# Electronic Supplementary Material (ESI) for Chemical Science.
# This journal is © The Royal Society of Chemistry 2016

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

data_rovis227-1
_database_code_depnum_ccdc_archive 'CCDC 1472771'
_audit_update_record             
;
2016-04-07 deposited with the CCDC.
2016-09-16 downloaded from the CCDC.
;
_audit_creation_date             2016-04-07
_audit_creation_method           
;
Olex2 1.2
(compiled 2016.02.19 svn.r3266 for OlexSys, GUI svn.r5155)
;
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C18 H17 N O2'
_chemical_formula_sum            'C18 H17 N O2'
_chemical_formula_weight         279.32
_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 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

_cell_length_a                   8.5035(2)
_cell_length_b                   7.1303(2)
_cell_length_c                   23.6793(6)
_cell_angle_alpha                90
_cell_angle_beta                 95.7420(12)
_cell_angle_gamma                90
_cell_volume                     1428.53(6)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    7672
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      33.26
_cell_measurement_theta_min      2.64
_shelx_estimated_absorpt_T_max   0.991
_shelx_estimated_absorpt_T_min   0.979
_exptl_absorpt_coefficient_mu    0.085
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   .
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.299
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             592
_exptl_crystal_preparation       ?
_exptl_crystal_recrystallization_method 'Vapor diffusion'
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.124
_exptl_crystal_size_min          0.107
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0926
_diffrn_reflns_av_unetI/netI     0.0945
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.984
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       36
_diffrn_reflns_limit_l_min       -36
_diffrn_reflns_number            30307
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.984
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         33.388
_diffrn_reflns_theta_min         2.985
_diffrn_ambient_temperature      99.77
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.984
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_special_details          ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3163
_reflns_number_total             5464
_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       ?
_computing_data_collection       ?
_computing_data_reduction        ?
_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    'XS (Sheldrick, 2008)'
_refine_diff_density_max         0.536
_refine_diff_density_min         -0.287
_refine_diff_density_rms         0.076
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.033
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     192
_refine_ls_number_reflns         5464
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1350
_refine_ls_R_factor_gt           0.0685
_refine_ls_restrained_S_all      1.033
_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)+(0.0840P)²+0.2020P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1558
_refine_ls_wR_factor_ref         0.1811
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C7(H7), C8(H8)
2.b Aromatic/amide H refined with riding coordinates:
 N3(H3), C4(H4), C13(H13), C14(H14), C16(H16), C17(H17), C18(H18), C19(H19),
 C20(H20)
2.c Idealised Me refined as rotating group:
 C15(H15A,H15B,H15C), C21(H21A,H21B,H21C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.67072(13) 0.34438(17) 0.00548(5) 0.0180(3) Uani 1 1 d . . . . .
O2 O 0.97316(14) -0.23988(19) 0.05114(6) 0.0232(3) Uani 1 1 d . . . . .
N3 N 0.44084(16) 0.3146(2) 0.04481(6) 0.0155(3) Uani 1 1 d . . . . .
H3 H 0.4122 0.4252 0.0309 0.019 Uiso 1 1 calc R . . . .
C4 C 0.77911(18) -0.0066(2) 0.04523(7) 0.0150(3) Uani 1 1 d . . . . .
H4 H 0.8446 0.0653 0.0232 0.018 Uiso 1 1 calc R . . . .
C5 C 0.63344(18) 0.0637(2) 0.05753(6) 0.0130(3) Uani 1 1 d . . . . .
C6 C 0.53477(18) -0.0415(2) 0.08984(6) 0.0137(3) Uani 1 1 d . . . . .
C7 C 0.37776(18) 0.0313(2) 0.10148(6) 0.0136(3) Uani 1 1 d . . . . .
H7 H 0.2913 -0.0640 0.1006 0.016 Uiso 1 1 calc R . . . .
C8 C 0.33086(18) 0.2188(2) 0.07688(7) 0.0144(3) Uani 1 1 d . . . . .
H8 H 0.2172 0.2310 0.0618 0.017 Uiso 1 1 calc R . . . .
C9 C 0.58374(18) 0.2508(2) 0.03413(7) 0.0135(3) Uani 1 1 d . . . . .
C10 C 0.82834(19) -0.1830(2) 0.06533(7) 0.0158(3) Uani 1 1 d . . . . .
C11 C 0.36163(18) 0.2012(2) 0.14153(7) 0.0146(3) Uani 1 1 d . . . . .
C12 C 0.21689(18) 0.2069(2) 0.17321(7) 0.0142(3) Uani 1 1 d . . . . .
C13 C 0.73074(19) -0.2900(3) 0.09686(7) 0.0175(3) Uani 1 1 d . . . . .
H13 H 0.7635 -0.4109 0.1102 0.021 Uiso 1 1 calc R . . . .
C14 C 0.58537(19) -0.2186(2) 0.10859(7) 0.0167(3) Uani 1 1 d . . . . .
H14 H 0.5192 -0.2922 0.1299 0.020 Uiso 1 1 calc R . . . .
C15 C 0.51076(19) 0.2856(3) 0.17096(7) 0.0171(3) Uani 1 1 d . . . . .
H15A H 0.5395 0.2196 0.2068 0.026 Uiso 1 1 calc GR . . . .
H15B H 0.4930 0.4186 0.1787 0.026 Uiso 1 1 calc GR . . . .
H15C H 0.5966 0.2735 0.1465 0.026 Uiso 1 1 calc GR . . . .
C16 C 0.07653(19) 0.1151(3) 0.15316(7) 0.0184(4) Uani 1 1 d . . . . .
H16 H 0.0726 0.0455 0.1189 0.022 Uiso 1 1 calc R . . . .
C17 C 0.2171(2) 0.3097(3) 0.22375(8) 0.0197(4) Uani 1 1 d . . . . .
H17 H 0.3104 0.3734 0.2385 0.024 Uiso 1 1 calc R . . . .
C18 C -0.0578(2) 0.1240(3) 0.18257(8) 0.0230(4) Uani 1 1 d . . . . .
H18 H -0.1509 0.0584 0.1687 0.028 Uiso 1 1 calc R . . . .
C19 C -0.0552(2) 0.2286(3) 0.23211(8) 0.0240(4) Uani 1 1 d . . . . .
H19 H -0.1470 0.2376 0.2518 0.029 Uiso 1 1 calc R . . . .
C20 C 0.0826(2) 0.3196(3) 0.25254(8) 0.0231(4) Uani 1 1 d . . . . .
H20 H 0.0854 0.3899 0.2867 0.028 Uiso 1 1 calc R . . . .
C21 C 1.0328(2) -0.4149(3) 0.07369(10) 0.0314(5) Uani 1 1 d . . . . .
H21A H 1.1371 -0.4387 0.0609 0.047 Uiso 1 1 calc GR . . . .
H21B H 0.9603 -0.5160 0.0604 0.047 Uiso 1 1 calc GR . . . .
H21C H 1.0420 -0.4100 0.1153 0.047 Uiso 1 1 calc GR . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C9 1.2461(19) . ?
O2 C10 1.3700(19) . ?
O2 C21 1.430(2) . ?
N3 C8 1.435(2) . ?
N3 C9 1.345(2) . ?
C4 C5 1.394(2) . ?
C4 C10 1.394(2) . ?
C5 C6 1.407(2) . ?
C5 C9 1.489(2) . ?
C6 C7 1.484(2) . ?
C6 C14 1.392(2) . ?
C7 C8 1.497(2) . ?
C7 C11 1.553(2) . ?
C8 C11 1.532(2) . ?
C10 C13 1.398(2) . ?
C11 C12 1.505(2) . ?
C11 C15 1.510(2) . ?
C12 C16 1.402(2) . ?
C12 C17 1.403(2) . ?
C13 C14 1.390(2) . ?
C16 C18 1.397(2) . ?
C17 C20 1.391(2) . ?
C18 C19 1.388(3) . ?
C19 C20 1.384(3) . ?

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
C10 O2 C21 117.45(13) . . ?
C9 N3 C8 125.98(14) . . ?
C10 C4 C5 119.75(15) . . ?
C4 C5 C6 120.82(15) . . ?
C4 C5 C9 118.01(14) . . ?
C6 C5 C9 121.15(14) . . ?
C5 C6 C7 120.72(15) . . ?
C14 C6 C5 118.35(14) . . ?
C14 C6 C7 120.88(14) . . ?
C6 C7 C8 116.74(13) . . ?
C6 C7 C11 121.50(14) . . ?
C8 C7 C11 60.29(11) . . ?
N3 C8 C7 117.95(13) . . ?
N3 C8 C11 120.84(14) . . ?
C7 C8 C11 61.67(11) . . ?
O1 C9 N3 121.19(15) . . ?
O1 C9 C5 121.36(14) . . ?
N3 C9 C5 117.45(14) . . ?
O2 C10 C4 115.48(14) . . ?
O2 C10 C13 124.44(15) . . ?
C4 C10 C13 120.07(14) . . ?
C8 C11 C7 58.03(10) . . ?
C12 C11 C7 116.89(14) . . ?
C12 C11 C8 115.43(13) . . ?
C12 C11 C15 116.76(14) . . ?
C15 C11 C7 118.13(13) . . ?
C15 C11 C8 118.68(14) . . ?
C16 C12 C11 121.99(15) . . ?
C16 C12 C17 117.46(15) . . ?
C17 C12 C11 120.53(15) . . ?
C14 C13 C10 119.60(16) . . ?
C13 C14 C6 121.41(15) . . ?
C18 C16 C12 121.38(16) . . ?
C20 C17 C12 120.91(16) . . ?
C19 C18 C16 120.08(17) . . ?
C20 C19 C18 119.22(16) . . ?
C19 C20 C17 120.94(17) . . ?

_shelx_SHELXL_version_number     2014/7
_olex2_submission_original_sample_id Rovis227
_olex2_submission_special_instructions 'No special instructions were received'
