Olex2 1.2
(compiled 2017.03.28 svn.r3405 for OlexSys, GUI svn.r5337)
;
_shelx_SHELXL_version_number     2016/6
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C21 H23 N O4'
_chemical_formula_sum            'C21 H23 N O4'
_chemical_formula_weight         353.40
_chemical_melting_point          ?
_chemical_oxdiff_formula         C21H23NO4
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      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   9.4667(5)
_cell_length_b                   10.5554(6)
_cell_length_c                   10.6002(6)
_cell_angle_alpha                62.334(6)
_cell_angle_beta                 83.248(5)
_cell_angle_gamma                79.062(5)
_cell_volume                     920.55(10)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    4636
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      72.5330
_cell_measurement_theta_min      4.6260
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.715
_exptl_absorpt_correction_T_max  0.764
_exptl_absorpt_correction_T_min  0.602
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.43 (Rigaku Oxford Diffraction, 2015)
Numerical absorption correction based on gaussian integration over
			a multifaceted crystal model
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.275
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       prism
_exptl_crystal_F_000             376
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
-2 -6 -5 0.0925
-1 -4 3 0.2448
-6 -1 0 0.1148
6 0 0 0.1160
-6 0 0 0.1318
-2 3 -4 0.2482
-3 4 -1 0.2338
1 4 -3 0.2602
6 4 4 0.1265
2 6 5 0.1632
5 -2 -2 0.1362
1 -6 -5 0.1103

_exptl_crystal_size_max          0.562
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.247
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
-1.9500 -6.0597 -5.2434 -0.8833 0.4194 -0.0532
-1.1730 -3.9734 3.0667 -0.1423 0.0705 -0.9873
-6.1037 -0.5424 -0.2655 -0.6034 -0.7876 -0.1249
6.1794 -0.2790 -0.1798 0.5320 0.8824 0.0839
-5.6976 -0.0128 0.2629 -0.5003 -0.7941 -0.1270
-1.6901 2.9565 -3.7251 -0.2213 -0.3576 0.9073
-3.4930 3.7394 -1.3421 -0.1816 -0.7528 0.6328
1.1732 3.9742 -3.0658 0.1425 -0.0706 0.9873
5.6579 3.9902 3.6092 0.9886 0.3222 0.0787
1.8355 5.6637 5.1818 0.8452 -0.3997 0.0087
5.3025 -1.9315 -2.0617 0.2301 0.9644 0.1305
1.2353 -5.6480 -5.1989 -0.5668 0.8227 0.0426

_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0172
_diffrn_reflns_av_unetI/netI     0.0176
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            8033
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         68.225
_diffrn_reflns_theta_min         4.713
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2529
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 0.999
_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     13.00  40.00   1.00    1.00    --  -38.08  77.00  30.00   27
  2  ω    -59.00  40.00   1.00    1.00    --  -38.08  38.00-180.00   99
  3  ω    -66.00  29.00   1.00    1.00    --  -38.08  38.00 -30.00   95
  4  ω    -73.00 -33.00   1.00    1.00    --  -38.08  77.00  30.00   40
  5  ω   -114.00 -19.00   1.00    1.00    --  -38.08 -57.00  30.00   95
  6  ω     44.00  71.00   1.00    1.00    --   38.08-125.00 -60.00   27
  7  ω     27.00  90.00   1.00    1.00    --   38.08-125.00-120.00   63
  8  ω    101.00 127.00   1.00    1.66    --  108.60 -45.00 -90.00   26
  9  ω     88.00 115.00   1.00    1.66    --  108.60-111.00-180.00   27
 10  ω     30.00  75.00   1.00    1.66    --  108.60 -45.00 -90.00   45
 11  ω     32.00 108.00   1.00    1.66    --  108.60 -95.00 -90.00   76
 12  ω     40.00 178.00   1.00    1.66    --  108.60 -15.00   0.00  138
 13  ω    103.00 178.00   1.00    1.66    --  108.60 111.00 -30.00   75
 14  ω    112.00 160.00   1.00    1.66    --  108.60 111.00  60.00   48
 15  ω     70.00 143.00   1.00    1.66    --  108.60 -30.00 120.00   73
 16  ω     49.00 125.00   1.00    1.66    --  108.60 -77.00  60.00   76
 17  ω     29.00  55.00   1.00    1.66    --  108.60 -95.00 150.00   26
 18  ω     29.00  56.00   1.00    1.66    --  108.60 -30.00 120.00   27
 19  ω     29.00 115.00   1.00    1.66    --  108.60-111.00  30.00   86
 20  ω    102.00 171.00   1.00    1.66    --  108.60 111.00-180.00   69
 21  ω     67.00  95.00   1.00    1.00    --   38.33-125.00 -30.00   28
 22  ω     63.00  89.00   1.00    1.66    --  108.60 178.00-180.00   26
 23  ω    125.00 150.00   1.00    1.66    --  108.60 178.00-180.00   25
 24  ω    130.00 156.00   1.00    1.66    --  108.60 111.00 -60.00   26
 25  ω     74.00 131.00   1.00    1.66    --  108.60  77.00 -30.00   57
 26  ω   -116.00  -6.00   1.00    1.00    --  -38.33 -57.00-180.00  110
 27  ω   -116.00  -6.00   1.00    1.00    --  -38.33 -57.00  90.00  110
 28  ω   -122.00  -2.00   1.00    1.00    --  -38.33 -77.00 -60.00  120
 29  ω      2.00  61.00   1.00    1.00    --   38.33  77.00-180.00   59
 30  ω      1.00  82.00   1.00    1.00    --   38.33 -99.00  30.00   81
;
_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      0.0906967000
_diffrn_orient_matrix_UB_12      0.0597409000
_diffrn_orient_matrix_UB_13      0.0656816000
_diffrn_orient_matrix_UB_21      0.1380054000
_diffrn_orient_matrix_UB_22      -0.0844822000
_diffrn_orient_matrix_UB_23      -0.0336788000
_diffrn_orient_matrix_UB_31      0.0152211000
_diffrn_orient_matrix_UB_32      0.1307921000
_diffrn_orient_matrix_UB_33      -0.1466607000
_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                3030
_reflns_number_total             3369
_reflns_odcompleteness_completeness 99.76
_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 1.171.38.43 (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.43 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43 (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         0.260
_refine_diff_density_min         -0.156
_refine_diff_density_rms         0.032
_refine_ls_extinction_coef       0.0194(12)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2016/6 (Sheldrick 2016)'
_refine_ls_goodness_of_fit_ref   1.055
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     237
_refine_ls_number_reflns         3369
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0448
_refine_ls_R_factor_gt           0.0401
_refine_ls_restrained_S_all      1.055
_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)+(0.0560P)²+0.1907P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1119
_refine_ls_wR_factor_ref         0.1163
_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:
 C1(H1)
2.b Secondary CH2 refined with riding coordinates:
 C8(H8A,H8B), C3(H3A,H3B), C7(H7A,H7B), C5(H5A,H5B), C6(H6A,H6B)
2.c Aromatic/amide H refined with riding coordinates:
 C10(H10), C17(H17), C13(H13), C11(H11), C14(H14), C21(H21), C18(H18),
 C19(H19), C20(H20)
2.d Idealised Me refined as rotating group:
 C15(H15A,H15B,H15C)
;
_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 0.50719(11) 0.37066(11) 0.71697(13) 0.0570(3) Uani 1 1 d . . . . .
O3 O 0.59815(14) -0.11479(13) 0.67112(12) 0.0669(3) Uani 1 1 d . . . . .
O4 O 0.06189(12) 0.69528(13) 0.87345(14) 0.0658(3) Uani 1 1 d . . . . .
O1 O 0.73526(14) 0.06830(14) 0.97568(11) 0.0678(4) Uani 1 1 d . . . . .
N1 N 0.66059(15) 0.05965(13) 0.78717(12) 0.0501(3) Uani 1 1 d . . . . .
C4 C 0.71619(15) 0.12574(16) 0.84750(14) 0.0450(3) Uani 1 1 d . . . . .
C9 C 0.40421(15) 0.46050(14) 0.75422(15) 0.0446(3) Uani 1 1 d . . . . .
C10 C 0.27572(16) 0.40833(15) 0.80958(15) 0.0479(3) Uani 1 1 d . . . . .
H10 H 0.264290 0.318441 0.819744 0.057 Uiso 1 1 calc R . . . .
C16 C 0.90519(15) 0.26346(15) 0.67265(15) 0.0439(3) Uani 1 1 d . . . . .
C12 C 0.18011(16) 0.62335(15) 0.83298(15) 0.0468(3) Uani 1 1 d . . . . .
C2 C 0.76298(15) 0.27223(15) 0.75068(15) 0.0444(3) Uani 1 1 d . . . . .
C17 C 1.02723(16) 0.19086(16) 0.75209(16) 0.0501(4) Uani 1 1 d . . . . .
H17 H 1.019492 0.150654 0.850979 0.060 Uiso 1 1 calc R . . . .
C13 C 0.30799(16) 0.67593(15) 0.77772(16) 0.0495(4) Uani 1 1 d . . . . .
H13 H 0.318930 0.766229 0.766818 0.059 Uiso 1 1 calc R . . . .
C11 C 0.16506(16) 0.48822(16) 0.84958(16) 0.0505(4) Uani 1 1 d . . . . .
H11 H 0.079568 0.451645 0.887996 0.061 Uiso 1 1 calc R . . . .
C14 C 0.42070(16) 0.59430(15) 0.73822(16) 0.0497(4) Uani 1 1 d . . . . .
H14 H 0.506886 0.629863 0.701135 0.060 Uiso 1 1 calc R . . . .
C1 C 0.64862(16) 0.40276(16) 0.68886(17) 0.0511(4) Uani 1 1 d . . . . .
H1 H 0.669857 0.480852 0.595289 0.061 Uiso 1 1 calc R . . . .
C8 C 0.61815(19) 0.12343(17) 0.63951(15) 0.0544(4) Uani 1 1 d . . . . .
H8A H 0.665762 0.206958 0.581480 0.065 Uiso 1 1 calc R . . . .
H8B H 0.514996 0.155369 0.634059 0.065 Uiso 1 1 calc R . . . .
C21 C 0.91903(18) 0.3218(2) 0.52630(17) 0.0623(4) Uani 1 1 d . . . . .
H21 H 0.838321 0.370545 0.471357 0.075 Uiso 1 1 calc R . . . .
C18 C 1.16004(17) 0.17754(18) 0.68617(19) 0.0572(4) Uani 1 1 d . . . . .
H18 H 1.241030 0.128490 0.740614 0.069 Uiso 1 1 calc R . . . .
C3 C 0.73079(17) 0.37969(18) 0.81131(18) 0.0559(4) Uani 1 1 d . . . . .
H3A H 0.681024 0.349929 0.903647 0.067 Uiso 1 1 calc R . . . .
H3B H 0.800990 0.442918 0.792655 0.067 Uiso 1 1 calc R . . . .
C19 C 1.17253(18) 0.23678(19) 0.54004(19) 0.0618(4) Uani 1 1 d . . . . .
H19 H 1.261958 0.228492 0.495339 0.074 Uiso 1 1 calc R . . . .
C7 C 0.6590(2) 0.01341(19) 0.58444(17) 0.0628(4) Uani 1 1 d . . . . .
H7A H 0.626293 0.054709 0.487972 0.075 Uiso 1 1 calc R . . . .
H7B H 0.763022 -0.010905 0.581451 0.075 Uiso 1 1 calc R . . . .
C5 C 0.6064(2) -0.07765(18) 0.87702(17) 0.0626(4) Uani 1 1 d . . . . .
H5A H 0.502403 -0.059448 0.887309 0.075 Uiso 1 1 calc R . . . .
H5B H 0.645832 -0.121477 0.971074 0.075 Uiso 1 1 calc R . . . .
C15 C 0.0628(2) 0.84324(19) 0.8357(2) 0.0677(5) Uani 1 1 d . . . . .
H15A H 0.075608 0.896475 0.734166 0.102 Uiso 1 1 calc GR . . . .
H15B H 0.140364 0.850662 0.881417 0.102 Uiso 1 1 calc GR . . . .
H15C H -0.026974 0.882442 0.865862 0.102 Uiso 1 1 calc GR . . . .
C6 C 0.6481(2) -0.17894(19) 0.81212(19) 0.0665(5) Uani 1 1 d . . . . .
H6A H 0.752044 -0.204282 0.810284 0.080 Uiso 1 1 calc R . . . .
H6B H 0.607487 -0.267150 0.870004 0.080 Uiso 1 1 calc R . . . .
C20 C 1.0525(2) 0.3082(2) 0.46051(19) 0.0711(5) Uani 1 1 d . . . . .
H20 H 1.060674 0.347748 0.361678 0.085 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 C9 1.3827(17) . ?
O2 C1 1.4073(18) . ?
O3 C7 1.4227(19) . ?
O3 C6 1.422(2) . ?
O4 C12 1.3712(18) . ?
O4 C15 1.422(2) . ?
O1 C4 1.2238(17) . ?
N1 C4 1.3436(19) . ?
N1 C8 1.4599(18) . ?
N1 C5 1.468(2) . ?
C4 C2 1.523(2) . ?
C9 C10 1.383(2) . ?
C9 C14 1.379(2) . ?
C10 H10 0.9300 . ?
C10 C11 1.371(2) . ?
C16 C2 1.5056(19) . ?
C16 C17 1.387(2) . ?
C16 C21 1.378(2) . ?
C12 C13 1.380(2) . ?
C12 C11 1.387(2) . ?
C2 C1 1.504(2) . ?
C2 C3 1.514(2) . ?
C17 H17 0.9300 . ?
C17 C18 1.381(2) . ?
C13 H13 0.9300 . ?
C13 C14 1.392(2) . ?
C11 H11 0.9300 . ?
C14 H14 0.9300 . ?
C1 H1 0.9800 . ?
C1 C3 1.490(2) . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C8 C7 1.498(2) . ?
C21 H21 0.9300 . ?
C21 C20 1.385(2) . ?
C18 H18 0.9300 . ?
C18 C19 1.375(2) . ?
C3 H3A 0.9700 . ?
C3 H3B 0.9700 . ?
C19 H19 0.9300 . ?
C19 C20 1.371(3) . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C5 H5A 0.9700 . ?
C5 H5B 0.9700 . ?
C5 C6 1.494(2) . ?
C15 H15A 0.9600 . ?
C15 H15B 0.9600 . ?
C15 H15C 0.9600 . ?
C6 H6A 0.9700 . ?
C6 H6B 0.9700 . ?
C20 H20 0.9300 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C9 O2 C1 117.42(11) . . ?
C6 O3 C7 110.00(12) . . ?
C12 O4 C15 117.38(13) . . ?
C4 N1 C8 126.36(12) . . ?
C4 N1 C5 119.98(12) . . ?
C8 N1 C5 112.35(13) . . ?
O1 C4 N1 121.62(14) . . ?
O1 C4 C2 120.16(13) . . ?
N1 C4 C2 118.14(12) . . ?
O2 C9 C10 115.13(12) . . ?
C14 C9 O2 125.14(13) . . ?
C14 C9 C10 119.73(13) . . ?
C9 C10 H10 119.8 . . ?
C11 C10 C9 120.47(13) . . ?
C11 C10 H10 119.8 . . ?
C17 C16 C2 118.38(12) . . ?
C21 C16 C2 122.98(13) . . ?
C21 C16 C17 118.63(14) . . ?
O4 C12 C13 125.04(13) . . ?
O4 C12 C11 115.47(13) . . ?
C13 C12 C11 119.48(13) . . ?
C16 C2 C4 114.04(12) . . ?
C16 C2 C3 118.38(12) . . ?
C1 C2 C4 118.44(12) . . ?
C1 C2 C16 121.15(12) . . ?
C1 C2 C3 59.18(10) . . ?
C3 C2 C4 114.50(12) . . ?
C16 C17 H17 119.6 . . ?
C18 C17 C16 120.82(14) . . ?
C18 C17 H17 119.6 . . ?
C12 C13 H13 119.9 . . ?
C12 C13 C14 120.22(13) . . ?
C14 C13 H13 119.9 . . ?
C10 C11 C12 120.27(13) . . ?
C10 C11 H11 119.9 . . ?
C12 C11 H11 119.9 . . ?
C9 C14 C13 119.81(13) . . ?
C9 C14 H14 120.1 . . ?
C13 C14 H14 120.1 . . ?
O2 C1 C2 114.15(12) . . ?
O2 C1 H1 117.3 . . ?
O2 C1 C3 117.71(14) . . ?
C2 C1 H1 117.3 . . ?
C3 C1 C2 60.74(10) . . ?
C3 C1 H1 117.3 . . ?
N1 C8 H8A 109.8 . . ?
N1 C8 H8B 109.8 . . ?
N1 C8 C7 109.56(13) . . ?
H8A C8 H8B 108.2 . . ?
C7 C8 H8A 109.8 . . ?
C7 C8 H8B 109.8 . . ?
C16 C21 H21 119.8 . . ?
C16 C21 C20 120.39(16) . . ?
C20 C21 H21 119.8 . . ?
C17 C18 H18 120.0 . . ?
C19 C18 C17 119.99(15) . . ?
C19 C18 H18 120.0 . . ?
C2 C3 H3A 117.8 . . ?
C2 C3 H3B 117.8 . . ?
C1 C3 C2 60.07(10) . . ?
C1 C3 H3A 117.8 . . ?
C1 C3 H3B 117.8 . . ?
H3A C3 H3B 114.9 . . ?
C18 C19 H19 120.2 . . ?
C20 C19 C18 119.67(15) . . ?
C20 C19 H19 120.2 . . ?
O3 C7 C8 111.83(13) . . ?
O3 C7 H7A 109.2 . . ?
O3 C7 H7B 109.3 . . ?
C8 C7 H7A 109.3 . . ?
C8 C7 H7B 109.2 . . ?
H7A C7 H7B 107.9 . . ?
N1 C5 H5A 109.6 . . ?
N1 C5 H5B 109.6 . . ?
N1 C5 C6 110.37(13) . . ?
H5A C5 H5B 108.1 . . ?
C6 C5 H5A 109.6 . . ?
C6 C5 H5B 109.6 . . ?
O4 C15 H15A 109.5 . . ?
O4 C15 H15B 109.5 . . ?
O4 C15 H15C 109.5 . . ?
H15A C15 H15B 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
O3 C6 C5 110.94(14) . . ?
O3 C6 H6A 109.5 . . ?
O3 C6 H6B 109.5 . . ?
C5 C6 H6A 109.5 . . ?
C5 C6 H6B 109.5 . . ?
H6A C6 H6B 108.0 . . ?
C21 C20 H20 119.8 . . ?
C19 C20 C21 120.50(16) . . ?
C19 C20 H20 119.8 . . ?

_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 1.331
_oxdiff_exptl_absorpt_empirical_full_min 0.669
