# Electronic Supplementary Material (ESI) for Chemical Science.
# 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. 
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#######################################################################

data_carter1_0m
_database_code_depnum_ccdc_archive 'CCDC 1578266'
_audit_update_record             
;
2017-10-05 deposited with the CCDC.
2017-12-14 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C22 H25 N O4'
_chemical_formula_sum            'C22 H25 N O4'
_chemical_formula_weight         367.43

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'

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

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

_cell_length_a                   10.3192(3)
_cell_length_b                   11.0867(4)
_cell_length_c                   17.4057(6)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1991.31(12)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    7921
_cell_measurement_theta_min      4.73
_cell_measurement_theta_max      66.58

_exptl_crystal_description       BLOCK
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.226
_exptl_crystal_F_000             784
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.300
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.200
_exptl_absorpt_coefficient_mu    0.680
_shelx_estimated_absorpt_T_min   0.822
_shelx_estimated_absorpt_T_max   0.876
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.79
_exptl_absorpt_correction_T_max  0.89
_exptl_absorpt_process_details   sadabs
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            25795
_diffrn_reflns_av_unetI/netI     0.0223
_diffrn_reflns_av_R_equivalents  0.0414
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         4.729
_diffrn_reflns_theta_max         66.627
_diffrn_reflns_theta_full        66.627
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_point_group_measured_fraction_full 0.997
_reflns_number_total             3512
_reflns_number_gt                3382
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.742
_reflns_Friedel_fraction_max     0.997
_reflns_Friedel_fraction_full    0.997

_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. 
;

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0375P)²+0.2781P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
; 
 Flack x determined using 1411 quotients [(I+)-(I-)]/[(I+)+(I-)] 
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259). 
;
_refine_ls_abs_structure_Flack   0.03(6)
_chemical_absolute_configuration unk
_refine_ls_number_reflns         3512
_refine_ls_number_parameters     248
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0296
_refine_ls_R_factor_gt           0.0280
_refine_ls_wR_factor_ref         0.0691
_refine_ls_wR_factor_gt          0.0682
_refine_ls_goodness_of_fit_ref   1.095
_refine_ls_restrained_S_all      1.095
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.78201(12) 0.00727(10) 0.82624(7) 0.0165(3) Uani 1 1 d . . . . .
O2 O 0.91820(11) 0.16789(11) 0.81979(7) 0.0186(3) Uani 1 1 d . . . . .
O3 O 0.50141(14) -0.06386(13) 0.87741(8) 0.0312(3) Uani 1 1 d . . . . .
O4 O 0.52517(13) 0.11530(12) 0.81991(8) 0.0245(3) Uani 1 1 d . . . . .
N1 N 0.73659(13) 0.16891(13) 0.89677(8) 0.0141(3) Uani 1 1 d . . . . .
C1 C 0.87950(19) -0.02473(18) 0.69947(10) 0.0214(4) Uani 1 1 d . . . . .
H24 H 0.7937 -0.0125 0.6766 0.032 Uiso 1 1 calc R U . . .
H1 H 0.9289 -0.0820 0.6681 0.032 Uiso 1 1 calc R U . . .
H25 H 0.9257 0.0524 0.7015 0.032 Uiso 1 1 calc R U . . .
C2 C 0.86452(19) -0.07431(17) 0.77984(10) 0.0194(4) Uani 1 1 d . . . . .
C3 C 0.82158(16) 0.11868(16) 0.84441(9) 0.0141(4) Uani 1 1 d . . . . .
C4 C 0.64244(16) 0.08865(15) 0.93605(10) 0.0150(4) Uani 1 1 d . . . . .
C5 C 0.71260(17) -0.00792(16) 0.98414(10) 0.0153(4) Uani 1 1 d . . . . .
C6 C 0.64578(19) -0.10642(17) 1.01412(11) 0.0204(4) Uani 1 1 d . . . . .
H20 H 0.5563 -0.1162 1.0028 0.024 Uiso 1 1 calc R U . . .
C7 C 0.7082(2) -0.19044(17) 1.06025(11) 0.0255(4) Uani 1 1 d . . . . .
H21 H 0.6614 -0.2578 1.0795 0.031 Uiso 1 1 calc R U . . .
C8 C 0.8383(2) -0.17686(19) 1.07845(11) 0.0269(4) Uani 1 1 d . . . . .
H2 H 0.8813 -0.2350 1.1094 0.032 Uiso 1 1 calc R U . . .
C9 C 0.7838(2) -0.18898(18) 0.77892(13) 0.0348(5) Uani 1 1 d . . . . .
H3 H 0.7703 -0.2171 0.8317 0.052 Uiso 1 1 calc R U . . .
H5 H 0.8292 -0.2514 0.7495 0.052 Uiso 1 1 calc R U . . .
H4 H 0.6997 -0.1724 0.7550 0.052 Uiso 1 1 calc R U . . .
C10 C 0.9927(2) -0.0945(2) 0.82015(12) 0.0336(5) Uani 1 1 d . . . . .
H8 H 1.0461 -0.0217 0.8158 0.050 Uiso 1 1 calc R U . . .
H6 H 1.0380 -0.1625 0.7962 0.050 Uiso 1 1 calc R U . . .
H7 H 0.9771 -0.1124 0.8745 0.050 Uiso 1 1 calc R U . . .
C11 C 0.55693(17) 0.16415(17) 0.99110(10) 0.0178(4) Uani 1 1 d . . . . .
H16 H 0.4955 0.2137 0.9609 0.021 Uiso 1 1 calc R U . . .
H9 H 0.5061 0.1097 1.0246 0.021 Uiso 1 1 calc R U . . .
C12 C 0.64184(18) 0.24592(16) 1.04028(10) 0.0188(4) Uani 1 1 d . . . . .
H14 H 0.5884 0.2888 1.0788 0.023 Uiso 1 1 calc R U . . .
H15 H 0.7081 0.1977 1.0677 0.023 Uiso 1 1 calc R U . . .
C13 C 0.70590(16) 0.33489(17) 0.98702(10) 0.0167(4) Uani 1 1 d . . . . .
C14 C 0.74361(15) 0.29464(16) 0.91403(10) 0.0147(4) Uani 1 1 d . . . . .
C15 C 0.78466(17) 0.37787(16) 0.85918(10) 0.0176(4) Uani 1 1 d . . . . .
H13 H 0.8038 0.3518 0.8084 0.021 Uiso 1 1 calc R U . . .
C16 C 0.79770(17) 0.49865(17) 0.87849(11) 0.0214(4) Uani 1 1 d . . . . .
H10 H 0.8273 0.5546 0.8411 0.026 Uiso 1 1 calc R U . . .
C17 C 0.76796(18) 0.53824(17) 0.95184(12) 0.0236(4) Uani 1 1 d . . . . .
H12 H 0.7802 0.6204 0.9656 0.028 Uiso 1 1 calc R U . . .
C18 C 0.72011(17) 0.45662(17) 1.00498(11) 0.0205(4) Uani 1 1 d . . . . .
H11 H 0.6965 0.4842 1.0547 0.025 Uiso 1 1 calc R U . . .
C19 C 0.55036(17) 0.03418(17) 0.87520(11) 0.0198(4) Uani 1 1 d . . . . .
C20 C 0.4412(2) 0.0716(2) 0.75952(13) 0.0348(5) Uani 1 1 d . . . . .
H17 H 0.4791 -0.0009 0.7364 0.052 Uiso 1 1 calc R U . . .
H19 H 0.4315 0.1340 0.7201 0.052 Uiso 1 1 calc R U . . .
H18 H 0.3560 0.0520 0.7811 0.052 Uiso 1 1 calc R U . . .
C21 C 0.90455(19) -0.07758(19) 1.05093(11) 0.0253(4) Uani 1 1 d . . . . .
H22 H 0.9932 -0.0665 1.0639 0.030 Uiso 1 1 calc R U . . .
C22 C 0.84223(18) 0.00634(17) 1.00439(10) 0.0192(4) Uani 1 1 d . . . . .
H23 H 0.8889 0.0744 0.9861 0.023 Uiso 1 1 calc R U . . .


_geom_special_details            
; 
 All esds (except the esd in the dihedral angle between two l.s. planes) 
 are estimated using the full covariance matrix.  The cell esds are taken 
 into account individually in the estimation of esds in distances, angles 
 and torsion angles; correlations between esds in cell parameters are only 
 used when they are defined by crystal symmetry.  An approximate (isotropic) 
 treatment of cell esds is used for estimating esds involving l.s. planes. 
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C3 1.339(2) . ?
O1 C2 1.482(2) . ?
O2 C3 1.215(2) . ?
O3 C19 1.199(2) . ?
O4 C19 1.343(2) . ?
O4 C20 1.446(2) . ?
N1 C3 1.382(2) . ?
N1 C14 1.428(2) . ?
N1 C4 1.484(2) . ?
C1 C2 1.511(2) . ?
C1 H24 0.9800 . ?
C1 H1 0.9800 . ?
C1 H25 0.9800 . ?
C2 C10 1.514(3) . ?
C2 C9 1.520(3) . ?
C4 C5 1.540(2) . ?
C4 C19 1.546(2) . ?
C4 C11 1.548(2) . ?
C5 C22 1.392(3) . ?
C5 C6 1.393(3) . ?
C6 C7 1.388(3) . ?
C6 H20 0.9500 . ?
C7 C8 1.388(3) . ?
C7 H21 0.9500 . ?
C8 C21 1.381(3) . ?
C8 H2 0.9500 . ?
C9 H3 0.9800 . ?
C9 H5 0.9800 . ?
C9 H4 0.9800 . ?
C10 H8 0.9800 . ?
C10 H6 0.9800 . ?
C10 H7 0.9800 . ?
C11 C12 1.524(3) . ?
C11 H16 0.9900 . ?
C11 H9 0.9900 . ?
C12 C13 1.506(2) . ?
C12 H14 0.9900 . ?
C12 H15 0.9900 . ?
C13 C18 1.393(3) . ?
C13 C14 1.402(2) . ?
C14 C15 1.394(2) . ?
C15 C16 1.387(3) . ?
C15 H13 0.9500 . ?
C16 C17 1.385(3) . ?
C16 H10 0.9500 . ?
C17 C18 1.385(3) . ?
C17 H12 0.9500 . ?
C18 H11 0.9500 . ?
C20 H17 0.9800 . ?
C20 H19 0.9800 . ?
C20 H18 0.9800 . ?
C21 C22 1.391(3) . ?
C21 H22 0.9500 . ?
C22 H23 0.9500 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C3 O1 C2 121.10(13) . . ?
C19 O4 C20 114.36(16) . . ?
C3 N1 C14 120.00(14) . . ?
C3 N1 C4 118.52(14) . . ?
C14 N1 C4 121.44(14) . . ?
C2 C1 H24 109.5 . . ?
C2 C1 H1 109.5 . . ?
H24 C1 H1 109.5 . . ?
C2 C1 H25 109.5 . . ?
H24 C1 H25 109.5 . . ?
H1 C1 H25 109.5 . . ?
O1 C2 C1 109.96(14) . . ?
O1 C2 C10 109.87(14) . . ?
C1 C2 C10 113.17(17) . . ?
O1 C2 C9 101.61(15) . . ?
C1 C2 C9 110.52(16) . . ?
C10 C2 C9 111.10(18) . . ?
O2 C3 O1 125.56(16) . . ?
O2 C3 N1 124.92(16) . . ?
O1 C3 N1 109.51(14) . . ?
N1 C4 C5 111.07(14) . . ?
N1 C4 C19 108.73(14) . . ?
C5 C4 C19 112.94(14) . . ?
N1 C4 C11 109.51(14) . . ?
C5 C4 C11 107.90(13) . . ?
C19 C4 C11 106.55(14) . . ?
C22 C5 C6 118.02(17) . . ?
C22 C5 C4 120.69(16) . . ?
C6 C5 C4 121.07(16) . . ?
C7 C6 C5 120.87(18) . . ?
C7 C6 H20 119.6 . . ?
C5 C6 H20 119.6 . . ?
C8 C7 C6 120.54(19) . . ?
C8 C7 H21 119.7 . . ?
C6 C7 H21 119.7 . . ?
C21 C8 C7 119.07(19) . . ?
C21 C8 H2 120.5 . . ?
C7 C8 H2 120.5 . . ?
C2 C9 H3 109.5 . . ?
C2 C9 H5 109.5 . . ?
H3 C9 H5 109.5 . . ?
C2 C9 H4 109.5 . . ?
H3 C9 H4 109.5 . . ?
H5 C9 H4 109.5 . . ?
C2 C10 H8 109.5 . . ?
C2 C10 H6 109.5 . . ?
H8 C10 H6 109.5 . . ?
C2 C10 H7 109.5 . . ?
H8 C10 H7 109.5 . . ?
H6 C10 H7 109.5 . . ?
C12 C11 C4 109.97(14) . . ?
C12 C11 H16 109.7 . . ?
C4 C11 H16 109.7 . . ?
C12 C11 H9 109.7 . . ?
C4 C11 H9 109.7 . . ?
H16 C11 H9 108.2 . . ?
C13 C12 C11 107.22(15) . . ?
C13 C12 H14 110.3 . . ?
C11 C12 H14 110.3 . . ?
C13 C12 H15 110.3 . . ?
C11 C12 H15 110.3 . . ?
H14 C12 H15 108.5 . . ?
C18 C13 C14 118.86(16) . . ?
C18 C13 C12 122.85(16) . . ?
C14 C13 C12 118.11(16) . . ?
C15 C14 C13 119.64(16) . . ?
C15 C14 N1 121.18(15) . . ?
C13 C14 N1 119.17(15) . . ?
C16 C15 C14 120.18(17) . . ?
C16 C15 H13 119.9 . . ?
C14 C15 H13 119.9 . . ?
C15 C16 C17 120.53(18) . . ?
C15 C16 H10 119.7 . . ?
C17 C16 H10 119.7 . . ?
C18 C17 C16 119.19(17) . . ?
C18 C17 H12 120.4 . . ?
C16 C17 H12 120.4 . . ?
C17 C18 C13 121.37(17) . . ?
C17 C18 H11 119.3 . . ?
C13 C18 H11 119.3 . . ?
O3 C19 O4 123.27(17) . . ?
O3 C19 C4 126.24(17) . . ?
O4 C19 C4 110.39(15) . . ?
O4 C20 H17 109.5 . . ?
O4 C20 H19 109.5 . . ?
H17 C20 H19 109.5 . . ?
O4 C20 H18 109.5 . . ?
H17 C20 H18 109.5 . . ?
H19 C20 H18 109.5 . . ?
C8 C21 C22 120.41(19) . . ?
C8 C21 H22 119.8 . . ?
C22 C21 H22 119.8 . . ?
C5 C22 C21 121.04(18) . . ?
C5 C22 H23 119.5 . . ?
C21 C22 H23 119.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C3 O1 C2 C1 -66.2(2) . . . . ?
C3 O1 C2 C10 59.0(2) . . . . ?
C3 O1 C2 C9 176.69(15) . . . . ?
C2 O1 C3 O2 7.8(2) . . . . ?
C2 O1 C3 N1 -171.22(13) . . . . ?
C14 N1 C3 O2 12.9(2) . . . . ?
C4 N1 C3 O2 -164.96(16) . . . . ?
C14 N1 C3 O1 -168.15(14) . . . . ?
C4 N1 C3 O1 14.03(19) . . . . ?
C3 N1 C4 C5 61.46(18) . . . . ?
C14 N1 C4 C5 -116.33(17) . . . . ?
C3 N1 C4 C19 -63.40(19) . . . . ?
C14 N1 C4 C19 118.80(16) . . . . ?
C3 N1 C4 C11 -179.46(14) . . . . ?
C14 N1 C4 C11 2.7(2) . . . . ?
N1 C4 C5 C22 17.9(2) . . . . ?
C19 C4 C5 C22 140.32(16) . . . . ?
C11 C4 C5 C22 -102.18(18) . . . . ?
N1 C4 C5 C6 -167.73(15) . . . . ?
C19 C4 C5 C6 -45.3(2) . . . . ?
C11 C4 C5 C6 72.2(2) . . . . ?
C22 C5 C6 C7 -2.6(3) . . . . ?
C4 C5 C6 C7 -177.14(16) . . . . ?
C5 C6 C7 C8 1.0(3) . . . . ?
C6 C7 C8 C21 0.9(3) . . . . ?
N1 C4 C11 C12 -48.39(19) . . . . ?
C5 C4 C11 C12 72.62(18) . . . . ?
C19 C4 C11 C12 -165.82(14) . . . . ?
C4 C11 C12 C13 65.09(18) . . . . ?
C11 C12 C13 C18 138.64(17) . . . . ?
C11 C12 C13 C14 -36.4(2) . . . . ?
C18 C13 C14 C15 -5.0(2) . . . . ?
C12 C13 C14 C15 170.20(16) . . . . ?
C18 C13 C14 N1 176.29(15) . . . . ?
C12 C13 C14 N1 -8.5(2) . . . . ?
C3 N1 C14 C15 30.8(2) . . . . ?
C4 N1 C14 C15 -151.48(16) . . . . ?
C3 N1 C14 C13 -150.56(15) . . . . ?
C4 N1 C14 C13 27.2(2) . . . . ?
C13 C14 C15 C16 5.0(3) . . . . ?
N1 C14 C15 C16 -176.36(16) . . . . ?
C14 C15 C16 C17 -1.2(3) . . . . ?
C15 C16 C17 C18 -2.5(3) . . . . ?
C16 C17 C18 C13 2.4(3) . . . . ?
C14 C13 C18 C17 1.3(3) . . . . ?
C12 C13 C18 C17 -173.63(17) . . . . ?
C20 O4 C19 O3 -4.5(3) . . . . ?
C20 O4 C19 C4 179.02(15) . . . . ?
N1 C4 C19 O3 147.47(18) . . . . ?
C5 C4 C19 O3 23.7(3) . . . . ?
C11 C4 C19 O3 -94.6(2) . . . . ?
N1 C4 C19 O4 -36.14(19) . . . . ?
C5 C4 C19 O4 -159.90(14) . . . . ?
C11 C4 C19 O4 81.80(17) . . . . ?
C7 C8 C21 C22 -1.2(3) . . . . ?
C6 C5 C22 C21 2.3(3) . . . . ?
C4 C5 C22 C21 176.85(16) . . . . ?
C8 C21 C22 C5 -0.4(3) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
C1 H25 O2 0.98 2.42 3.018(2) 118.5 .
C10 H8 O2 0.98 2.48 3.009(3) 113.4 .

_refine_diff_density_max         0.138
_refine_diff_density_min         -0.193
_refine_diff_density_rms         0.044

####################################################################### 
# 
# 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_OIC270A
_database_code_depnum_ccdc_archive 'CCDC 1578269'
_audit_update_record             
;
2017-10-05 deposited with the CCDC.
2017-12-14 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C20 H23 N O2'
_chemical_formula_sum            'C20 H23 N O2'
_chemical_formula_weight         309.39

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'

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

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

_cell_length_a                   6.1094(3)
_cell_length_b                   14.2823(6)
_cell_length_c                   19.8409(8)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1731.24(13)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    9924
_cell_measurement_theta_min      3.81
_cell_measurement_theta_max      66.63

_exptl_crystal_description       BLOCK
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.187
_exptl_crystal_F_000             664
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.180
_exptl_absorpt_coefficient_mu    0.599
_shelx_estimated_absorpt_T_min   0.890
_shelx_estimated_absorpt_T_max   0.900
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.82
_exptl_absorpt_correction_T_max  0.92
_exptl_absorpt_process_details   sadabs
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            11998
_diffrn_reflns_av_unetI/netI     0.0283
_diffrn_reflns_av_R_equivalents  0.0313
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_theta_min         3.813
_diffrn_reflns_theta_max         66.624
_diffrn_reflns_theta_full        66.624
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measured_fraction_theta_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.991
_diffrn_reflns_point_group_measured_fraction_full 0.992
_reflns_number_total             3043
_reflns_number_gt                2918
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.704
_reflns_Friedel_fraction_max     0.987
_reflns_Friedel_fraction_full    0.988

_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. 
;

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0351P)²+0.2503P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
; 
 Flack x determined using 1181 quotients [(I+)-(I-)]/[(I+)+(I-)] 
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259). 
;
_refine_ls_abs_structure_Flack   0.08(7)
_chemical_absolute_configuration syn
_refine_ls_number_reflns         3043
_refine_ls_number_parameters     211
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0303
_refine_ls_R_factor_gt           0.0285
_refine_ls_wR_factor_ref         0.0698
_refine_ls_wR_factor_gt          0.0687
_refine_ls_goodness_of_fit_ref   1.091
_refine_ls_restrained_S_all      1.091
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.75160(19) 0.58743(8) 0.43607(6) 0.0182(3) Uani 1 1 d . . . . .
O2 O 0.43094(19) 0.52071(8) 0.46631(6) 0.0236(3) Uani 1 1 d . . . . .
N1 N 0.9681(2) 0.43039(10) 0.47275(7) 0.0165(3) Uani 1 1 d . . . . .
H1N H 1.0642 0.4772 0.4651 0.020 Uiso 1 1 d R U . . .
C1 C 0.5041(3) 0.72287(13) 0.43505(10) 0.0269(4) Uani 1 1 d . . . . .
H5 H 0.3752 0.6870 0.4491 0.040 Uiso 1 1 calc R U . . .
H1 H 0.4576 0.7769 0.4082 0.040 Uiso 1 1 calc R U . . .
H6 H 0.5835 0.7447 0.4750 0.040 Uiso 1 1 calc R U . . .
C2 C 0.6521(3) 0.66129(12) 0.39323(8) 0.0196(4) Uani 1 1 d . . . . .
C3 C 0.6281(3) 0.52481(12) 0.46834(9) 0.0168(4) Uani 1 1 d . . . . .
C4 C 0.7740(3) 0.45786(11) 0.51027(8) 0.0157(4) Uani 1 1 d . . . . .
C5 C 0.9418(3) 0.37179(11) 0.41673(8) 0.0164(3) Uani 1 1 d . . . . .
C6 C 1.1036(3) 0.36937(13) 0.36679(9) 0.0206(4) Uani 1 1 d . . . . .
H14 H 1.2226 0.4121 0.3687 0.025 Uiso 1 1 calc R U . . .
C7 C 1.0914(3) 0.30531(14) 0.31485(9) 0.0259(4) Uani 1 1 d . . . . .
H15 H 1.2043 0.3031 0.2820 0.031 Uiso 1 1 calc R U . . .
C8 C 0.9149(3) 0.24399(15) 0.31025(9) 0.0286(4) Uani 1 1 d . . . . .
H2 H 0.9063 0.1999 0.2745 0.034 Uiso 1 1 calc R U . . .
C9 C 0.5353(4) 0.61661(15) 0.33384(10) 0.0352(5) Uani 1 1 d . . . . .
H24 H 0.6346 0.5729 0.3112 0.053 Uiso 1 1 calc R U . . .
H4 H 0.4899 0.6654 0.3021 0.053 Uiso 1 1 calc R U . . .
H3 H 0.4061 0.5827 0.3500 0.053 Uiso 1 1 calc R U . . .
C10 C 0.8522(3) 0.71524(14) 0.37027(10) 0.0289(4) Uani 1 1 d . . . . .
H9 H 0.9271 0.7417 0.4096 0.043 Uiso 1 1 calc R U . . .
H7 H 0.8071 0.7660 0.3400 0.043 Uiso 1 1 calc R U . . .
H8 H 0.9518 0.6730 0.3463 0.043 Uiso 1 1 calc R U . . .
C11 C 0.6450(3) 0.36874(12) 0.52799(9) 0.0173(3) Uani 1 1 d . . . . .
H17 H 0.7329 0.3303 0.5595 0.021 Uiso 1 1 calc R U . . .
H18 H 0.5082 0.3867 0.5514 0.021 Uiso 1 1 calc R U . . .
C12 C 0.5878(3) 0.30999(12) 0.46624(9) 0.0197(4) Uani 1 1 d . . . . .
H16 H 0.5624 0.2445 0.4807 0.024 Uiso 1 1 calc R U . . .
H10 H 0.4496 0.3337 0.4466 0.024 Uiso 1 1 calc R U . . .
C13 C 0.7622(3) 0.31073(12) 0.41246(9) 0.0182(4) Uani 1 1 d . . . . .
C14 C 0.7523(3) 0.24843(13) 0.35862(9) 0.0242(4) Uani 1 1 d . . . . .
H11 H 0.6300 0.2077 0.3550 0.029 Uiso 1 1 calc R U . . .
C15 C 0.8359(3) 0.50621(11) 0.57620(9) 0.0173(4) Uani 1 1 d . . . . .
C16 C 1.0432(3) 0.49615(12) 0.60429(9) 0.0202(4) Uani 1 1 d . . . . .
H23 H 1.1548 0.4647 0.5798 0.024 Uiso 1 1 calc R U . . .
C17 C 1.0877(3) 0.53190(13) 0.66800(9) 0.0242(4) Uani 1 1 d . . . . .
H22 H 1.2293 0.5242 0.6869 0.029 Uiso 1 1 calc R U . . .
C18 C 0.9274(3) 0.57869(13) 0.70414(9) 0.0240(4) Uani 1 1 d . . . . .
H19 H 0.9581 0.6026 0.7478 0.029 Uiso 1 1 calc R U . . .
C19 C 0.7218(3) 0.59013(13) 0.67576(9) 0.0251(4) Uani 1 1 d . . . . .
H21 H 0.6114 0.6229 0.6999 0.030 Uiso 1 1 calc R U . . .
C20 C 0.6765(3) 0.55428(12) 0.61270(9) 0.0216(4) Uani 1 1 d . . . . .
H20 H 0.5348 0.5625 0.5939 0.026 Uiso 1 1 calc R U . . .


_geom_special_details            
; 
 All esds (except the esd in the dihedral angle between two l.s. planes) 
 are estimated using the full covariance matrix.  The cell esds are taken 
 into account individually in the estimation of esds in distances, angles 
 and torsion angles; correlations between esds in cell parameters are only 
 used when they are defined by crystal symmetry.  An approximate (isotropic) 
 treatment of cell esds is used for estimating esds involving l.s. planes. 
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C3 1.334(2) . ?
O1 C2 1.485(2) . ?
O2 C3 1.207(2) . ?
N1 C5 1.401(2) . ?
N1 C4 1.454(2) . ?
N1 H1N 0.9023 . ?
C1 C2 1.510(3) . ?
C1 H5 0.9800 . ?
C1 H1 0.9800 . ?
C1 H6 0.9800 . ?
C2 C10 1.515(3) . ?
C2 C9 1.518(3) . ?
C3 C4 1.549(2) . ?
C4 C15 1.527(2) . ?
C4 C11 1.538(2) . ?
C5 C6 1.400(2) . ?
C5 C13 1.404(2) . ?
C6 C7 1.380(3) . ?
C6 H14 0.9500 . ?
C7 C8 1.392(3) . ?
C7 H15 0.9500 . ?
C8 C14 1.383(3) . ?
C8 H2 0.9500 . ?
C9 H24 0.9800 . ?
C9 H4 0.9800 . ?
C9 H3 0.9800 . ?
C10 H9 0.9800 . ?
C10 H7 0.9800 . ?
C10 H8 0.9800 . ?
C11 C12 1.525(2) . ?
C11 H17 0.9900 . ?
C11 H18 0.9900 . ?
C12 C13 1.508(2) . ?
C12 H16 0.9900 . ?
C12 H10 0.9900 . ?
C13 C14 1.392(3) . ?
C14 H11 0.9500 . ?
C15 C16 1.391(2) . ?
C15 C20 1.394(2) . ?
C16 C17 1.390(3) . ?
C16 H23 0.9500 . ?
C17 C18 1.385(3) . ?
C17 H22 0.9500 . ?
C18 C19 1.386(3) . ?
C18 H19 0.9500 . ?
C19 C20 1.380(3) . ?
C19 H21 0.9500 . ?
C20 H20 0.9500 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C3 O1 C2 121.31(13) . . ?
C5 N1 C4 118.28(13) . . ?
C5 N1 H1N 112.6 . . ?
C4 N1 H1N 114.6 . . ?
C2 C1 H5 109.5 . . ?
C2 C1 H1 109.5 . . ?
H5 C1 H1 109.5 . . ?
C2 C1 H6 109.5 . . ?
H5 C1 H6 109.5 . . ?
H1 C1 H6 109.5 . . ?
O1 C2 C1 110.14(13) . . ?
O1 C2 C10 101.72(14) . . ?
C1 C2 C10 110.62(15) . . ?
O1 C2 C9 109.77(15) . . ?
C1 C2 C9 112.95(17) . . ?
C10 C2 C9 111.08(16) . . ?
O2 C3 O1 125.53(16) . . ?
O2 C3 C4 124.21(15) . . ?
O1 C3 C4 110.26(13) . . ?
N1 C4 C15 111.00(13) . . ?
N1 C4 C11 108.16(13) . . ?
C15 C4 C11 107.78(13) . . ?
N1 C4 C3 111.15(13) . . ?
C15 C4 C3 108.87(13) . . ?
C11 C4 C3 109.81(13) . . ?
C6 C5 N1 119.70(15) . . ?
C6 C5 C13 119.58(16) . . ?
N1 C5 C13 120.57(15) . . ?
C7 C6 C5 120.46(16) . . ?
C7 C6 H14 119.8 . . ?
C5 C6 H14 119.8 . . ?
C6 C7 C8 120.52(17) . . ?
C6 C7 H15 119.7 . . ?
C8 C7 H15 119.7 . . ?
C14 C8 C7 118.82(17) . . ?
C14 C8 H2 120.6 . . ?
C7 C8 H2 120.6 . . ?
C2 C9 H24 109.5 . . ?
C2 C9 H4 109.5 . . ?
H24 C9 H4 109.5 . . ?
C2 C9 H3 109.5 . . ?
H24 C9 H3 109.5 . . ?
H4 C9 H3 109.5 . . ?
C2 C10 H9 109.5 . . ?
C2 C10 H7 109.5 . . ?
H9 C10 H7 109.5 . . ?
C2 C10 H8 109.5 . . ?
H9 C10 H8 109.5 . . ?
H7 C10 H8 109.5 . . ?
C12 C11 C4 112.90(14) . . ?
C12 C11 H17 109.0 . . ?
C4 C11 H17 109.0 . . ?
C12 C11 H18 109.0 . . ?
C4 C11 H18 109.0 . . ?
H17 C11 H18 107.8 . . ?
C13 C12 C11 113.75(14) . . ?
C13 C12 H16 108.8 . . ?
C11 C12 H16 108.8 . . ?
C13 C12 H10 108.8 . . ?
C11 C12 H10 108.8 . . ?
H16 C12 H10 107.7 . . ?
C14 C13 C5 118.51(17) . . ?
C14 C13 C12 120.54(15) . . ?
C5 C13 C12 120.91(15) . . ?
C8 C14 C13 122.07(17) . . ?
C8 C14 H11 119.0 . . ?
C13 C14 H11 119.0 . . ?
C16 C15 C20 118.60(16) . . ?
C16 C15 C4 121.48(15) . . ?
C20 C15 C4 119.64(15) . . ?
C17 C16 C15 120.29(17) . . ?
C17 C16 H23 119.9 . . ?
C15 C16 H23 119.9 . . ?
C18 C17 C16 120.64(17) . . ?
C18 C17 H22 119.7 . . ?
C16 C17 H22 119.7 . . ?
C17 C18 C19 119.14(17) . . ?
C17 C18 H19 120.4 . . ?
C19 C18 H19 120.4 . . ?
C20 C19 C18 120.43(17) . . ?
C20 C19 H21 119.8 . . ?
C18 C19 H21 119.8 . . ?
C19 C20 C15 120.89(17) . . ?
C19 C20 H20 119.6 . . ?
C15 C20 H20 119.6 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C3 O1 C2 C1 60.83(19) . . . . ?
C3 O1 C2 C10 178.17(14) . . . . ?
C3 O1 C2 C9 -64.1(2) . . . . ?
C2 O1 C3 O2 0.4(3) . . . . ?
C2 O1 C3 C4 -178.76(13) . . . . ?
C5 N1 C4 C15 169.66(13) . . . . ?
C5 N1 C4 C11 51.62(18) . . . . ?
C5 N1 C4 C3 -69.00(17) . . . . ?
O2 C3 C4 N1 138.89(17) . . . . ?
O1 C3 C4 N1 -41.91(18) . . . . ?
O2 C3 C4 C15 -98.54(19) . . . . ?
O1 C3 C4 C15 80.66(16) . . . . ?
O2 C3 C4 C11 19.2(2) . . . . ?
O1 C3 C4 C11 -161.55(13) . . . . ?
C4 N1 C5 C6 158.15(15) . . . . ?
C4 N1 C5 C13 -26.3(2) . . . . ?
N1 C5 C6 C7 173.38(15) . . . . ?
C13 C5 C6 C7 -2.3(2) . . . . ?
C5 C6 C7 C8 1.9(3) . . . . ?
C6 C7 C8 C14 0.0(3) . . . . ?
N1 C4 C11 C12 -55.65(17) . . . . ?
C15 C4 C11 C12 -175.73(13) . . . . ?
C3 C4 C11 C12 65.80(17) . . . . ?
C4 C11 C12 C13 35.53(19) . . . . ?
C6 C5 C13 C14 0.8(2) . . . . ?
N1 C5 C13 C14 -174.81(15) . . . . ?
C6 C5 C13 C12 178.57(15) . . . . ?
N1 C5 C13 C12 3.0(2) . . . . ?
C11 C12 C13 C14 168.87(15) . . . . ?
C11 C12 C13 C5 -8.9(2) . . . . ?
C7 C8 C14 C13 -1.5(3) . . . . ?
C5 C13 C14 C8 1.1(3) . . . . ?
C12 C13 C14 C8 -176.71(17) . . . . ?
N1 C4 C15 C16 -19.1(2) . . . . ?
C11 C4 C15 C16 99.20(17) . . . . ?
C3 C4 C15 C16 -141.74(15) . . . . ?
N1 C4 C15 C20 167.15(15) . . . . ?
C11 C4 C15 C20 -74.58(19) . . . . ?
C3 C4 C15 C20 44.49(19) . . . . ?
C20 C15 C16 C17 1.2(2) . . . . ?
C4 C15 C16 C17 -172.60(16) . . . . ?
C15 C16 C17 C18 -0.6(3) . . . . ?
C16 C17 C18 C19 -0.5(3) . . . . ?
C17 C18 C19 C20 0.9(3) . . . . ?
C18 C19 C20 C15 -0.2(3) . . . . ?
C16 C15 C20 C19 -0.9(3) . . . . ?
C4 C15 C20 C19 173.10(15) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
C9 H3 O2 0.98 2.48 3.032(2) 115.5 .
C1 H5 O2 0.98 2.42 2.987(2) 116.1 .
C9 H3 O2 0.98 2.48 3.032(2) 115.5 .
C1 H5 O2 0.98 2.42 2.987(2) 116.1 .
N1 H1N O2 0.90 2.33 3.1104(18) 145.4 1_655
N1 H1N O2 0.90 2.33 3.1104(18) 145.4 1_655
C1 H5 O2 0.98 2.42 2.987(2) 116.1 .
C9 H3 O2 0.98 2.48 3.032(2) 115.5 .

_refine_diff_density_max         0.152
_refine_diff_density_min         -0.169
_refine_diff_density_rms         0.034

####################################################################### 
# 
# 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_OIC276v_0m
_database_code_depnum_ccdc_archive 'CCDC 1578268'
_audit_update_record             
;
2017-10-05 deposited with the CCDC.
2017-12-14 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C27 H21 N O2'
_chemical_formula_sum            'C27 H21 N O2'
_chemical_formula_weight         391.45

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

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

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   7.9717(3)
_cell_length_b                   9.2791(4)
_cell_length_c                   14.2492(6)
_cell_angle_alpha                95.3798(16)
_cell_angle_beta                 105.3362(17)
_cell_angle_gamma                98.2795(16)
_cell_volume                     996.24(7)
_cell_formula_units_Z            2
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    9968
_cell_measurement_theta_min      3.247
_cell_measurement_theta_max      66.741

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.305
_exptl_crystal_F_000             412
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.180
_exptl_crystal_size_mid          0.080
_exptl_crystal_size_min          0.050
_exptl_absorpt_coefficient_mu    0.647
_shelx_estimated_absorpt_T_min   0.892
_shelx_estimated_absorpt_T_max   0.968
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6965
_exptl_absorpt_correction_T_max  0.7528
_exptl_absorpt_process_details   SADABS
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            29236
_diffrn_reflns_av_unetI/netI     0.0194
_diffrn_reflns_av_R_equivalents  0.0356
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         3.247
_diffrn_reflns_theta_max         66.736
_diffrn_reflns_theta_full        66.736
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measured_fraction_theta_full 0.991
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_reflns_Laue_measured_fraction_full 0.991
_diffrn_reflns_point_group_measured_fraction_max 0.991
_diffrn_reflns_point_group_measured_fraction_full 0.991
_reflns_number_total             3496
_reflns_number_gt                3086
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
; 
 Reflections were merged by SHELXL according to the crystal 
 class for the calculation of statistics and refinement. 
  
 _reflns_Friedel_fraction is defined as the number of unique 
 Friedel pairs measured divided by the number that would be 
 possible theoretically, ignoring centric projections and 
 systematic absences. 
;

_computing_data_collection       ?
_computing_cell_refinement       'SAINT v8.37A (Bruker, 2015)'
_computing_data_reduction        'SAINT v8.37A (Bruker, 2015)'
_computing_structure_solution    'XS (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0390P)²+0.3085P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_extinction_coef       0.0114(8)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         3496
_refine_ls_number_parameters     272
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0387
_refine_ls_R_factor_gt           0.0321
_refine_ls_wR_factor_ref         0.0805
_refine_ls_wR_factor_gt          0.0768
_refine_ls_goodness_of_fit_ref   1.038
_refine_ls_restrained_S_all      1.038
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.20142(15) -0.06166(13) 0.11868(8) 0.0155(3) Uani 1 1 d . . . . .
C2 C 0.35472(15) -0.07864(13) 0.09161(8) 0.0176(3) Uani 1 1 d . . . . .
H2 H 0.4320 0.0052 0.0848 0.021 Uiso 1 1 calc R U . . .
C3 C 0.39368(16) -0.21813(14) 0.07471(8) 0.0199(3) Uani 1 1 d . . . . .
H3 H 0.4979 -0.2293 0.0565 0.024 Uiso 1 1 calc R U . . .
C4 C 0.28137(16) -0.34151(14) 0.08422(8) 0.0208(3) Uani 1 1 d . . . . .
H4 H 0.3069 -0.4371 0.0713 0.025 Uiso 1 1 calc R U . . .
C5 C 0.13166(16) -0.32353(13) 0.11282(8) 0.0195(3) Uani 1 1 d . . . . .
H5 H 0.0554 -0.4080 0.1197 0.023 Uiso 1 1 calc R U . . .
C6 C 0.08962(15) -0.18491(13) 0.13182(8) 0.0165(3) Uani 1 1 d . . . . .
C7 C -0.06886(15) -0.17058(13) 0.16910(8) 0.0186(3) Uani 1 1 d . . . . .
H7A H -0.0381 -0.1801 0.2400 0.022 Uiso 1 1 calc R U . . .
H7B H -0.1669 -0.2519 0.1343 0.022 Uiso 1 1 calc R U . . .
C8 C -0.13099(15) -0.02414(13) 0.15421(8) 0.0168(3) Uani 1 1 d . . . . .
H8A H -0.2177 -0.0108 0.1914 0.020 Uiso 1 1 calc R U . . .
H8B H -0.1898 -0.0241 0.0837 0.020 Uiso 1 1 calc R U . . .
C9 C 0.02650(14) 0.10214(12) 0.18959(8) 0.0156(3) Uani 1 1 d . . . . .
C10 C -0.01991(15) 0.24927(12) 0.15425(8) 0.0165(3) Uani 1 1 d . . . . .
H10 H -0.1145 0.2257 0.0902 0.020 Uiso 1 1 calc R U . . .
C11 C 0.22472(15) 0.20825(13) 0.10935(8) 0.0163(3) Uani 1 1 d . . . . .
C12 C 0.11530(15) 0.11991(12) 0.30014(8) 0.0154(3) Uani 1 1 d . . . . .
C13 C 0.29534(15) 0.14134(12) 0.33836(8) 0.0163(3) Uani 1 1 d . . . . .
H13 H 0.3672 0.1409 0.2948 0.020 Uiso 1 1 calc R U . . .
C14 C 0.37731(15) 0.16417(12) 0.44126(8) 0.0176(3) Uani 1 1 d . . . . .
C15 C 0.56289(16) 0.18391(13) 0.48141(9) 0.0213(3) Uani 1 1 d . . . . .
H15 H 0.6368 0.1862 0.4389 0.026 Uiso 1 1 calc R U . . .
C16 C 0.63667(17) 0.19974(14) 0.58087(9) 0.0254(3) Uani 1 1 d . . . . .
H16 H 0.7614 0.2126 0.6068 0.030 Uiso 1 1 calc R U . . .
C17 C 0.52944(18) 0.19721(14) 0.64528(9) 0.0259(3) Uani 1 1 d . . . . .
H17 H 0.5820 0.2074 0.7142 0.031 Uiso 1 1 calc R U . . .
C18 C 0.35033(17) 0.18014(13) 0.60877(9) 0.0229(3) Uani 1 1 d . . . . .
H18 H 0.2790 0.1793 0.6527 0.027 Uiso 1 1 calc R U . . .
C19 C 0.26928(16) 0.16370(12) 0.50615(8) 0.0186(3) Uani 1 1 d . . . . .
C20 C 0.08377(16) 0.14537(13) 0.46510(8) 0.0193(3) Uani 1 1 d . . . . .
H20 H 0.0100 0.1487 0.5076 0.023 Uiso 1 1 calc R U . . .
C21 C 0.00902(16) 0.12303(13) 0.36604(8) 0.0181(3) Uani 1 1 d . . . . .
H21 H -0.1159 0.1093 0.3406 0.022 Uiso 1 1 calc R U . . .
C22 C -0.07919(15) 0.34889(12) 0.22279(8) 0.0177(3) Uani 1 1 d . . . . .
C23 C -0.26009(16) 0.34023(13) 0.20883(9) 0.0226(3) Uani 1 1 d . . . . .
H23 H -0.3410 0.2824 0.1520 0.027 Uiso 1 1 calc R U . . .
C24 C -0.32301(18) 0.41542(15) 0.27729(10) 0.0290(3) Uani 1 1 d . . . . .
H24 H -0.4466 0.4089 0.2674 0.035 Uiso 1 1 calc R U . . .
C25 C -0.20554(19) 0.49993(14) 0.36008(10) 0.0290(3) Uani 1 1 d . . . . .
H25 H -0.2482 0.5481 0.4086 0.035 Uiso 1 1 calc R U . . .
C26 C -0.02545(18) 0.51407(14) 0.37200(9) 0.0257(3) Uani 1 1 d . . . . .
H26 H 0.0549 0.5753 0.4276 0.031 Uiso 1 1 calc R U . . .
C27 C 0.03866(17) 0.44001(13) 0.30387(9) 0.0207(3) Uani 1 1 d . . . . .
H27 H 0.1623 0.4512 0.3123 0.025 Uiso 1 1 calc R U . . .
N1 N 0.15391(12) 0.07883(10) 0.13388(7) 0.0151(2) Uani 1 1 d . . . . .
O1 O 0.14231(10) 0.31713(9) 0.13613(6) 0.0183(2) Uani 1 1 d . . . . .
O2 O 0.34198(11) 0.23151(9) 0.07063(6) 0.0213(2) 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
C1 C2 1.4001(16) . ?
C1 C6 1.4043(17) . ?
C1 N1 1.4222(15) . ?
C2 C3 1.3881(17) . ?
C2 H2 0.9500 . ?
C3 C4 1.3888(18) . ?
C3 H3 0.9500 . ?
C4 C5 1.3856(17) . ?
C4 H4 0.9500 . ?
C5 C6 1.3953(16) . ?
C5 H5 0.9500 . ?
C6 C7 1.5120(16) . ?
C7 C8 1.5261(16) . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C8 C9 1.5278(16) . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C9 N1 1.4717(14) . ?
C9 C12 1.5290(15) . ?
C9 C10 1.5589(15) . ?
C10 O1 1.4519(14) . ?
C10 C22 1.4941(16) . ?
C10 H10 1.0000 . ?
C11 O2 1.2090(14) . ?
C11 O1 1.3598(14) . ?
C11 N1 1.3678(15) . ?
C12 C13 1.3711(16) . ?
C12 C21 1.4223(16) . ?
C13 C14 1.4202(16) . ?
C13 H13 0.9500 . ?
C14 C15 1.4156(17) . ?
C14 C19 1.4204(17) . ?
C15 C16 1.3678(17) . ?
C15 H15 0.9500 . ?
C16 C17 1.4096(19) . ?
C16 H16 0.9500 . ?
C17 C18 1.3641(18) . ?
C17 H17 0.9500 . ?
C18 C19 1.4174(16) . ?
C18 H18 0.9500 . ?
C19 C20 1.4175(17) . ?
C20 C21 1.3620(16) . ?
C20 H20 0.9500 . ?
C21 H21 0.9500 . ?
C22 C23 1.3920(17) . ?
C22 C27 1.3951(17) . ?
C23 C24 1.3863(18) . ?
C23 H23 0.9500 . ?
C24 C25 1.3835(19) . ?
C24 H24 0.9500 . ?
C25 C26 1.3855(19) . ?
C25 H25 0.9500 . ?
C26 C27 1.3837(18) . ?
C26 H26 0.9500 . ?
C27 H27 0.9500 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 C1 C6 120.24(11) . . ?
C2 C1 N1 121.76(10) . . ?
C6 C1 N1 118.00(10) . . ?
C3 C2 C1 119.95(11) . . ?
C3 C2 H2 120.0 . . ?
C1 C2 H2 120.0 . . ?
C2 C3 C4 120.48(11) . . ?
C2 C3 H3 119.8 . . ?
C4 C3 H3 119.8 . . ?
C5 C4 C3 119.19(11) . . ?
C5 C4 H4 120.4 . . ?
C3 C4 H4 120.4 . . ?
C4 C5 C6 121.92(11) . . ?
C4 C5 H5 119.0 . . ?
C6 C5 H5 119.0 . . ?
C5 C6 C1 118.17(10) . . ?
C5 C6 C7 119.81(10) . . ?
C1 C6 C7 121.99(10) . . ?
C6 C7 C8 112.53(9) . . ?
C6 C7 H7A 109.1 . . ?
C8 C7 H7A 109.1 . . ?
C6 C7 H7B 109.1 . . ?
C8 C7 H7B 109.1 . . ?
H7A C7 H7B 107.8 . . ?
C7 C8 C9 109.98(9) . . ?
C7 C8 H8A 109.7 . . ?
C9 C8 H8A 109.7 . . ?
C7 C8 H8B 109.7 . . ?
C9 C8 H8B 109.7 . . ?
H8A C8 H8B 108.2 . . ?
N1 C9 C8 108.54(9) . . ?
N1 C9 C12 110.81(9) . . ?
C8 C9 C12 113.42(9) . . ?
N1 C9 C10 98.36(8) . . ?
C8 C9 C10 112.32(9) . . ?
C12 C9 C10 112.34(9) . . ?
O1 C10 C22 111.99(9) . . ?
O1 C10 C9 102.77(8) . . ?
C22 C10 C9 116.48(9) . . ?
O1 C10 H10 108.4 . . ?
C22 C10 H10 108.4 . . ?
C9 C10 H10 108.4 . . ?
O2 C11 O1 121.86(10) . . ?
O2 C11 N1 128.90(11) . . ?
O1 C11 N1 109.24(9) . . ?
C13 C12 C21 118.62(10) . . ?
C13 C12 C9 122.12(10) . . ?
C21 C12 C9 119.16(10) . . ?
C12 C13 C14 121.83(10) . . ?
C12 C13 H13 119.1 . . ?
C14 C13 H13 119.1 . . ?
C15 C14 C13 122.25(11) . . ?
C15 C14 C19 118.82(11) . . ?
C13 C14 C19 118.91(11) . . ?
C16 C15 C14 120.59(12) . . ?
C16 C15 H15 119.7 . . ?
C14 C15 H15 119.7 . . ?
C15 C16 C17 120.64(12) . . ?
C15 C16 H16 119.7 . . ?
C17 C16 H16 119.7 . . ?
C18 C17 C16 120.08(11) . . ?
C18 C17 H17 120.0 . . ?
C16 C17 H17 120.0 . . ?
C17 C18 C19 120.83(12) . . ?
C17 C18 H18 119.6 . . ?
C19 C18 H18 119.6 . . ?
C18 C19 C20 122.68(11) . . ?
C18 C19 C14 119.02(11) . . ?
C20 C19 C14 118.29(11) . . ?
C21 C20 C19 121.38(11) . . ?
C21 C20 H20 119.3 . . ?
C19 C20 H20 119.3 . . ?
C20 C21 C12 120.92(11) . . ?
C20 C21 H21 119.5 . . ?
C12 C21 H21 119.5 . . ?
C23 C22 C27 119.34(11) . . ?
C23 C22 C10 117.85(10) . . ?
C27 C22 C10 122.59(11) . . ?
C24 C23 C22 120.46(12) . . ?
C24 C23 H23 119.8 . . ?
C22 C23 H23 119.8 . . ?
C25 C24 C23 119.93(12) . . ?
C25 C24 H24 120.0 . . ?
C23 C24 H24 120.0 . . ?
C24 C25 C26 119.74(12) . . ?
C24 C25 H25 120.1 . . ?
C26 C25 H25 120.1 . . ?
C27 C26 C25 120.73(12) . . ?
C27 C26 H26 119.6 . . ?
C25 C26 H26 119.6 . . ?
C26 C27 C22 119.67(12) . . ?
C26 C27 H27 120.2 . . ?
C22 C27 H27 120.2 . . ?
C11 N1 C1 127.59(9) . . ?
C11 N1 C9 111.19(9) . . ?
C1 N1 C9 120.98(9) . . ?
C11 O1 C10 108.12(9) . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
C2 H2 O2 0.95 2.32 2.9346(15) 121.5 .

_refine_diff_density_max         0.250
_refine_diff_density_min         -0.186
_refine_diff_density_rms         0.033

####################################################################### 
# 
# 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_CARTERN2_0m
_database_code_depnum_ccdc_archive 'CCDC 1578267'
_audit_update_record             
;
2017-10-05 deposited with the CCDC.
2017-12-14 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C23 H27 N O4'
_chemical_formula_sum            'C23 H27 N O4'
_chemical_formula_weight         381.45

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_H-M_alt        'P 21'
_space_group_name_Hall           'P 2yb'

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

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

_cell_length_a                   9.4950(3)
_cell_length_b                   8.8357(3)
_cell_length_c                   12.0617(4)
_cell_angle_alpha                90
_cell_angle_beta                 90.258(2)
_cell_angle_gamma                90
_cell_volume                     1011.91(6)
_cell_formula_units_Z            2
_cell_measurement_temperature    97(2)
_cell_measurement_reflns_used    8464
_cell_measurement_theta_min      3.66
_cell_measurement_theta_max      66.52

_exptl_crystal_description       PLATE
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.252
_exptl_crystal_F_000             408
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.320
_exptl_crystal_size_mid          0.120
_exptl_crystal_size_min          0.090
_exptl_absorpt_coefficient_mu    0.687
_shelx_estimated_absorpt_T_min   0.810
_shelx_estimated_absorpt_T_max   0.941
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.87
_exptl_absorpt_correction_T_max  0.91
_exptl_absorpt_process_details   sadabs
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      97(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            14554
_diffrn_reflns_av_unetI/netI     0.0424
_diffrn_reflns_av_R_equivalents  0.0511
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         3.664
_diffrn_reflns_theta_max         66.614
_diffrn_reflns_theta_full        66.614
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.974
_diffrn_reflns_point_group_measured_fraction_full 0.975
_reflns_number_total             3491
_reflns_number_gt                3116
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.825
_reflns_Friedel_fraction_max     0.949
_reflns_Friedel_fraction_full    0.949

_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. 
;

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0411P)²+0.0980P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_extinction_coef       0.0107(11)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_abs_structure_details 
; 
 Flack x determined using 1271 quotients [(I+)-(I-)]/[(I+)+(I-)] 
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259). 
;
_refine_ls_abs_structure_Flack   0.11(12)
_chemical_absolute_configuration unk
_refine_ls_number_reflns         3491
_refine_ls_number_parameters     258
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0418
_refine_ls_R_factor_gt           0.0337
_refine_ls_wR_factor_ref         0.0786
_refine_ls_wR_factor_gt          0.0753
_refine_ls_goodness_of_fit_ref   1.016
_refine_ls_restrained_S_all      1.016
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.42033(16) 0.45132(19) 0.77104(13) 0.0207(4) Uani 1 1 d . . . . .
O2 O 0.10783(18) 0.4009(2) 0.65782(15) 0.0269(5) Uani 1 1 d . . . . .
O3 O 0.32006(17) 0.5368(2) 0.92919(14) 0.0263(4) Uani 1 1 d . . . . .
O4 O 0.04227(17) 0.5412(2) 0.51142(14) 0.0295(5) Uani 1 1 d . . . . .
N1 N 0.2693(2) 0.6449(2) 0.76022(16) 0.0196(5) Uani 1 1 d . . . . .
C1 C 0.4335(3) 0.2281(4) 0.8933(2) 0.0360(7) Uani 1 1 d . . . . .
H10 H 0.3978 0.2767 0.9605 0.054 Uiso 1 1 calc R U . . .
H1 H 0.4948 0.1433 0.9138 0.054 Uiso 1 1 calc R U . . .
H9 H 0.3542 0.1904 0.8489 0.054 Uiso 1 1 calc R U . . .
C2 C 0.5165(2) 0.3421(3) 0.8261(2) 0.0218(6) Uani 1 1 d . . . . .
C3 C 0.3357(2) 0.5426(3) 0.8297(2) 0.0193(5) Uani 1 1 d . . . . .
C4 C 0.3232(2) 0.6734(3) 0.64601(19) 0.0190(6) Uani 1 1 d . . . . .
C5 C 0.4808(3) 0.7055(3) 0.6515(2) 0.0211(6) Uani 1 1 d . . . . .
C6 C 0.5355(3) 0.7883(3) 0.7403(2) 0.0249(6) Uani 1 1 d . . . . .
H25 H 0.4743 0.8196 0.7980 0.030 Uiso 1 1 calc R U . . .
C7 C 0.6766(3) 0.8258(3) 0.7463(2) 0.0295(6) Uani 1 1 d . . . . .
H22 H 0.7110 0.8837 0.8070 0.035 Uiso 1 1 calc R U . . .
C8 C 0.7678(3) 0.7794(3) 0.6643(2) 0.0307(7) Uani 1 1 d . . . . .
H2 H 0.8649 0.8046 0.6684 0.037 Uiso 1 1 calc R U . . .
C9 C -0.0388(3) 0.3625(3) 0.6758(2) 0.0328(7) Uani 1 1 d . . . . .
H3 H -0.0975 0.4523 0.6635 0.049 Uiso 1 1 calc R U . . .
H4 H -0.0510 0.3267 0.7520 0.049 Uiso 1 1 calc R U . . .
H5 H -0.0671 0.2826 0.6239 0.049 Uiso 1 1 calc R U . . .
C10 C 0.1327(3) 0.4959(3) 0.5733(2) 0.0216(6) Uani 1 1 d . . . . .
C11 C 0.2860(2) 0.5392(3) 0.5678(2) 0.0208(5) Uani 1 1 d . . . . .
H27 H 0.3094 0.5674 0.4906 0.025 Uiso 1 1 calc R U . . .
H26 H 0.3442 0.4505 0.5883 0.025 Uiso 1 1 calc R U . . .
C12 C 0.6250(3) 0.4257(4) 0.8944(3) 0.0370(7) Uani 1 1 d . . . . .
H6 H 0.6737 0.4995 0.8476 0.055 Uiso 1 1 calc R U . . .
H8 H 0.6934 0.3534 0.9246 0.055 Uiso 1 1 calc R U . . .
H7 H 0.5782 0.4785 0.9555 0.055 Uiso 1 1 calc R U . . .
C13 C 0.5849(3) 0.2663(3) 0.7268(2) 0.0279(6) Uani 1 1 d . . . . .
H12 H 0.5121 0.2183 0.6810 0.042 Uiso 1 1 calc R U . . .
H11 H 0.6517 0.1894 0.7527 0.042 Uiso 1 1 calc R U . . .
H13 H 0.6348 0.3424 0.6829 0.042 Uiso 1 1 calc R U . . .
C14 C 0.1612(3) 0.7385(3) 0.8058(2) 0.0238(6) Uani 1 1 d . . . . .
C15 C 0.1516(3) 0.8897(3) 0.7749(2) 0.0285(7) Uani 1 1 d . . . . .
C16 C 0.2397(3) 0.9454(3) 0.6808(2) 0.0317(7) Uani 1 1 d . . . . .
H17 H 0.3346 0.9745 0.7077 0.038 Uiso 1 1 calc R U . . .
H16 H 0.1953 1.0348 0.6458 0.038 Uiso 1 1 calc R U . . .
C17 C 0.2502(3) 0.8164(3) 0.5982(2) 0.0246(6) Uani 1 1 d . . . . .
H15 H 0.3035 0.8516 0.5327 0.030 Uiso 1 1 calc R U . . .
H14 H 0.1542 0.7889 0.5729 0.030 Uiso 1 1 calc R U . . .
C18 C 0.0494(3) 0.9802(4) 0.8252(3) 0.0379(8) Uani 1 1 d . . . . .
H18 H 0.0425 1.0839 0.8053 0.045 Uiso 1 1 calc R U . . .
C19 C -0.0418(3) 0.9218(4) 0.9031(2) 0.0452(9) Uani 1 1 d . . . . .
H21 H -0.1077 0.9859 0.9390 0.054 Uiso 1 1 calc R U . . .
C20 C -0.0364(3) 0.7693(4) 0.9284(2) 0.0408(9) Uani 1 1 d . . . . .
H20 H -0.1012 0.7277 0.9798 0.049 Uiso 1 1 calc R U . . .
C21 C 0.0634(3) 0.6764(4) 0.8788(2) 0.0298(7) Uani 1 1 d . . . . .
H19 H 0.0650 0.5711 0.8947 0.036 Uiso 1 1 calc R U . . .
C22 C 0.7164(3) 0.6955(3) 0.5757(2) 0.0287(7) Uani 1 1 d . . . . .
H24 H 0.7787 0.6620 0.5195 0.034 Uiso 1 1 calc R U . . .
C23 C 0.5739(3) 0.6603(3) 0.5690(2) 0.0236(6) Uani 1 1 d . . . . .
H23 H 0.5396 0.6045 0.5072 0.028 Uiso 1 1 calc R U . . .


_geom_special_details            
; 
 All esds (except the esd in the dihedral angle between two l.s. planes) 
 are estimated using the full covariance matrix.  The cell esds are taken 
 into account individually in the estimation of esds in distances, angles 
 and torsion angles; correlations between esds in cell parameters are only 
 used when they are defined by crystal symmetry.  An approximate (isotropic) 
 treatment of cell esds is used for estimating esds involving l.s. planes. 
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C3 1.343(3) . ?
O1 C2 1.483(3) . ?
O2 C10 1.342(3) . ?
O2 C9 1.450(3) . ?
O3 C3 1.211(3) . ?
O4 C10 1.204(3) . ?
N1 C3 1.382(3) . ?
N1 C14 1.430(3) . ?
N1 C4 1.493(3) . ?
C1 C2 1.517(4) . ?
C1 H10 0.9800 . ?
C1 H1 0.9800 . ?
C1 H9 0.9800 . ?
C2 C12 1.510(4) . ?
C2 C13 1.520(3) . ?
C4 C5 1.524(3) . ?
C4 C17 1.551(3) . ?
C4 C11 1.555(3) . ?
C5 C23 1.393(4) . ?
C5 C6 1.396(4) . ?
C6 C7 1.382(4) . ?
C6 H25 0.9500 . ?
C7 C8 1.380(4) . ?
C7 H22 0.9500 . ?
C8 C22 1.387(4) . ?
C8 H2 0.9500 . ?
C9 H3 0.9800 . ?
C9 H4 0.9800 . ?
C9 H5 0.9800 . ?
C10 C11 1.507(3) . ?
C11 H27 0.9900 . ?
C11 H26 0.9900 . ?
C12 H6 0.9800 . ?
C12 H8 0.9800 . ?
C12 H7 0.9800 . ?
C13 H12 0.9800 . ?
C13 H11 0.9800 . ?
C13 H13 0.9800 . ?
C14 C15 1.390(4) . ?
C14 C21 1.395(4) . ?
C15 C18 1.398(4) . ?
C15 C16 1.496(4) . ?
C16 C17 1.518(4) . ?
C16 H17 0.9900 . ?
C16 H16 0.9900 . ?
C17 H15 0.9900 . ?
C17 H14 0.9900 . ?
C18 C19 1.380(5) . ?
C18 H18 0.9500 . ?
C19 C20 1.383(5) . ?
C19 H21 0.9500 . ?
C20 C21 1.390(4) . ?
C20 H20 0.9500 . ?
C21 H19 0.9500 . ?
C22 C23 1.390(4) . ?
C22 H24 0.9500 . ?
C23 H23 0.9500 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C3 O1 C2 121.59(18) . . ?
C10 O2 C9 115.6(2) . . ?
C3 N1 C14 118.09(19) . . ?
C3 N1 C4 120.85(18) . . ?
C14 N1 C4 120.4(2) . . ?
C2 C1 H10 109.5 . . ?
C2 C1 H1 109.5 . . ?
H10 C1 H1 109.5 . . ?
C2 C1 H9 109.5 . . ?
H10 C1 H9 109.5 . . ?
H1 C1 H9 109.5 . . ?
O1 C2 C12 110.1(2) . . ?
O1 C2 C1 110.5(2) . . ?
C12 C2 C1 112.8(2) . . ?
O1 C2 C13 101.47(19) . . ?
C12 C2 C13 110.7(2) . . ?
C1 C2 C13 110.7(2) . . ?
O3 C3 O1 125.0(2) . . ?
O3 C3 N1 124.8(2) . . ?
O1 C3 N1 110.2(2) . . ?
N1 C4 C5 109.38(19) . . ?
N1 C4 C17 109.06(19) . . ?
C5 C4 C17 107.5(2) . . ?
N1 C4 C11 110.68(19) . . ?
C5 C4 C11 112.9(2) . . ?
C17 C4 C11 107.2(2) . . ?
C23 C5 C6 117.6(2) . . ?
C23 C5 C4 122.8(2) . . ?
C6 C5 C4 119.5(2) . . ?
C7 C6 C5 121.5(2) . . ?
C7 C6 H25 119.2 . . ?
C5 C6 H25 119.2 . . ?
C8 C7 C6 120.2(3) . . ?
C8 C7 H22 119.9 . . ?
C6 C7 H22 119.9 . . ?
C7 C8 C22 119.4(2) . . ?
C7 C8 H2 120.3 . . ?
C22 C8 H2 120.3 . . ?
O2 C9 H3 109.5 . . ?
O2 C9 H4 109.5 . . ?
H3 C9 H4 109.5 . . ?
O2 C9 H5 109.5 . . ?
H3 C9 H5 109.5 . . ?
H4 C9 H5 109.5 . . ?
O4 C10 O2 123.5(2) . . ?
O4 C10 C11 125.1(2) . . ?
O2 C10 C11 111.4(2) . . ?
C10 C11 C4 112.54(19) . . ?
C10 C11 H27 109.1 . . ?
C4 C11 H27 109.1 . . ?
C10 C11 H26 109.1 . . ?
C4 C11 H26 109.1 . . ?
H27 C11 H26 107.8 . . ?
C2 C12 H6 109.5 . . ?
C2 C12 H8 109.5 . . ?
H6 C12 H8 109.5 . . ?
C2 C12 H7 109.5 . . ?
H6 C12 H7 109.5 . . ?
H8 C12 H7 109.5 . . ?
C2 C13 H12 109.5 . . ?
C2 C13 H11 109.5 . . ?
H12 C13 H11 109.5 . . ?
C2 C13 H13 109.5 . . ?
H12 C13 H13 109.5 . . ?
H11 C13 H13 109.5 . . ?
C15 C14 C21 120.3(2) . . ?
C15 C14 N1 119.9(2) . . ?
C21 C14 N1 119.8(3) . . ?
C14 C15 C18 118.6(3) . . ?
C14 C15 C16 118.9(2) . . ?
C18 C15 C16 122.2(3) . . ?
C15 C16 C17 106.8(2) . . ?
C15 C16 H17 110.4 . . ?
C17 C16 H17 110.4 . . ?
C15 C16 H16 110.4 . . ?
C17 C16 H16 110.4 . . ?
H17 C16 H16 108.6 . . ?
C16 C17 C4 113.4(2) . . ?
C16 C17 H15 108.9 . . ?
C4 C17 H15 108.9 . . ?
C16 C17 H14 108.9 . . ?
C4 C17 H14 108.9 . . ?
H15 C17 H14 107.7 . . ?
C19 C18 C15 121.3(3) . . ?
C19 C18 H18 119.3 . . ?
C15 C18 H18 119.3 . . ?
C18 C19 C20 119.5(3) . . ?
C18 C19 H21 120.3 . . ?
C20 C19 H21 120.3 . . ?
C19 C20 C21 120.3(3) . . ?
C19 C20 H20 119.8 . . ?
C21 C20 H20 119.8 . . ?
C20 C21 C14 119.7(3) . . ?
C20 C21 H19 120.1 . . ?
C14 C21 H19 120.1 . . ?
C8 C22 C23 120.3(3) . . ?
C8 C22 H24 119.9 . . ?
C23 C22 H24 119.9 . . ?
C22 C23 C5 121.0(3) . . ?
C22 C23 H23 119.5 . . ?
C5 C23 H23 119.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C3 O1 C2 C12 -63.8(3) . . . . ?
C3 O1 C2 C1 61.5(3) . . . . ?
C3 O1 C2 C13 179.0(2) . . . . ?
C2 O1 C3 O3 -6.6(4) . . . . ?
C2 O1 C3 N1 173.1(2) . . . . ?
C14 N1 C3 O3 -8.3(4) . . . . ?
C4 N1 C3 O3 162.6(2) . . . . ?
C14 N1 C3 O1 172.0(2) . . . . ?
C4 N1 C3 O1 -17.0(3) . . . . ?
C3 N1 C4 C5 -50.1(3) . . . . ?
C14 N1 C4 C5 120.6(2) . . . . ?
C3 N1 C4 C17 -167.5(2) . . . . ?
C14 N1 C4 C17 3.2(3) . . . . ?
C3 N1 C4 C11 74.8(3) . . . . ?
C14 N1 C4 C11 -114.4(2) . . . . ?
N1 C4 C5 C23 145.3(2) . . . . ?
C17 C4 C5 C23 -96.3(3) . . . . ?
C11 C4 C5 C23 21.7(3) . . . . ?
N1 C4 C5 C6 -37.0(3) . . . . ?
C17 C4 C5 C6 81.3(3) . . . . ?
C11 C4 C5 C6 -160.7(2) . . . . ?
C23 C5 C6 C7 0.6(4) . . . . ?
C4 C5 C6 C7 -177.1(2) . . . . ?
C5 C6 C7 C8 -1.0(4) . . . . ?
C6 C7 C8 C22 0.3(4) . . . . ?
C9 O2 C10 O4 -4.1(4) . . . . ?
C9 O2 C10 C11 175.1(2) . . . . ?
O4 C10 C11 C4 94.7(3) . . . . ?
O2 C10 C11 C4 -84.4(3) . . . . ?
N1 C4 C11 C10 50.1(3) . . . . ?
C5 C4 C11 C10 173.1(2) . . . . ?
C17 C4 C11 C10 -68.7(3) . . . . ?
C3 N1 C14 C15 139.9(3) . . . . ?
C4 N1 C14 C15 -31.1(3) . . . . ?
C3 N1 C14 C21 -41.8(3) . . . . ?
C4 N1 C14 C21 147.2(2) . . . . ?
C21 C14 C15 C18 5.0(4) . . . . ?
N1 C14 C15 C18 -176.8(2) . . . . ?
C21 C14 C15 C16 -168.4(2) . . . . ?
N1 C14 C15 C16 9.9(4) . . . . ?
C14 C15 C16 C17 34.5(3) . . . . ?
C18 C15 C16 C17 -138.6(3) . . . . ?
C15 C16 C17 C4 -61.8(3) . . . . ?
N1 C4 C17 C16 43.1(3) . . . . ?
C5 C4 C17 C16 -75.4(3) . . . . ?
C11 C4 C17 C16 163.0(2) . . . . ?
C14 C15 C18 C19 -0.7(4) . . . . ?
C16 C15 C18 C19 172.5(3) . . . . ?
C15 C18 C19 C20 -3.0(4) . . . . ?
C18 C19 C20 C21 2.3(4) . . . . ?
C19 C20 C21 C14 1.9(4) . . . . ?
C15 C14 C21 C20 -5.7(4) . . . . ?
N1 C14 C21 C20 176.1(2) . . . . ?
C7 C8 C22 C23 0.8(4) . . . . ?
C8 C22 C23 C5 -1.3(4) . . . . ?
C6 C5 C23 C22 0.5(4) . . . . ?
C4 C5 C23 C22 178.2(2) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
C1 H10 O3 0.98 2.44 2.965(4) 113.0 .
C11 H26 O1 0.99 2.32 2.866(3) 114.0 .
C12 H7 O3 0.98 2.52 3.087(3) 116.5 .
C17 H14 O4 0.99 2.54 3.300(3) 133.2 .

_refine_diff_density_max         0.161
_refine_diff_density_min         -0.141
_refine_diff_density_rms         0.033

