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

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_180709_zyc_2_60
_audit_block_doi                 10.5517/ccdc.csd.cc20912g
_database_code_depnum_ccdc_archive 'CCDC 1855724'
_audit_update_record             
;
2018-07-13 deposited with the CCDC.
2018-12-18 downloaded from the CCDC.
;
_audit_creation_date             2018-07-09
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2016/6
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C24 H22 O'
_chemical_formula_sum            'C24 H22 O'
_chemical_formula_weight         326.41
_chemical_melting_point          ?
_chemical_oxdiff_formula         'c h n o'
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      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                   8.4646(7)
_cell_length_b                   10.2366(11)
_cell_length_c                   11.8274(12)
_cell_angle_alpha                77.022(9)
_cell_angle_beta                 69.293(8)
_cell_angle_gamma                74.924(8)
_cell_volume                     915.61(16)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    1569
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      29.2613
_cell_measurement_theta_min      2.5765
_shelx_estimated_absorpt_T_max   0.974
_shelx_estimated_absorpt_T_min   0.970
_exptl_absorpt_coefficient_mu    0.070
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.93737
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.184
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             348
_exptl_crystal_size_max          0.43
_exptl_crystal_size_mid          0.4
_exptl_crystal_size_min          0.38
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0336
_diffrn_reflns_av_unetI/netI     0.0518
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            5997
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.350
_diffrn_reflns_theta_min         2.582
_diffrn_ambient_temperature      296.15
_diffrn_detector_area_resol_mean 10.3592
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega  -67.00   19.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      -11.4683  -77.0000 -120.0000 86

#__ type_ start__ end____ width___ exp.time_
  2 omega  -56.00   35.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -       11.7808  -38.0000    0.0000 91

#__ type_ start__ end____ width___ exp.time_
  3 omega  -15.00   80.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -       11.7808   38.0000 -180.0000 95
;
_diffrn_measurement_device_type  'Xcalibur, Atlas, Gemini ultra'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      0.0063942000
_diffrn_orient_matrix_UB_12      -0.0496019000
_diffrn_orient_matrix_UB_13      -0.0355557000
_diffrn_orient_matrix_UB_21      0.0613308000
_diffrn_orient_matrix_UB_22      0.0309690000
_diffrn_orient_matrix_UB_23      -0.0498842000
_diffrn_orient_matrix_UB_31      0.0674604000
_diffrn_orient_matrix_UB_32      -0.0429369000
_diffrn_orient_matrix_UB_33      0.0211742000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'Enhance (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2007
_reflns_number_total             3358
_reflns_odcompleteness_completeness 99.63
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
;
_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    'ShelXS (Sheldrick, 2008)'
_refine_diff_density_max         0.194
_refine_diff_density_min         -0.258
_refine_diff_density_rms         0.061
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.031
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     228
_refine_ls_number_reflns         3358
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1055
_refine_ls_R_factor_gt           0.0624
_refine_ls_restrained_S_all      1.031
_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)+(0.0996P)²+0.0501P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1570
_refine_ls_wR_factor_ref         0.1984
_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 Secondary CH2 refined with riding coordinates:
 C1(H1A,H1B), C2(H2A,H2B)
2.b Aromatic/amide H refined with riding coordinates:
 C10(H10), C11(H11), C12(H12), C13(H13), C14(H14), C17(H17), C18(H18),
 C19(H19), C20(H20), C21(H21)
2.c X=CH2 refined with riding coordinates:
 C23(H23A,H23B)
2.d Idealised Me refined as rotating group:
 C15(H15A,H15B,H15C), C24(H24A,H24B,H24C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O -0.1671(3) 0.9578(2) 0.18210(17) 0.0932(7) Uani 1 1 d . . . . .
C1 C 0.0094(3) 0.8968(3) 0.1386(2) 0.0736(8) Uani 1 1 d . . . . .
H1A H 0.077329 0.965453 0.091874 0.088 Uiso 1 1 calc R . . . .
H1B H 0.026450 0.829593 0.087055 0.088 Uiso 1 1 calc R . . . .
C2 C -0.2372(3) 0.9150(3) 0.3089(3) 0.0704(8) Uani 1 1 d . . . . .
H2A H -0.315671 0.854362 0.323709 0.085 Uiso 1 1 calc R . . . .
H2B H -0.299021 0.993165 0.351196 0.085 Uiso 1 1 calc R . . . .
C3 C -0.0845(3) 0.8413(2) 0.3511(2) 0.0523(6) Uani 1 1 d . . . . .
C4 C 0.0601(3) 0.8296(2) 0.2511(2) 0.0525(6) Uani 1 1 d . . . . .
C5 C 0.2212(3) 0.7663(2) 0.26159(19) 0.0488(6) Uani 1 1 d . . . . .
C6 C 0.2320(3) 0.7135(2) 0.38015(19) 0.0466(5) Uani 1 1 d . . . . .
C7 C 0.0832(3) 0.7260(2) 0.48231(18) 0.0449(5) Uani 1 1 d . . . . .
C8 C -0.0780(3) 0.7915(2) 0.46900(19) 0.0485(6) Uani 1 1 d . . . . .
C9 C 0.3738(3) 0.7559(2) 0.1496(2) 0.0560(6) Uani 1 1 d . . . . .
C10 C 0.3823(4) 0.6833(3) 0.0620(3) 0.0846(9) Uani 1 1 d . . . . .
H10 H 0.292559 0.639751 0.074367 0.102 Uiso 1 1 calc R . . . .
C11 C 0.5204(5) 0.6735(4) -0.0434(3) 0.1002(11) Uani 1 1 d . . . . .
H11 H 0.523517 0.623672 -0.101265 0.120 Uiso 1 1 calc R . . . .
C12 C 0.6535(4) 0.7376(4) -0.0629(3) 0.0938(10) Uani 1 1 d . . . . .
H12 H 0.747747 0.730867 -0.133525 0.113 Uiso 1 1 calc R . . . .
C13 C 0.6466(4) 0.8106(3) 0.0214(3) 0.0842(9) Uani 1 1 d . . . . .
H13 H 0.736359 0.854305 0.008318 0.101 Uiso 1 1 calc R . . . .
C14 C 0.5074(3) 0.8209(3) 0.1270(2) 0.0705(8) Uani 1 1 d . . . . .
H14 H 0.504082 0.872622 0.183498 0.085 Uiso 1 1 calc R . . . .
C15 C 0.4035(3) 0.6422(3) 0.3972(2) 0.0630(7) Uani 1 1 d . . . . .
H15A H 0.456456 0.707132 0.410738 0.094 Uiso 1 1 calc GR . . . .
H15B H 0.476773 0.602728 0.325367 0.094 Uiso 1 1 calc GR . . . .
H15C H 0.386498 0.571355 0.466479 0.094 Uiso 1 1 calc GR . . . .
C16 C 0.0983(3) 0.6710(2) 0.60755(19) 0.0478(6) Uani 1 1 d . . . . .
C17 C 0.1336(3) 0.7508(3) 0.6718(2) 0.0661(7) Uani 1 1 d . . . . .
H17 H 0.142087 0.841120 0.638608 0.079 Uiso 1 1 calc R . . . .
C18 C 0.1568(4) 0.6993(3) 0.7847(2) 0.0776(8) Uani 1 1 d . . . . .
H18 H 0.181577 0.754532 0.826220 0.093 Uiso 1 1 calc R . . . .
C19 C 0.1431(3) 0.5671(4) 0.8351(2) 0.0796(9) Uani 1 1 d . . . . .
H19 H 0.160712 0.531177 0.910228 0.095 Uiso 1 1 calc R . . . .
C20 C 0.1036(4) 0.4890(3) 0.7741(2) 0.0780(8) Uani 1 1 d . . . . .
H20 H 0.091727 0.399615 0.808740 0.094 Uiso 1 1 calc R . . . .
C21 C 0.0808(3) 0.5398(3) 0.6621(2) 0.0646(7) Uani 1 1 d . . . . .
H21 H 0.053011 0.484492 0.622270 0.078 Uiso 1 1 calc R . . . .
C22 C -0.2383(3) 0.8093(3) 0.5746(2) 0.0596(7) Uani 1 1 d . . . . .
C23 C -0.2817(4) 0.9251(3) 0.6316(3) 0.0931(10) Uani 1 1 d . . . . .
H23A H -0.383625 0.939887 0.695860 0.112 Uiso 1 1 calc R . . . .
H23B H -0.208702 0.987330 0.605268 0.112 Uiso 1 1 calc R . . . .
C24 C -0.3413(4) 0.7121(4) 0.6093(3) 0.1007(11) Uani 1 1 d . . . . .
H24A H -0.361132 0.696692 0.538665 0.151 Uiso 1 1 calc GR . . . .
H24B H -0.449587 0.744414 0.667475 0.151 Uiso 1 1 calc GR . . . .
H24C H -0.284443 0.627986 0.645549 0.151 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
O1 C1 1.415(3) . ?
O1 C2 1.415(3) . ?
C1 H1A 0.9700 . ?
C1 H1B 0.9700 . ?
C1 C4 1.505(3) . ?
C2 H2A 0.9700 . ?
C2 H2B 0.9700 . ?
C2 C3 1.507(3) . ?
C3 C4 1.369(3) . ?
C3 C8 1.388(3) . ?
C4 C5 1.385(3) . ?
C5 C6 1.411(3) . ?
C5 C9 1.488(3) . ?
C6 C7 1.405(3) . ?
C6 C15 1.507(3) . ?
C7 C8 1.401(3) . ?
C7 C16 1.500(3) . ?
C8 C22 1.487(3) . ?
C9 C10 1.378(4) . ?
C9 C14 1.375(3) . ?
C10 H10 0.9300 . ?
C10 C11 1.377(4) . ?
C11 H11 0.9300 . ?
C11 C12 1.374(5) . ?
C12 H12 0.9300 . ?
C12 C13 1.351(5) . ?
C13 H13 0.9300 . ?
C13 C14 1.383(4) . ?
C14 H14 0.9300 . ?
C15 H15A 0.9600 . ?
C15 H15B 0.9600 . ?
C15 H15C 0.9600 . ?
C16 C17 1.379(3) . ?
C16 C21 1.374(3) . ?
C17 H17 0.9300 . ?
C17 C18 1.383(3) . ?
C18 H18 0.9300 . ?
C18 C19 1.368(4) . ?
C19 H19 0.9300 . ?
C19 C20 1.357(4) . ?
C20 H20 0.9300 . ?
C20 C21 1.372(3) . ?
C21 H21 0.9300 . ?
C22 C23 1.397(4) . ?
C22 C24 1.391(4) . ?
C23 H23A 0.9300 . ?
C23 H23B 0.9300 . ?
C24 H24A 0.9600 . ?
C24 H24B 0.9600 . ?
C24 H24C 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
C1 O1 C2 111.03(18) . . ?
O1 C1 H1A 110.7 . . ?
O1 C1 H1B 110.7 . . ?
O1 C1 C4 105.4(2) . . ?
H1A C1 H1B 108.8 . . ?
C4 C1 H1A 110.7 . . ?
C4 C1 H1B 110.7 . . ?
O1 C2 H2A 110.7 . . ?
O1 C2 H2B 110.7 . . ?
O1 C2 C3 105.2(2) . . ?
H2A C2 H2B 108.8 . . ?
C3 C2 H2A 110.7 . . ?
C3 C2 H2B 110.7 . . ?
C4 C3 C2 108.76(19) . . ?
C4 C3 C8 121.98(19) . . ?
C8 C3 C2 129.3(2) . . ?
C3 C4 C1 108.5(2) . . ?
C3 C4 C5 121.95(18) . . ?
C5 C4 C1 129.5(2) . . ?
C4 C5 C6 117.5(2) . . ?
C4 C5 C9 119.62(18) . . ?
C6 C5 C9 122.90(19) . . ?
C5 C6 C15 119.92(19) . . ?
C7 C6 C5 120.25(18) . . ?
C7 C6 C15 119.83(17) . . ?
C6 C7 C16 119.25(17) . . ?
C8 C7 C6 121.01(18) . . ?
C8 C7 C16 119.73(18) . . ?
C3 C8 C7 117.3(2) . . ?
C3 C8 C22 119.83(19) . . ?
C7 C8 C22 122.84(18) . . ?
C10 C9 C5 120.2(2) . . ?
C14 C9 C5 122.3(2) . . ?
C14 C9 C10 117.5(2) . . ?
C9 C10 H10 119.2 . . ?
C11 C10 C9 121.6(3) . . ?
C11 C10 H10 119.2 . . ?
C10 C11 H11 120.1 . . ?
C12 C11 C10 119.7(3) . . ?
C12 C11 H11 120.1 . . ?
C11 C12 H12 120.3 . . ?
C13 C12 C11 119.5(3) . . ?
C13 C12 H12 120.3 . . ?
C12 C13 H13 119.6 . . ?
C12 C13 C14 120.8(3) . . ?
C14 C13 H13 119.6 . . ?
C9 C14 C13 120.9(3) . . ?
C9 C14 H14 119.5 . . ?
C13 C14 H14 119.5 . . ?
C6 C15 H15A 109.5 . . ?
C6 C15 H15B 109.5 . . ?
C6 C15 H15C 109.5 . . ?
H15A C15 H15B 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
C17 C16 C7 120.6(2) . . ?
C21 C16 C7 122.0(2) . . ?
C21 C16 C17 117.3(2) . . ?
C16 C17 H17 119.3 . . ?
C16 C17 C18 121.3(2) . . ?
C18 C17 H17 119.3 . . ?
C17 C18 H18 120.0 . . ?
C19 C18 C17 120.0(3) . . ?
C19 C18 H18 120.0 . . ?
C18 C19 H19 120.4 . . ?
C20 C19 C18 119.1(2) . . ?
C20 C19 H19 120.4 . . ?
C19 C20 H20 119.5 . . ?
C19 C20 C21 121.0(3) . . ?
C21 C20 H20 119.5 . . ?
C16 C21 H21 119.4 . . ?
C20 C21 C16 121.2(3) . . ?
C20 C21 H21 119.4 . . ?
C23 C22 C8 118.6(2) . . ?
C24 C22 C8 118.3(3) . . ?
C24 C22 C23 123.1(3) . . ?
C22 C23 H23A 120.0 . . ?
C22 C23 H23B 120.0 . . ?
H23A C23 H23B 120.0 . . ?
C22 C24 H24A 109.5 . . ?
C22 C24 H24B 109.5 . . ?
C22 C24 H24C 109.5 . . ?
H24A C24 H24B 109.5 . . ?
H24A C24 H24C 109.5 . . ?
H24B C24 H24C 109.5 . . ?

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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_180604_zyc_2_35
_audit_block_doi                 10.5517/ccdc.csd.cc20268l
_database_code_depnum_ccdc_archive 'CCDC 1849158'
_audit_update_record             
;
2018-06-13 deposited with the CCDC.
2018-12-18 downloaded from the CCDC.
;
_audit_creation_date             2018-06-05
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2016/6
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C24 H22 O2'
_chemical_formula_sum            'C24 H22 O2'
_chemical_formula_weight         342.41
_chemical_melting_point          ?
_chemical_oxdiff_formula         'c h n o'
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

_cell_length_a                   6.8864(5)
_cell_length_b                   33.272(3)
_cell_length_c                   8.5011(8)
_cell_angle_alpha                90
_cell_angle_beta                 104.932(8)
_cell_angle_gamma                90
_cell_volume                     1882.0(3)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    1931
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      29.2773
_cell_measurement_theta_min      3.0551
_shelx_estimated_absorpt_T_max   0.972
_shelx_estimated_absorpt_T_min   0.964
_exptl_absorpt_coefficient_mu    0.075
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.94205
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'light yellow'
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.208
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             728
_exptl_crystal_size_max          0.49
_exptl_crystal_size_mid          0.46
_exptl_crystal_size_min          0.38
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0345
_diffrn_reflns_av_unetI/netI     0.0526
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       40
_diffrn_reflns_limit_k_min       -30
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            7378
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.348
_diffrn_reflns_theta_min         3.486
_diffrn_ambient_temperature      293.15
_diffrn_detector_area_resol_mean 10.3592
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega  -34.00   64.00   1.0000    7.0000
omega____ theta____ kappa____ phi______ frames
    -      -11.4683   38.0000   90.0000 98

#__ type_ start__ end____ width___ exp.time_
  2 omega    8.00   85.00   1.0000    7.0000
omega____ theta____ kappa____ phi______ frames
    -       11.7808   38.0000    0.0000 77
;
_diffrn_measurement_device_type  'Xcalibur, Atlas, Gemini ultra'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      0.0217074000
_diffrn_orient_matrix_UB_12      0.0077296000
_diffrn_orient_matrix_UB_13      0.0804368000
_diffrn_orient_matrix_UB_21      -0.0677412000
_diffrn_orient_matrix_UB_22      0.0160971000
_diffrn_orient_matrix_UB_23      -0.0273782000
_diffrn_orient_matrix_UB_31      -0.0793860000
_diffrn_orient_matrix_UB_32      -0.0116370000
_diffrn_orient_matrix_UB_33      0.0154950000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'Enhance (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2370
_reflns_number_total             3441
_reflns_odcompleteness_completeness 99.52
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
;
_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         0.149
_refine_diff_density_min         -0.186
_refine_diff_density_rms         0.042
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.064
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     237
_refine_ls_number_reflns         3441
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0921
_refine_ls_R_factor_gt           0.0602
_refine_ls_restrained_S_all      1.064
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0481P)²+0.4590P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1251
_refine_ls_wR_factor_ref         0.1457
_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, All O(H) groups
2.a Secondary CH2 refined with riding coordinates:
 C7(H7A,H7B), C8(H8A,H8B), C15(H15A,H15B)
2.b Aromatic/amide H refined with riding coordinates:
 C10(H10), C11(H11), C12(H12), C13(H13), C14(H14), C17(H17), C18(H18),
 C19(H19), C20(H20), C21(H21)
2.c X=CH2 refined with riding coordinates:
 C23(H23A,H23B)
2.d Idealised Me refined as rotating group:
 C24(H24A,H24B,H24C)
2.e Idealised tetrahedral OH refined as rotating group:
 O2(H2)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O -0.2202(3) 0.64473(7) 0.2757(2) 0.0920(7) Uani 1 1 d . . . . .
O2 O 0.4000(2) 0.64092(6) 1.04098(19) 0.0628(5) Uani 1 1 d . . . . .
H2 H 0.504054 0.639542 1.114085 0.094 Uiso 1 1 calc GR . . . .
C1 C 0.1274(3) 0.66828(6) 0.6724(2) 0.0396(5) Uani 1 1 d . . . . .
C2 C 0.3044(3) 0.64705(6) 0.7472(2) 0.0386(5) Uani 1 1 d . . . . .
C3 C 0.3620(3) 0.61297(7) 0.6720(2) 0.0407(5) Uani 1 1 d . . . . .
C4 C 0.2501(3) 0.60017(7) 0.5186(3) 0.0456(5) Uani 1 1 d . . . . .
C5 C 0.0828(3) 0.62300(7) 0.4422(3) 0.0490(6) Uani 1 1 d . . . . .
C6 C 0.0229(3) 0.65579(7) 0.5164(3) 0.0450(5) Uani 1 1 d . . . . .
C7 C -0.1674(4) 0.67251(9) 0.4077(3) 0.0638(7) Uani 1 1 d . . . . .
H7A H -0.272383 0.674053 0.464763 0.077 Uiso 1 1 calc R . . . .
H7B H -0.145035 0.699120 0.369212 0.077 Uiso 1 1 calc R . . . .
C8 C -0.0652(4) 0.61607(10) 0.2807(3) 0.0756(8) Uani 1 1 d . . . . .
H8A H -0.002876 0.620416 0.191943 0.091 Uiso 1 1 calc R . . . .
H8B H -0.118098 0.588923 0.273455 0.091 Uiso 1 1 calc R . . . .
C9 C 0.0449(3) 0.70108(7) 0.7548(3) 0.0409(5) Uani 1 1 d . . . . .
C10 C -0.0034(3) 0.73848(7) 0.6841(3) 0.0509(6) Uani 1 1 d . . . . .
H10 H 0.021383 0.743738 0.583598 0.061 Uiso 1 1 calc R . . . .
C11 C -0.0871(4) 0.76805(8) 0.7587(3) 0.0595(7) Uani 1 1 d . . . . .
H11 H -0.118774 0.792880 0.708473 0.071 Uiso 1 1 calc R . . . .
C12 C -0.1237(3) 0.76096(9) 0.9062(3) 0.0641(7) Uani 1 1 d . . . . .
H12 H -0.179129 0.780996 0.957341 0.077 Uiso 1 1 calc R . . . .
C13 C -0.0780(4) 0.72386(9) 0.9796(3) 0.0644(7) Uani 1 1 d . . . . .
H13 H -0.103416 0.718936 1.080160 0.077 Uiso 1 1 calc R . . . .
C14 C 0.0049(3) 0.69414(8) 0.9047(3) 0.0533(6) Uani 1 1 d . . . . .
H14 H 0.034303 0.669227 0.954716 0.064 Uiso 1 1 calc R . . . .
C15 C 0.4376(3) 0.66187(7) 0.9061(3) 0.0490(6) Uani 1 1 d . . . . .
H15A H 0.577222 0.658291 0.905502 0.059 Uiso 1 1 calc R . . . .
H15B H 0.414493 0.690355 0.917340 0.059 Uiso 1 1 calc R . . . .
C16 C 0.5455(3) 0.59019(7) 0.7583(3) 0.0425(5) Uani 1 1 d . . . . .
C17 C 0.5438(3) 0.56349(8) 0.8825(3) 0.0586(7) Uani 1 1 d . . . . .
H17 H 0.424934 0.559243 0.912758 0.070 Uiso 1 1 calc R . . . .
C18 C 0.7154(4) 0.54297(8) 0.9627(3) 0.0694(8) Uani 1 1 d . . . . .
H18 H 0.710589 0.524814 1.044744 0.083 Uiso 1 1 calc R . . . .
C19 C 0.8912(4) 0.54931(8) 0.9215(4) 0.0706(8) Uani 1 1 d . . . . .
H19 H 1.007645 0.536094 0.977252 0.085 Uiso 1 1 calc R . . . .
C20 C 0.8955(4) 0.57503(10) 0.7989(4) 0.0821(9) Uani 1 1 d . . . . .
H20 H 1.015224 0.579171 0.769737 0.099 Uiso 1 1 calc R . . . .
C21 C 0.7243(4) 0.59509(9) 0.7169(4) 0.0707(8) Uani 1 1 d . . . . .
H21 H 0.729741 0.612272 0.631853 0.085 Uiso 1 1 calc R . . . .
C22 C 0.2966(4) 0.56266(8) 0.4390(3) 0.0584(7) Uani 1 1 d . . . . .
C23 C 0.2412(5) 0.52584(10) 0.4910(5) 0.1046(12) Uani 1 1 d . . . . .
H23A H 0.268006 0.502223 0.441963 0.125 Uiso 1 1 calc R . . . .
H23B H 0.177204 0.524794 0.574829 0.125 Uiso 1 1 calc R . . . .
C24 C 0.3937(6) 0.56552(12) 0.3126(4) 0.1111(13) Uani 1 1 d . . . . .
H24A H 0.329483 0.585854 0.236775 0.167 Uiso 1 1 calc GR . . . .
H24B H 0.385516 0.540148 0.257529 0.167 Uiso 1 1 calc GR . . . .
H24C H 0.532187 0.572518 0.357252 0.167 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
O1 C7 1.427(3) . ?
O1 C8 1.423(3) . ?
O2 H2 0.8200 . ?
O2 C15 1.422(3) . ?
C1 C2 1.411(3) . ?
C1 C6 1.399(3) . ?
C1 C9 1.486(3) . ?
C2 C3 1.408(3) . ?
C2 C15 1.507(3) . ?
C3 C4 1.399(3) . ?
C3 C16 1.494(3) . ?
C4 C5 1.393(3) . ?
C4 C22 1.493(3) . ?
C5 C6 1.376(3) . ?
C5 C8 1.502(3) . ?
C6 C7 1.502(3) . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C9 C10 1.384(3) . ?
C9 C14 1.391(3) . ?
C10 H10 0.9300 . ?
C10 C11 1.375(3) . ?
C11 H11 0.9300 . ?
C11 C12 1.361(4) . ?
C12 H12 0.9300 . ?
C12 C13 1.383(4) . ?
C13 H13 0.9300 . ?
C13 C14 1.377(3) . ?
C14 H14 0.9300 . ?
C15 H15A 0.9700 . ?
C15 H15B 0.9700 . ?
C16 C17 1.382(3) . ?
C16 C21 1.375(3) . ?
C17 H17 0.9300 . ?
C17 C18 1.382(3) . ?
C18 H18 0.9300 . ?
C18 C19 1.360(4) . ?
C19 H19 0.9300 . ?
C19 C20 1.355(4) . ?
C20 H20 0.9300 . ?
C20 C21 1.378(4) . ?
C21 H21 0.9300 . ?
C22 C23 1.389(4) . ?
C22 C24 1.407(4) . ?
C23 H23A 0.9300 . ?
C23 H23B 0.9300 . ?
C24 H24A 0.9600 . ?
C24 H24B 0.9600 . ?
C24 H24C 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
C8 O1 C7 111.94(18) . . ?
C15 O2 H2 109.5 . . ?
C2 C1 C9 123.11(18) . . ?
C6 C1 C2 116.9(2) . . ?
C6 C1 C9 119.94(18) . . ?
C1 C2 C15 119.73(19) . . ?
C3 C2 C1 120.70(18) . . ?
C3 C2 C15 119.52(18) . . ?
C2 C3 C16 119.16(18) . . ?
C4 C3 C2 121.09(19) . . ?
C4 C3 C16 119.75(19) . . ?
C3 C4 C22 123.1(2) . . ?
C5 C4 C3 117.3(2) . . ?
C5 C4 C22 119.5(2) . . ?
C4 C5 C8 128.9(2) . . ?
C6 C5 C4 121.9(2) . . ?
C6 C5 C8 109.1(2) . . ?
C1 C6 C7 128.9(2) . . ?
C5 C6 C1 121.90(19) . . ?
C5 C6 C7 109.18(19) . . ?
O1 C7 C6 104.4(2) . . ?
O1 C7 H7A 110.9 . . ?
O1 C7 H7B 110.9 . . ?
C6 C7 H7A 110.9 . . ?
C6 C7 H7B 110.9 . . ?
H7A C7 H7B 108.9 . . ?
O1 C8 C5 104.5(2) . . ?
O1 C8 H8A 110.8 . . ?
O1 C8 H8B 110.8 . . ?
C5 C8 H8A 110.8 . . ?
C5 C8 H8B 110.8 . . ?
H8A C8 H8B 108.9 . . ?
C10 C9 C1 122.28(19) . . ?
C10 C9 C14 117.7(2) . . ?
C14 C9 C1 120.0(2) . . ?
C9 C10 H10 119.2 . . ?
C11 C10 C9 121.7(2) . . ?
C11 C10 H10 119.2 . . ?
C10 C11 H11 120.0 . . ?
C12 C11 C10 120.0(2) . . ?
C12 C11 H11 120.0 . . ?
C11 C12 H12 120.1 . . ?
C11 C12 C13 119.7(2) . . ?
C13 C12 H12 120.1 . . ?
C12 C13 H13 119.8 . . ?
C14 C13 C12 120.3(2) . . ?
C14 C13 H13 119.8 . . ?
C9 C14 H14 119.7 . . ?
C13 C14 C9 120.6(2) . . ?
C13 C14 H14 119.7 . . ?
O2 C15 C2 111.54(18) . . ?
O2 C15 H15A 109.3 . . ?
O2 C15 H15B 109.3 . . ?
C2 C15 H15A 109.3 . . ?
C2 C15 H15B 109.3 . . ?
H15A C15 H15B 108.0 . . ?
C17 C16 C3 121.90(19) . . ?
C21 C16 C3 120.9(2) . . ?
C21 C16 C17 117.2(2) . . ?
C16 C17 H17 119.4 . . ?
C16 C17 C18 121.3(2) . . ?
C18 C17 H17 119.4 . . ?
C17 C18 H18 120.0 . . ?
C19 C18 C17 120.1(3) . . ?
C19 C18 H18 120.0 . . ?
C18 C19 H19 120.2 . . ?
C20 C19 C18 119.5(2) . . ?
C20 C19 H19 120.2 . . ?
C19 C20 H20 119.7 . . ?
C19 C20 C21 120.6(3) . . ?
C21 C20 H20 119.7 . . ?
C16 C21 C20 121.3(3) . . ?
C16 C21 H21 119.4 . . ?
C20 C21 H21 119.4 . . ?
C23 C22 C4 119.0(2) . . ?
C23 C22 C24 121.7(3) . . ?
C24 C22 C4 119.3(3) . . ?
C22 C23 H23A 120.0 . . ?
C22 C23 H23B 120.0 . . ?
H23A C23 H23B 120.0 . . ?
C22 C24 H24A 109.5 . . ?
C22 C24 H24B 109.5 . . ?
C22 C24 H24C 109.5 . . ?
H24A C24 H24B 109.5 . . ?
H24A C24 H24C 109.5 . . ?
H24B C24 H24C 109.5 . . ?

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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_171115_zyc_1_79
_audit_block_doi                 10.5517/ccdc.csd.cc20267k
_database_code_depnum_ccdc_archive 'CCDC 1849157'
_audit_update_record             
;
2018-06-13 deposited with the CCDC.
2018-12-18 downloaded from the CCDC.
;
_audit_creation_date             2017-11-16
_audit_creation_method           
;
Olex2 1.2
(compiled 2017.03.28 svn.r3405 for OlexSys, GUI svn.r5381)
;
_shelx_SHELXL_version_number     2016/6
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C27 H23 N O2'
_chemical_formula_sum            'C27 H23 N O2'
_chemical_formula_weight         393.46
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C H N O'
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      orthorhombic
_space_group_IT_number           61
_space_group_name_H-M_alt        'P b c a'
_space_group_name_Hall           '-P 2ac 2ab'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'x, -y-1/2, z-1/2'
'-x-1/2, y-1/2, z'

_cell_length_a                   37.682(4)
_cell_length_b                   6.9971(4)
_cell_length_c                   15.2009(9)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     4007.9(5)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    5148
_cell_measurement_temperature    150.0
_cell_measurement_theta_max      29.3215
_cell_measurement_theta_min      3.1986
_shelx_estimated_absorpt_T_max   0.984
_shelx_estimated_absorpt_T_min   0.961
_exptl_absorpt_coefficient_mu    0.082
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.63525
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.304
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             1664
_exptl_crystal_size_max          0.49
_exptl_crystal_size_mid          0.4
_exptl_crystal_size_min          0.2
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0793
_diffrn_reflns_av_unetI/netI     0.0452
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       35
_diffrn_reflns_limit_h_min       -45
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            23799
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.350
_diffrn_reflns_theta_min         3.250
_diffrn_ambient_temperature      150.0
_diffrn_detector_area_resol_mean 10.3592
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega  -85.00   18.00   1.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -      -11.6246  -77.0000 -150.0000 103

#__ type_ start__ end____ width___ exp.time_
  2 omega  -14.00   77.00   1.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -       11.9371   38.0000  150.0000 91

#__ type_ start__ end____ width___ exp.time_
  3 omega  -59.00   39.00   1.0000    8.0000
omega____ theta____ kappa____ phi______ frames
    -       11.9371  -77.0000    0.0000 98
;
_diffrn_measurement_device_type  'Xcalibur, Atlas, Gemini ultra'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      -0.0185705000
_diffrn_orient_matrix_UB_12      0.0123219000
_diffrn_orient_matrix_UB_13      -0.0048515000
_diffrn_orient_matrix_UB_21      -0.0028992000
_diffrn_orient_matrix_UB_22      -0.0915730000
_diffrn_orient_matrix_UB_23      0.0186831000
_diffrn_orient_matrix_UB_31      -0.0008447000
_diffrn_orient_matrix_UB_32      0.0416502000
_diffrn_orient_matrix_UB_33      0.0425118000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'Enhance (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2837
_reflns_number_total             3672
_reflns_odcompleteness_completeness 99.59
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
;
_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         0.200
_refine_diff_density_min         -0.226
_refine_diff_density_rms         0.053
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.137
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     272
_refine_ls_number_reflns         3672
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0937
_refine_ls_R_factor_gt           0.0717
_refine_ls_restrained_S_all      1.137
_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)+(0.0246P)²+6.3068P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1322
_refine_ls_wR_factor_ref         0.1440
_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 Secondary CH2 refined with riding coordinates:
 C9(H9A,H9B), C16(H16A,H16B), C17(H17A,H17B)
2.b Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C3(H3), C4(H4), C8(H8), C15(H15), C22(H22), C23(H23),
 C24(H24), C25(H25), C26(H26), C27(H27)
2.c X=CH2 refined with riding coordinates:
 C19(H19A,H19B)
2.d Idealised Me refined as rotating group:
 C20(H20A,H20B,H20C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.26394(5) 0.2399(3) 0.59575(14) 0.0369(5) Uani 1 1 d . . . . .
O2 O 0.50473(7) -0.3810(4) 0.64906(15) 0.0542(7) Uani 1 1 d . . . . .
N1 N 0.44063(6) 0.1591(3) 0.57785(15) 0.0293(6) Uani 1 1 d . . . . .
C1 C 0.46519(8) -0.2641(5) 0.46075(19) 0.0340(7) Uani 1 1 d . . . . .
H1 H 0.479120 -0.374368 0.472435 0.041 Uiso 1 1 calc R . . . .
C2 C 0.44883(8) -0.2391(5) 0.3792(2) 0.0375(7) Uani 1 1 d . . . . .
H2 H 0.450898 -0.335863 0.335686 0.045 Uiso 1 1 calc R . . . .
C3 C 0.42963(9) -0.0751(5) 0.3609(2) 0.0413(8) Uani 1 1 d . . . . .
H3 H 0.419183 -0.060815 0.304370 0.050 Uiso 1 1 calc R . . . .
C4 C 0.42520(8) 0.0694(5) 0.42282(19) 0.0355(7) Uani 1 1 d . . . . .
H4 H 0.412094 0.181878 0.409874 0.043 Uiso 1 1 calc R . . . .
C5 C 0.44082(7) 0.0412(4) 0.50430(18) 0.0288(6) Uani 1 1 d . . . . .
C6 C 0.46059(7) -0.1234(4) 0.52468(18) 0.0275(6) Uani 1 1 d . . . . .
C7 C 0.47270(8) -0.1008(4) 0.61418(18) 0.0305(7) Uani 1 1 d . . . . .
C8 C 0.45985(8) 0.0722(4) 0.64248(19) 0.0312(7) Uani 1 1 d . . . . .
H8 H 0.463815 0.124245 0.699359 0.037 Uiso 1 1 calc R . . . .
C9 C 0.42419(8) 0.3472(4) 0.5844(2) 0.0309(7) Uani 1 1 d . . . . .
H9A H 0.436134 0.434642 0.542614 0.037 Uiso 1 1 calc R . . . .
H9B H 0.428101 0.397627 0.644433 0.037 Uiso 1 1 calc R . . . .
C10 C 0.38471(8) 0.3480(4) 0.56529(17) 0.0249(6) Uani 1 1 d . . . . .
C11 C 0.36098(7) 0.2231(4) 0.60860(17) 0.0238(6) Uani 1 1 d . . . . .
C12 C 0.32538(7) 0.2368(4) 0.58546(17) 0.0255(6) Uani 1 1 d . . . . .
C13 C 0.31304(7) 0.3657(4) 0.52368(17) 0.0247(6) Uani 1 1 d . . . . .
C14 C 0.33589(7) 0.4930(4) 0.48177(17) 0.0239(6) Uani 1 1 d . . . . .
C15 C 0.37190(7) 0.4798(4) 0.50409(17) 0.0258(6) Uani 1 1 d . . . . .
H15 H 0.388244 0.563918 0.476450 0.031 Uiso 1 1 calc R . . . .
C16 C 0.29424(8) 0.1313(4) 0.6233(2) 0.0324(7) Uani 1 1 d . . . . .
H16A H 0.293103 -0.000749 0.600024 0.039 Uiso 1 1 calc R . . . .
H16B H 0.295726 0.126002 0.688258 0.039 Uiso 1 1 calc R . . . .
C17 C 0.27342(7) 0.3454(4) 0.5176(2) 0.0336(7) Uani 1 1 d . . . . .
H17A H 0.261751 0.472134 0.516949 0.040 Uiso 1 1 calc R . . . .
H17B H 0.266562 0.274383 0.463941 0.040 Uiso 1 1 calc R . . . .
C18 C 0.37215(8) 0.0878(4) 0.67991(18) 0.0280(6) Uani 1 1 d . . . . .
C19 C 0.38080(9) 0.1550(5) 0.75842(19) 0.0413(8) Uani 1 1 d . . . . .
H19A H 0.386892 0.069323 0.804489 0.050 Uiso 1 1 calc R . . . .
H19B H 0.380927 0.288925 0.768705 0.050 Uiso 1 1 calc R . . . .
C20 C 0.37156(9) -0.1214(4) 0.6605(2) 0.0375(8) Uani 1 1 d . . . . .
H20A H 0.348071 -0.157373 0.638336 0.056 Uiso 1 1 calc GR . . . .
H20B H 0.376682 -0.193043 0.714386 0.056 Uiso 1 1 calc GR . . . .
H20C H 0.389552 -0.150929 0.615947 0.056 Uiso 1 1 calc GR . . . .
C21 C 0.32308(8) 0.6400(4) 0.41861(18) 0.0266(6) Uani 1 1 d . . . . .
C22 C 0.33606(8) 0.8268(4) 0.4220(2) 0.0342(7) Uani 1 1 d . . . . .
H22 H 0.353356 0.859171 0.464967 0.041 Uiso 1 1 calc R . . . .
C23 C 0.32433(9) 0.9654(5) 0.3644(2) 0.0405(8) Uani 1 1 d . . . . .
H23 H 0.333279 1.091981 0.368499 0.049 Uiso 1 1 calc R . . . .
C24 C 0.29938(9) 0.9197(5) 0.3002(2) 0.0406(8) Uani 1 1 d . . . . .
H24 H 0.291544 1.014163 0.259778 0.049 Uiso 1 1 calc R . . . .
C25 C 0.28610(8) 0.7361(5) 0.2958(2) 0.0368(7) Uani 1 1 d . . . . .
H25 H 0.268960 0.704241 0.252356 0.044 Uiso 1 1 calc R . . . .
C26 C 0.29773(8) 0.5975(4) 0.35475(19) 0.0309(7) Uani 1 1 d . . . . .
H26 H 0.288244 0.471899 0.351432 0.037 Uiso 1 1 calc R . . . .
C27 C 0.49389(8) -0.2213(5) 0.6686(2) 0.0388(8) Uani 1 1 d . . . . .
H27 H 0.500173 -0.173620 0.724992 0.047 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
O1 C16 1.434(3) . ?
O1 C17 1.443(3) . ?
O2 C27 1.226(4) . ?
N1 C5 1.389(4) . ?
N1 C8 1.364(4) . ?
N1 C9 1.458(4) . ?
C1 H1 0.9500 . ?
C1 C2 1.395(4) . ?
C1 C6 1.394(4) . ?
C2 H2 0.9500 . ?
C2 C3 1.385(5) . ?
C3 H3 0.9500 . ?
C3 C4 1.392(4) . ?
C4 H4 0.9500 . ?
C4 C5 1.385(4) . ?
C5 C6 1.406(4) . ?
C6 C7 1.444(4) . ?
C7 C8 1.373(4) . ?
C7 C27 1.426(4) . ?
C8 H8 0.9500 . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C9 C10 1.516(4) . ?
C10 C11 1.413(4) . ?
C10 C15 1.396(4) . ?
C11 C12 1.390(4) . ?
C11 C18 1.499(4) . ?
C12 C13 1.382(4) . ?
C12 C16 1.501(4) . ?
C13 C14 1.393(4) . ?
C13 C17 1.503(4) . ?
C14 C15 1.401(4) . ?
C14 C21 1.487(4) . ?
C15 H15 0.9500 . ?
C16 H16A 0.9900 . ?
C16 H16B 0.9900 . ?
C17 H17A 0.9900 . ?
C17 H17B 0.9900 . ?
C18 C19 1.324(4) . ?
C18 C20 1.493(4) . ?
C19 H19A 0.9500 . ?
C19 H19B 0.9500 . ?
C20 H20A 0.9800 . ?
C20 H20B 0.9800 . ?
C20 H20C 0.9800 . ?
C21 C22 1.397(4) . ?
C21 C26 1.394(4) . ?
C22 H22 0.9500 . ?
C22 C23 1.379(4) . ?
C23 H23 0.9500 . ?
C23 C24 1.392(5) . ?
C24 H24 0.9500 . ?
C24 C25 1.380(5) . ?
C25 H25 0.9500 . ?
C25 C26 1.391(4) . ?
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
C16 O1 C17 108.3(2) . . ?
C5 N1 C9 126.3(2) . . ?
C8 N1 C5 108.2(2) . . ?
C8 N1 C9 125.4(2) . . ?
C2 C1 H1 120.8 . . ?
C6 C1 H1 120.8 . . ?
C6 C1 C2 118.4(3) . . ?
C1 C2 H2 119.5 . . ?
C3 C2 C1 120.9(3) . . ?
C3 C2 H2 119.5 . . ?
C2 C3 H3 119.1 . . ?
C2 C3 C4 121.9(3) . . ?
C4 C3 H3 119.1 . . ?
C3 C4 H4 121.6 . . ?
C5 C4 C3 116.8(3) . . ?
C5 C4 H4 121.6 . . ?
N1 C5 C6 108.2(2) . . ?
C4 C5 N1 129.3(3) . . ?
C4 C5 C6 122.6(3) . . ?
C1 C6 C5 119.4(3) . . ?
C1 C6 C7 134.0(3) . . ?
C5 C6 C7 106.6(3) . . ?
C8 C7 C6 106.3(3) . . ?
C8 C7 C27 122.5(3) . . ?
C27 C7 C6 131.2(3) . . ?
N1 C8 C7 110.8(3) . . ?
N1 C8 H8 124.6 . . ?
C7 C8 H8 124.6 . . ?
N1 C9 H9A 108.7 . . ?
N1 C9 H9B 108.7 . . ?
N1 C9 C10 114.1(2) . . ?
H9A C9 H9B 107.6 . . ?
C10 C9 H9A 108.7 . . ?
C10 C9 H9B 108.7 . . ?
C11 C10 C9 122.0(2) . . ?
C15 C10 C9 118.0(3) . . ?
C15 C10 C11 120.0(3) . . ?
C10 C11 C18 123.3(2) . . ?
C12 C11 C10 116.7(2) . . ?
C12 C11 C18 119.8(2) . . ?
C11 C12 C16 128.6(3) . . ?
C13 C12 C11 122.8(3) . . ?
C13 C12 C16 108.6(2) . . ?
C12 C13 C14 121.3(3) . . ?
C12 C13 C17 108.3(2) . . ?
C14 C13 C17 130.3(3) . . ?
C13 C14 C15 116.5(2) . . ?
C13 C14 C21 122.5(2) . . ?
C15 C14 C21 121.1(2) . . ?
C10 C15 C14 122.7(3) . . ?
C10 C15 H15 118.7 . . ?
C14 C15 H15 118.7 . . ?
O1 C16 C12 104.5(2) . . ?
O1 C16 H16A 110.9 . . ?
O1 C16 H16B 110.9 . . ?
C12 C16 H16A 110.9 . . ?
C12 C16 H16B 110.9 . . ?
H16A C16 H16B 108.9 . . ?
O1 C17 C13 104.1(2) . . ?
O1 C17 H17A 110.9 . . ?
O1 C17 H17B 110.9 . . ?
C13 C17 H17A 110.9 . . ?
C13 C17 H17B 110.9 . . ?
H17A C17 H17B 108.9 . . ?
C19 C18 C11 119.8(3) . . ?
C19 C18 C20 122.0(3) . . ?
C20 C18 C11 118.1(2) . . ?
C18 C19 H19A 120.0 . . ?
C18 C19 H19B 120.0 . . ?
H19A C19 H19B 120.0 . . ?
C18 C20 H20A 109.5 . . ?
C18 C20 H20B 109.5 . . ?
C18 C20 H20C 109.5 . . ?
H20A C20 H20B 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
C22 C21 C14 120.6(3) . . ?
C26 C21 C14 121.6(3) . . ?
C26 C21 C22 117.7(3) . . ?
C21 C22 H22 119.3 . . ?
C23 C22 C21 121.5(3) . . ?
C23 C22 H22 119.3 . . ?
C22 C23 H23 120.0 . . ?
C22 C23 C24 120.0(3) . . ?
C24 C23 H23 120.0 . . ?
C23 C24 H24 120.2 . . ?
C25 C24 C23 119.5(3) . . ?
C25 C24 H24 120.2 . . ?
C24 C25 H25 119.9 . . ?
C24 C25 C26 120.2(3) . . ?
C26 C25 H25 119.9 . . ?
C21 C26 H26 119.5 . . ?
C25 C26 C21 121.1(3) . . ?
C25 C26 H26 119.5 . . ?
O2 C27 C7 125.8(3) . . ?
O2 C27 H27 117.1 . . ?
C7 C27 H27 117.1 . . ?

_olex2_submission_special_instructions 'No special instructions were received'
