# Electronic Supplementary Material (ESI) for Green Chemistry.
# This journal is © The Royal Society of Chemistry 2023

####################################################################### 
# 
# 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_con037v_0ms
_database_code_depnum_ccdc_archive 'CCDC 2218009'
loop_
_audit_author_name
_audit_author_address
'M. Concepcion Gimeno'
;Instituto de Sintesis Quimica y Catalisis Homogenea
Spain
;
_audit_update_record             
;
2022-11-07 deposited with the CCDC.	2023-05-31 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            'C24 H21 N'
_chemical_formula_weight         323.42

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'

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

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

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

_cell_length_a                   7.6105(10)
_cell_length_b                   12.1722(14)
_cell_length_c                   19.257(2)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1783.9(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    9759
_cell_measurement_theta_min      2.37
_cell_measurement_theta_max      28.28

_exptl_crystal_description       prism
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.204
_exptl_crystal_F_000             688
_exptl_transmission_factor_min   0.978
_exptl_transmission_factor_max   0.990
_exptl_crystal_size_max          0.330
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.140
_exptl_absorpt_coefficient_mu    0.069
_shelx_estimated_absorpt_T_min   0.978
_shelx_estimated_absorpt_T_max   0.990
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.978
_exptl_absorpt_correction_T_max  0.990
_exptl_absorpt_process_details   SADABS
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker Venture'
_diffrn_measurement_method       'w rotations'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            30439
_diffrn_reflns_av_unetI/netI     0.0306
_diffrn_reflns_av_R_equivalents  0.0477
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_theta_min         1.979
_diffrn_reflns_theta_max         28.311
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measured_fraction_theta_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             4423
_reflns_number_gt                4259
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.751
_reflns_Friedel_fraction_max     0.999
_reflns_Friedel_fraction_full    1.000

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

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          
;
 Refined as a 2-component inversion twin.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0444P)²+0.2363P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   0(3)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         4423
_refine_ls_number_parameters     228
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0321
_refine_ls_R_factor_gt           0.0308
_refine_ls_wR_factor_ref         0.0822
_refine_ls_wR_factor_gt          0.0812
_refine_ls_goodness_of_fit_ref   1.043
_refine_ls_restrained_S_all      1.043
_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
N1 N 0.14261(16) 0.59830(10) 0.80776(6) 0.0244(3) Uani 1 1 d . . . . .
C1 C 0.13842(19) 0.90200(13) 0.80867(8) 0.0274(3) Uani 1 1 d . . . . .
H1 H 0.104454 0.964639 0.834861 0.033 Uiso 1 1 calc R U . . .
C2 C 0.2221(2) 0.91664(12) 0.74408(8) 0.0266(3) Uani 1 1 d . . . . .
H19 H 0.242384 0.988910 0.727256 0.032 Uiso 1 1 calc R U . . .
C3 C 0.27547(18) 0.82744(12) 0.70469(7) 0.0238(3) Uani 1 1 d . . . . .
H18 H 0.332301 0.838194 0.661290 0.029 Uiso 1 1 calc R U . . .
C4 C 0.24439(17) 0.72115(12) 0.72975(7) 0.0210(3) Uani 1 1 d . . . . .
C5 C 0.27965(17) 0.61247(11) 0.70433(7) 0.0211(3) Uani 1 1 d . . . . .
C6 C 0.36278(18) 0.58304(11) 0.63561(7) 0.0209(3) Uani 1 1 d . . . . .
H6 H 0.281136 0.607049 0.597853 0.025 Uiso 1 1 calc R U . . .
C7 C 0.38854(17) 0.46062(11) 0.62894(7) 0.0217(3) Uani 1 1 d . . . . .
H17 H 0.470109 0.426503 0.659428 0.026 Uiso 1 1 calc R U . . .
C8 C 0.30524(18) 0.39705(12) 0.58346(7) 0.0212(3) Uani 1 1 d . . . . .
H16 H 0.222164 0.431497 0.553764 0.025 Uiso 1 1 calc R U . . .
C9 C 0.33069(17) 0.27772(12) 0.57513(7) 0.0205(3) Uani 1 1 d . . . . .
C10 C 0.42640(18) 0.21466(12) 0.62294(7) 0.0236(3) Uani 1 1 d . . . . .
H13 H 0.473781 0.248618 0.663217 0.028 Uiso 1 1 calc R U . . .
C11 C 0.45252(19) 0.10344(13) 0.61201(8) 0.0271(3) Uani 1 1 d . . . . .
H14 H 0.516873 0.061653 0.645019 0.032 Uiso 1 1 calc R U . . .
C12 C 0.3853(2) 0.05234(12) 0.55307(8) 0.0275(3) Uani 1 1 d . . . . .
H2 H 0.406020 -0.023609 0.545210 0.033 Uiso 1 1 calc R U . . .
C13 C 0.10482(18) 0.79851(13) 0.83461(7) 0.0247(3) Uani 1 1 d . . . . .
H21 H 0.047123 0.788610 0.877911 0.030 Uiso 1 1 calc R U . . .
C14 C 0.15892(17) 0.70881(12) 0.79474(7) 0.0219(3) Uani 1 1 d . . . . .
C15 C 0.0703(2) 0.55102(14) 0.87083(8) 0.0315(3) Uani 1 1 d . . . . .
H3 H 0.147128 0.568574 0.910133 0.047 Uiso 1 1 calc R U . . .
H4 H 0.061943 0.471091 0.865679 0.047 Uiso 1 1 calc R U . . .
H5 H -0.046986 0.581486 0.879239 0.047 Uiso 1 1 calc R U . . .
C16 C 0.21648(18) 0.54132(12) 0.75330(7) 0.0239(3) Uani 1 1 d . . . . .
H20 H 0.222682 0.463524 0.750189 0.029 Uiso 1 1 calc R U . . .
C17 C 0.54015(17) 0.63956(11) 0.62372(7) 0.0200(3) Uani 1 1 d . . . . .
C18 C 0.64600(18) 0.67325(12) 0.67871(7) 0.0237(3) Uani 1 1 d . . . . .
H11 H 0.605219 0.665017 0.725048 0.028 Uiso 1 1 calc R U . . .
C19 C 0.81069(19) 0.71880(13) 0.66659(8) 0.0264(3) Uani 1 1 d . . . . .
H10 H 0.881947 0.741066 0.704578 0.032 Uiso 1 1 calc R U . . .
C20 C 0.87108(19) 0.73179(12) 0.59922(8) 0.0269(3) Uani 1 1 d . . . . .
H7 H 0.983854 0.762552 0.590912 0.032 Uiso 1 1 calc R U . . .
C21 C 0.7659(2) 0.69959(12) 0.54382(8) 0.0263(3) Uani 1 1 d . . . . .
H9 H 0.805719 0.709584 0.497496 0.032 Uiso 1 1 calc R U . . .
C22 C 0.60231(19) 0.65275(11) 0.55627(7) 0.0232(3) Uani 1 1 d . . . . .
H8 H 0.532057 0.629451 0.518243 0.028 Uiso 1 1 calc R U . . .
C23 C 0.26003(18) 0.22462(12) 0.51698(7) 0.0236(3) Uani 1 1 d . . . . .
H12 H 0.192131 0.265462 0.484622 0.028 Uiso 1 1 calc R U . . .
C24 C 0.2876(2) 0.11315(12) 0.50584(8) 0.0272(3) Uani 1 1 d . . . . .
H15 H 0.239622 0.078552 0.465890 0.033 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
N1 C14 1.3739(18) . ?
N1 C16 1.3773(18) . ?
N1 C15 1.4524(18) . ?
C1 C13 1.379(2) . ?
C1 C2 1.409(2) . ?
C1 H1 0.9500 . ?
C2 C3 1.385(2) . ?
C2 H19 0.9500 . ?
C3 C4 1.401(2) . ?
C3 H18 0.9500 . ?
C4 C14 1.4185(18) . ?
C4 C5 1.4358(19) . ?
C5 C16 1.368(2) . ?
C5 C6 1.5098(18) . ?
C6 C7 1.5085(19) . ?
C6 C17 1.5323(19) . ?
C6 H6 1.0000 . ?
C7 C8 1.3296(19) . ?
C7 H17 0.9500 . ?
C8 C9 1.4741(19) . ?
C8 H16 0.9500 . ?
C9 C23 1.4002(18) . ?
C9 C10 1.4026(19) . ?
C10 C11 1.384(2) . ?
C10 H13 0.9500 . ?
C11 C12 1.392(2) . ?
C11 H14 0.9500 . ?
C12 C24 1.388(2) . ?
C12 H2 0.9500 . ?
C13 C14 1.397(2) . ?
C13 H21 0.9500 . ?
C15 H3 0.9800 . ?
C15 H4 0.9800 . ?
C15 H5 0.9800 . ?
C16 H20 0.9500 . ?
C17 C22 1.3916(19) . ?
C17 C18 1.3924(19) . ?
C18 C19 1.390(2) . ?
C18 H11 0.9500 . ?
C19 C20 1.385(2) . ?
C19 H10 0.9500 . ?
C20 C21 1.390(2) . ?
C20 H7 0.9500 . ?
C21 C22 1.390(2) . ?
C21 H9 0.9500 . ?
C22 H8 0.9500 . ?
C23 C24 1.390(2) . ?
C23 H12 0.9500 . ?
C24 H15 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
C14 N1 C16 108.50(12) . . ?
C14 N1 C15 125.08(13) . . ?
C16 N1 C15 126.29(13) . . ?
C13 C1 C2 121.28(13) . . ?
C13 C1 H1 119.4 . . ?
C2 C1 H1 119.4 . . ?
C3 C2 C1 121.12(14) . . ?
C3 C2 H19 119.4 . . ?
C1 C2 H19 119.4 . . ?
C2 C3 C4 119.06(13) . . ?
C2 C3 H18 120.5 . . ?
C4 C3 H18 120.5 . . ?
C3 C4 C14 118.63(12) . . ?
C3 C4 C5 134.57(12) . . ?
C14 C4 C5 106.80(12) . . ?
C16 C5 C4 106.42(12) . . ?
C16 C5 C6 126.97(13) . . ?
C4 C5 C6 126.57(12) . . ?
C7 C6 C5 111.31(11) . . ?
C7 C6 C17 108.44(11) . . ?
C5 C6 C17 113.18(11) . . ?
C7 C6 H6 107.9 . . ?
C5 C6 H6 107.9 . . ?
C17 C6 H6 107.9 . . ?
C8 C7 C6 124.68(13) . . ?
C8 C7 H17 117.7 . . ?
C6 C7 H17 117.7 . . ?
C7 C8 C9 125.63(13) . . ?
C7 C8 H16 117.2 . . ?
C9 C8 H16 117.2 . . ?
C23 C9 C10 118.14(13) . . ?
C23 C9 C8 119.43(13) . . ?
C10 C9 C8 122.41(12) . . ?
C11 C10 C9 120.66(13) . . ?
C11 C10 H13 119.7 . . ?
C9 C10 H13 119.7 . . ?
C10 C11 C12 120.54(14) . . ?
C10 C11 H14 119.7 . . ?
C12 C11 H14 119.7 . . ?
C24 C12 C11 119.53(14) . . ?
C24 C12 H2 120.2 . . ?
C11 C12 H2 120.2 . . ?
C1 C13 C14 117.40(13) . . ?
C1 C13 H21 121.3 . . ?
C14 C13 H21 121.3 . . ?
N1 C14 C13 129.67(13) . . ?
N1 C14 C4 107.82(12) . . ?
C13 C14 C4 122.51(13) . . ?
N1 C15 H3 109.5 . . ?
N1 C15 H4 109.5 . . ?
H3 C15 H4 109.5 . . ?
N1 C15 H5 109.5 . . ?
H3 C15 H5 109.5 . . ?
H4 C15 H5 109.5 . . ?
C5 C16 N1 110.46(13) . . ?
C5 C16 H20 124.8 . . ?
N1 C16 H20 124.8 . . ?
C22 C17 C18 118.63(13) . . ?
C22 C17 C6 119.39(12) . . ?
C18 C17 C6 121.89(12) . . ?
C19 C18 C17 120.76(13) . . ?
C19 C18 H11 119.6 . . ?
C17 C18 H11 119.6 . . ?
C20 C19 C18 120.11(14) . . ?
C20 C19 H10 119.9 . . ?
C18 C19 H10 119.9 . . ?
C19 C20 C21 119.70(13) . . ?
C19 C20 H7 120.2 . . ?
C21 C20 H7 120.2 . . ?
C22 C21 C20 119.94(13) . . ?
C22 C21 H9 120.0 . . ?
C20 C21 H9 120.0 . . ?
C21 C22 C17 120.85(13) . . ?
C21 C22 H8 119.6 . . ?
C17 C22 H8 119.6 . . ?
C24 C23 C9 121.08(14) . . ?
C24 C23 H12 119.5 . . ?
C9 C23 H12 119.5 . . ?
C12 C24 C23 120.02(14) . . ?
C12 C24 H15 120.0 . . ?
C23 C24 H15 120.0 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C13 C1 C2 C3 -0.7(2) . . . . ?
C1 C2 C3 C4 0.3(2) . . . . ?
C2 C3 C4 C14 0.09(19) . . . . ?
C2 C3 C4 C5 179.99(14) . . . . ?
C3 C4 C5 C16 -179.97(15) . . . . ?
C14 C4 C5 C16 -0.07(14) . . . . ?
C3 C4 C5 C6 -2.4(2) . . . . ?
C14 C4 C5 C6 177.47(12) . . . . ?
C16 C5 C6 C7 -6.38(19) . . . . ?
C4 C5 C6 C7 176.58(12) . . . . ?
C16 C5 C6 C17 -128.81(15) . . . . ?
C4 C5 C6 C17 54.15(18) . . . . ?
C5 C6 C7 C8 113.78(15) . . . . ?
C17 C6 C7 C8 -121.09(14) . . . . ?
C6 C7 C8 C9 178.79(13) . . . . ?
C7 C8 C9 C23 -167.94(14) . . . . ?
C7 C8 C9 C10 10.9(2) . . . . ?
C23 C9 C10 C11 1.1(2) . . . . ?
C8 C9 C10 C11 -177.74(13) . . . . ?
C9 C10 C11 C12 0.5(2) . . . . ?
C10 C11 C12 C24 -1.6(2) . . . . ?
C2 C1 C13 C14 0.7(2) . . . . ?
C16 N1 C14 C13 -179.82(14) . . . . ?
C15 N1 C14 C13 -3.7(2) . . . . ?
C16 N1 C14 C4 0.52(15) . . . . ?
C15 N1 C14 C4 176.62(13) . . . . ?
C1 C13 C14 N1 -179.99(14) . . . . ?
C1 C13 C14 C4 -0.4(2) . . . . ?
C3 C4 C14 N1 179.65(12) . . . . ?
C5 C4 C14 N1 -0.28(14) . . . . ?
C3 C4 C14 C13 -0.04(19) . . . . ?
C5 C4 C14 C13 -179.97(12) . . . . ?
C4 C5 C16 N1 0.39(16) . . . . ?
C6 C5 C16 N1 -177.13(12) . . . . ?
C14 N1 C16 C5 -0.58(16) . . . . ?
C15 N1 C16 C5 -176.63(13) . . . . ?
C7 C6 C17 C22 78.50(15) . . . . ?
C5 C6 C17 C22 -157.48(12) . . . . ?
C7 C6 C17 C18 -98.09(15) . . . . ?
C5 C6 C17 C18 25.92(18) . . . . ?
C22 C17 C18 C19 -0.2(2) . . . . ?
C6 C17 C18 C19 176.40(13) . . . . ?
C17 C18 C19 C20 0.4(2) . . . . ?
C18 C19 C20 C21 0.3(2) . . . . ?
C19 C20 C21 C22 -1.2(2) . . . . ?
C20 C21 C22 C17 1.4(2) . . . . ?
C18 C17 C22 C21 -0.6(2) . . . . ?
C6 C17 C22 C21 -177.35(12) . . . . ?
C10 C9 C23 C24 -1.7(2) . . . . ?
C8 C9 C23 C24 177.25(13) . . . . ?
C11 C12 C24 C23 1.1(2) . . . . ?
C9 C23 C24 C12 0.6(2) . . . . ?

_refine_diff_density_max         0.176
_refine_diff_density_min         -0.166
_refine_diff_density_rms         0.033

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

data_mo_con08v_0ms
_database_code_depnum_ccdc_archive 'CCDC 2252454'
loop_
_audit_author_name
_audit_author_address
'M. Concepcion Gimeno'
;Instituto de Sintesis Quimica y Catalisis Homogenea
Spain
;
_audit_update_record             
;
2023-03-29 deposited with the CCDC.	2023-05-31 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            'C23 H23 N'
_chemical_formula_weight         313.42

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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

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

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

_cell_length_a                   15.447(3)
_cell_length_b                   5.6795(11)
_cell_length_c                   21.658(4)
_cell_angle_alpha                90
_cell_angle_beta                 108.34(3)
_cell_angle_gamma                90
_cell_volume                     1803.6(7)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    7437
_cell_measurement_theta_min      2.81
_cell_measurement_theta_max      28.13

_exptl_crystal_description       needle
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.154
_exptl_crystal_F_000             672
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.160
_exptl_crystal_size_mid          0.130
_exptl_crystal_size_min          0.060
_exptl_absorpt_coefficient_mu    0.066
_shelx_estimated_absorpt_T_min   0.989
_shelx_estimated_absorpt_T_max   0.996
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6565
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_process_details   SADABS
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'APEX Venture'
_diffrn_measurement_method       'ω rotations'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            22521
_diffrn_reflns_av_unetI/netI     0.0240
_diffrn_reflns_av_R_equivalents  0.0362
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_theta_min         1.981
_diffrn_reflns_theta_max         25.499
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_point_group_measured_fraction_full 0.997
_reflns_number_total             3334
_reflns_number_gt                2822
_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       Apex4
_computing_cell_refinement       Apex4
_computing_data_reduction        Apex4
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_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)+(0.1597P)²+2.0613P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3334
_refine_ls_number_parameters     219
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1029
_refine_ls_R_factor_gt           0.0925
_refine_ls_wR_factor_ref         0.2781
_refine_ls_wR_factor_gt          0.2656
_refine_ls_goodness_of_fit_ref   1.057
_refine_ls_restrained_S_all      1.057
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.82396(17) 0.7049(5) 0.84923(12) 0.0325(6) Uani 1 1 d . . . . .
H1 H 0.853807 0.553816 0.843503 0.039 Uiso 1 1 calc R U . . .
C2 C 0.88954(16) 0.9049(5) 0.84857(12) 0.0318(6) Uani 1 1 d . . . . .
C3 C 0.89565(19) 0.9945(5) 0.79020(13) 0.0387(7) Uani 1 1 d . . . . .
H3 H 0.856613 0.933693 0.750274 0.046 Uiso 1 1 calc R U . . .
C4 C 0.95711(19) 1.1696(5) 0.78904(13) 0.0396(7) Uani 1 1 d . . . . .
H4 H 0.960186 1.226323 0.748521 0.048 Uiso 1 1 calc R U . . .
C5 C 1.01401(19) 1.2627(5) 0.84611(14) 0.0404(7) Uani 1 1 d . . . . .
H5 H 1.056563 1.382501 0.845306 0.048 Uiso 1 1 calc R U . . .
C6 C 1.0082(2) 1.1790(6) 0.90452(14) 0.0453(8) Uani 1 1 d . . . . .
H6 H 1.046935 1.242524 0.944164 0.054 Uiso 1 1 calc R U . . .
C7 C 0.94662(19) 1.0038(6) 0.90616(13) 0.0418(7) Uani 1 1 d . . . . .
H7 H 0.943108 0.950147 0.946843 0.050 Uiso 1 1 calc R U . . .
C8 C 0.80253(17) 0.6896(5) 0.91245(12) 0.0325(6) Uani 1 1 d . . . . .
H8 H 0.777361 0.826083 0.925584 0.039 Uiso 1 1 calc R U . . .
C9 C 0.81543(19) 0.5046(5) 0.95131(14) 0.0422(7) Uani 1 1 d . . . . .
H9 H 0.845636 0.373108 0.940269 0.051 Uiso 1 1 calc R U . . .
C10 C 0.78671(18) 0.4820(5) 1.01167(13) 0.0394(7) Uani 1 1 d . . . . .
C11 C 0.8153(3) 0.2833(6) 1.04993(18) 0.0576(9) Uani 1 1 d . . . . .
H11 H 0.852449 0.169916 1.038084 0.069 Uiso 1 1 calc R U . . .
C12 C 0.7899(3) 0.2487(6) 1.10584(16) 0.0588(9) Uani 1 1 d . . . . .
H12 H 0.809115 0.112816 1.132164 0.071 Uiso 1 1 calc R U . . .
C13 C 0.7352(3) 0.4203(7) 1.12195(16) 0.0594(10) Uani 1 1 d . . . . .
H13 H 0.716990 0.399998 1.159604 0.071 Uiso 1 1 calc R U . . .
C14 C 0.7084(3) 0.6128(7) 1.08484(18) 0.0616(10) Uani 1 1 d . . . . .
H14 H 0.672092 0.728427 1.096728 0.074 Uiso 1 1 calc R U . . .
C15 C 0.7338(2) 0.6438(7) 1.02844(16) 0.0546(9) Uani 1 1 d . . . . .
H15 H 0.713634 0.779008 1.001980 0.065 Uiso 1 1 calc R U . . .
C16 C 0.73471(18) 0.7246(5) 0.79387(12) 0.0350(6) Uani 1 1 d . . . . .
C17 C 0.7074(2) 0.5413(7) 0.74931(15) 0.0516(8) Uani 1 1 d . . . . .
H17 H 0.746062 0.408062 0.753825 0.062 Uiso 1 1 calc R U . . .
C18 C 0.6268(3) 0.5456(7) 0.69918(17) 0.0597(9) Uani 1 1 d . . . . .
H18 H 0.610934 0.417398 0.669560 0.072 Uiso 1 1 calc R U . . .
C19 C 0.5696(2) 0.7321(8) 0.69171(14) 0.0574(10) Uani 1 1 d . . . . .
C20 C 0.5959(2) 0.9218(7) 0.73761(15) 0.0520(9) Uani 1 1 d . . . . .
H20 H 0.557462 1.054981 0.734008 0.062 Uiso 1 1 calc R U . . .
C21 C 0.6778(2) 0.9078(6) 0.78698(14) 0.0432(7) Uani 1 1 d . . . . .
H21 H 0.694625 1.033318 0.817412 0.052 Uiso 1 1 calc R U . . .
C22 C 0.4668(4) 0.5918(11) 0.5901(2) 0.107(2) Uani 1 1 d . . . . .
H22A H 0.513852 0.605109 0.568735 0.160 Uiso 1 1 calc R U . . .
H22B H 0.407129 0.629257 0.558914 0.160 Uiso 1 1 calc R U . . .
H22C H 0.466020 0.430639 0.606148 0.160 Uiso 1 1 calc R U . . .
C23 C 0.4316(3) 0.9454(14) 0.6356(3) 0.114(2) Uani 1 1 d . . . . .
H23A H 0.461128 1.079022 0.621814 0.171 Uiso 1 1 calc R U . . .
H23B H 0.423287 0.981120 0.677700 0.171 Uiso 1 1 calc R U . . .
H23C H 0.372006 0.916451 0.603211 0.171 Uiso 1 1 calc R U . . .
N1 N 0.4857(2) 0.7468(10) 0.64161(17) 0.0952(15) Uani 1 1 d . . . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 C8 1.509(3) . ?
C1 C16 1.520(4) . ?
C1 C2 1.525(4) . ?
C2 C3 1.393(4) . ?
C2 C7 1.399(4) . ?
C3 C4 1.381(4) . ?
C4 C5 1.377(4) . ?
C5 C6 1.381(4) . ?
C6 C7 1.384(4) . ?
C8 C9 1.322(4) . ?
C9 C10 1.512(4) . ?
C10 C15 1.354(5) . ?
C10 C11 1.387(5) . ?
C11 C12 1.399(5) . ?
C12 C13 1.403(6) . ?
C13 C14 1.343(5) . ?
C14 C15 1.406(5) . ?
C16 C21 1.340(4) . ?
C16 C17 1.392(4) . ?
C17 C18 1.371(5) . ?
C18 C19 1.356(6) . ?
C19 N1 1.407(4) . ?
C19 C20 1.435(5) . ?
C20 C21 1.378(5) . ?
C22 N1 1.378(7) . ?
C23 N1 1.386(8) . ?

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 C1 C16 108.5(2) . . ?
C8 C1 C2 112.8(2) . . ?
C16 C1 C2 112.2(2) . . ?
C3 C2 C7 117.3(3) . . ?
C3 C2 C1 121.0(2) . . ?
C7 C2 C1 121.7(2) . . ?
C4 C3 C2 121.5(2) . . ?
C5 C4 C3 120.6(3) . . ?
C4 C5 C6 118.9(3) . . ?
C5 C6 C7 121.0(3) . . ?
C6 C7 C2 120.7(3) . . ?
C9 C8 C1 126.3(3) . . ?
C8 C9 C10 126.3(3) . . ?
C15 C10 C11 119.8(3) . . ?
C15 C10 C9 122.7(3) . . ?
C11 C10 C9 117.4(3) . . ?
C10 C11 C12 120.5(3) . . ?
C11 C12 C13 118.2(3) . . ?
C14 C13 C12 120.9(3) . . ?
C13 C14 C15 120.2(4) . . ?
C10 C15 C14 120.3(3) . . ?
C21 C16 C17 117.3(3) . . ?
C21 C16 C1 123.1(3) . . ?
C17 C16 C1 119.6(3) . . ?
C18 C17 C16 122.5(3) . . ?
C19 C18 C17 120.2(3) . . ?
C18 C19 N1 123.1(4) . . ?
C18 C19 C20 118.2(3) . . ?
N1 C19 C20 118.8(4) . . ?
C21 C20 C19 119.0(3) . . ?
C16 C21 C20 122.8(3) . . ?
C22 N1 C23 118.5(4) . . ?
C22 N1 C19 119.7(4) . . ?
C23 N1 C19 120.2(5) . . ?

_refine_diff_density_max         0.910
_refine_diff_density_min         -0.326
_refine_diff_density_rms         0.069

