# 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. 
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data_cc_amr4_31bp_0m_pl
_database_code_depnum_ccdc_archive 'CCDC 1571341'
_audit_update_record             
;
2017-08-29 deposited with the CCDC.
2018-01-08 downloaded from the CCDC.
;
_audit_creation_date             2017-07-20
_audit_creation_method           
;
Olex2 1.2
(compiled 2016.02.19 svn.r3266 for OlexSys, GUI svn.r5155)
;
_chemical_name_common            ?
_chemical_name_systematic        
(Z)-4-((2,4-dimethoxypyrimidin-5-yl)(phenyl)methylene)-2-methyl-3,4-dihydroisoquinolin-1(2H)-one
_chemical_formula_moiety         'C23 H21 N3 O3'
_chemical_formula_sum            'C23 H21 N3 O3'
_chemical_formula_weight         387.43
_chemical_melting_point          '186-188 degree centigrade'
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           15
_space_group_name_H-M_alt        'I 1 2/a 1'
_space_group_name_Hall           '-I 2ya'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y, -z'
'x+1/2, y+1/2, z+1/2'
'-x+1, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y, z'
'-x+1/2, -y+1/2, -z+1/2'
'x, -y+1/2, z+1/2'

_cell_length_a                   12.091(4)
_cell_length_b                   12.635(5)
_cell_length_c                   25.986(10)
_cell_angle_alpha                90
_cell_angle_beta                 92.324(14)
_cell_angle_gamma                90
_cell_volume                     3967(3)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    3837
_cell_measurement_temperature    273.15
_cell_measurement_theta_max      23.59
_cell_measurement_theta_min      2.77
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.088
_exptl_absorpt_correction_T_max  0.7455
_exptl_absorpt_correction_T_min  0.6600
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2014/5 (Bruker,2014/5) was used for absorption correction.
wR2(int) was 0.0928 before and 0.0488 after correction.
The Ratio of minimum to maximum transmission is 0.8853.
The λ/2 correction factor is 0.00150.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            white
_exptl_crystal_colour_primary    white
_exptl_crystal_density_diffrn    1.298
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             1632
_exptl_crystal_size_max          0.5
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.1
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0670
_diffrn_reflns_av_unetI/netI     0.0514
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       32
_diffrn_reflns_limit_l_min       -32
_diffrn_reflns_number            24976
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.992
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.697
_diffrn_reflns_theta_min         2.332
_diffrn_ambient_temperature      273.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.992
_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_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2202
_reflns_number_total             4158
_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  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    ?
_refine_diff_density_max         0.191
_refine_diff_density_min         -0.241
_refine_diff_density_rms         0.046
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.038
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     265
_refine_ls_number_reflns         4158
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1165
_refine_ls_R_factor_gt           0.0563
_refine_ls_restrained_S_all      1.038
_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)+(0.0870P)²+0.2205P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1404
_refine_ls_wR_factor_ref         0.1729
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C00R(H00A,H00B)
2.b Aromatic/amide H refined with riding coordinates:
 C00Z(H00Z), C010(H010), C011(H011), C014(H014), C015(H015), C019(H019),
 C01A(H01A), C01B(H01B), C01D(H01D), C01K(H01K)
2.c Idealised Me refined as rotating group:
 C01G(H01C,H01E,H01F), C01H(H01G,H01H,H01I), C01L(H01J,H01L,H01M)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_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
O001 O 0.22448(14) 0.32671(12) 0.07471(7) 0.0648(5) Uani 1 1 d . . . . .
O008 O 0.08079(19) -0.07480(14) 0.22945(7) 0.0847(7) Uani 1 1 d . . . . .
O004 O 0.22486(15) 0.64491(12) 0.15221(7) 0.0663(5) Uani 1 1 d . . . . .
N005 N 0.22355(16) 0.48880(14) 0.11342(7) 0.0515(5) Uani 1 1 d . . . . .
N00A N 0.08938(18) 0.10294(15) 0.22237(8) 0.0592(6) Uani 1 1 d . . . . .
N00C N 0.07789(18) 0.53667(14) 0.16716(8) 0.0581(6) Uani 1 1 d . . . . .
C00E C 0.01847(18) 0.26466(15) 0.11259(8) 0.0441(5) Uani 1 1 d . . . . .
C00G C 0.07457(19) 0.36670(16) 0.12532(8) 0.0455(6) Uani 1 1 d . . . . .
C00I C 0.17560(19) 0.39685(16) 0.10467(9) 0.0471(6) Uani 1 1 d . . . . .
C00J C 0.1707(2) 0.55249(17) 0.14446(9) 0.0503(6) Uani 1 1 d . . . . .
C00L C -0.01383(18) 0.25038(17) 0.05677(9) 0.0471(6) Uani 1 1 d . . . . .
C00N C -0.00321(18) 0.19274(16) 0.14879(9) 0.0452(5) Uani 1 1 d . . . . .
C00P C -0.07252(19) 0.09716(17) 0.14067(9) 0.0498(6) Uani 1 1 d . . . . .
C00R C 0.0419(2) 0.20271(17) 0.20352(9) 0.0570(7) Uani 1 1 d . . . . .
H00A H 0.0984 0.2572 0.2053 0.068 Uiso 1 1 calc R . . . .
H00B H -0.0171 0.2240 0.2255 0.068 Uiso 1 1 calc R . . . .
C00W C 0.0462(2) 0.00824(19) 0.20955(10) 0.0601(7) Uani 1 1 d . . . . .
C00Y C -0.0466(2) 0.00795(17) 0.17029(10) 0.0567(7) Uani 1 1 d . . . . .
C00Z C 0.0188(2) 0.16215(19) 0.03025(10) 0.0577(6) Uani 1 1 d . . . . .
H00Z H 0.0630 0.1116 0.0470 0.069 Uiso 1 1 calc R . . . .
C010 C -0.0770(2) 0.3263(2) 0.03084(10) 0.0619(7) Uani 1 1 d . . . . .
H010 H -0.0976 0.3876 0.0478 0.074 Uiso 1 1 calc R . . . .
C011 C 0.0305(2) 0.44107(17) 0.15643(9) 0.0569(7) Uani 1 1 d . . . . .
H011 H -0.0362 0.4255 0.1713 0.068 Uiso 1 1 calc R . . . .
C014 C -0.1652(2) 0.0944(2) 0.10703(11) 0.0658(7) Uani 1 1 d . . . . .
H014 H -0.1850 0.1543 0.0880 0.079 Uiso 1 1 calc R . . . .
C015 C -0.0134(2) 0.1473(2) -0.02116(11) 0.0724(8) Uani 1 1 d . . . . .
H015 H 0.0090 0.0873 -0.0386 0.087 Uiso 1 1 calc R . . . .
C019 C -0.1097(2) 0.3109(3) -0.02062(11) 0.0757(8) Uani 1 1 d . . . . .
H019 H -0.1531 0.3616 -0.0378 0.091 Uiso 1 1 calc R . . . .
C01A C -0.0786(3) 0.2222(3) -0.04602(12) 0.0802(9) Uani 1 1 d . . . . .
H01A H -0.1016 0.2122 -0.0803 0.096 Uiso 1 1 calc R . . . .
C01B C -0.1087(3) -0.0837(2) 0.16372(12) 0.0751(9) Uani 1 1 d . . . . .
H01B H -0.0897 -0.1441 0.1825 0.090 Uiso 1 1 calc R . . . .
C01D C -0.2273(3) 0.0038(2) 0.10184(13) 0.0824(9) Uani 1 1 d . . . . .
H01D H -0.2893 0.0028 0.0795 0.099 Uiso 1 1 calc R . . . .
C01G C 0.1705(3) 0.1099(2) 0.26515(12) 0.0842(9) Uani 1 1 d . . . . .
H01C H 0.2210 0.1667 0.2591 0.126 Uiso 1 1 calc GR . . . .
H01E H 0.2107 0.0445 0.2681 0.126 Uiso 1 1 calc GR . . . .
H01F H 0.1333 0.1230 0.2965 0.126 Uiso 1 1 calc GR . . . .
C01H C 0.1808(3) 0.7169(2) 0.18798(12) 0.0909(11) Uani 1 1 d . . . . .
H01G H 0.1050 0.7319 0.1782 0.136 Uiso 1 1 calc GR . . . .
H01H H 0.2228 0.7813 0.1882 0.136 Uiso 1 1 calc GR . . . .
H01I H 0.1847 0.6861 0.2218 0.136 Uiso 1 1 calc GR . . . .
C01K C -0.1983(3) -0.0852(2) 0.12949(14) 0.0876(10) Uani 1 1 d . . . . .
H01K H -0.2396 -0.1468 0.1250 0.105 Uiso 1 1 calc R . . . .
C01L C 0.3321(2) 0.3556(3) 0.05670(14) 0.0977(11) Uani 1 1 d . . . . .
H01J H 0.3581 0.3010 0.0346 0.147 Uiso 1 1 calc GR . . . .
H01L H 0.3832 0.3641 0.0856 0.147 Uiso 1 1 calc GR . . . .
H01M H 0.3263 0.4210 0.0379 0.147 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
O001 C00I 1.333(3) . ?
O001 C01L 1.447(3) . ?
O008 C00W 1.235(3) . ?
O004 C00J 1.350(3) . ?
O004 C01H 1.420(3) . ?
N005 C00I 1.314(3) . ?
N005 C00J 1.322(3) . ?
N00A C00R 1.461(3) . ?
N00A C00W 1.342(3) . ?
N00A C01G 1.455(3) . ?
N00C C00J 1.304(3) . ?
N00C C011 1.361(3) . ?
C00E C00G 1.488(3) . ?
C00E C00L 1.498(3) . ?
C00E C00N 1.341(3) . ?
C00G C00I 1.407(3) . ?
C00G C011 1.362(3) . ?
C00L C00Z 1.377(3) . ?
C00L C010 1.384(3) . ?
C00N C00P 1.480(3) . ?
C00N C00R 1.508(3) . ?
C00P C00Y 1.393(3) . ?
C00P C014 1.393(4) . ?
C00R H00A 0.9700 . ?
C00R H00B 0.9700 . ?
C00W C00Y 1.486(4) . ?
C00Y C01B 1.386(3) . ?
C00Z H00Z 0.9300 . ?
C00Z C015 1.389(4) . ?
C010 H010 0.9300 . ?
C010 C019 1.393(4) . ?
C011 H011 0.9300 . ?
C014 H014 0.9300 . ?
C014 C01D 1.373(4) . ?
C015 H015 0.9300 . ?
C015 C01A 1.376(4) . ?
C019 H019 0.9300 . ?
C019 C01A 1.361(4) . ?
C01A H01A 0.9300 . ?
C01B H01B 0.9300 . ?
C01B C01K 1.374(5) . ?
C01D H01D 0.9300 . ?
C01D C01K 1.372(4) . ?
C01G H01C 0.9600 . ?
C01G H01E 0.9600 . ?
C01G H01F 0.9600 . ?
C01H H01G 0.9600 . ?
C01H H01H 0.9600 . ?
C01H H01I 0.9600 . ?
C01K H01K 0.9300 . ?
C01L H01J 0.9600 . ?
C01L H01L 0.9600 . ?
C01L H01M 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
C00I O001 C01L 116.53(19) . . ?
C00J O004 C01H 117.3(2) . . ?
C00I N005 C00J 115.0(2) . . ?
C00W N00A C00R 122.9(2) . . ?
C00W N00A C01G 119.1(2) . . ?
C01G N00A C00R 116.6(2) . . ?
C00J N00C C011 114.0(2) . . ?
C00G C00E C00L 114.73(17) . . ?
C00N C00E C00G 122.1(2) . . ?
C00N C00E C00L 123.16(19) . . ?
C00I C00G C00E 123.03(19) . . ?
C011 C00G C00E 123.0(2) . . ?
C011 C00G C00I 114.0(2) . . ?
O001 C00I C00G 117.1(2) . . ?
N005 C00I O001 119.1(2) . . ?
N005 C00I C00G 123.9(2) . . ?
N005 C00J O004 111.9(2) . . ?
N00C C00J O004 119.1(2) . . ?
N00C C00J N005 129.0(2) . . ?
C00Z C00L C00E 120.9(2) . . ?
C00Z C00L C010 118.8(2) . . ?
C010 C00L C00E 120.3(2) . . ?
C00E C00N C00P 125.3(2) . . ?
C00E C00N C00R 122.1(2) . . ?
C00P C00N C00R 112.58(18) . . ?
C00Y C00P C00N 117.9(2) . . ?
C014 C00P C00N 123.1(2) . . ?
C014 C00P C00Y 118.9(2) . . ?
N00A C00R C00N 111.48(18) . . ?
N00A C00R H00A 109.3 . . ?
N00A C00R H00B 109.3 . . ?
C00N C00R H00A 109.3 . . ?
C00N C00R H00B 109.3 . . ?
H00A C00R H00B 108.0 . . ?
O008 C00W N00A 122.2(3) . . ?
O008 C00W C00Y 121.2(2) . . ?
N00A C00W C00Y 116.6(2) . . ?
C00P C00Y C00W 121.6(2) . . ?
C01B C00Y C00P 119.9(3) . . ?
C01B C00Y C00W 118.5(2) . . ?
C00L C00Z H00Z 119.5 . . ?
C00L C00Z C015 121.1(2) . . ?
C015 C00Z H00Z 119.5 . . ?
C00L C010 H010 120.0 . . ?
C00L C010 C019 120.0(2) . . ?
C019 C010 H010 120.0 . . ?
N00C C011 C00G 124.2(2) . . ?
N00C C011 H011 117.9 . . ?
C00G C011 H011 117.9 . . ?
C00P C014 H014 119.8 . . ?
C01D C014 C00P 120.3(3) . . ?
C01D C014 H014 119.8 . . ?
C00Z C015 H015 120.3 . . ?
C01A C015 C00Z 119.5(3) . . ?
C01A C015 H015 120.3 . . ?
C010 C019 H019 119.8 . . ?
C01A C019 C010 120.5(3) . . ?
C01A C019 H019 119.8 . . ?
C015 C01A H01A 119.9 . . ?
C019 C01A C015 120.2(3) . . ?
C019 C01A H01A 119.9 . . ?
C00Y C01B H01B 120.0 . . ?
C01K C01B C00Y 120.0(3) . . ?
C01K C01B H01B 120.0 . . ?
C014 C01D H01D 119.8 . . ?
C01K C01D C014 120.3(3) . . ?
C01K C01D H01D 119.8 . . ?
N00A C01G H01C 109.5 . . ?
N00A C01G H01E 109.5 . . ?
N00A C01G H01F 109.5 . . ?
H01C C01G H01E 109.5 . . ?
H01C C01G H01F 109.5 . . ?
H01E C01G H01F 109.5 . . ?
O004 C01H H01G 109.5 . . ?
O004 C01H H01H 109.5 . . ?
O004 C01H H01I 109.5 . . ?
H01G C01H H01H 109.5 . . ?
H01G C01H H01I 109.5 . . ?
H01H C01H H01I 109.5 . . ?
C01B C01K H01K 119.8 . . ?
C01D C01K C01B 120.4(3) . . ?
C01D C01K H01K 119.8 . . ?
O001 C01L H01J 109.5 . . ?
O001 C01L H01L 109.5 . . ?
O001 C01L H01M 109.5 . . ?
H01J C01L H01L 109.5 . . ?
H01J C01L H01M 109.5 . . ?
H01L C01L H01M 109.5 . . ?

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
O008 C00W C00Y C00P -167.7(2) . . . . ?
O008 C00W C00Y C01B 12.8(4) . . . . ?
N00A C00W C00Y C00P 12.9(4) . . . . ?
N00A C00W C00Y C01B -166.6(2) . . . . ?
C00E C00G C00I O001 -3.8(3) . . . . ?
C00E C00G C00I N005 176.4(2) . . . . ?
C00E C00G C011 N00C -177.4(2) . . . . ?
C00E C00L C00Z C015 178.3(2) . . . . ?
C00E C00L C010 C019 -177.9(2) . . . . ?
C00E C00N C00P C00Y 149.1(2) . . . . ?
C00E C00N C00P C014 -34.4(3) . . . . ?
C00E C00N C00R N00A -133.2(2) . . . . ?
C00G C00E C00L C00Z 126.3(2) . . . . ?
C00G C00E C00L C010 -53.5(3) . . . . ?
C00G C00E C00N C00P 170.6(2) . . . . ?
C00G C00E C00N C00R -9.0(3) . . . . ?
C00I N005 C00J O004 179.36(19) . . . . ?
C00I N005 C00J N00C -0.3(4) . . . . ?
C00I C00G C011 N00C 0.2(4) . . . . ?
C00J N005 C00I O001 -178.5(2) . . . . ?
C00J N005 C00I C00G 1.2(3) . . . . ?
C00J N00C C011 C00G 0.6(4) . . . . ?
C00L C00E C00G C00I -61.1(3) . . . . ?
C00L C00E C00G C011 116.3(2) . . . . ?
C00L C00E C00N C00P -7.9(3) . . . . ?
C00L C00E C00N C00R 172.5(2) . . . . ?
C00L C00Z C015 C01A 0.2(4) . . . . ?
C00L C010 C019 C01A -1.0(4) . . . . ?
C00N C00E C00G C00I 120.3(2) . . . . ?
C00N C00E C00G C011 -62.3(3) . . . . ?
C00N C00E C00L C00Z -55.2(3) . . . . ?
C00N C00E C00L C010 125.1(2) . . . . ?
C00N C00P C00Y C00W 1.0(3) . . . . ?
C00N C00P C00Y C01B -179.5(2) . . . . ?
C00N C00P C014 C01D -178.9(2) . . . . ?
C00P C00N C00R N00A 47.1(3) . . . . ?
C00P C00Y C01B C01K -2.5(4) . . . . ?
C00P C014 C01D C01K -0.4(4) . . . . ?
C00R N00A C00W O008 -173.1(2) . . . . ?
C00R N00A C00W C00Y 6.4(3) . . . . ?
C00R C00N C00P C00Y -31.2(3) . . . . ?
C00R C00N C00P C014 145.2(2) . . . . ?
C00W N00A C00R C00N -36.3(3) . . . . ?
C00W C00Y C01B C01K 177.0(3) . . . . ?
C00Y C00P C014 C01D -2.4(4) . . . . ?
C00Y C01B C01K C01D -0.3(5) . . . . ?
C00Z C00L C010 C019 2.3(4) . . . . ?
C00Z C015 C01A C019 1.1(4) . . . . ?
C010 C00L C00Z C015 -1.9(4) . . . . ?
C010 C019 C01A C015 -0.7(4) . . . . ?
C011 N00C C00J O004 179.8(2) . . . . ?
C011 N00C C00J N005 -0.5(4) . . . . ?
C011 C00G C00I O001 178.6(2) . . . . ?
C011 C00G C00I N005 -1.1(3) . . . . ?
C014 C00P C00Y C00W -175.6(2) . . . . ?
C014 C00P C00Y C01B 3.9(4) . . . . ?
C014 C01D C01K C01B 1.8(5) . . . . ?
C01G N00A C00R C00N 157.5(2) . . . . ?
C01G N00A C00W O008 -7.3(4) . . . . ?
C01G N00A C00W C00Y 172.2(2) . . . . ?
C01H O004 C00J N005 -175.3(2) . . . . ?
C01H O004 C00J N00C 4.4(3) . . . . ?
C01L O001 C00I N005 4.0(3) . . . . ?
C01L O001 C00I C00G -175.7(2) . . . . ?

_shelx_SHELXL_version_number     2014/7
_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_cc_amr4_140a2_0m_a
_database_code_depnum_ccdc_archive 'CCDC 1571343'
_audit_update_record             
;
2017-08-29 deposited with the CCDC.
2018-01-08 downloaded from the CCDC.
;
_audit_creation_date             2017-07-02
_audit_creation_method           
;
Olex2 1.2
(compiled 2015.01.26 svn.r3150 for OlexSys, GUI svn.r4998)
;
_chemical_name_common            ?
_chemical_name_systematic        isoquinolin-4-yldiphenylmethanol
_chemical_formula_moiety         'C22 H17 N O'
_chemical_formula_sum            'C22 H17 N O'
_chemical_formula_weight         311.36
_chemical_melting_point          '168-170 degree centigrade'
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                   10.117(3)
_cell_length_b                   13.923(4)
_cell_length_c                   12.307(4)
_cell_angle_alpha                90
_cell_angle_beta                 99.313(2)
_cell_angle_gamma                90
_cell_volume                     1710.8(9)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    3060
_cell_measurement_temperature    296.15
_cell_measurement_theta_max      25.702
_cell_measurement_theta_min      8.496
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.074
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6789
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2014/5 (Bruker,2014/5) was used for absorption correction.
wR2(int) was 0.0919 before and 0.0482 after correction.
The Ratio of minimum to maximum transmission is 0.9105.
The λ/2 correction factor is 0.00150.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            white
_exptl_crystal_colour_primary    white
_exptl_crystal_density_diffrn    1.209
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             656
_exptl_crystal_size_max          0.5
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.1
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0473
_diffrn_reflns_av_unetI/netI     0.0379
_diffrn_reflns_Laue_measured_fraction_full 0.961
_diffrn_reflns_Laue_measured_fraction_max 0.958
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            15040
_diffrn_reflns_point_group_measured_fraction_full 0.961
_diffrn_reflns_point_group_measured_fraction_max 0.958
_diffrn_reflns_theta_full        26.000
_diffrn_reflns_theta_max         27.225
_diffrn_reflns_theta_min         8.465
_diffrn_ambient_temperature      296.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.961
_diffrn_measured_fraction_theta_max 0.958
_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_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2720
_reflns_number_total             3644
_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       ?
_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  'ShelXL (Sheldrick, 2008)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.189
_refine_diff_density_min         -0.154
_refine_diff_density_rms         0.029
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.032
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     218
_refine_ls_number_reflns         3644
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0670
_refine_ls_R_factor_gt           0.0458
_refine_ls_restrained_S_all      1.032
_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)+(0.0460P)²+0.3050P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1019
_refine_ls_wR_factor_ref         0.1131
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All O(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C008(H008), C00A(H00A), C00B(H00B), C00C(H00C), C00D(H00D), C00E(H00E),
 C00F(H00F), C00G(H00G), C00H(H00H), C00I(H00I), C00J(H00J), C00K(H00K),
 C00L(H00L), C00M(H00M), C00N(H00N), C00O(H00O)
2.b Idealised tetrahedral OH refined as rotating group:
 O001(H001)
;
_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
O001 O 0.70078(9) 0.70277(6) 0.19989(7) 0.0349(2) Uani 1 1 d . . . . .
H001 H 0.7439 0.7512 0.2202 0.052 Uiso 1 1 calc GR . . . .
N002 N 0.65421(12) 0.37028(7) 0.23341(10) 0.0377(3) Uani 1 1 d . . . . .
C003 C 0.64226(12) 0.54378(8) 0.24182(10) 0.0280(3) Uani 1 1 d . . . . .
C004 C 0.70575(12) 0.63801(8) 0.29003(10) 0.0285(3) Uani 1 1 d . . . . .
C005 C 0.51365(12) 0.54236(8) 0.17249(10) 0.0293(3) Uani 1 1 d . . . . .
C006 C 0.85450(13) 0.62548(8) 0.34031(11) 0.0335(3) Uani 1 1 d . . . . .
C007 C 0.46258(13) 0.45151(9) 0.13445(11) 0.0340(3) Uani 1 1 d . . . . .
C008 C 0.70398(13) 0.45806(8) 0.26832(11) 0.0323(3) Uani 1 1 d . . . . .
H008 H 0.7868 0.4595 0.3139 0.039 Uiso 1 1 calc R . . . .
C009 C 0.62121(13) 0.67423(9) 0.37461(11) 0.0350(3) Uani 1 1 d . . . . .
C00A C 0.43308(14) 0.62355(9) 0.13960(12) 0.0380(3) Uani 1 1 d . . . . .
H00A H 0.4632 0.6843 0.1633 0.046 Uiso 1 1 calc R . . . .
C00B C 0.53836(14) 0.36905(9) 0.16854(12) 0.0393(3) Uani 1 1 d . . . . .
H00B H 0.5038 0.3098 0.1433 0.047 Uiso 1 1 calc R . . . .
C00C C 0.33772(15) 0.44440(11) 0.06413(13) 0.0455(4) Uani 1 1 d . . . . .
H00C H 0.3061 0.3846 0.0379 0.055 Uiso 1 1 calc R . . . .
C00D C 0.56394(14) 0.76456(10) 0.36731(14) 0.0446(4) Uani 1 1 d . . . . .
H00D H 0.5779 0.8057 0.3108 0.054 Uiso 1 1 calc R . . . .
C00E C 0.94373(15) 0.60138(11) 0.27005(14) 0.0482(4) Uani 1 1 d . . . . .
H00E H 0.9117 0.5893 0.1962 0.058 Uiso 1 1 calc R . . . .
C00F C 0.90600(16) 0.64354(10) 0.44948(13) 0.0455(4) Uani 1 1 d . . . . .
H00F H 0.8482 0.6592 0.4984 0.055 Uiso 1 1 calc R . . . .
C00G C 0.31181(15) 0.61402(11) 0.07368(13) 0.0454(4) Uani 1 1 d . . . . .
H00G H 0.2599 0.6684 0.0542 0.055 Uiso 1 1 calc R . . . .
C00H C 0.26397(15) 0.52409(11) 0.03476(14) 0.0494(4) Uani 1 1 d . . . . .
H00H H 0.1817 0.5191 -0.0112 0.059 Uiso 1 1 calc R . . . .
C00I C 0.59821(18) 0.61538(11) 0.46098(14) 0.0529(4) Uani 1 1 d . . . . .
H00I H 0.6350 0.5540 0.4673 0.063 Uiso 1 1 calc R . . . .
C00J C 0.48551(17) 0.79429(14) 0.44406(19) 0.0651(5) Uani 1 1 d . . . . .
H00J H 0.4466 0.8550 0.4378 0.078 Uiso 1 1 calc R . . . .
C00K C 1.0428(2) 0.63858(12) 0.48705(18) 0.0642(5) Uani 1 1 d . . . . .
H00K H 1.0759 0.6522 0.5604 0.077 Uiso 1 1 calc R . . . .
C00L C 1.07990(18) 0.59510(14) 0.3087(2) 0.0691(6) Uani 1 1 d . . . . .
H00L H 1.1385 0.5780 0.2610 0.083 Uiso 1 1 calc R . . . .
C00M C 1.12853(19) 0.61406(14) 0.4176(2) 0.0734(6) Uani 1 1 d . . . . .
H00M H 1.2200 0.6101 0.4434 0.088 Uiso 1 1 calc R . . . .
C00N C 0.5219(2) 0.64636(15) 0.53720(17) 0.0716(6) Uani 1 1 d . . . . .
H00N H 0.5091 0.6063 0.5951 0.086 Uiso 1 1 calc R . . . .
C00O C 0.4650(2) 0.73552(17) 0.52833(19) 0.0750(6) Uani 1 1 d . . . . .
H00O H 0.4126 0.7560 0.5794 0.090 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
O001 H001 0.8200 . ?
O001 C004 1.4241(15) . ?
N002 C008 1.3645(16) . ?
N002 C00B 1.3072(19) . ?
C003 C004 1.5371(16) . ?
C003 C005 1.4361(18) . ?
C003 C008 1.3618(17) . ?
C004 C006 1.5417(18) . ?
C004 C009 1.5355(18) . ?
C005 C007 1.4170(17) . ?
C005 C00A 1.4139(18) . ?
C006 C00E 1.388(2) . ?
C006 C00F 1.383(2) . ?
C007 C00B 1.4063(19) . ?
C007 C00C 1.415(2) . ?
C008 H008 0.9300 . ?
C009 C00D 1.381(2) . ?
C009 C00I 1.391(2) . ?
C00A H00A 0.9300 . ?
C00A C00G 1.363(2) . ?
C00B H00B 0.9300 . ?
C00C H00C 0.9300 . ?
C00C C00H 1.353(2) . ?
C00D H00D 0.9300 . ?
C00D C00J 1.391(2) . ?
C00E H00E 0.9300 . ?
C00E C00L 1.386(2) . ?
C00F H00F 0.9300 . ?
C00F C00K 1.388(2) . ?
C00G H00G 0.9300 . ?
C00G C00H 1.399(2) . ?
C00H H00H 0.9300 . ?
C00I H00I 0.9300 . ?
C00I C00N 1.377(2) . ?
C00J H00J 0.9300 . ?
C00J C00O 1.363(3) . ?
C00K H00K 0.9300 . ?
C00K C00M 1.356(3) . ?
C00L H00L 0.9300 . ?
C00L C00M 1.376(3) . ?
C00M H00M 0.9300 . ?
C00N H00N 0.9300 . ?
C00N C00O 1.366(3) . ?
C00O H00O 0.9300 . ?

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
C004 O001 H001 109.5 . . ?
C00B N002 C008 116.92(11) . . ?
C005 C003 C004 121.53(10) . . ?
C008 C003 C004 120.59(11) . . ?
C008 C003 C005 117.81(10) . . ?
O001 C004 C003 106.25(10) . . ?
O001 C004 C006 107.06(10) . . ?
O001 C004 C009 111.53(10) . . ?
C003 C004 C006 112.22(9) . . ?
C009 C004 C003 107.35(10) . . ?
C009 C004 C006 112.32(10) . . ?
C007 C005 C003 117.09(10) . . ?
C00A C005 C003 125.74(11) . . ?
C00A C005 C007 117.16(12) . . ?
C00E C006 C004 117.92(12) . . ?
C00F C006 C004 123.99(13) . . ?
C00F C006 C00E 117.92(13) . . ?
C00B C007 C005 118.57(12) . . ?
C00B C007 C00C 121.01(12) . . ?
C00C C007 C005 120.42(12) . . ?
N002 C008 H008 117.3 . . ?
C003 C008 N002 125.31(12) . . ?
C003 C008 H008 117.3 . . ?
C00D C009 C004 121.91(13) . . ?
C00D C009 C00I 117.75(14) . . ?
C00I C009 C004 120.33(12) . . ?
C005 C00A H00A 119.5 . . ?
C00G C00A C005 120.94(12) . . ?
C00G C00A H00A 119.5 . . ?
N002 C00B C007 124.27(11) . . ?
N002 C00B H00B 117.9 . . ?
C007 C00B H00B 117.9 . . ?
C007 C00C H00C 119.8 . . ?
C00H C00C C007 120.35(13) . . ?
C00H C00C H00C 119.8 . . ?
C009 C00D H00D 119.8 . . ?
C009 C00D C00J 120.40(17) . . ?
C00J C00D H00D 119.8 . . ?
C006 C00E H00E 119.6 . . ?
C00L C00E C006 120.78(17) . . ?
C00L C00E H00E 119.6 . . ?
C006 C00F H00F 119.6 . . ?
C006 C00F C00K 120.86(17) . . ?
C00K C00F H00F 119.6 . . ?
C00A C00G H00G 119.4 . . ?
C00A C00G C00H 121.27(13) . . ?
C00H C00G H00G 119.4 . . ?
C00C C00H C00G 119.81(13) . . ?
C00C C00H H00H 120.1 . . ?
C00G C00H H00H 120.1 . . ?
C009 C00I H00I 119.4 . . ?
C00N C00I C009 121.16(17) . . ?
C00N C00I H00I 119.4 . . ?
C00D C00J H00J 119.6 . . ?
C00O C00J C00D 120.79(17) . . ?
C00O C00J H00J 119.6 . . ?
C00F C00K H00K 119.8 . . ?
C00M C00K C00F 120.48(18) . . ?
C00M C00K H00K 119.8 . . ?
C00E C00L H00L 120.0 . . ?
C00M C00L C00E 120.09(19) . . ?
C00M C00L H00L 120.0 . . ?
C00K C00M C00L 119.85(17) . . ?
C00K C00M H00M 120.1 . . ?
C00L C00M H00M 120.1 . . ?
C00I C00N H00N 119.8 . . ?
C00O C00N C00I 120.41(19) . . ?
C00O C00N H00N 119.8 . . ?
C00J C00O C00N 119.48(16) . . ?
C00J C00O H00O 120.3 . . ?
C00N C00O H00O 120.3 . . ?

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
O001 C004 C006 C00E -51.58(14) . . . . ?
O001 C004 C006 C00F 123.53(13) . . . . ?
O001 C004 C009 C00D -7.70(16) . . . . ?
O001 C004 C009 C00I 171.26(12) . . . . ?
C003 C004 C006 C00E 64.63(14) . . . . ?
C003 C004 C006 C00F -120.27(13) . . . . ?
C003 C004 C009 C00D -123.70(12) . . . . ?
C003 C004 C009 C00I 55.26(15) . . . . ?
C003 C005 C007 C00B 1.49(18) . . . . ?
C003 C005 C007 C00C -178.79(12) . . . . ?
C003 C005 C00A C00G -179.73(13) . . . . ?
C004 C003 C005 C007 -178.52(11) . . . . ?
C004 C003 C005 C00A 0.94(19) . . . . ?
C004 C003 C008 N002 177.53(12) . . . . ?
C004 C006 C00E C00L 175.83(14) . . . . ?
C004 C006 C00F C00K -174.48(13) . . . . ?
C004 C009 C00D C00J 178.60(13) . . . . ?
C004 C009 C00I C00N -179.57(15) . . . . ?
C005 C003 C004 O001 -51.01(14) . . . . ?
C005 C003 C004 C006 -167.70(11) . . . . ?
C005 C003 C004 C009 68.43(14) . . . . ?
C005 C003 C008 N002 0.70(19) . . . . ?
C005 C007 C00B N002 -0.2(2) . . . . ?
C005 C007 C00C C00H -1.8(2) . . . . ?
C005 C00A C00G C00H -1.1(2) . . . . ?
C006 C004 C009 C00D 112.49(13) . . . . ?
C006 C004 C009 C00I -68.55(15) . . . . ?
C006 C00E C00L C00M -0.9(3) . . . . ?
C006 C00F C00K C00M -1.3(2) . . . . ?
C007 C005 C00A C00G -0.3(2) . . . . ?
C007 C00C C00H C00G 0.3(2) . . . . ?
C008 N002 C00B C007 -0.9(2) . . . . ?
C008 C003 C004 O001 132.28(12) . . . . ?
C008 C003 C004 C006 15.58(16) . . . . ?
C008 C003 C004 C009 -108.29(13) . . . . ?
C008 C003 C005 C007 -1.71(18) . . . . ?
C008 C003 C005 C00A 177.74(13) . . . . ?
C009 C004 C006 C00E -174.32(11) . . . . ?
C009 C004 C006 C00F 0.79(16) . . . . ?
C009 C00D C00J C00O 0.7(2) . . . . ?
C009 C00I C00N C00O 1.2(3) . . . . ?
C00A C005 C007 C00B -178.01(12) . . . . ?
C00A C005 C007 C00C 1.7(2) . . . . ?
C00A C00G C00H C00C 1.1(2) . . . . ?
C00B N002 C008 C003 0.6(2) . . . . ?
C00B C007 C00C C00H 177.94(15) . . . . ?
C00C C007 C00B N002 -179.91(14) . . . . ?
C00D C009 C00I C00N -0.6(2) . . . . ?
C00D C00J C00O C00N -0.1(3) . . . . ?
C00E C006 C00F C00K 0.6(2) . . . . ?
C00E C00L C00M C00K 0.2(3) . . . . ?
C00F C006 C00E C00L 0.4(2) . . . . ?
C00F C00K C00M C00L 0.8(3) . . . . ?
C00I C009 C00D C00J -0.4(2) . . . . ?
C00I C00N C00O C00J -0.8(3) . . . . ?

_shelx_SHELXL_version_number     2014/7
_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_cc_amr4_152_0m
_database_code_depnum_ccdc_archive 'CCDC 1571342'
_audit_update_record             
;
2017-08-29 deposited with the CCDC.
2018-01-08 downloaded from the CCDC.
;
_audit_creation_date             2017-07-20
_audit_creation_method           
;
Olex2 1.2
(compiled 2016.02.19 svn.r3266 for OlexSys, GUI svn.r5155)
;
_chemical_name_common            ?
_chemical_name_systematic        4-benzhydrylisoquinolin-1(2H)-one
_chemical_formula_moiety         'C22 H17 N O'
_chemical_formula_sum            'C22 H17 N O'
_chemical_formula_weight         311.36
_chemical_melting_point          '242-244 degree centigrade'
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      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   6.6454(2)
_cell_length_b                   8.8659(4)
_cell_length_c                   15.1694(5)
_cell_angle_alpha                94.198(3)
_cell_angle_beta                 102.080(2)
_cell_angle_gamma                102.439(2)
_cell_volume                     846.86(5)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    3698
_cell_measurement_temperature    296.15
_cell_measurement_theta_max      26.146
_cell_measurement_theta_min      2.370
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.075
_exptl_absorpt_correction_T_max  0.7454
_exptl_absorpt_correction_T_min  0.6826
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            white
_exptl_crystal_colour_primary    white
_exptl_crystal_density_diffrn    1.221
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             328
_exptl_crystal_size_max          0.45
_exptl_crystal_size_mid          0.29
_exptl_crystal_size_min          0.1
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0361
_diffrn_reflns_av_unetI/netI     0.0341
_diffrn_reflns_Laue_measured_fraction_full 0.986
_diffrn_reflns_Laue_measured_fraction_max 0.984
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            12644
_diffrn_reflns_point_group_measured_fraction_full 0.986
_diffrn_reflns_point_group_measured_fraction_max 0.984
_diffrn_reflns_theta_full        26.000
_diffrn_reflns_theta_max         26.379
_diffrn_reflns_theta_min         2.593
_diffrn_ambient_temperature      296.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.986
_diffrn_measured_fraction_theta_max 0.984
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       ?
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2285
_reflns_number_total             3416
_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  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.158
_refine_diff_density_min         -0.156
_refine_diff_density_rms         0.030
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.996
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     217
_refine_ls_number_reflns         3416
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0743
_refine_ls_R_factor_gt           0.0458
_refine_ls_restrained_S_all      0.996
_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)+(0.0850P)²+0.0260P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1258
_refine_ls_wR_factor_ref         0.1416
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups
2.a Ternary CH refined with riding coordinates:
 C009(H009)
2.b Aromatic/amide H refined with riding coordinates:
 N002(H002), C007(H007), C00A(H00A), C00B(H00B), C00D(H00D), C00E(H00E),
 C00F(H00F), C00G(H00G), C00H(H00H), C00I(H00I), C00J(H00J), C00K(H00K),
 C00L(H00L), C00M(H00M), C00N(H00N), C00O(H00O)
;
_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
O001 O 0.82393(15) 0.33639(13) 0.52470(7) 0.0507(3) Uani 1 1 d . . . . .
N002 N 0.75873(18) 0.50481(15) 0.42329(8) 0.0435(3) Uani 1 1 d . . . . .
H002 H 0.8901 0.5534 0.4383 0.052 Uiso 1 1 calc R . . . .
C003 C 0.3353(2) 0.35489(17) 0.36847(9) 0.0391(4) Uani 1 1 d . . . . .
C004 C 0.4172(2) 0.49118(17) 0.32819(9) 0.0391(4) Uani 1 1 d . . . . .
C005 C 0.6963(2) 0.37932(18) 0.46493(9) 0.0401(4) Uani 1 1 d . . . . .
C006 C 0.4738(2) 0.29973(17) 0.43495(9) 0.0384(4) Uani 1 1 d . . . . .
C007 C 0.6247(2) 0.55963(18) 0.35819(9) 0.0423(4) Uani 1 1 d . . . . .
H007 H 0.6800 0.6482 0.3337 0.051 Uiso 1 1 calc R . . . .
C008 C 0.3768(2) 0.71136(18) 0.23225(9) 0.0449(4) Uani 1 1 d . . . . .
C009 C 0.2712(2) 0.55630(18) 0.25771(9) 0.0438(4) Uani 1 1 d . . . . .
H009 H 0.1589 0.5767 0.2863 0.053 Uiso 1 1 calc R . . . .
C00A C 0.1219(2) 0.2717(2) 0.34526(10) 0.0496(4) Uani 1 1 d . . . . .
H00A H 0.0246 0.3072 0.3034 0.059 Uiso 1 1 calc R . . . .
C00B C 0.4014(2) 0.16624(19) 0.47335(10) 0.0468(4) Uani 1 1 d . . . . .
H00B H 0.4946 0.1326 0.5180 0.056 Uiso 1 1 calc R . . . .
C00C C 0.1605(2) 0.44135(19) 0.17307(10) 0.0502(4) Uani 1 1 d . . . . .
C00D C 0.1950(2) 0.0843(2) 0.44601(11) 0.0549(4) Uani 1 1 d . . . . .
H00D H 0.1491 -0.0077 0.4695 0.066 Uiso 1 1 calc R . . . .
C00E C 0.0546(3) 0.1401(2) 0.38276(11) 0.0574(5) Uani 1 1 d . . . . .
H00E H -0.0871 0.0871 0.3657 0.069 Uiso 1 1 calc R . . . .
C00F C 0.5197(3) 0.7231(2) 0.17729(11) 0.0583(5) Uani 1 1 d . . . . .
H00F H 0.5518 0.6335 0.1539 0.070 Uiso 1 1 calc R . . . .
C00G C 0.3307(3) 0.8462(2) 0.26402(12) 0.0635(5) Uani 1 1 d . . . . .
H00G H 0.2351 0.8410 0.3012 0.076 Uiso 1 1 calc R . . . .
C00H C 0.2558(3) 0.3349(2) 0.13863(11) 0.0687(5) Uani 1 1 d . . . . .
H00H H 0.3926 0.3313 0.1673 0.082 Uiso 1 1 calc R . . . .
C00I C -0.0419(3) 0.4443(2) 0.12771(12) 0.0720(6) Uani 1 1 d . . . . .
H00I H -0.1086 0.5160 0.1498 0.086 Uiso 1 1 calc R . . . .
C00J C 0.6159(3) 0.8666(3) 0.15661(13) 0.0743(6) Uani 1 1 d . . . . .
H00J H 0.7148 0.8735 0.1209 0.089 Uiso 1 1 calc R . . . .
C00K C 0.5644(4) 0.9991(3) 0.18909(14) 0.0842(7) Uani 1 1 d . . . . .
H00K H 0.6268 1.0956 0.1746 0.101 Uiso 1 1 calc R . . . .
C00L C 0.4227(4) 0.9886(3) 0.24219(15) 0.0852(7) Uani 1 1 d . . . . .
H00L H 0.3875 1.0780 0.2639 0.102 Uiso 1 1 calc R . . . .
C00M C 0.1478(5) 0.2322(3) 0.06085(14) 0.0988(8) Uani 1 1 d . . . . .
H00M H 0.2121 0.1591 0.0385 0.119 Uiso 1 1 calc R . . . .
C00N C -0.0518(5) 0.2380(3) 0.01718(15) 0.1095(10) Uani 1 1 d . . . . .
H00N H -0.1224 0.1701 -0.0351 0.131 Uiso 1 1 calc R . . . .
C00O C -0.1464(4) 0.3434(3) 0.05056(15) 0.0994(8) Uani 1 1 d . . . . .
H00O H -0.2824 0.3474 0.0211 0.119 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
O001 C005 1.2464(16) . ?
N002 H002 0.8600 . ?
N002 C005 1.3501(19) . ?
N002 C007 1.3761(17) . ?
C003 C004 1.447(2) . ?
C003 C006 1.4074(19) . ?
C003 C00A 1.407(2) . ?
C004 C007 1.346(2) . ?
C004 C009 1.5217(19) . ?
C005 C006 1.454(2) . ?
C006 C00B 1.394(2) . ?
C007 H007 0.9300 . ?
C008 C009 1.519(2) . ?
C008 C00F 1.382(2) . ?
C008 C00G 1.375(2) . ?
C009 H009 0.9800 . ?
C009 C00C 1.523(2) . ?
C00A H00A 0.9300 . ?
C00A C00E 1.365(2) . ?
C00B H00B 0.9300 . ?
C00B C00D 1.368(2) . ?
C00C C00H 1.374(2) . ?
C00C C00I 1.384(2) . ?
C00D H00D 0.9300 . ?
C00D C00E 1.389(2) . ?
C00E H00E 0.9300 . ?
C00F H00F 0.9300 . ?
C00F C00J 1.385(3) . ?
C00G H00G 0.9300 . ?
C00G C00L 1.375(3) . ?
C00H H00H 0.9300 . ?
C00H C00M 1.394(3) . ?
C00I H00I 0.9300 . ?
C00I C00O 1.375(3) . ?
C00J H00J 0.9300 . ?
C00J C00K 1.378(3) . ?
C00K H00K 0.9300 . ?
C00K C00L 1.355(3) . ?
C00L H00L 0.9300 . ?
C00M H00M 0.9300 . ?
C00M C00N 1.367(4) . ?
C00N H00N 0.9300 . ?
C00N C00O 1.357(4) . ?
C00O H00O 0.9300 . ?

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
C005 N002 H002 118.1 . . ?
C005 N002 C007 123.90(12) . . ?
C007 N002 H002 118.1 . . ?
C006 C003 C004 119.29(13) . . ?
C006 C003 C00A 116.81(14) . . ?
C00A C003 C004 123.90(13) . . ?
C003 C004 C009 120.74(12) . . ?
C007 C004 C003 117.10(13) . . ?
C007 C004 C009 122.12(14) . . ?
O001 C005 N002 121.21(13) . . ?
O001 C005 C006 123.29(15) . . ?
N002 C005 C006 115.50(12) . . ?
C003 C006 C005 121.04(14) . . ?
C00B C006 C003 120.81(13) . . ?
C00B C006 C005 118.15(13) . . ?
N002 C007 H007 118.4 . . ?
C004 C007 N002 123.15(14) . . ?
C004 C007 H007 118.4 . . ?
C00F C008 C009 122.25(14) . . ?
C00G C008 C009 119.95(14) . . ?
C00G C008 C00F 117.80(17) . . ?
C004 C009 H009 106.0 . . ?
C004 C009 C00C 113.55(13) . . ?
C008 C009 C004 113.68(12) . . ?
C008 C009 H009 106.0 . . ?
C008 C009 C00C 110.77(12) . . ?
C00C C009 H009 106.0 . . ?
C003 C00A H00A 119.3 . . ?
C00E C00A C003 121.49(14) . . ?
C00E C00A H00A 119.3 . . ?
C006 C00B H00B 119.6 . . ?
C00D C00B C006 120.70(14) . . ?
C00D C00B H00B 119.6 . . ?
C00H C00C C009 122.31(14) . . ?
C00H C00C C00I 118.14(16) . . ?
C00I C00C C009 119.54(15) . . ?
C00B C00D H00D 120.4 . . ?
C00B C00D C00E 119.15(16) . . ?
C00E C00D H00D 120.4 . . ?
C00A C00E C00D 120.92(15) . . ?
C00A C00E H00E 119.5 . . ?
C00D C00E H00E 119.5 . . ?
C008 C00F H00F 119.6 . . ?
C008 C00F C00J 120.78(18) . . ?
C00J C00F H00F 119.6 . . ?
C008 C00G H00G 119.2 . . ?
C008 C00G C00L 121.60(19) . . ?
C00L C00G H00G 119.2 . . ?
C00C C00H H00H 119.9 . . ?
C00C C00H C00M 120.1(2) . . ?
C00M C00H H00H 119.9 . . ?
C00C C00I H00I 119.4 . . ?
C00O C00I C00C 121.3(2) . . ?
C00O C00I H00I 119.4 . . ?
C00F C00J H00J 120.1 . . ?
C00K C00J C00F 119.75(19) . . ?
C00K C00J H00J 120.1 . . ?
C00J C00K H00K 120.1 . . ?
C00L C00K C00J 119.9(2) . . ?
C00L C00K H00K 120.1 . . ?
C00G C00L H00L 119.9 . . ?
C00K C00L C00G 120.2(2) . . ?
C00K C00L H00L 119.9 . . ?
C00H C00M H00M 119.7 . . ?
C00N C00M C00H 120.5(2) . . ?
C00N C00M H00M 119.7 . . ?
C00M C00N H00N 120.2 . . ?
C00O C00N C00M 119.6(2) . . ?
C00O C00N H00N 120.2 . . ?
C00I C00O H00O 119.9 . . ?
C00N C00O C00I 120.3(2) . . ?
C00N C00O H00O 119.9 . . ?

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
O001 C005 C006 C003 178.69(12) . . . . ?
O001 C005 C006 C00B -1.84(19) . . . . ?
N002 C005 C006 C003 -1.55(18) . . . . ?
N002 C005 C006 C00B 177.93(12) . . . . ?
C003 C004 C007 N002 0.9(2) . . . . ?
C003 C004 C009 C008 172.09(11) . . . . ?
C003 C004 C009 C00C -60.06(17) . . . . ?
C003 C006 C00B C00D 1.2(2) . . . . ?
C003 C00A C00E C00D 0.5(2) . . . . ?
C004 C003 C006 C005 1.25(19) . . . . ?
C004 C003 C006 C00B -178.21(11) . . . . ?
C004 C003 C00A C00E 177.34(13) . . . . ?
C004 C009 C00C C00H -34.2(2) . . . . ?
C004 C009 C00C C00I 146.78(16) . . . . ?
C005 N002 C007 C004 -1.3(2) . . . . ?
C005 C006 C00B C00D -178.25(13) . . . . ?
C006 C003 C004 C007 -0.86(19) . . . . ?
C006 C003 C004 C009 -178.59(12) . . . . ?
C006 C003 C00A C00E -2.6(2) . . . . ?
C006 C00B C00D C00E -3.4(2) . . . . ?
C007 N002 C005 O001 -178.68(12) . . . . ?
C007 N002 C005 C006 1.55(19) . . . . ?
C007 C004 C009 C008 -5.52(19) . . . . ?
C007 C004 C009 C00C 122.33(15) . . . . ?
C008 C009 C00C C00H 95.12(18) . . . . ?
C008 C009 C00C C00I -83.89(18) . . . . ?
C008 C00F C00J C00K -1.8(3) . . . . ?
C008 C00G C00L C00K -0.8(3) . . . . ?
C009 C004 C007 N002 178.55(12) . . . . ?
C009 C008 C00F C00J -178.92(14) . . . . ?
C009 C008 C00G C00L -179.79(16) . . . . ?
C009 C00C C00H C00M -179.92(17) . . . . ?
C009 C00C C00I C00O 179.39(18) . . . . ?
C00A C003 C004 C007 179.17(13) . . . . ?
C00A C003 C004 C009 1.4(2) . . . . ?
C00A C003 C006 C005 -178.78(12) . . . . ?
C00A C003 C006 C00B 1.76(19) . . . . ?
C00B C00D C00E C00A 2.5(2) . . . . ?
C00C C00H C00M C00N 1.2(3) . . . . ?
C00C C00I C00O C00N 0.0(4) . . . . ?
C00F C008 C009 C004 74.66(17) . . . . ?
C00F C008 C009 C00C -54.61(18) . . . . ?
C00F C008 C00G C00L 0.1(3) . . . . ?
C00F C00J C00K C00L 1.0(3) . . . . ?
C00G C008 C009 C004 -105.48(16) . . . . ?
C00G C008 C009 C00C 125.25(15) . . . . ?
C00G C008 C00F C00J 1.2(2) . . . . ?
C00H C00C C00I C00O 0.3(3) . . . . ?
C00H C00M C00N C00O -0.8(4) . . . . ?
C00I C00C C00H C00M -0.9(3) . . . . ?
C00J C00K C00L C00G 0.2(3) . . . . ?
C00M C00N C00O C00I 0.3(4) . . . . ?

_shelx_SHELXL_version_number     2014/7
_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_cc_amr3_103b_0m
_database_code_depnum_ccdc_archive 'CCDC 1571344'
_audit_update_record             
;
2017-08-29 deposited with the CCDC.
2018-01-08 downloaded from the CCDC.
;
_audit_creation_date             2017-07-20
_audit_creation_method           
;
Olex2 1.2
(compiled 2016.02.19 svn.r3266 for OlexSys, GUI svn.r5155)
;
_chemical_name_common            ?
_chemical_name_systematic        
2-methyl-4-(3-oxo-1-phenyl-1,3-dihydroisobenzofuran-1-yl)isoquinolin-1(2H)-one
_chemical_formula_moiety         'C24 H17 N O3'
_chemical_formula_sum            'C24 H17 N O3'
_chemical_formula_weight         367.38
_chemical_melting_point          'greater than 270 degree centigrade'
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           15
_space_group_name_H-M_alt        'C 1 2/c 1'
_space_group_name_Hall           '-C 2yc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z-1/2'

_cell_length_a                   20.6490(17)
_cell_length_b                   10.8202(8)
_cell_length_c                   20.1324(17)
_cell_angle_alpha                90
_cell_angle_beta                 126.199(2)
_cell_angle_gamma                90
_cell_volume                     3629.8(5)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    5380
_cell_measurement_temperature    273(2)
_cell_measurement_theta_max      25.137
_cell_measurement_theta_min      2.776
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.089
_exptl_absorpt_correction_T_max  0.7454
_exptl_absorpt_correction_T_min  0.6395
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2014/5 (Bruker,2014/5) was used for absorption correction.
wR2(int) was 0.1403 before and 0.0594 after correction.
The Ratio of minimum to maximum transmission is 0.8579.
The λ/2 correction factor is 0.00150.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            white
_exptl_crystal_colour_primary    white
_exptl_crystal_density_diffrn    1.345
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1536
_exptl_crystal_size_max          0.5
_exptl_crystal_size_mid          0.26
_exptl_crystal_size_min          0.13
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.1134
_diffrn_reflns_av_unetI/netI     0.0651
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.986
_diffrn_reflns_limit_h_max       25
_diffrn_reflns_limit_h_min       -25
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            40405
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.986
_diffrn_reflns_theta_full        26.000
_diffrn_reflns_theta_max         26.683
_diffrn_reflns_theta_min         2.190
_diffrn_ambient_temperature      273.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.986
_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_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2482
_reflns_number_total             3787
_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       ?
_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  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.271
_refine_diff_density_min         -0.258
_refine_diff_density_rms         0.088
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.035
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     254
_refine_ls_number_reflns         3787
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0773
_refine_ls_R_factor_gt           0.0405
_refine_ls_restrained_S_all      1.035
_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)+(0.0960P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1194
_refine_ls_wR_factor_ref         0.1620
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C00B(H00B), C00C(H00C), C00F(H00F), C00G(H00G), C00H(H00H), C00K(H00K),
 C00L(H00L), C00M(H00M), C00N(H00N), C00O(H00O), C00P(H00P), C00Q(H00Q),
 C00R(H00R), C00S(H00S)
2.b Idealised Me refined as rotating group:
 C00J(H00A,H00D,H00E)
;
_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
O001 O 0.61924(7) 0.88420(13) 0.69570(8) 0.0371(4) Uani 1 1 d . . . . .
O002 O 0.80243(7) 0.89742(17) 0.54381(9) 0.0522(5) Uani 1 1 d . . . . .
O003 O 0.63373(10) 1.03143(17) 0.78110(10) 0.0630(5) Uani 1 1 d . . . . .
N004 N 0.81028(8) 0.82458(16) 0.65355(9) 0.0348(4) Uani 1 1 d . . . . .
C005 C 0.71756(10) 0.8481(2) 0.83200(11) 0.0369(5) Uani 1 1 d . . . . .
C006 C 0.76762(10) 0.8639(2) 0.57310(12) 0.0359(5) Uani 1 1 d . . . . .
C007 C 0.69435(9) 0.79676(19) 0.65214(11) 0.0309(4) Uani 1 1 d . . . . .
C008 C 0.72089(10) 0.75012(19) 0.79062(11) 0.0322(5) Uani 1 1 d . . . . .
C009 C 0.68052(10) 0.86365(19) 0.52798(11) 0.0322(4) Uani 1 1 d . . . . .
C00A C 0.59839(10) 0.6637(2) 0.66228(11) 0.0344(5) Uani 1 1 d . . . . .
C00B C 0.77378(10) 0.79481(19) 0.69051(11) 0.0328(5) Uani 1 1 d . . . . .
H00B H 0.8063 0.7719 0.7457 0.039 Uiso 1 1 calc R . . . .
C00C C 0.63474(11) 0.9017(2) 0.44593(11) 0.0404(5) Uani 1 1 d . . . . .
H00C H 0.6599 0.9209 0.4213 0.049 Uiso 1 1 calc R . . . .
C00D C 0.64333(10) 0.83314(18) 0.56587(11) 0.0306(4) Uani 1 1 d . . . . .
C00E C 0.65916(10) 0.76929(18) 0.69868(11) 0.0315(4) Uani 1 1 d . . . . .
C00F C 0.77336(11) 0.6535(2) 0.83343(12) 0.0387(5) Uani 1 1 d . . . . .
H00F H 0.7754 0.5860 0.8061 0.046 Uiso 1 1 calc R . . . .
C00G C 0.51590(11) 0.8825(2) 0.43854(12) 0.0431(5) Uani 1 1 d . . . . .
H00G H 0.4604 0.8895 0.4084 0.052 Uiso 1 1 calc R . . . .
C00H C 0.55945(10) 0.8442(2) 0.51881(11) 0.0377(5) Uani 1 1 d . . . . .
H00H H 0.5332 0.8253 0.5424 0.045 Uiso 1 1 calc R . . . .
C00I C 0.65490(11) 0.9335(2) 0.77188(12) 0.0412(5) Uani 1 1 d . . . . .
C00J C 0.89768(10) 0.8241(2) 0.70275(13) 0.0464(6) Uani 1 1 d . . . . .
H00A H 0.9142 0.7949 0.6698 0.070 Uiso 1 1 calc GR . . . .
H00D H 0.9189 0.7707 0.7494 0.070 Uiso 1 1 calc GR . . . .
H00E H 0.9175 0.9065 0.7214 0.070 Uiso 1 1 calc GR . . . .
C00K C 0.55332(11) 0.9111(2) 0.40161(12) 0.0457(6) Uani 1 1 d . . . . .
H00K H 0.5231 0.9365 0.3469 0.055 Uiso 1 1 calc R . . . .
C00L C 0.53203(11) 0.6661(2) 0.66370(13) 0.0466(6) Uani 1 1 d . . . . .
H00L H 0.5233 0.7335 0.6861 0.056 Uiso 1 1 calc R . . . .
C00M C 0.82273(11) 0.6609(2) 0.91835(12) 0.0434(5) Uani 1 1 d . . . . .
H00M H 0.8591 0.5975 0.9485 0.052 Uiso 1 1 calc R . . . .
C00N C 0.76718(12) 0.8559(2) 0.91738(13) 0.0492(6) Uani 1 1 d . . . . .
H00N H 0.7651 0.9231 0.9448 0.059 Uiso 1 1 calc R . . . .
C00O C 0.61097(12) 0.5609(2) 0.63059(12) 0.0435(5) Uani 1 1 d . . . . .
H00O H 0.6557 0.5574 0.6301 0.052 Uiso 1 1 calc R . . . .
C00P C 0.81949(12) 0.7597(2) 0.95946(13) 0.0507(6) Uani 1 1 d . . . . .
H00P H 0.8533 0.7613 1.0167 0.061 Uiso 1 1 calc R . . . .
C00Q C 0.47886(12) 0.5676(3) 0.63153(15) 0.0567(7) Uani 1 1 d . . . . .
H00Q H 0.4340 0.5702 0.6318 0.068 Uiso 1 1 calc R . . . .
C00R C 0.49118(13) 0.4673(3) 0.59965(14) 0.0568(7) Uani 1 1 d . . . . .
H00R H 0.4549 0.4020 0.5780 0.068 Uiso 1 1 calc R . . . .
C00S C 0.55761(13) 0.4633(2) 0.59972(14) 0.0551(6) Uani 1 1 d . . . . .
H00S H 0.5668 0.3943 0.5788 0.066 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
O001 C00E 1.473(2) . ?
O001 C00I 1.358(2) . ?
O002 C006 1.223(2) . ?
O003 C00I 1.202(3) . ?
N004 C006 1.377(2) . ?
N004 C00B 1.374(2) . ?
N004 C00J 1.458(2) . ?
C005 C008 1.375(3) . ?
C005 C00I 1.464(3) . ?
C005 C00N 1.390(3) . ?
C006 C009 1.460(2) . ?
C007 C00B 1.338(2) . ?
C007 C00D 1.456(2) . ?
C007 C00E 1.516(2) . ?
C008 C00E 1.519(2) . ?
C008 C00F 1.381(3) . ?
C009 C00C 1.395(3) . ?
C009 C00D 1.405(2) . ?
C00A C00E 1.526(3) . ?
C00A C00L 1.387(3) . ?
C00A C00O 1.382(3) . ?
C00B H00B 0.9300 . ?
C00C H00C 0.9300 . ?
C00C C00K 1.364(3) . ?
C00D C00H 1.405(2) . ?
C00F H00F 0.9300 . ?
C00F C00M 1.382(3) . ?
C00G H00G 0.9300 . ?
C00G C00H 1.369(3) . ?
C00G C00K 1.387(3) . ?
C00H H00H 0.9300 . ?
C00J H00A 0.9600 . ?
C00J H00D 0.9600 . ?
C00J H00E 0.9600 . ?
C00K H00K 0.9300 . ?
C00L H00L 0.9300 . ?
C00L C00Q 1.386(3) . ?
C00M H00M 0.9300 . ?
C00M C00P 1.377(3) . ?
C00N H00N 0.9300 . ?
C00N C00P 1.374(3) . ?
C00O H00O 0.9300 . ?
C00O C00S 1.381(3) . ?
C00P H00P 0.9300 . ?
C00Q H00Q 0.9300 . ?
C00Q C00R 1.359(4) . ?
C00R H00R 0.9300 . ?
C00R C00S 1.372(3) . ?
C00S H00S 0.9300 . ?

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
C00I O001 C00E 111.60(14) . . ?
C006 N004 C00J 118.39(15) . . ?
C00B N004 C006 122.35(15) . . ?
C00B N004 C00J 119.08(15) . . ?
C008 C005 C00I 108.76(17) . . ?
C008 C005 C00N 122.15(19) . . ?
C00N C005 C00I 129.1(2) . . ?
O002 C006 N004 120.59(16) . . ?
O002 C006 C009 124.01(18) . . ?
N004 C006 C009 115.39(15) . . ?
C00B C007 C00D 118.01(15) . . ?
C00B C007 C00E 120.77(15) . . ?
C00D C007 C00E 121.12(14) . . ?
C005 C008 C00E 109.09(17) . . ?
C005 C008 C00F 120.47(18) . . ?
C00F C008 C00E 130.42(18) . . ?
C00C C009 C006 117.42(16) . . ?
C00C C009 C00D 120.45(16) . . ?
C00D C009 C006 122.03(16) . . ?
C00L C00A C00E 121.22(19) . . ?
C00O C00A C00E 119.93(16) . . ?
C00O C00A C00L 118.8(2) . . ?
N004 C00B H00B 117.9 . . ?
C007 C00B N004 124.13(16) . . ?
C007 C00B H00B 117.9 . . ?
C009 C00C H00C 119.7 . . ?
C00K C00C C009 120.51(17) . . ?
C00K C00C H00C 119.7 . . ?
C009 C00D C007 117.96(15) . . ?
C009 C00D C00H 117.74(16) . . ?
C00H C00D C007 124.26(16) . . ?
O001 C00E C007 105.67(15) . . ?
O001 C00E C008 102.21(14) . . ?
O001 C00E C00A 109.29(13) . . ?
C007 C00E C008 114.60(13) . . ?
C007 C00E C00A 114.09(15) . . ?
C008 C00E C00A 110.08(16) . . ?
C008 C00F H00F 121.2 . . ?
C008 C00F C00M 117.5(2) . . ?
C00M C00F H00F 121.2 . . ?
C00H C00G H00G 119.5 . . ?
C00H C00G C00K 120.97(17) . . ?
C00K C00G H00G 119.5 . . ?
C00D C00H H00H 119.7 . . ?
C00G C00H C00D 120.69(17) . . ?
C00G C00H H00H 119.7 . . ?
O001 C00I C005 108.10(18) . . ?
O003 C00I O001 121.10(18) . . ?
O003 C00I C005 130.80(19) . . ?
N004 C00J H00A 109.5 . . ?
N004 C00J H00D 109.5 . . ?
N004 C00J H00E 109.5 . . ?
H00A C00J H00D 109.5 . . ?
H00A C00J H00E 109.5 . . ?
H00D C00J H00E 109.5 . . ?
C00C C00K C00G 119.63(18) . . ?
C00C C00K H00K 120.2 . . ?
C00G C00K H00K 120.2 . . ?
C00A C00L H00L 120.1 . . ?
C00Q C00L C00A 119.7(2) . . ?
C00Q C00L H00L 120.1 . . ?
C00F C00M H00M 119.1 . . ?
C00P C00M C00F 121.8(2) . . ?
C00P C00M H00M 119.1 . . ?
C005 C00N H00N 121.5 . . ?
C00P C00N C005 117.0(2) . . ?
C00P C00N H00N 121.5 . . ?
C00A C00O H00O 119.8 . . ?
C00S C00O C00A 120.42(19) . . ?
C00S C00O H00O 119.8 . . ?
C00M C00P H00P 119.4 . . ?
C00N C00P C00M 121.1(2) . . ?
C00N C00P H00P 119.4 . . ?
C00L C00Q H00Q 119.4 . . ?
C00R C00Q C00L 121.1(2) . . ?
C00R C00Q H00Q 119.4 . . ?
C00Q C00R H00R 120.3 . . ?
C00Q C00R C00S 119.4(2) . . ?
C00S C00R H00R 120.3 . . ?
C00O C00S H00S 119.7 . . ?
C00R C00S C00O 120.5(2) . . ?
C00R C00S H00S 119.7 . . ?

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
O002 C006 C009 C00C 1.4(3) . . . . ?
O002 C006 C009 C00D -175.2(2) . . . . ?
N004 C006 C009 C00C -179.42(19) . . . . ?
N004 C006 C009 C00D 4.0(3) . . . . ?
C005 C008 C00E O001 -3.26(19) . . . . ?
C005 C008 C00E C007 110.51(18) . . . . ?
C005 C008 C00E C00A -119.30(17) . . . . ?
C005 C008 C00F C00M -1.3(3) . . . . ?
C005 C00N C00P C00M 0.6(3) . . . . ?
C006 N004 C00B C007 2.4(3) . . . . ?
C006 C009 C00C C00K -175.9(2) . . . . ?
C006 C009 C00D C007 -2.2(3) . . . . ?
C006 C009 C00D C00H 175.50(19) . . . . ?
C007 C00D C00H C00G 178.1(2) . . . . ?
C008 C005 C00I O001 2.4(2) . . . . ?
C008 C005 C00I O003 -177.6(2) . . . . ?
C008 C005 C00N C00P -1.0(3) . . . . ?
C008 C00F C00M C00P 0.9(3) . . . . ?
C009 C00C C00K C00G 0.0(4) . . . . ?
C009 C00D C00H C00G 0.5(3) . . . . ?
C00A C00L C00Q C00R 1.1(3) . . . . ?
C00A C00O C00S C00R 0.4(3) . . . . ?
C00B N004 C006 O002 175.1(2) . . . . ?
C00B N004 C006 C009 -4.1(3) . . . . ?
C00B C007 C00D C009 0.2(3) . . . . ?
C00B C007 C00D C00H -177.3(2) . . . . ?
C00B C007 C00E O001 116.1(2) . . . . ?
C00B C007 C00E C008 4.4(3) . . . . ?
C00B C007 C00E C00A -123.8(2) . . . . ?
C00C C009 C00D C007 -178.62(19) . . . . ?
C00C C009 C00D C00H -0.9(3) . . . . ?
C00D C007 C00B N004 -0.2(3) . . . . ?
C00D C007 C00E O001 -60.2(2) . . . . ?
C00D C007 C00E C008 -171.91(17) . . . . ?
C00D C007 C00E C00A 59.9(2) . . . . ?
C00D C009 C00C C00K 0.7(3) . . . . ?
C00E O001 C00I O003 175.31(19) . . . . ?
C00E O001 C00I C005 -4.6(2) . . . . ?
C00E C007 C00B N004 -176.65(18) . . . . ?
C00E C007 C00D C009 176.61(18) . . . . ?
C00E C007 C00D C00H -0.9(3) . . . . ?
C00E C008 C00F C00M -179.27(18) . . . . ?
C00E C00A C00L C00Q -178.75(18) . . . . ?
C00E C00A C00O C00S 178.09(19) . . . . ?
C00F C008 C00E O001 174.88(18) . . . . ?
C00F C008 C00E C007 -71.3(3) . . . . ?
C00F C008 C00E C00A 58.8(2) . . . . ?
C00F C00M C00P C00N -0.5(3) . . . . ?
C00H C00G C00K C00C -0.4(4) . . . . ?
C00I O001 C00E C007 -115.35(16) . . . . ?
C00I O001 C00E C008 4.86(18) . . . . ?
C00I O001 C00E C00A 121.47(16) . . . . ?
C00I C005 C008 C00E 0.7(2) . . . . ?
C00I C005 C008 C00F -177.61(17) . . . . ?
C00I C005 C00N C00P 177.8(2) . . . . ?
C00J N004 C006 O002 0.1(3) . . . . ?
C00J N004 C006 C009 -179.12(18) . . . . ?
C00J N004 C00B C007 177.4(2) . . . . ?
C00K C00G C00H C00D 0.1(3) . . . . ?
C00L C00A C00E O001 -26.7(2) . . . . ?
C00L C00A C00E C007 -144.71(19) . . . . ?
C00L C00A C00E C008 84.8(2) . . . . ?
C00L C00A C00O C00S 1.1(3) . . . . ?
C00L C00Q C00R C00S 0.3(4) . . . . ?
C00N C005 C008 C00E 179.79(18) . . . . ?
C00N C005 C008 C00F 1.4(3) . . . . ?
C00N C005 C00I O001 -176.6(2) . . . . ?
C00N C005 C00I O003 3.5(4) . . . . ?
C00O C00A C00E O001 156.38(17) . . . . ?
C00O C00A C00E C007 38.3(2) . . . . ?
C00O C00A C00E C008 -92.1(2) . . . . ?
C00O C00A C00L C00Q -1.8(3) . . . . ?
C00Q C00R C00S C00O -1.1(4) . . . . ?

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