# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 2018

####################################################################### 
# 
# 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_mo_nrm_4146_0m_a_sqd_a
_database_code_depnum_ccdc_archive 'CCDC 1846706'
_audit_update_record             
;
2018-06-01 deposited with the CCDC.
2018-08-31 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2016/6
_shelx_SHELXL_version_number     2016/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C23 H22 N2 O'
_chemical_formula_sum            'C23 H22 N2 O'
_chemical_formula_weight         342.42

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'

_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                   5.1215(15)
_cell_length_b                   9.156(3)
_cell_length_c                   20.332(6)
_cell_angle_alpha                98.617(11)
_cell_angle_beta                 95.001(10)
_cell_angle_gamma                97.261(10)
_cell_volume                     929.6(5)
_cell_formula_units_Z            2
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    2491
_cell_measurement_theta_min      2.27
_cell_measurement_theta_max      26.43

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.223
_exptl_crystal_F_000             364
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.21
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.08
_exptl_absorpt_coefficient_mu    0.075
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6656
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_process_details   
;
 SADABS 2016/2: Krause, L., Herbst-Irmer, R., Sheldrick G.M. & Stalke D.,
 J. Appl. Cryst. 48 (2015) 3-10
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\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            14300
_diffrn_reflns_av_unetI/netI     0.0880
_diffrn_reflns_av_R_equivalents  0.0881
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_theta_min         2.273
_diffrn_reflns_theta_max         25.247
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             3348
_reflns_number_gt                1912
_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       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_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)+(0.0755P)²+0.1579P] 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_number_reflns         3348
_refine_ls_number_parameters     237
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1265
_refine_ls_R_factor_gt           0.0690
_refine_ls_wR_factor_ref         0.1673
_refine_ls_wR_factor_gt          0.1476
_refine_ls_goodness_of_fit_ref   1.025
_refine_ls_restrained_S_all      1.025
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

# SQUEEZE RESULTS (Version = 211017)
# Note: Data are Listed for all Voids in the P1 Unit Cell
# i.e. Centre of Gravity, Solvent Accessible Volume,
# Recovered number of Electrons in the Void and
# Details about the Squeezed Material
loop_
_platon_squeeze_void_nr
_platon_squeeze_void_average_x
_platon_squeeze_void_average_y
_platon_squeeze_void_average_z
_platon_squeeze_void_volume
_platon_squeeze_void_count_electrons
_platon_squeeze_void_content
1 -0.027 0.000 0.500 68 21 ' '
# Missing Reflections Below sin(th)/lambda = 0.25
loop_
_platon_missing_refln_index_h
_platon_missing_refln_index_k
_platon_missing_refln_index_l
_platon_missing_refln_theta
0 0 1 1.013
0 0 2 2.026
_platon_squeeze_void_probe_radius 1.20
_platon_squeeze_details          
;
TITL mo_NRM_4146_0m_a.res in P-1
CELL    5.1900    9.2100   20.4600     98.50     95.17     97.60
SPGR P-1
# Solvent Accessible Volume =        68
# Electrons Found in S.A.V. =        21
# Note: Atoms in Void are Labelled as Cxxx and Qxxx for all Others
Q101 0.733 0.947 0.481 !       9.95 eA-3
Q102 0.915 1.005 0.481 !       0.99 eA-3
Q103 0.492 0.036 0.451 !       0.86 eA-3
C104 0.262 0.031 0.454 !       0.81 eA-3
Q105 0.367 0.905 0.466 !       0.78 eA-3
Q106 0.121 0.682 0.027 !       0.74 eA-3
Q107 0.429 0.662 0.360 !       0.74 eA-3
Q108 0.431 0.062 0.157 !       0.74 eA-3
Q109 0.430 0.589 0.470 !       0.73 eA-3
Q110 0.514 0.844 0.473 !       0.72 eA-3
Q111 0.702 0.128 0.453 !       0.72 eA-3
Q112 0.626 0.619 0.361 !       0.71 eA-3
Q113 0.749 1.004 0.109 !       0.71 eA-3
Q114 0.687 0.098 0.139 !       0.71 eA-3
Q115 0.440 0.569 0.331 !       0.70 eA-3
Q116 0.309 0.813 0.235 !       0.69 eA-3
Q117 0.946 0.906 0.357 !       0.69 eA-3
Q118 0.125 0.849 0.328 !       0.69 eA-3
Q119 0.500 0.781 0.313 !       0.69 eA-3
Q120 0.868 0.621 0.329 !       0.68 eA-3
Q121 0.490 0.126 0.467 !       0.67 eA-3
Q122 0.443 0.814 0.095 !       0.67 eA-3
Q123 0.382 0.282 0.406 !       0.66 eA-3
Q124 0.507 0.121 0.034 !       0.66 eA-3
Q125 0.951 0.222 0.005 !       0.66 eA-3
Q126 0.880 0.684 0.282 !       0.66 eA-3
Q127 0.818 0.188 0.031 !       0.66 eA-3
Q128 1.001 0.717 0.437 !       0.65 eA-3
Q129 0.947 0.466 0.327 !       0.65 eA-3
Q130 0.446 0.379 0.222 !       0.64 eA-3
Q131 0.817 0.538 0.403 !       0.64 eA-3
Q132 0.429 0.217 0.502 !       0.64 eA-3
Q133 0.876 0.152 0.485 !       0.64 eA-3
Q134 0.759 0.287 0.345 !       0.64 eA-3
Q135 0.508 0.122 0.230 !       0.63 eA-3
Q136 0.622 0.032 0.419 !       0.63 eA-3
Q137 0.558 0.496 0.172 !       0.63 eA-3
Q138 0.745 0.633 0.436 !       0.63 eA-3
C139 0.700 0.782 0.473 !       0.62 eA-3
Q140 0.742 0.367 0.189 !       0.62 eA-3
Q141 0.311 0.157 0.344 !       0.61 eA-3
Q142 0.664 0.343 0.031 !       0.61 eA-3
Q143 0.293 0.834 0.419 !       0.61 eA-3
Q144 0.312 0.091 0.218 !       0.61 eA-3
Q145 0.500 0.783 0.049 !       0.60 eA-3
Q146 0.932 0.126 0.421 !       0.60 eA-3
Q147 0.256 0.781 0.297 !       0.60 eA-3
Q148 0.070 0.341 0.251 !       0.60 eA-3
C149 0.164 0.942 0.472 !       0.59 eA-3
Q150 0.878 0.832 0.264 !       0.59 eA-3
Q151 0.635 0.747 0.298 !       0.59 eA-3
Q152 0.557 0.698 0.233 !       0.59 eA-3
Q153 0.620 0.568 0.252 !       0.59 eA-3
Q154 0.058 0.466 0.450 !       0.59 eA-3
Q155 0.762 0.467 0.327 !       0.58 eA-3
Q156 0.938 0.256 0.502 !       0.58 eA-3
Q157 0.559 0.634 0.439 !       0.58 eA-3
Q158 0.388 0.567 0.033 !       0.58 eA-3
Q159 0.240 0.504 0.109 !       0.58 eA-3
Q160 0.755 0.812 0.329 !       0.57 eA-3
Q161 0.932 0.777 0.014 !       0.57 eA-3
Q162 0.762 0.219 0.499 !       0.57 eA-3
Q163 0.284 0.071 0.107 !       0.57 eA-3
Q164 0.698 0.130 0.233 !       0.57 eA-3
Q165 0.431 0.366 0.403 !       0.57 eA-3
Q166 0.433 0.250 0.108 !       0.57 eA-3
Q167 0.069 0.177 0.419 !       0.57 eA-3
Q168 0.742 0.596 0.392 !       0.56 eA-3
Q169 0.073 0.034 0.034 !       0.56 eA-3
Q170 0.695 0.626 0.296 !       0.56 eA-3
Q171 0.637 0.285 0.362 !       0.56 eA-3
Q172 0.315 0.312 0.140 !       0.56 eA-3
Q173 0.556 0.945 0.015 !       0.56 eA-3
Q174 0.677 0.847 0.391 !       0.56 eA-3
Q175 0.312 0.248 0.168 !       0.55 eA-3
Q176 0.767 0.179 0.159 !       0.55 eA-3
Q177 0.192 0.189 0.016 !       0.55 eA-3
Q178 0.738 0.215 0.204 !       0.55 eA-3
Q179 0.433 0.501 0.386 !       0.55 eA-3
C180 0.058 0.155 0.470 !       0.55 eA-3
Q181 0.895 0.255 0.239 !       0.55 eA-3
Q182 0.435 0.898 0.437 !       0.55 eA-3
Q183 0.426 0.500 0.330 !       0.54 eA-3
Q184 0.911 0.993 0.431 !       0.54 eA-3
Q185 0.068 0.281 0.282 !       0.54 eA-3
Q186 0.257 0.499 0.467 !       0.54 eA-3
Q187 1.011 0.349 0.468 !       0.53 eA-3
Q188 0.943 0.819 0.093 !       0.53 eA-3
Q189 0.763 0.599 0.282 !       0.53 eA-3
Q190 0.570 0.029 0.191 !       0.53 eA-3
Q191 0.619 0.470 0.015 !       0.53 eA-3
Q192 0.686 0.464 0.219 !       0.53 eA-3
Q193 0.752 0.873 0.139 !       0.53 eA-3
Q194 0.560 0.412 0.190 !       0.53 eA-3
Q195 0.493 0.444 0.079 !       0.53 eA-3
Q196 0.500 0.688 0.409 !       0.52 eA-3
Q197 0.440 0.947 0.145 !       0.52 eA-3
Q198 0.994 0.502 0.112 !       0.52 eA-3
Q199 0.810 0.126 0.263 !       0.52 eA-3
;

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 0.7931(4) 0.8757(2) 0.85362(10) 0.0241(5) Uani 1 1 d . . . . .
N1 N 0.5240(5) 0.7075(2) 0.77418(12) 0.0165(6) Uani 1 1 d . . . . .
N2 N 0.6869(5) 0.4398(3) 0.79549(12) 0.0210(6) Uani 1 1 d . . . . .
C1 C 0.7279(6) 0.8263(3) 0.79387(16) 0.0197(7) Uani 1 1 d . . . . .
C8 C 0.4273(6) 0.6349(3) 0.82738(15) 0.0194(7) Uani 1 1 d . . . . .
C12 C 0.4273(6) 0.4287(3) 0.89072(15) 0.0207(7) Uani 1 1 d . . . . .
C007 C 0.4305(6) 0.6538(3) 0.70751(15) 0.0188(7) Uani 1 1 d . . . . .
C13 C 0.5174(6) 0.4985(3) 0.83736(15) 0.0186(7) Uani 1 1 d . . . . .
C2 C 0.8588(6) 0.8837(3) 0.74046(15) 0.0192(7) Uani 1 1 d . . . . .
C00A C 0.5431(6) 0.7145(3) 0.65870(15) 0.0204(7) Uani 1 1 d . . . . .
H00A H 0.473240 0.681409 0.614423 0.025 Uiso 1 1 calc R U . . .
C9 C 0.2659(6) 0.6986(3) 0.86888(15) 0.0233(8) Uani 1 1 d . . . . .
H9 H 0.212404 0.789084 0.862186 0.028 Uiso 1 1 calc R U . . .
C7 C 0.7668(6) 0.8283(3) 0.67317(16) 0.0212(7) Uani 1 1 d . . . . .
C11 C 0.2556(6) 0.4979(4) 0.93175(16) 0.0277(8) Uani 1 1 d . . . . .
H11 H 0.194008 0.452093 0.966376 0.033 Uiso 1 1 calc R U . . .
C6 C 0.9009(6) 0.8865(3) 0.62366(16) 0.0241(8) Uani 1 1 d . . . . .
H6 H 0.838807 0.852485 0.578932 0.029 Uiso 1 1 calc R U . . .
C20 C -0.1553(6) 0.3693(3) 0.61020(15) 0.0243(8) Uani 1 1 d . . . . .
H20A H -0.107530 0.278501 0.624153 0.029 Uiso 1 1 calc R U . . .
H20B H -0.292001 0.402335 0.636628 0.029 Uiso 1 1 calc R U . . .
C18 C 0.1989(6) 0.5301(3) 0.69461(15) 0.0234(7) Uani 1 1 d . . . . .
H18A H 0.060154 0.560254 0.720993 0.028 Uiso 1 1 calc R U . . .
H18B H 0.254884 0.442250 0.709764 0.028 Uiso 1 1 calc R U . . .
C4 C 1.2108(6) 1.0445(3) 0.70667(17) 0.0273(8) Uani 1 1 d . . . . .
H4 H 1.359840 1.116322 0.717993 0.033 Uiso 1 1 calc R U . . .
C19 C 0.0860(6) 0.4890(3) 0.62205(15) 0.0214(7) Uani 1 1 d . . . . .
H19A H 0.222101 0.454039 0.595895 0.026 Uiso 1 1 calc R U . . .
H19B H 0.037557 0.577757 0.606215 0.026 Uiso 1 1 calc R U . . .
C3 C 1.0819(6) 0.9913(3) 0.75644(16) 0.0241(8) Uani 1 1 d . . . . .
H3 H 1.143776 1.027194 0.801033 0.029 Uiso 1 1 calc R U . . .
C16 C 0.7664(6) 0.3151(3) 0.80693(16) 0.0252(8) Uani 1 1 d . . . . .
H16 H 0.882717 0.274482 0.779107 0.030 Uiso 1 1 calc R U . . .
C5 C 1.1222(6) 0.9927(3) 0.63923(17) 0.0243(8) Uani 1 1 d . . . . .
C10 C 0.1779(6) 0.6302(4) 0.92189(16) 0.0284(8) Uani 1 1 d . . . . .
H10 H 0.067133 0.675188 0.950073 0.034 Uiso 1 1 calc R U . . .
C14 C 0.5180(7) 0.2933(3) 0.89990(16) 0.0276(8) Uani 1 1 d . . . . .
H14 H 0.462184 0.243042 0.933793 0.033 Uiso 1 1 calc R U . . .
C15 C 0.6883(7) 0.2376(3) 0.85846(16) 0.0298(8) Uani 1 1 d . . . . .
H15 H 0.752724 0.149243 0.864025 0.036 Uiso 1 1 calc R U . . .
C17 C 1.2696(7) 1.0519(4) 0.58575(18) 0.0352(9) Uani 1 1 d . . . . .
H17A H 1.453286 1.041048 0.593462 0.053 Uiso 1 1 calc R U . . .
H17B H 1.252928 1.155465 0.586930 0.053 Uiso 1 1 calc R U . . .
H17C H 1.196795 0.996845 0.542731 0.053 Uiso 1 1 calc R U . . .
C21 C -0.2600(7) 0.3381(4) 0.53647(16) 0.0352(9) Uani 1 1 d . . . . .
H21A H -0.307412 0.428116 0.522840 0.053 Uiso 1 1 calc R U . . .
H21B H -0.413264 0.263227 0.529449 0.053 Uiso 1 1 calc R U . . .
H21C H -0.125608 0.303377 0.510538 0.053 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 C1 1.232(3) . ?
N1 C007 1.391(4) . ?
N1 C1 1.394(4) . ?
N1 C8 1.444(3) . ?
N2 C16 1.305(4) . ?
N2 C13 1.370(4) . ?
C1 C2 1.454(4) . ?
C8 C9 1.353(4) . ?
C8 C13 1.421(4) . ?
C12 C11 1.408(4) . ?
C12 C14 1.409(4) . ?
C12 C13 1.421(4) . ?
C007 C00A 1.345(4) . ?
C007 C18 1.508(4) . ?
C2 C3 1.391(4) . ?
C2 C7 1.404(4) . ?
C00A C7 1.426(4) . ?
C00A H00A 0.9300 . ?
C9 C10 1.404(4) . ?
C9 H9 0.9300 . ?
C7 C6 1.399(4) . ?
C11 C10 1.359(4) . ?
C11 H11 0.9300 . ?
C6 C5 1.377(4) . ?
C6 H6 0.9300 . ?
C20 C21 1.520(4) . ?
C20 C19 1.521(4) . ?
C20 H20A 0.9700 . ?
C20 H20B 0.9700 . ?
C18 C19 1.511(4) . ?
C18 H18A 0.9700 . ?
C18 H18B 0.9700 . ?
C4 C3 1.371(4) . ?
C4 C5 1.398(5) . ?
C4 H4 0.9300 . ?
C19 H19A 0.9700 . ?
C19 H19B 0.9700 . ?
C3 H3 0.9300 . ?
C16 C15 1.408(4) . ?
C16 H16 0.9300 . ?
C5 C17 1.504(4) . ?
C10 H10 0.9300 . ?
C14 C15 1.357(5) . ?
C14 H14 0.9300 . ?
C15 H15 0.9300 . ?
C17 H17A 0.9600 . ?
C17 H17B 0.9600 . ?
C17 H17C 0.9600 . ?
C21 H21A 0.9600 . ?
C21 H21B 0.9600 . ?
C21 H21C 0.9600 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C007 N1 C1 123.0(2) . . ?
C007 N1 C8 121.2(2) . . ?
C1 N1 C8 115.6(2) . . ?
C16 N2 C13 116.9(3) . . ?
O1 C1 N1 120.6(3) . . ?
O1 C1 C2 123.2(3) . . ?
N1 C1 C2 116.2(3) . . ?
C9 C8 C13 120.7(3) . . ?
C9 C8 N1 121.0(3) . . ?
C13 C8 N1 118.2(3) . . ?
C11 C12 C14 123.5(3) . . ?
C11 C12 C13 118.9(3) . . ?
C14 C12 C13 117.6(3) . . ?
C00A C007 N1 119.8(3) . . ?
C00A C007 C18 123.6(3) . . ?
N1 C007 C18 116.5(2) . . ?
N2 C13 C8 119.0(3) . . ?
N2 C13 C12 122.7(2) . . ?
C8 C13 C12 118.3(3) . . ?
C3 C2 C7 119.9(3) . . ?
C3 C2 C1 119.5(3) . . ?
C7 C2 C1 120.6(3) . . ?
C007 C00A C7 121.6(3) . . ?
C007 C00A H00A 119.2 . . ?
C7 C00A H00A 119.2 . . ?
C8 C9 C10 121.0(3) . . ?
C8 C9 H9 119.5 . . ?
C10 C9 H9 119.5 . . ?
C6 C7 C2 118.3(3) . . ?
C6 C7 C00A 123.3(3) . . ?
C2 C7 C00A 118.4(3) . . ?
C10 C11 C12 121.5(3) . . ?
C10 C11 H11 119.3 . . ?
C12 C11 H11 119.3 . . ?
C5 C6 C7 121.9(3) . . ?
C5 C6 H6 119.0 . . ?
C7 C6 H6 119.0 . . ?
C21 C20 C19 109.9(2) . . ?
C21 C20 H20A 109.7 . . ?
C19 C20 H20A 109.7 . . ?
C21 C20 H20B 109.7 . . ?
C19 C20 H20B 109.7 . . ?
H20A C20 H20B 108.2 . . ?
C007 C18 C19 114.0(2) . . ?
C007 C18 H18A 108.7 . . ?
C19 C18 H18A 108.7 . . ?
C007 C18 H18B 108.7 . . ?
C19 C18 H18B 108.7 . . ?
H18A C18 H18B 107.6 . . ?
C3 C4 C5 121.1(3) . . ?
C3 C4 H4 119.4 . . ?
C5 C4 H4 119.4 . . ?
C18 C19 C20 113.5(2) . . ?
C18 C19 H19A 108.9 . . ?
C20 C19 H19A 108.9 . . ?
C18 C19 H19B 108.9 . . ?
C20 C19 H19B 108.9 . . ?
H19A C19 H19B 107.7 . . ?
C4 C3 C2 120.2(3) . . ?
C4 C3 H3 119.9 . . ?
C2 C3 H3 119.9 . . ?
N2 C16 C15 124.6(3) . . ?
N2 C16 H16 117.7 . . ?
C15 C16 H16 117.7 . . ?
C6 C5 C4 118.4(3) . . ?
C6 C5 C17 121.7(3) . . ?
C4 C5 C17 119.9(3) . . ?
C11 C10 C9 119.6(3) . . ?
C11 C10 H10 120.2 . . ?
C9 C10 H10 120.2 . . ?
C15 C14 C12 118.9(3) . . ?
C15 C14 H14 120.6 . . ?
C12 C14 H14 120.6 . . ?
C14 C15 C16 119.3(3) . . ?
C14 C15 H15 120.3 . . ?
C16 C15 H15 120.3 . . ?
C5 C17 H17A 109.5 . . ?
C5 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
C5 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
C20 C21 H21A 109.5 . . ?
C20 C21 H21B 109.5 . . ?
H21A C21 H21B 109.5 . . ?
C20 C21 H21C 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?

_refine_diff_density_max         0.219
_refine_diff_density_min         -0.243
_refine_diff_density_rms         0.057

####################################################################### 
# 
# 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_NMM-4163_a
_database_code_depnum_ccdc_archive 'CCDC 1846709'
_audit_update_record             
;
2018-06-01 deposited with the CCDC.
2018-08-31 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2016/6
_shelx_SHELXL_version_number     2016/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C29 H30 N2 O'
_chemical_formula_weight         422.55

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'

_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                   8.697(4)
_cell_length_b                   11.477(4)
_cell_length_c                   12.404(5)
_cell_angle_alpha                93.694(9)
_cell_angle_beta                 96.086(10)
_cell_angle_gamma                106.015(10)
_cell_volume                     1177.7(8)
_cell_formula_units_Z            2
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    967
_cell_measurement_theta_min      2.36
_cell_measurement_theta_max      23.73

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.192
_exptl_crystal_F_000             452
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.11
_exptl_absorpt_coefficient_mu    0.072
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6726
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_process_details   
;
 SADABS 2016/2: Krause, L., Herbst-Irmer, R., Sheldrick G.M. & Stalke D.,
 J. Appl. Cryst. 48 (2015) 3-10
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\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            11388
_diffrn_reflns_av_unetI/netI     0.0766
_diffrn_reflns_av_R_equivalents  0.0589
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         1.659
_diffrn_reflns_theta_max         25.248
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             4269
_reflns_number_gt                2532
_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       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_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)+(0.0853P)²+0.4233P] 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_number_reflns         4269
_refine_ls_number_parameters     292
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1124
_refine_ls_R_factor_gt           0.0657
_refine_ls_wR_factor_ref         0.1978
_refine_ls_wR_factor_gt          0.1645
_refine_ls_goodness_of_fit_ref   1.019
_refine_ls_restrained_S_all      1.019
_refine_ls_shift/su_max          0.001
_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 0.3628(2) -0.05784(17) 0.17307(16) 0.0379(5) Uani 1 1 d . . . . .
N1 N 0.4429(3) 0.14861(19) 0.18672(17) 0.0268(5) Uani 1 1 d . . . . .
N2 N 0.1470(3) 0.1863(2) 0.20975(18) 0.0315(6) Uani 1 1 d . . . . .
C10 C 0.3309(3) 0.1464(2) 0.0915(2) 0.0270(6) Uani 1 1 d . . . . .
C15 C 0.1802(3) 0.1648(2) 0.1060(2) 0.0275(6) Uani 1 1 d . . . . .
C14 C 0.0701(3) 0.1609(2) 0.0116(2) 0.0288(7) Uani 1 1 d . . . . .
C9 C 0.5352(3) 0.2611(2) 0.2413(2) 0.0282(6) Uani 1 1 d . . . . .
C1 C 0.4478(3) 0.0386(2) 0.2230(2) 0.0293(7) Uani 1 1 d . . . . .
C2 C 0.5577(3) 0.0451(2) 0.3220(2) 0.0272(6) Uani 1 1 d . . . . .
C8 C 0.6424(3) 0.2684(2) 0.3310(2) 0.0287(6) Uani 1 1 d . . . . .
C7 C 0.6544(3) 0.1572(2) 0.3743(2) 0.0272(6) Uani 1 1 d . . . . .
C11 C 0.3691(4) 0.1242(2) -0.0098(2) 0.0319(7) Uani 1 1 d . . . . .
H11 H 0.469226 0.112733 -0.017753 0.038 Uiso 1 1 calc R U . . .
C3 C 0.5650(3) -0.0625(3) 0.3657(2) 0.0326(7) Uani 1 1 d . . . . .
H3 H 0.500212 -0.136725 0.331100 0.039 Uiso 1 1 calc R U . . .
C6 C 0.7589(3) 0.1561(3) 0.4693(2) 0.0322(7) Uani 1 1 d . . . . .
H6 H 0.824802 0.229704 0.504409 0.039 Uiso 1 1 calc R U . . .
C5 C 0.7661(3) 0.0499(3) 0.5114(2) 0.0349(7) Uani 1 1 d . . . . .
C13 C 0.1119(4) 0.1361(2) -0.0926(2) 0.0360(7) Uani 1 1 d . . . . .
H13 H 0.039303 0.131749 -0.154462 0.043 Uiso 1 1 calc R U . . .
C20 C 0.5125(3) 0.3681(3) 0.1959(2) 0.0331(7) Uani 1 1 d . . . . .
C4 C 0.6660(4) -0.0605(3) 0.4588(2) 0.0370(7) Uani 1 1 d . . . . .
H4 H 0.667950 -0.133205 0.487198 0.044 Uiso 1 1 calc R U . . .
C16 C -0.0789(4) 0.1804(3) 0.0291(2) 0.0366(7) Uani 1 1 d . . . . .
H16 H -0.155615 0.178080 -0.029874 0.044 Uiso 1 1 calc R U . . .
C26 C 0.7426(3) 0.3903(3) 0.3862(2) 0.0354(7) Uani 1 1 d . . . . .
H26A H 0.754978 0.449888 0.333384 0.042 Uiso 1 1 calc R U . . .
H26B H 0.849150 0.384804 0.412691 0.042 Uiso 1 1 calc R U . . .
C12 C 0.2589(4) 0.1185(3) -0.1026(2) 0.0376(8) Uani 1 1 d . . . . .
H12 H 0.286281 0.102687 -0.171370 0.045 Uiso 1 1 calc R U . . .
C18 C 0.0059(4) 0.2037(3) 0.2186(2) 0.0393(8) Uani 1 1 d . . . . .
H18 H -0.019000 0.217971 0.288426 0.047 Uiso 1 1 calc R U . . .
C17 C -0.1096(4) 0.2023(3) 0.1313(3) 0.0427(8) Uani 1 1 d . . . . .
H17 H -0.206917 0.216383 0.143563 0.051 Uiso 1 1 calc R U . . .
C21 C 0.5019(4) 0.4625(3) 0.1666(3) 0.0431(8) Uani 1 1 d . . . . .
C27 C 0.6685(4) 0.4336(3) 0.4808(3) 0.0444(8) Uani 1 1 d . . . . .
H27A H 0.563659 0.441721 0.453384 0.053 Uiso 1 1 calc R U . . .
H27B H 0.651570 0.371845 0.531598 0.053 Uiso 1 1 calc R U . . .
C19 C 0.8785(4) 0.0513(3) 0.6131(2) 0.0483(9) Uani 1 1 d . . . . .
H19A H 0.985921 0.062280 0.595088 0.072 Uiso 1 1 calc R U . . .
H19B H 0.843471 -0.024524 0.644291 0.072 Uiso 1 1 calc R U . . .
H19C H 0.877694 0.117060 0.664778 0.072 Uiso 1 1 calc R U . . .
C28 C 0.7684(4) 0.5534(3) 0.5417(3) 0.0569(10) Uani 1 1 d . . . . .
H28A H 0.713334 0.573286 0.601308 0.068 Uiso 1 1 calc R U . . .
H28B H 0.871161 0.544462 0.572873 0.068 Uiso 1 1 calc R U . . .
C22 C 0.4855(5) 0.5801(3) 0.1345(3) 0.0622(11) Uani 1 1 d . . . . .
H22A H 0.470779 0.576499 0.055582 0.075 Uiso 1 1 calc R U . . .
H22B H 0.584590 0.643223 0.161031 0.075 Uiso 1 1 calc R U . . .
C29 C 0.7985(5) 0.6565(3) 0.4709(4) 0.0761(13) Uani 1 1 d . . . . .
H29A H 0.866928 0.643228 0.418301 0.114 Uiso 1 1 calc R U . . .
H29B H 0.850162 0.731704 0.515164 0.114 Uiso 1 1 calc R U . . .
H29C H 0.697709 0.660460 0.433768 0.114 Uiso 1 1 calc R U . . .
C23 C 0.3450(6) 0.6146(4) 0.1778(4) 0.0772(13) Uani 1 1 d . . . . .
H23A H 0.361605 0.618892 0.256700 0.093 Uiso 1 1 calc R U . . .
H23B H 0.347574 0.695497 0.158284 0.093 Uiso 1 1 calc R U . . .
C24 C 0.1858(6) 0.5335(4) 0.1398(4) 0.0924(16) Uani 1 1 d . . . . .
H24A H 0.182360 0.452335 0.159075 0.111 Uiso 1 1 calc R U . . .
H24B H 0.167869 0.529530 0.060907 0.111 Uiso 1 1 calc R U . . .
C25 C 0.0506(7) 0.5710(5) 0.1853(5) 0.114(2) Uani 1 1 d . . . . .
H25A H 0.066326 0.574119 0.263375 0.172 Uiso 1 1 calc R U . . .
H25B H -0.050516 0.512719 0.157465 0.172 Uiso 1 1 calc R U . . .
H25C H 0.050106 0.649854 0.164193 0.172 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 C1 1.232(3) . ?
N1 C1 1.377(3) . ?
N1 C9 1.403(3) . ?
N1 C10 1.443(3) . ?
N2 C18 1.311(4) . ?
N2 C15 1.371(3) . ?
C10 C11 1.360(4) . ?
C10 C15 1.411(4) . ?
C15 C14 1.422(4) . ?
C14 C16 1.410(4) . ?
C14 C13 1.412(4) . ?
C9 C8 1.357(4) . ?
C9 C20 1.437(4) . ?
C1 C2 1.458(4) . ?
C2 C3 1.394(4) . ?
C2 C7 1.401(4) . ?
C8 C7 1.442(4) . ?
C8 C26 1.504(4) . ?
C7 C6 1.413(4) . ?
C11 C12 1.403(4) . ?
C11 H11 0.9300 . ?
C3 C4 1.370(4) . ?
C3 H3 0.9300 . ?
C6 C5 1.371(4) . ?
C6 H6 0.9300 . ?
C5 C4 1.398(4) . ?
C5 C19 1.509(4) . ?
C13 C12 1.365(4) . ?
C13 H13 0.9300 . ?
C20 C21 1.188(4) . ?
C4 H4 0.9300 . ?
C16 C17 1.346(4) . ?
C16 H16 0.9300 . ?
C26 C27 1.517(4) . ?
C26 H26A 0.9700 . ?
C26 H26B 0.9700 . ?
C12 H12 0.9300 . ?
C18 C17 1.393(4) . ?
C18 H18 0.9300 . ?
C17 H17 0.9300 . ?
C21 C22 1.471(4) . ?
C27 C28 1.511(4) . ?
C27 H27A 0.9700 . ?
C27 H27B 0.9700 . ?
C19 H19A 0.9600 . ?
C19 H19B 0.9600 . ?
C19 H19C 0.9600 . ?
C28 C29 1.501(5) . ?
C28 H28A 0.9700 . ?
C28 H28B 0.9700 . ?
C22 C23 1.522(6) . ?
C22 H22A 0.9700 . ?
C22 H22B 0.9700 . ?
C29 H29A 0.9600 . ?
C29 H29B 0.9600 . ?
C29 H29C 0.9600 . ?
C23 C24 1.449(6) . ?
C23 H23A 0.9700 . ?
C23 H23B 0.9700 . ?
C24 C25 1.508(7) . ?
C24 H24A 0.9700 . ?
C24 H24B 0.9700 . ?
C25 H25A 0.9600 . ?
C25 H25B 0.9600 . ?
C25 H25C 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 N1 C9 122.9(2) . . ?
C1 N1 C10 117.7(2) . . ?
C9 N1 C10 119.3(2) . . ?
C18 N2 C15 116.4(2) . . ?
C11 C10 C15 120.9(2) . . ?
C11 C10 N1 120.4(2) . . ?
C15 C10 N1 118.7(2) . . ?
N2 C15 C10 118.8(2) . . ?
N2 C15 C14 123.0(3) . . ?
C10 C15 C14 118.2(2) . . ?
C16 C14 C13 123.6(3) . . ?
C16 C14 C15 116.6(2) . . ?
C13 C14 C15 119.7(3) . . ?
C8 C9 N1 121.8(2) . . ?
C8 C9 C20 121.7(2) . . ?
N1 C9 C20 116.5(2) . . ?
O1 C1 N1 120.5(2) . . ?
O1 C1 C2 123.5(2) . . ?
N1 C1 C2 115.9(2) . . ?
C3 C2 C7 119.6(2) . . ?
C3 C2 C1 119.2(2) . . ?
C7 C2 C1 121.3(2) . . ?
C9 C8 C7 118.6(3) . . ?
C9 C8 C26 120.6(2) . . ?
C7 C8 C26 120.8(2) . . ?
C2 C7 C6 118.0(2) . . ?
C2 C7 C8 119.4(2) . . ?
C6 C7 C8 122.6(3) . . ?
C10 C11 C12 120.6(3) . . ?
C10 C11 H11 119.7 . . ?
C12 C11 H11 119.7 . . ?
C4 C3 C2 121.1(3) . . ?
C4 C3 H3 119.5 . . ?
C2 C3 H3 119.5 . . ?
C5 C6 C7 122.1(3) . . ?
C5 C6 H6 119.0 . . ?
C7 C6 H6 119.0 . . ?
C6 C5 C4 118.8(3) . . ?
C6 C5 C19 121.0(3) . . ?
C4 C5 C19 120.2(3) . . ?
C12 C13 C14 120.0(3) . . ?
C12 C13 H13 120.0 . . ?
C14 C13 H13 120.0 . . ?
C21 C20 C9 174.1(3) . . ?
C3 C4 C5 120.5(3) . . ?
C3 C4 H4 119.8 . . ?
C5 C4 H4 119.8 . . ?
C17 C16 C14 119.8(3) . . ?
C17 C16 H16 120.1 . . ?
C14 C16 H16 120.1 . . ?
C8 C26 C27 112.6(2) . . ?
C8 C26 H26A 109.1 . . ?
C27 C26 H26A 109.1 . . ?
C8 C26 H26B 109.1 . . ?
C27 C26 H26B 109.1 . . ?
H26A C26 H26B 107.8 . . ?
C13 C12 C11 120.5(3) . . ?
C13 C12 H12 119.7 . . ?
C11 C12 H12 119.7 . . ?
N2 C18 C17 124.9(3) . . ?
N2 C18 H18 117.5 . . ?
C17 C18 H18 117.5 . . ?
C16 C17 C18 119.3(3) . . ?
C16 C17 H17 120.4 . . ?
C18 C17 H17 120.4 . . ?
C20 C21 C22 177.5(4) . . ?
C28 C27 C26 114.5(3) . . ?
C28 C27 H27A 108.6 . . ?
C26 C27 H27A 108.6 . . ?
C28 C27 H27B 108.6 . . ?
C26 C27 H27B 108.6 . . ?
H27A C27 H27B 107.6 . . ?
C5 C19 H19A 109.5 . . ?
C5 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
C5 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
C29 C28 C27 113.0(3) . . ?
C29 C28 H28A 109.0 . . ?
C27 C28 H28A 109.0 . . ?
C29 C28 H28B 109.0 . . ?
C27 C28 H28B 109.0 . . ?
H28A C28 H28B 107.8 . . ?
C21 C22 C23 113.3(3) . . ?
C21 C22 H22A 108.9 . . ?
C23 C22 H22A 108.9 . . ?
C21 C22 H22B 108.9 . . ?
C23 C22 H22B 108.9 . . ?
H22A C22 H22B 107.7 . . ?
C28 C29 H29A 109.5 . . ?
C28 C29 H29B 109.5 . . ?
H29A C29 H29B 109.5 . . ?
C28 C29 H29C 109.5 . . ?
H29A C29 H29C 109.5 . . ?
H29B C29 H29C 109.5 . . ?
C24 C23 C22 116.1(4) . . ?
C24 C23 H23A 108.3 . . ?
C22 C23 H23A 108.3 . . ?
C24 C23 H23B 108.3 . . ?
C22 C23 H23B 108.3 . . ?
H23A C23 H23B 107.4 . . ?
C23 C24 C25 114.2(5) . . ?
C23 C24 H24A 108.7 . . ?
C25 C24 H24A 108.7 . . ?
C23 C24 H24B 108.7 . . ?
C25 C24 H24B 108.7 . . ?
H24A C24 H24B 107.6 . . ?
C24 C25 H25A 109.5 . . ?
C24 C25 H25B 109.5 . . ?
H25A C25 H25B 109.5 . . ?
C24 C25 H25C 109.5 . . ?
H25A C25 H25C 109.5 . . ?
H25B C25 H25C 109.5 . . ?

_refine_diff_density_max         0.562
_refine_diff_density_min         -0.307
_refine_diff_density_rms         0.052

####################################################################### 
# 
# 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_NRM-4147_a
_database_code_depnum_ccdc_archive 'CCDC 1846708'
_audit_update_record             
;
2018-06-01 deposited with the CCDC.
2018-08-31 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2016/6
_shelx_SHELXL_version_number     2016/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C28 H34 N2 O Si'
_chemical_formula_sum            'C28 H34 N2 O Si'
_chemical_formula_weight         442.66

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'
Si Si 0.0817 0.0704 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/n'
_space_group_name_Hall           '-P 2yn'

_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+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   18.218(4)
_cell_length_b                   7.7675(18)
_cell_length_c                   18.549(4)
_cell_angle_alpha                90
_cell_angle_beta                 111.106(5)
_cell_angle_gamma                90
_cell_volume                     2448.8(9)
_cell_formula_units_Z            4
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    3779
_cell_measurement_theta_min      2.40
_cell_measurement_theta_max      25.89

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.201
_exptl_crystal_F_000             952
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.29
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.12
_exptl_absorpt_coefficient_mu    0.118
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.5648
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_process_details   
;
 SADABS 2016/2: Krause, L., Herbst-Irmer, R., Sheldrick G.M. & Stalke D.,
 J. Appl. Cryst. 48 (2015) 3-10
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\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            44246
_diffrn_reflns_av_unetI/netI     0.0974
_diffrn_reflns_av_R_equivalents  0.1315
_diffrn_reflns_limit_h_min       -22
_diffrn_reflns_limit_h_max       24
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         1.959
_diffrn_reflns_theta_max         28.401
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             6144
_reflns_number_gt                3868
_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       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_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)+(0.0859P)²+0.4204P] 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_number_reflns         6144
_refine_ls_number_parameters     296
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1056
_refine_ls_R_factor_gt           0.0592
_refine_ls_wR_factor_ref         0.1782
_refine_ls_wR_factor_gt          0.1460
_refine_ls_goodness_of_fit_ref   0.993
_refine_ls_restrained_S_all      0.993
_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
Si01 Si 0.42039(4) 0.75474(7) 0.17136(3) 0.02187(17) Uani 1 1 d . . . . .
N1 N 0.54521(11) 0.7401(2) 0.32399(10) 0.0222(4) Uani 1 1 d . . . . .
N2 N 0.45855(11) 0.6627(2) 0.41474(10) 0.0246(4) Uani 1 1 d . . . . .
O1 O 0.64736(11) 0.7664(2) 0.43868(10) 0.0453(5) Uani 1 1 d . . . . .
C7 C 0.61284(12) 0.4455(3) 0.28980(12) 0.0216(5) Uani 1 1 d . . . . .
C11 C 0.50636(12) 0.8760(3) 0.34929(12) 0.0217(4) Uani 1 1 d . . . . .
C16 C 0.46056(12) 0.8307(3) 0.39401(12) 0.0213(4) Uani 1 1 d . . . . .
C9 C 0.50555(13) 0.6548(3) 0.25380(12) 0.0215(4) Uani 1 1 d . . . . .
C2 C 0.65259(13) 0.5362(3) 0.35698(12) 0.0233(5) Uani 1 1 d . . . . .
C8 C 0.53884(13) 0.5098(3) 0.23899(13) 0.0237(5) Uani 1 1 d . . . . .
H8 H 0.512381 0.449452 0.193766 0.028 Uiso 1 1 calc R U . . .
C15 C 0.41947(13) 0.9636(3) 0.41592(12) 0.0239(5) Uani 1 1 d . . . . .
C6 C 0.64821(13) 0.2961(3) 0.27395(13) 0.0261(5) Uani 1 1 d . . . . .
H6 H 0.622369 0.234774 0.228846 0.031 Uiso 1 1 calc R U . . .
C26 C 0.33795(13) 0.8370(3) 0.20174(13) 0.0255(5) Uani 1 1 d . . . . .
H26 H 0.361193 0.926424 0.240550 0.031 Uiso 1 1 calc R U . . .
C1 C 0.61687(14) 0.6884(3) 0.37765(13) 0.0282(5) Uani 1 1 d . . . . .
C12 C 0.51476(14) 1.0435(3) 0.33203(13) 0.0268(5) Uani 1 1 d . . . . .
H12 H 0.547629 1.071302 0.305309 0.032 Uiso 1 1 calc R U . . .
C20 C 0.46833(14) 0.9418(3) 0.13792(13) 0.0287(5) Uani 1 1 d . . . . .
H20 H 0.471550 1.036882 0.173676 0.034 Uiso 1 1 calc R U . . .
C14 C 0.42676(13) 1.1353(3) 0.39416(13) 0.0284(5) Uani 1 1 d . . . . .
H14 H 0.398753 1.222158 0.407319 0.034 Uiso 1 1 calc R U . . .
C5 C 0.71977(14) 0.2391(3) 0.32342(14) 0.0273(5) Uani 1 1 d . . . . .
C4 C 0.75949(14) 0.3348(3) 0.38961(14) 0.0295(5) Uani 1 1 d . . . . .
H4 H 0.808845 0.299032 0.422689 0.035 Uiso 1 1 calc R U . . .
C13 C 0.47398(14) 1.1752(3) 0.35438(14) 0.0298(5) Uani 1 1 d . . . . .
H13 H 0.479501 1.289128 0.341828 0.036 Uiso 1 1 calc R U . . .
C3 C 0.72653(14) 0.4818(3) 0.40666(13) 0.0299(5) Uani 1 1 d . . . . .
H3 H 0.753455 0.544439 0.451071 0.036 Uiso 1 1 calc R U . . .
C17 C 0.37369(14) 0.9162(3) 0.45986(13) 0.0303(5) Uani 1 1 d . . . . .
H17 H 0.345105 0.998805 0.474890 0.036 Uiso 1 1 calc R U . . .
C19 C 0.41591(14) 0.6274(3) 0.45687(13) 0.0284(5) Uani 1 1 d . . . . .
H19 H 0.414929 0.513879 0.472452 0.034 Uiso 1 1 calc R U . . .
C21 C 0.55284(15) 0.9048(3) 0.14426(15) 0.0359(6) Uani 1 1 d . . . . .
H21A H 0.553529 0.805883 0.113476 0.054 Uiso 1 1 calc R U . . .
H21B H 0.584710 0.882708 0.197247 0.054 Uiso 1 1 calc R U . . .
H21C H 0.573363 1.002543 0.126029 0.054 Uiso 1 1 calc R U . . .
C18 C 0.37175(14) 0.7488(3) 0.48005(13) 0.0310(5) Uani 1 1 d . . . . .
H18 H 0.341616 0.714994 0.508782 0.037 Uiso 1 1 calc R U . . .
C23 C 0.37834(15) 0.5934(3) 0.09015(14) 0.0334(6) Uani 1 1 d . . . . .
H23 H 0.331423 0.650942 0.054494 0.040 Uiso 1 1 calc R U . . .
C27 C 0.27185(15) 0.9243(3) 0.13613(14) 0.0355(6) Uani 1 1 d . . . . .
H27A H 0.251492 0.845876 0.093566 0.053 Uiso 1 1 calc R U . . .
H27B H 0.292026 1.025004 0.119602 0.053 Uiso 1 1 calc R U . . .
H27C H 0.230512 0.957017 0.154023 0.053 Uiso 1 1 calc R U . . .
C28 C 0.30342(15) 0.7031(3) 0.24066(15) 0.0364(6) Uani 1 1 d . . . . .
H28A H 0.276680 0.760202 0.270015 0.055 Uiso 1 1 calc R U . . .
H28B H 0.344999 0.633007 0.274495 0.055 Uiso 1 1 calc R U . . .
H28C H 0.266843 0.631760 0.201971 0.055 Uiso 1 1 calc R U . . .
C22 C 0.42168(16) 1.0106(3) 0.05717(14) 0.0394(6) Uani 1 1 d . . . . .
H22A H 0.448260 1.108797 0.046690 0.059 Uiso 1 1 calc R U . . .
H22B H 0.369997 1.043775 0.054499 0.059 Uiso 1 1 calc R U . . .
H22C H 0.417472 0.922527 0.019590 0.059 Uiso 1 1 calc R U . . .
C24 C 0.42647(18) 0.5506(4) 0.03985(15) 0.0448(7) Uani 1 1 d . . . . .
H24A H 0.471818 0.484287 0.069375 0.067 Uiso 1 1 calc R U . . .
H24B H 0.443094 0.655321 0.022877 0.067 Uiso 1 1 calc R U . . .
H24C H 0.394707 0.485175 -0.004273 0.067 Uiso 1 1 calc R U . . .
C10 C 0.75568(17) 0.0760(3) 0.30706(17) 0.0446(7) Uani 1 1 d . . . . .
H10A H 0.745726 -0.016907 0.336440 0.067 Uiso 1 1 calc R U . . .
H10B H 0.811421 0.091252 0.321356 0.067 Uiso 1 1 calc R U . . .
H10C H 0.732784 0.049608 0.252956 0.067 Uiso 1 1 calc R U . . .
C25 C 0.34612(17) 0.4273(3) 0.11245(18) 0.0473(7) Uani 1 1 d . . . . .
H25A H 0.318055 0.362882 0.066623 0.071 Uiso 1 1 calc R U . . .
H25B H 0.311154 0.455772 0.138947 0.071 Uiso 1 1 calc R U . . .
H25C H 0.388988 0.359473 0.145717 0.071 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
Si01 C26 1.895(2) . ?
Si01 C23 1.896(2) . ?
Si01 C9 1.908(2) . ?
Si01 C20 1.910(2) . ?
N1 C1 1.386(3) . ?
N1 C9 1.407(3) . ?
N1 C11 1.441(3) . ?
N2 C19 1.314(3) . ?
N2 C16 1.365(3) . ?
O1 C1 1.227(3) . ?
C7 C2 1.387(3) . ?
C7 C6 1.409(3) . ?
C7 C8 1.428(3) . ?
C11 C12 1.361(3) . ?
C11 C16 1.417(3) . ?
C16 C15 1.418(3) . ?
C9 C8 1.353(3) . ?
C2 C3 1.396(3) . ?
C2 C1 1.465(3) . ?
C8 H8 0.9300 . ?
C15 C17 1.409(3) . ?
C15 C14 1.413(3) . ?
C6 C5 1.370(3) . ?
C6 H6 0.9300 . ?
C26 C28 1.525(3) . ?
C26 C27 1.528(3) . ?
C26 H26 0.9800 . ?
C12 C13 1.411(3) . ?
C12 H12 0.9300 . ?
C20 C22 1.528(3) . ?
C20 C21 1.529(3) . ?
C20 H20 0.9800 . ?
C14 C13 1.356(3) . ?
C14 H14 0.9300 . ?
C5 C4 1.394(3) . ?
C5 C10 1.506(3) . ?
C4 C3 1.379(3) . ?
C4 H4 0.9300 . ?
C13 H13 0.9300 . ?
C3 H3 0.9300 . ?
C17 C18 1.357(3) . ?
C17 H17 0.9300 . ?
C19 C18 1.404(3) . ?
C19 H19 0.9300 . ?
C21 H21A 0.9600 . ?
C21 H21B 0.9600 . ?
C21 H21C 0.9600 . ?
C18 H18 0.9300 . ?
C23 C24 1.530(3) . ?
C23 C25 1.535(4) . ?
C23 H23 0.9800 . ?
C27 H27A 0.9600 . ?
C27 H27B 0.9600 . ?
C27 H27C 0.9600 . ?
C28 H28A 0.9600 . ?
C28 H28B 0.9600 . ?
C28 H28C 0.9600 . ?
C22 H22A 0.9600 . ?
C22 H22B 0.9600 . ?
C22 H22C 0.9600 . ?
C24 H24A 0.9600 . ?
C24 H24B 0.9600 . ?
C24 H24C 0.9600 . ?
C10 H10A 0.9600 . ?
C10 H10B 0.9600 . ?
C10 H10C 0.9600 . ?
C25 H25A 0.9600 . ?
C25 H25B 0.9600 . ?
C25 H25C 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
C26 Si01 C23 108.81(11) . . ?
C26 Si01 C9 113.69(10) . . ?
C23 Si01 C9 110.32(10) . . ?
C26 Si01 C20 110.12(10) . . ?
C23 Si01 C20 110.23(11) . . ?
C9 Si01 C20 103.58(10) . . ?
C1 N1 C9 124.44(17) . . ?
C1 N1 C11 115.11(17) . . ?
C9 N1 C11 119.86(17) . . ?
C19 N2 C16 116.64(19) . . ?
C2 C7 C6 118.4(2) . . ?
C2 C7 C8 118.57(19) . . ?
C6 C7 C8 123.0(2) . . ?
C12 C11 C16 120.99(19) . . ?
C12 C11 N1 120.90(19) . . ?
C16 C11 N1 118.09(18) . . ?
N2 C16 C11 118.92(18) . . ?
N2 C16 C15 123.03(19) . . ?
C11 C16 C15 118.04(19) . . ?
C8 C9 N1 117.48(19) . . ?
C8 C9 Si01 118.07(16) . . ?
N1 C9 Si01 123.27(15) . . ?
C7 C2 C3 120.4(2) . . ?
C7 C2 C1 120.5(2) . . ?
C3 C2 C1 119.0(2) . . ?
C9 C8 C7 122.9(2) . . ?
C9 C8 H8 118.6 . . ?
C7 C8 H8 118.6 . . ?
C17 C15 C14 123.2(2) . . ?
C17 C15 C16 117.3(2) . . ?
C14 C15 C16 119.4(2) . . ?
C5 C6 C7 121.5(2) . . ?
C5 C6 H6 119.2 . . ?
C7 C6 H6 119.2 . . ?
C28 C26 C27 109.8(2) . . ?
C28 C26 Si01 114.64(16) . . ?
C27 C26 Si01 113.23(15) . . ?
C28 C26 H26 106.2 . . ?
C27 C26 H26 106.2 . . ?
Si01 C26 H26 106.2 . . ?
O1 C1 N1 121.1(2) . . ?
O1 C1 C2 122.9(2) . . ?
N1 C1 C2 115.97(19) . . ?
C11 C12 C13 120.5(2) . . ?
C11 C12 H12 119.7 . . ?
C13 C12 H12 119.7 . . ?
C22 C20 C21 109.29(19) . . ?
C22 C20 Si01 115.24(17) . . ?
C21 C20 Si01 113.42(16) . . ?
C22 C20 H20 106.0 . . ?
C21 C20 H20 106.0 . . ?
Si01 C20 H20 106.0 . . ?
C13 C14 C15 121.0(2) . . ?
C13 C14 H14 119.5 . . ?
C15 C14 H14 119.5 . . ?
C6 C5 C4 119.0(2) . . ?
C6 C5 C10 121.0(2) . . ?
C4 C5 C10 120.0(2) . . ?
C3 C4 C5 120.9(2) . . ?
C3 C4 H4 119.6 . . ?
C5 C4 H4 119.6 . . ?
C14 C13 C12 119.9(2) . . ?
C14 C13 H13 120.0 . . ?
C12 C13 H13 120.0 . . ?
C4 C3 C2 119.7(2) . . ?
C4 C3 H3 120.1 . . ?
C2 C3 H3 120.1 . . ?
C18 C17 C15 119.3(2) . . ?
C18 C17 H17 120.3 . . ?
C15 C17 H17 120.3 . . ?
N2 C19 C18 124.7(2) . . ?
N2 C19 H19 117.7 . . ?
C18 C19 H19 117.7 . . ?
C20 C21 H21A 109.5 . . ?
C20 C21 H21B 109.5 . . ?
H21A C21 H21B 109.5 . . ?
C20 C21 H21C 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
C17 C18 C19 119.0(2) . . ?
C17 C18 H18 120.5 . . ?
C19 C18 H18 120.5 . . ?
C24 C23 C25 109.9(2) . . ?
C24 C23 Si01 118.18(18) . . ?
C25 C23 Si01 115.20(18) . . ?
C24 C23 H23 103.9 . . ?
C25 C23 H23 103.9 . . ?
Si01 C23 H23 103.9 . . ?
C26 C27 H27A 109.5 . . ?
C26 C27 H27B 109.5 . . ?
H27A C27 H27B 109.5 . . ?
C26 C27 H27C 109.5 . . ?
H27A C27 H27C 109.5 . . ?
H27B C27 H27C 109.5 . . ?
C26 C28 H28A 109.5 . . ?
C26 C28 H28B 109.5 . . ?
H28A C28 H28B 109.5 . . ?
C26 C28 H28C 109.5 . . ?
H28A C28 H28C 109.5 . . ?
H28B C28 H28C 109.5 . . ?
C20 C22 H22A 109.5 . . ?
C20 C22 H22B 109.5 . . ?
H22A C22 H22B 109.5 . . ?
C20 C22 H22C 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
C23 C24 H24A 109.5 . . ?
C23 C24 H24B 109.5 . . ?
H24A C24 H24B 109.5 . . ?
C23 C24 H24C 109.5 . . ?
H24A C24 H24C 109.5 . . ?
H24B C24 H24C 109.5 . . ?
C5 C10 H10A 109.5 . . ?
C5 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
C5 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
C23 C25 H25A 109.5 . . ?
C23 C25 H25B 109.5 . . ?
H25A C25 H25B 109.5 . . ?
C23 C25 H25C 109.5 . . ?
H25A C25 H25C 109.5 . . ?
H25B C25 H25C 109.5 . . ?

_refine_diff_density_max         0.380
_refine_diff_density_min         -0.448
_refine_diff_density_rms         0.066

