data_ia817b
_publ_requested_journal           JACS
_publ_contact_author_name        'Ivan Aprahamian'
_publ_contact_author_address     
'Department of Chemistry, Dartmouth College, Hanover, New Hampshire 03755, USA.'
_publ_contact_author_email       ivan.aprahamian@dartmouth.edu
_publ_contact_author_phone       '(603) 646-9666'
_publ_contact_author_fax         '(603) 646-3946'
loop_
_publ_author_name
_publ_author_address
'Aprahamian, Ivan'
'Department of Chemistry, Dartmouth College, Hanover, New Hampshire 03755, USA.'
_audit_creation_date             2017-08-18
_audit_creation_method           
;
Olex2 1.2-alpha
(compiled 2017.08.10 svn.r3458 for OlexSys, GUI svn.r5375)
;
_shelxl_version_number           2014/6
_publ_contact_author_id_orcid    ?
_publ_section_references         
;
Dolomanov, O.V., Bourhis, L.J., Gildea, R.J, Howard, J.A.K. & Puschmann, H.
 (2009), J. Appl. Cryst. 42, 339-341.

Sheldrick, G.M. (2008). Acta Cryst. A64, 112-122.

Sheldrick, G.M. (2015). Acta Cryst. A71, 3-8.
;
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C19 H23 N3 O2'
_chemical_formula_sum            'C19 H23 N3 O2'
_chemical_formula_weight         325.40
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

_cell_length_a                   13.9142(2)
_cell_length_b                   8.66870(10)
_cell_length_c                   15.2614(2)
_cell_angle_alpha                90
_cell_angle_beta                 106.4280(10)
_cell_angle_gamma                90
_cell_volume                     1765.65(4)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9904
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      72.18
_cell_measurement_theta_min      3.02
_shelx_estimated_absorpt_T_max   0.786
_shelx_estimated_absorpt_T_min   0.770
_exptl_absorpt_coefficient_mu    0.646
_exptl_absorpt_correction_T_max  0.7536
_exptl_absorpt_correction_T_min  0.6766
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'SADABS-2012/1 (Bruker,2012) was used for absorption correction. wR2(int) was 0.0751 before and 0.0455 after correction. The Ratio of minimum to maximum transmission is 0.8978. The λ/2 correction factor is 0.0015.'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.224
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       chunk
_exptl_crystal_F_000             696
_exptl_crystal_recrystallization_method 'used as received'
_exptl_crystal_size_max          0.426
_exptl_crystal_size_mid          0.4
_exptl_crystal_size_min          0.391
_exptl_special_details           
;
Data was collected using a BRUKER CCD (charge coupled device) based
diffractometer equipped with an Oxford low-temperature apparatus operating at
173 K.  A suitable crystal was chosen and mounted on a nylon loop using 
Paratone oil.  Data  were measured using omega and phi scans of 1.0° per frame 
for 30 s. The total number of images were based on 
results from the program COSMO where redundancy was expected to be 4 and 
completeness to 0.83Å to 100%. Cell parameters were
retrieved using APEX II software and refined using SAINT on all observed
reflections.Data reduction was performed using the SAINT software which 
corrects for Lp. Scaling and absorption corrections were applied using SADABS6 
multi-scan technique, supplied by George Sheldrick.  The structures are solved 
by the direct method using the SHELXS-97 program and refined by least squares 
method on F2, SHELXL-97, incorporated in OLEX2. 
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0296
_diffrn_reflns_av_unetI/netI     0.0239
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.990
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            17872
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.990
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         72.191
_diffrn_reflns_theta_min         3.311
_diffrn_ambient_temperature      173(2)
_diffrn_detector_area_resol_mean 836.6
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.990
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'ω and φ'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_source                   'sealed tube'
_diffrn_standards_interval_count .
_diffrn_standards_interval_time  .
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3019
_reflns_number_total             3458
_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       'SAINT v8.34A (Bruker, 2013)'
_computing_data_collection       'COSMO (BRUKER, V1.61, 2009)'
_computing_data_reduction        'SAINT v8.34A (Bruker, 2013)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.168
_refine_diff_density_min         -0.165
_refine_diff_density_rms         0.032
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.039
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     221
_refine_ls_number_reflns         3458
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0416
_refine_ls_R_factor_gt           0.0361
_refine_ls_restrained_S_all      1.039
_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)+(0.0473P)²+0.3793P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0940
_refine_ls_wR_factor_ref         0.0982
_refine_special_details          
;
The structure was refined by Least Squares using version 2014/6 
of XL (Sheldrick, 2008) incorporated in Olex2 (Dolomanov et al., 2009). 
All non-hydrogen atoms were refined anisotropically. 
Hydrogen atom positions were calculated geometrically and refined using the riding model.
;
_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)
2.b Aromatic/amide H refined with riding coordinates:
 C4(H4), C5(H5), C7(H7), C8(H8), C15(H15), C16(H16), C17(H17), C18(H18),
 C19(H19)
2.c Idealised Me refined as rotating group:
 C10(H10A,H10B,H10C), C11(H11A,H11B,H11C), C12(H12A,H12B,H12C), C13(H13A,H13B,
 H13C)
;
_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 0.07685(6) 0.51748(10) 0.24554(6) 0.0403(2) Uani 1 1 d . . . . .
O2 O 0.14628(7) 0.72705(11) 0.32660(6) 0.0437(2) Uani 1 1 d . . . . .
N1 N 0.25731(7) 0.62745(12) 0.17903(7) 0.0347(2) Uani 1 1 d . . . . .
N2 N 0.17049(7) 0.71755(12) 0.12892(6) 0.0344(2) Uani 1 1 d . . . . .
N3 N 0.53331(8) 0.21477(14) 0.50663(7) 0.0433(3) Uani 1 1 d . . . . .
C1 C 0.24408(8) 0.57526(13) 0.25343(7) 0.0303(2) Uani 1 1 d . . . . .
C2 C 0.15005(8) 0.61809(14) 0.27940(7) 0.0326(3) Uani 1 1 d . . . . .
C3 C 0.31974(8) 0.48185(13) 0.31748(7) 0.0297(2) Uani 1 1 d . . . . .
C4 C 0.41424(9) 0.45266(14) 0.30543(8) 0.0340(3) Uani 1 1 d . . . . .
H4 H 0.4300 0.4937 0.2534 0.041 Uiso 1 1 calc R . . . .
C5 C 0.48473(8) 0.36597(15) 0.36720(8) 0.0361(3) Uani 1 1 d . . . . .
H5 H 0.5482 0.3485 0.3571 0.043 Uiso 1 1 calc R . . . .
C6 C 0.46436(9) 0.30234(13) 0.44551(8) 0.0337(3) Uani 1 1 d . . . . .
C7 C 0.36957(9) 0.33269(15) 0.45733(8) 0.0361(3) Uani 1 1 d . . . . .
H7 H 0.3533 0.2923 0.5092 0.043 Uiso 1 1 calc R . . . .
C8 C 0.30005(8) 0.41992(14) 0.39497(8) 0.0338(3) Uani 1 1 d . . . . .
H8 H 0.2367 0.4385 0.4050 0.041 Uiso 1 1 calc R . . . .
C9 C -0.02134(9) 0.55354(19) 0.25836(10) 0.0484(3) Uani 1 1 d . . . . .
H9A H -0.0128 0.6224 0.3118 0.058 Uiso 1 1 calc R . . . .
H9B H -0.0540 0.4574 0.2701 0.058 Uiso 1 1 calc R . . . .
C10 C -0.08523(10) 0.63039(18) 0.17495(10) 0.0491(3) Uani 1 1 d . . . . .
H10A H -0.0936 0.5617 0.1223 0.074 Uiso 1 1 calc GR . . . .
H10B H -0.0532 0.7264 0.1642 0.074 Uiso 1 1 calc GR . . . .
H10C H -0.1510 0.6536 0.1834 0.074 Uiso 1 1 calc GR . . . .
C11 C 0.51306(10) 0.15777(17) 0.58882(9) 0.0461(3) Uani 1 1 d . . . . .
H11A H 0.5143 0.2439 0.6307 0.069 Uiso 1 1 calc GR . . . .
H11B H 0.5643 0.0821 0.6184 0.069 Uiso 1 1 calc GR . . . .
H11C H 0.4469 0.1087 0.5730 0.069 Uiso 1 1 calc GR . . . .
C12 C 0.63475(10) 0.19913(18) 0.49935(10) 0.0500(3) Uani 1 1 d . . . . .
H12A H 0.6328 0.1532 0.4402 0.075 Uiso 1 1 calc GR . . . .
H12B H 0.6736 0.1326 0.5486 0.075 Uiso 1 1 calc GR . . . .
H12C H 0.6663 0.3011 0.5043 0.075 Uiso 1 1 calc GR . . . .
C13 C 0.12179(10) 0.63846(17) 0.04345(9) 0.0443(3) Uani 1 1 d . . . . .
H13A H 0.1643 0.6454 0.0022 0.066 Uiso 1 1 calc GR . . . .
H13B H 0.0569 0.6871 0.0148 0.066 Uiso 1 1 calc GR . . . .
H13C H 0.1115 0.5298 0.0560 0.066 Uiso 1 1 calc GR . . . .
C14 C 0.19307(8) 0.87527(14) 0.12469(7) 0.0318(2) Uani 1 1 d . . . . .
C15 C 0.13931(9) 0.96928(15) 0.05342(8) 0.0378(3) Uani 1 1 d . . . . .
H15 H 0.0906 0.9253 0.0030 0.045 Uiso 1 1 calc R . . . .
C16 C 0.15699(10) 1.12718(17) 0.05611(9) 0.0457(3) Uani 1 1 d . . . . .
H16 H 0.1192 1.1903 0.0077 0.055 Uiso 1 1 calc R . . . .
C17 C 0.22835(11) 1.19425(16) 0.12779(10) 0.0471(3) Uani 1 1 d . . . . .
H17 H 0.2397 1.3024 0.1291 0.057 Uiso 1 1 calc R . . . .
C18 C 0.28289(11) 1.10097(16) 0.19744(10) 0.0459(3) Uani 1 1 d . . . . .
H18 H 0.3331 1.1453 0.2467 0.055 Uiso 1 1 calc R . . . .
C19 C 0.26553(9) 0.94400(15) 0.19654(8) 0.0395(3) Uani 1 1 d . . . . .
H19 H 0.3034 0.8820 0.2455 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 C2 1.3294(14) . ?
O1 C9 1.4676(15) . ?
O2 C2 1.1979(15) . ?
N1 N2 1.4600(13) . ?
N1 C1 1.2829(15) . ?
N2 C13 1.4598(15) . ?
N2 C14 1.4084(16) . ?
N3 C6 1.3640(15) . ?
N3 C11 1.4480(18) . ?
N3 C12 1.4532(17) . ?
C1 C2 1.5166(16) . ?
C1 C3 1.4620(15) . ?
C3 C4 1.4014(16) . ?
C3 C8 1.3946(16) . ?
C4 H4 0.9500 . ?
C4 C5 1.3756(17) . ?
C5 H5 0.9500 . ?
C5 C6 1.4158(17) . ?
C6 C7 1.4056(17) . ?
C7 H7 0.9500 . ?
C7 C8 1.3757(16) . ?
C8 H8 0.9500 . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C9 C10 1.4881(19) . ?
C10 H10A 0.9800 . ?
C10 H10B 0.9800 . ?
C10 H10C 0.9800 . ?
C11 H11A 0.9800 . ?
C11 H11B 0.9800 . ?
C11 H11C 0.9800 . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12C 0.9800 . ?
C13 H13A 0.9800 . ?
C13 H13B 0.9800 . ?
C13 H13C 0.9800 . ?
C14 C15 1.3951(16) . ?
C14 C19 1.3960(17) . ?
C15 H15 0.9500 . ?
C15 C16 1.389(2) . ?
C16 H16 0.9500 . ?
C16 C17 1.381(2) . ?
C17 H17 0.9500 . ?
C17 C18 1.380(2) . ?
C18 H18 0.9500 . ?
C18 C19 1.3813(19) . ?
C19 H19 0.9500 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 O1 C9 116.63(10) . . ?
C1 N1 N2 110.35(9) . . ?
C13 N2 N1 108.85(9) . . ?
C14 N2 N1 112.41(9) . . ?
C14 N2 C13 117.91(10) . . ?
C6 N3 C11 120.71(11) . . ?
C6 N3 C12 120.68(11) . . ?
C11 N3 C12 117.75(11) . . ?
N1 C1 C2 119.69(10) . . ?
N1 C1 C3 122.05(10) . . ?
C3 C1 C2 118.17(9) . . ?
O1 C2 C1 111.13(10) . . ?
O2 C2 O1 126.30(11) . . ?
O2 C2 C1 122.54(11) . . ?
C4 C3 C1 122.49(10) . . ?
C8 C3 C1 120.21(10) . . ?
C8 C3 C4 117.29(10) . . ?
C3 C4 H4 119.3 . . ?
C5 C4 C3 121.48(11) . . ?
C5 C4 H4 119.3 . . ?
C4 C5 H5 119.4 . . ?
C4 C5 C6 121.15(11) . . ?
C6 C5 H5 119.4 . . ?
N3 C6 C5 121.61(11) . . ?
N3 C6 C7 121.36(11) . . ?
C7 C6 C5 117.03(11) . . ?
C6 C7 H7 119.5 . . ?
C8 C7 C6 121.05(11) . . ?
C8 C7 H7 119.5 . . ?
C3 C8 H8 119.0 . . ?
C7 C8 C3 122.00(11) . . ?
C7 C8 H8 119.0 . . ?
O1 C9 H9A 109.8 . . ?
O1 C9 H9B 109.8 . . ?
O1 C9 C10 109.56(11) . . ?
H9A C9 H9B 108.2 . . ?
C10 C9 H9A 109.8 . . ?
C10 C9 H9B 109.8 . . ?
C9 C10 H10A 109.5 . . ?
C9 C10 H10B 109.5 . . ?
C9 C10 H10C 109.5 . . ?
H10A C10 H10B 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
N3 C11 H11A 109.5 . . ?
N3 C11 H11B 109.5 . . ?
N3 C11 H11C 109.5 . . ?
H11A C11 H11B 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
N3 C12 H12A 109.5 . . ?
N3 C12 H12B 109.5 . . ?
N3 C12 H12C 109.5 . . ?
H12A C12 H12B 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
N2 C13 H13A 109.5 . . ?
N2 C13 H13B 109.5 . . ?
N2 C13 H13C 109.5 . . ?
H13A C13 H13B 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
C15 C14 N2 121.70(11) . . ?
C15 C14 C19 118.17(11) . . ?
C19 C14 N2 119.94(10) . . ?
C14 C15 H15 120.0 . . ?
C16 C15 C14 120.07(12) . . ?
C16 C15 H15 120.0 . . ?
C15 C16 H16 119.3 . . ?
C17 C16 C15 121.33(12) . . ?
C17 C16 H16 119.3 . . ?
C16 C17 H17 120.7 . . ?
C18 C17 C16 118.64(13) . . ?
C18 C17 H17 120.7 . . ?
C17 C18 H18 119.6 . . ?
C17 C18 C19 120.88(13) . . ?
C19 C18 H18 119.6 . . ?
C14 C19 H19 119.5 . . ?
C18 C19 C14 120.90(12) . . ?
C18 C19 H19 119.5 . . ?


_journal_year                    2017
_olex2_diffrn_ambient_temperature_device 'Oxford Cryosystems'
_olex2_exptl_crystal_mounting_method 
'The crystal was mounted on a nylon loop with paratone oil'
_olex2_submission_original_sample_id 'BHS-HzNCH3, methyl'
_olex2_submission_special_instructions 'No special instructions were received'

