# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# 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. 
# 
#######################################################################

data_4d
_database_code_depnum_ccdc_archive 'CCDC 1442061'
_audit_update_record             
;
2015-12-11 deposited with the CCDC.
2016-12-06 downloaded from the CCDC.
;
#============================================================================
_audit_creation_date             2015-04-17
_audit_creation_method           CRYSTALS_ver_14.43

_oxford_structure_analysis_title 026lp14
_chemical_name_systematic        .
_chemical_melting_point          'decomposition at 551 K'

_cell_length_a                   13.5987(2)
_cell_length_b                   7.2344(1)
_cell_length_c                   13.7418(2)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1351.90(3)

_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_H-M   'P b c n '
_symmetry_space_group_name_Hall  '-P 2n 2ab'
loop_
_symmetry_equiv_pos_as_xyz
x,y,z
-x,-y,-z
x+1/2,y+1/2,-z+1/2
-x+1/2,-y+1/2,z+1/2
x+1/2,-y+1/2,-z
-x+1/2,y+1/2,z
-x,y,-z+1/2
x,-y,z+1/2

loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_Cromer_Mann_a1
_atom_type_scat_Cromer_Mann_b1
_atom_type_scat_Cromer_Mann_a2
_atom_type_scat_Cromer_Mann_b2
_atom_type_scat_Cromer_Mann_a3
_atom_type_scat_Cromer_Mann_b3
_atom_type_scat_Cromer_Mann_a4
_atom_type_scat_Cromer_Mann_b4
_atom_type_scat_Cromer_Mann_c
_atom_type_scat_source
C 0.0181 0.0091 2.3100 20.8439 1.0200 10.2075 1.5886 0.5687 0.8650 51.6512
0.2156 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
H 0.0000 0.0000 0.4930 10.5109 0.3229 26.1257 0.1402 3.1424 0.0408 57.7998
0.0030 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
Cl 0.3639 0.7018 11.4604 0.0104 7.1964 1.1662 6.2556 18.5194 1.6455 47.7784
-9.5574 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
N 0.0311 0.0180 12.2126 0.0057 3.1322 9.8933 2.0125 28.9975 1.1663 0.5826
-11.5290 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
O 0.0492 0.0322 3.0485 13.2771 2.2868 5.7011 1.5463 0.3239 0.8670 32.9089
0.2508 'International Tables Vol C 4.2.6.8 and 6.1.1.4'


_cell_formula_units_Z            4

# Given Formula = C16 H10 Cl2 N2 O2 
# Dc =      1.64 Fooo =    680.00 Mu =     44.02 M =    166.59
# Found Formula = C16 H10 Cl2 N2 O2 
# Dc =      1.64 FOOO =    680.00 Mu =     44.02 M =    166.59

_chemical_formula_sum            'C16 H10 Cl2 N2 O2'
_chemical_formula_moiety         'C16 H10 Cl2 N2 O2'
_chemical_compound_source        .
_chemical_formula_weight         333.17


_cell_measurement_reflns_used    6892
_cell_measurement_theta_min      3
_cell_measurement_theta_max      76
_cell_measurement_temperature    150

_exptl_crystal_description       block
_exptl_crystal_colour            clear_pale_colourless
_exptl_crystal_size_min          0.18
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_max          0.25

_exptl_crystal_density_diffrn    1.637
_exptl_crystal_density_meas      .
_exptl_crystal_density_method    'not measured'
# Non-dispersive F(000): 
_exptl_crystal_F_000             680
_exptl_absorpt_coefficient_mu    4.402

# Sheldrick geometric approximatio 0.41 0.45 
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'CrysAlis, (Oxford Diffraction, 2002)'
_exptl_absorpt_correction_T_min  0.29
_exptl_absorpt_correction_T_max  0.45
_diffrn_measurement_device_type  'Oxford Diffraction SuperNova'
_diffrn_measurement_device       Area
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54180
_diffrn_measurement_method       ω

# If a reference occurs more than once, delete the author 
# and date from subsequent references. 
_computing_data_collection       'SuperNova, (Oxford Diffraction, 2010)'
_computing_cell_refinement       'CrysAlis, (Oxford Diffraction, 2002)'
_computing_data_reduction        'CrysAlis, (Oxford Diffraction, 2002)'
_computing_structure_solution    'Superflip (Palatinus & Chapuis, 2007)'
_computing_structure_refinement  'CRYSTALS (Betteridge et al., 2003)'
_computing_publication_material  'CRYSTALS (Betteridge et al., 2003)'
_computing_molecular_graphics    'CAMERON (Watkin et al., 1996)'

_diffrn_standards_interval_time  .
_diffrn_standards_interval_count .
_diffrn_standards_number         0
_diffrn_standards_decay_%        .

_diffrn_ambient_temperature      150
_diffrn_reflns_number            11819
_reflns_number_total             1413
_diffrn_reflns_av_R_equivalents  0.024
# Number of reflections with Friedels Law is 1413 
# Theoretical number of reflections is about 2834 


_diffrn_reflns_theta_min         6.442
_diffrn_reflns_theta_max         76.293
_diffrn_measured_fraction_theta_max 0.996

_diffrn_reflns_theta_full        76.293
_diffrn_measured_fraction_theta_full 0.996


_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       17
_reflns_limit_h_min              0
_reflns_limit_h_max              17
_reflns_limit_k_min              0
_reflns_limit_k_max              9
_reflns_limit_l_min              0
_reflns_limit_l_max              17

_oxford_diffrn_Wilson_B_factor   1.75
_oxford_diffrn_Wilson_scale      0.04

_atom_sites_solution_primary     Other #heavy,direct,difmap,geom
# _atom_sites_solution_secondary  difmap
_atom_sites_solution_hydrogens   difmap

_refine_diff_density_min         -0.33
_refine_diff_density_max         0.31


# The current dictionary definitions do not cover the 
# situation where the reflections used for refinement were 
# selected by a user-defined sigma threshold 


# The values actually used during refinement 
_oxford_reflns_threshold_expression_ref I>-3.0\s(I)
_refine_ls_number_reflns         1406
_refine_ls_number_restraints     0
_refine_ls_number_parameters     100
_oxford_refine_ls_R_factor_ref   0.0287
_refine_ls_wR_factor_ref         0.0761
_refine_ls_goodness_of_fit_ref   1.0054
_refine_ls_shift/su_max          0.0007165
_refine_ls_shift/su_mean         0.0000589


# The values computed with all filters except I/sigma 
_oxford_reflns_number_all        1407
_refine_ls_R_factor_all          0.0287
_refine_ls_wR_factor_all         0.0768

# The values computed with a 2 sigma cutoff - a la SHELX 
_reflns_threshold_expression     I>2.0σ(I)
_reflns_number_gt                1326
_refine_ls_R_factor_gt           0.0274
_refine_ls_wR_factor_gt          0.0748

# choose from: rm (reference molecule of known chirality), 
# ad (anomolous dispersion - Flack), rmad (rm and ad), 
# syn (from synthesis), unk (unknown) or . (not applicable). 
_chemical_absolute_configuration .


_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_hydrogen_treatment    constr #undef, noref, refall,
# refxyz, refU, constr or mixed
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
;
 Method= Modified Sheldrick 
 w=1/[σ²(F²) + ( 0.04P)² + 0.66P] 
 ,where P=(max(Fo²,0) + 2Fc²)/3 
;

# Uequiv = arithmetic mean of Ui i.e. Ueqiv = (U1+U2+U3)/3

# Replace last . with number of unfound hydrogen atoms attached to an atom.

# ..._refinement_flags_... 
# . no refinement constraints           S special position constraint on site
# G rigid group refinement of site      R riding atom
# D distance or angle restraint on site T thermal displacement constraints
# U Uiso or Uij restraint (rigid bond)  P partial occupancy constraint


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_occupancy
_atom_site_adp_type
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
_atom_site_attached_hydrogens
Cl1 Cl 0.84538(2) 0.50449(5) 0.50430(2) 0.0297 1.0000 Uani . . . . . .
C2 C 0.76483(9) 0.54506(17) 0.40853(9) 0.0207 1.0000 Uani . . . . . .
C3 C 0.80201(9) 0.61278(17) 0.32160(9) 0.0201 1.0000 Uani . . . . . .
C4 C 0.73889(9) 0.64183(17) 0.24338(8) 0.0191 1.0000 Uani . . . . . .
C5 C 0.63951(9) 0.60568(17) 0.25494(8) 0.0182 1.0000 Uani . . . . . .
N6 N 0.56817(7) 0.64920(14) 0.18030(7) 0.0183 1.0000 Uani . . . . . .
C7 C 0.50657(9) 0.50419(17) 0.15169(10) 0.0196 1.0000 Uani . . . . . .
C8 C 0.60231(9) 0.54309(16) 0.34442(9) 0.0189 1.0000 Uani . . . . . .
C9 C 0.66534(9) 0.50858(16) 0.42176(9) 0.0205 1.0000 Uani . . . . . .
O10 O 0.53857(7) 0.35216(13) 0.13139(7) 0.0280 1.0000 Uani . . . . . .
C11 C 0.52340(9) 0.83128(16) 0.19893(8) 0.0190 1.0000 Uani . . . . . .
H31 H 0.8709 0.6447 0.3156 0.0229 1.0000 Uiso R . . . . .
H41 H 0.7642 0.6900 0.1823 0.0222 1.0000 Uiso R . . . . .
H91 H 0.6406 0.4583 0.4821 0.0246 1.0000 Uiso R . . . . .
H111 H 0.5745 0.9192 0.1946 0.0221 1.0000 Uiso R . . . . .
H112 H 0.4741 0.8467 0.1483 0.0210 1.0000 Uiso R . . . . .

_refine_ls_extinction_method     None
_oxford_refine_ls_scale          5.60(14)
loop_
_geom_bond_atom_site_label_1
_geom_bond_site_symmetry_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
Cl1 . C2 . 1.7372(12) yes
C2 . C3 . 1.3866(17) yes
C2 . C9 . 1.3904(18) yes
C3 . C4 . 1.3916(17) yes
C3 . H31 . 0.969 no
C4 . C5 . 1.3856(17) yes
C4 . H41 . 0.971 no
C5 . N6 . 1.4465(15) yes
C5 . C8 . 1.4046(16) yes
N6 . C7 . 1.3989(16) yes
N6 . C11 . 1.4736(15) yes
C7 . C8 7_655 1.5080(16) yes
C7 . O10 . 1.2153(16) yes
C8 . C9 . 1.3880(17) yes
C9 . H91 . 0.967 no
C11 . C11 7_655 1.541(2) yes
C11 . H111 . 0.943 no
C11 . H112 . 0.973 no
loop_
_geom_angle_atom_site_label_1
_geom_angle_site_symmetry_1
_geom_angle_atom_site_label_2
_geom_angle_site_symmetry_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
Cl1 . C2 . C3 . 118.84(9) yes
Cl1 . C2 . C9 . 118.85(10) yes
C3 . C2 . C9 . 122.31(11) yes
C2 . C3 . C4 . 119.60(11) yes
C2 . C3 . H31 . 120.7 no
C4 . C3 . H31 . 119.6 no
C3 . C4 . C5 . 118.98(11) yes
C3 . C4 . H41 . 120.2 no
C5 . C4 . H41 . 120.8 no
C4 . C5 . N6 . 122.12(10) yes
C4 . C5 . C8 . 120.83(11) yes
N6 . C5 . C8 . 116.70(10) yes
C5 . N6 . C7 . 115.95(10) yes
C5 . N6 . C11 . 110.39(9) yes
C7 . N6 . C11 . 118.15(9) yes
C8 7_655 C7 . N6 . 115.98(10) yes
C8 7_655 C7 . O10 . 121.91(11) yes
N6 . C7 . O10 . 121.92(11) yes
C7 7_655 C8 . C5 . 116.42(11) yes
C7 7_655 C8 . C9 . 123.06(11) yes
C5 . C8 . C9 . 120.39(11) yes
C2 . C9 . C8 . 117.82(11) yes
C2 . C9 . H91 . 121.5 no
C8 . C9 . H91 . 120.6 no
C11 7_655 C11 . N6 . 109.20(7) yes
C11 7_655 C11 . H111 . 111.2 no
N6 . C11 . H111 . 106.7 no
C11 7_655 C11 . H112 . 111.5 no
N6 . C11 . H112 . 105.3 no
H111 . C11 . H112 . 112.6 no


_iucr_refine_instructions_details_constraints 
;
#
# Punched on 17/04/15 at 16:20:38
#
#LIST     12                                                                    
BLOCK SCALE X'S, U'S 
RIDE C   (   3,X'S) H   (  31,X'S) 
RIDE C   (   4,X'S) H   (  41,X'S) 
RIDE C   (   9,X'S) H   (  91,X'S) 
RIDE C   (  11,X'S) H   ( 111,X'S) H   ( 112,X'S) 
END                                                                             
;


_iucr_refine_instructions_details_restraints 
;
#
# Punched on 17/04/15 at 16:20:38
#
#LIST     16                                                                    
NO 
REM   HREST   START (DO NOT REMOVE THIS LINE) 
REM   HREST   END (DO NOT REMOVE THIS LINE) 
END                                                                             
;

# Manually omitted reflections

loop_
_oxford_refln_omitted_index_h
_oxford_refln_omitted_index_k
_oxford_refln_omitted_index_l
_oxford_refln_omitted_flag
_oxford_refln_omitted_details
0 2 0 x .
####################################################################### 
# 
# 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_5a
_database_code_depnum_ccdc_archive 'CCDC 1442062'
_audit_update_record             
;
2015-12-11 deposited with the CCDC.
2016-12-06 downloaded from the CCDC.
;
#============================================================================
_audit_creation_date             2015-04-17
_audit_creation_method           CRYSTALS_ver_14.43

_oxford_structure_analysis_title 052lp15
_chemical_name_systematic        .
_chemical_melting_point          'decomposition at 348-350 K'


_cell_length_a                   9.6458(2)
_cell_length_b                   14.7532(2)
_cell_length_c                   11.0237(2)
_cell_angle_alpha                90
_cell_angle_beta                 109.3728(18)
_cell_angle_gamma                90
_cell_volume                     1479.92(5)

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 21/n '
_symmetry_space_group_name_Hall  '-P 2yn'
loop_
_symmetry_equiv_pos_as_xyz
x,y,z
-x,-y,-z
x+1/2,-y+1/2,z+1/2
-x+1/2,y+1/2,-z+1/2

loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_Cromer_Mann_a1
_atom_type_scat_Cromer_Mann_b1
_atom_type_scat_Cromer_Mann_a2
_atom_type_scat_Cromer_Mann_b2
_atom_type_scat_Cromer_Mann_a3
_atom_type_scat_Cromer_Mann_b3
_atom_type_scat_Cromer_Mann_a4
_atom_type_scat_Cromer_Mann_b4
_atom_type_scat_Cromer_Mann_c
_atom_type_scat_source
C 0.0181 0.0091 2.3100 20.8439 1.0200 10.2075 1.5886 0.5687 0.8650 51.6512
0.2156 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
H 0.0000 0.0000 0.4930 10.5109 0.3229 26.1257 0.1402 3.1424 0.0408 57.7998
0.0030 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
N 0.0311 0.0180 12.2126 0.0057 3.1322 9.8933 2.0125 28.9975 1.1663 0.5826
-11.5290 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
O 0.0492 0.0322 3.0485 13.2771 2.2868 5.7011 1.5463 0.3239 0.8670 32.9089
0.2508 'International Tables Vol C 4.2.6.8 and 6.1.1.4'


_cell_formula_units_Z            4

# Given Formula = C19 H18 N2 O1 
# Dc =      1.30 Fooo =    616.00 Mu =      6.41 M =    290.36
# Found Formula = C19 H18 N2 O1 
# Dc =      1.30 FOOO =    616.00 Mu =      6.41 M =    290.36

_chemical_formula_sum            'C19 H18 N2 O1'
_chemical_formula_moiety         'C19 H18 N2 O1'
_chemical_compound_source        .
_chemical_formula_weight         290.36


_cell_measurement_reflns_used    7704
_cell_measurement_theta_min      3
_cell_measurement_theta_max      76
_cell_measurement_temperature    150

_exptl_crystal_description       prism
_exptl_crystal_colour            clear_pale_colourless
_exptl_crystal_size_min          0.18
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_max          0.20

_exptl_crystal_density_diffrn    1.303
_exptl_crystal_density_meas      .
_exptl_crystal_density_method    'not measured'
# Non-dispersive F(000): 
_exptl_crystal_F_000             616
_exptl_absorpt_coefficient_mu    0.641

# Sheldrick geometric approximatio 0.88 0.89 
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'CrysAlis, (Oxford Diffraction, 2002)'
_exptl_absorpt_correction_T_min  0.83
_exptl_absorpt_correction_T_max  0.89
_diffrn_measurement_device_type  'Oxford Diffraction SuperNova'
_diffrn_measurement_device       Area
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54180
_diffrn_measurement_method       ω

# If a reference occurs more than once, delete the author 
# and date from subsequent references. 
_computing_data_collection       'SuperNova, (Oxford Diffraction, 2010)'
_computing_cell_refinement       'CrysAlis, (Oxford Diffraction, 2002)'
_computing_data_reduction        'CrysAlis, (Oxford Diffraction, 2002)'
_computing_structure_solution    'Superflip (Palatinus & Chapuis, 2007)'
_computing_structure_refinement  'CRYSTALS (Betteridge et al., 2003)'
_computing_publication_material  'CRYSTALS (Betteridge et al., 2003)'
_computing_molecular_graphics    'CAMERON (Watkin et al., 1996)'

_diffrn_standards_interval_time  .
_diffrn_standards_interval_count .
_diffrn_standards_number         0
_diffrn_standards_decay_%        .

_diffrn_ambient_temperature      150
_diffrn_reflns_number            13631
_reflns_number_total             3080
_diffrn_reflns_av_R_equivalents  0.019
# Number of reflections with Friedels Law is 3080 
# Theoretical number of reflections is about 6213 


_diffrn_reflns_theta_min         5.204
_diffrn_reflns_theta_max         76.404
_diffrn_measured_fraction_theta_max 0.994

_diffrn_reflns_theta_full        74.876
_diffrn_measured_fraction_theta_full 0.998


_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       13
_reflns_limit_h_min              -12
_reflns_limit_h_max              11
_reflns_limit_k_min              0
_reflns_limit_k_max              18
_reflns_limit_l_min              0
_reflns_limit_l_max              13

_oxford_diffrn_Wilson_B_factor   1.94
_oxford_diffrn_Wilson_scale      0.02

_atom_sites_solution_primary     Other #heavy,direct,difmap,geom
# _atom_sites_solution_secondary  difmap
_atom_sites_solution_hydrogens   difmap

_refine_diff_density_min         -0.21
_refine_diff_density_max         0.27


# The current dictionary definitions do not cover the 
# situation where the reflections used for refinement were 
# selected by a user-defined sigma threshold 


# The values actually used during refinement 
_oxford_reflns_threshold_expression_ref I>-3.0\s(I)
_refine_ls_number_reflns         3068
_refine_ls_number_restraints     0
_refine_ls_number_parameters     199
_oxford_refine_ls_R_factor_ref   0.0406
_refine_ls_wR_factor_ref         0.0984
_refine_ls_goodness_of_fit_ref   0.9881
_refine_ls_shift/su_max          0.0002284
_refine_ls_shift/su_mean         0.0000366


# The values computed with all filters except I/sigma 
_oxford_reflns_number_all        3068
_refine_ls_R_factor_all          0.0406
_refine_ls_wR_factor_all         0.0984

# The values computed with a 2 sigma cutoff - a la SHELX 
_reflns_threshold_expression     I>2.0σ(I)
_reflns_number_gt                2840
_refine_ls_R_factor_gt           0.0382
_refine_ls_wR_factor_gt          0.0962

# choose from: rm (reference molecule of known chirality), 
# ad (anomolous dispersion - Flack), rmad (rm and ad), 
# syn (from synthesis), unk (unknown) or . (not applicable). 
_chemical_absolute_configuration .


_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_hydrogen_treatment    constr #undef, noref, refall,
# refxyz, refU, constr or mixed
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
;
 Method= Modified Sheldrick 
 w=1/[σ²(F²) + ( 0.05P)² + 0.72P] 
 ,where P=(max(Fo²,0) + 2Fc²)/3 
;

# Uequiv = arithmetic mean of Ui i.e. Ueqiv = (U1+U2+U3)/3

# Replace last . with number of unfound hydrogen atoms attached to an atom.

# ..._refinement_flags_... 
# . no refinement constraints           S special position constraint on site
# G rigid group refinement of site      R riding atom
# D distance or angle restraint on site T thermal displacement constraints
# U Uiso or Uij restraint (rigid bond)  P partial occupancy constraint


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_occupancy
_atom_site_adp_type
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
_atom_site_attached_hydrogens
O1 O 0.72266(9) 0.12139(6) 0.67299(9) 0.0264 1.0000 Uani . . . . . .
C2 C 0.65491(12) 0.18047(7) 0.59894(10) 0.0188 1.0000 Uani . . . . . .
N3 N 0.51131(10) 0.16816(6) 0.51865(9) 0.0199 1.0000 Uani . . . . . .
C4 C 0.41034(12) 0.13304(8) 0.57887(11) 0.0207 1.0000 Uani . . . . . .
C5 C 0.38529(12) 0.18702(8) 0.67438(11) 0.0204 1.0000 Uani . . . . . .
C6 C 0.46967(12) 0.27317(7) 0.71611(11) 0.0199 1.0000 Uani . . . . . .
N7 N 0.48873(10) 0.33189(6) 0.61986(9) 0.0200 1.0000 Uani . . . . . .
C8 C 0.63832(12) 0.34613(8) 0.62338(11) 0.0197 1.0000 Uani . . . . . .
C9 C 0.71949(12) 0.27314(7) 0.60019(10) 0.0187 1.0000 Uani . . . . . .
C10 C 0.86189(12) 0.28681(8) 0.59939(11) 0.0215 1.0000 Uani . . . . . .
C11 C 0.92498(13) 0.37287(8) 0.61981(12) 0.0253 1.0000 Uani . . . . . .
C12 C 0.84480(14) 0.44398(8) 0.64696(13) 0.0283 1.0000 Uani . . . . . .
C13 C 0.70272(14) 0.43107(8) 0.64850(12) 0.0260 1.0000 Uani . . . . . .
C14 C 1.07747(15) 0.38851(10) 0.61536(16) 0.0386 1.0000 Uani . . . . . .
C15 C 0.39009(13) 0.31771(8) 0.48780(11) 0.0242 1.0000 Uani . . . . . .
C16 C 0.44292(13) 0.23868(8) 0.42366(11) 0.0236 1.0000 Uani . . . . . .
C17 C 0.52874(14) 0.29427(9) 0.83962(12) 0.0271 1.0000 Uani . . . . . .
C18 C 0.28391(13) 0.15709(8) 0.73108(12) 0.0243 1.0000 Uani . . . . . .
C19 C 0.20635(13) 0.07623(8) 0.69319(13) 0.0272 1.0000 Uani . . . . . .
C20 C 0.23281(14) 0.02504(8) 0.59655(13) 0.0285 1.0000 Uani . . . . . .
C21 C 0.33447(13) 0.05279(8) 0.53946(12) 0.0258 1.0000 Uani . . . . . .
C22 C 0.09722(15) 0.04591(10) 0.75575(16) 0.0359 1.0000 Uani . . . . . .
H101 H 0.9133 0.2353 0.5847 0.0279 1.0000 Uiso R . . . . .
H121 H 0.8868 0.5028 0.6633 0.0352 1.0000 Uiso R . . . . .
H131 H 0.6510 0.4810 0.6703 0.0310 1.0000 Uiso R . . . . .
H141 H 1.1169 0.4461 0.6520 0.0626 1.0000 Uiso R . . . . .
H142 H 1.1415 0.3422 0.6596 0.0625 1.0000 Uiso R . . . . .
H143 H 1.0821 0.3883 0.5282 0.0629 1.0000 Uiso R . . . . .
H151 H 0.3921 0.3745 0.4400 0.0313 1.0000 Uiso R . . . . .
H152 H 0.2860 0.3049 0.4863 0.0302 1.0000 Uiso R . . . . .
H161 H 0.5205 0.2578 0.3878 0.0284 1.0000 Uiso R . . . . .
H162 H 0.3558 0.2105 0.3528 0.0303 1.0000 Uiso R . . . . .
H171 H 0.5843 0.3492 0.8666 0.0351 1.0000 Uiso R . . . . .
H172 H 0.5192 0.2532 0.9033 0.0355 1.0000 Uiso R . . . . .
H181 H 0.2702 0.1940 0.8012 0.0310 1.0000 Uiso R . . . . .
H201 H 0.1774 -0.0303 0.5684 0.0360 1.0000 Uiso R . . . . .
H211 H 0.3512 0.0159 0.4716 0.0331 1.0000 Uiso R . . . . .
H221 H 0.0900 -0.0201 0.7567 0.0558 1.0000 Uiso R . . . . .
H222 H 0.1191 0.0686 0.8437 0.0562 1.0000 Uiso R . . . . .
H223 H 0.0035 0.0701 0.7108 0.0562 1.0000 Uiso R . . . . .

_refine_ls_extinction_method     None
_oxford_refine_ls_scale          6.62(17)
loop_
_geom_bond_atom_site_label_1
_geom_bond_site_symmetry_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
O1 . C2 . 1.2245(14) yes
C2 . N3 . 1.3863(15) yes
C2 . C9 . 1.5005(15) yes
N3 . C4 . 1.4445(14) yes
N3 . C16 . 1.4683(15) yes
C4 . C5 . 1.4035(16) yes
C4 . C21 . 1.3839(16) yes
C5 . C6 . 1.4971(16) yes
C5 . C18 . 1.3955(16) yes
C6 . N7 . 1.4280(14) yes
C6 . C17 . 1.3269(17) yes
N7 . C8 . 1.4459(14) yes
N7 . C15 . 1.4660(15) yes
C8 . C9 . 1.4039(16) yes
C8 . C13 . 1.3853(16) yes
C9 . C10 . 1.3912(16) yes
C10 . C11 . 1.3936(17) yes
C10 . H101 . 0.950 no
C11 . C12 . 1.3935(18) yes
C11 . C14 . 1.5057(17) yes
C12 . C13 . 1.3893(17) yes
C12 . H121 . 0.949 no
C13 . H131 . 0.963 no
C14 . H141 . 0.964 no
C14 . H142 . 0.941 no
C14 . H143 . 0.977 no
C15 . C16 . 1.5356(17) yes
C15 . H151 . 0.994 no
C15 . H152 . 1.017 no
C16 . H161 . 0.996 no
C16 . H162 . 1.027 no
C17 . H171 . 0.963 no
C17 . H172 . 0.955 no
C18 . C19 . 1.3964(17) yes
C18 . H181 . 0.990 no
C19 . C20 . 1.3967(19) yes
C19 . C22 . 1.5051(17) yes
C20 . C21 . 1.3909(18) yes
C20 . H201 . 0.968 no
C21 . H211 . 0.980 no
C22 . H221 . 0.976 no
C22 . H222 . 0.980 no
C22 . H223 . 0.945 no
loop_
_geom_angle_atom_site_label_1
_geom_angle_site_symmetry_1
_geom_angle_atom_site_label_2
_geom_angle_site_symmetry_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
O1 . C2 . N3 . 122.12(10) yes
O1 . C2 . C9 . 120.95(10) yes
N3 . C2 . C9 . 116.68(10) yes
C2 . N3 . C4 . 115.89(9) yes
C2 . N3 . C16 . 118.68(9) yes
C4 . N3 . C16 . 111.72(9) yes
N3 . C4 . C5 . 116.83(10) yes
N3 . C4 . C21 . 121.97(11) yes
C5 . C4 . C21 . 121.08(11) yes
C4 . C5 . C6 . 120.06(10) yes
C4 . C5 . C18 . 118.49(11) yes
C6 . C5 . C18 . 121.42(10) yes
C5 . C6 . N7 . 118.53(10) yes
C5 . C6 . C17 . 121.27(11) yes
N7 . C6 . C17 . 120.18(11) yes
C6 . N7 . C8 . 116.20(9) yes
C6 . N7 . C15 . 116.75(9) yes
C8 . N7 . C15 . 111.14(9) yes
N7 . C8 . C9 . 119.71(10) yes
N7 . C8 . C13 . 120.94(10) yes
C9 . C8 . C13 . 119.35(10) yes
C2 . C9 . C8 . 116.46(10) yes
C2 . C9 . C10 . 122.67(10) yes
C8 . C9 . C10 . 120.09(10) yes
C9 . C10 . C11 . 120.68(11) yes
C9 . C10 . H101 . 117.2 no
C11 . C10 . H101 . 122.1 no
C10 . C11 . C12 . 118.48(11) yes
C10 . C11 . C14 . 120.89(11) yes
C12 . C11 . C14 . 120.62(11) yes
C11 . C12 . C13 . 121.29(11) yes
C11 . C12 . H121 . 119.8 no
C13 . C12 . H121 . 118.9 no
C12 . C13 . C8 . 120.02(11) yes
C12 . C13 . H131 . 119.5 no
C8 . C13 . H131 . 120.4 no
C11 . C14 . H141 . 112.1 no
C11 . C14 . H142 . 110.6 no
H141 . C14 . H142 . 108.9 no
C11 . C14 . H143 . 113.3 no
H141 . C14 . H143 . 105.9 no
H142 . C14 . H143 . 105.7 no
N7 . C15 . C16 . 111.12(9) yes
N7 . C15 . H151 . 106.6 no
C16 . C15 . H151 . 109.2 no
N7 . C15 . H152 . 110.8 no
C16 . C15 . H152 . 109.1 no
H151 . C15 . H152 . 110.0 no
C15 . C16 . N3 . 110.41(9) yes
C15 . C16 . H161 . 112.1 no
N3 . C16 . H161 . 105.3 no
C15 . C16 . H162 . 110.2 no
N3 . C16 . H162 . 108.5 no
H161 . C16 . H162 . 110.2 no
C6 . C17 . H171 . 121.3 no
C6 . C17 . H172 . 119.5 no
H171 . C17 . H172 . 119.1 no
C5 . C18 . C19 . 121.46(11) yes
C5 . C18 . H181 . 118.1 no
C19 . C18 . H181 . 120.4 no
C18 . C19 . C20 . 118.34(11) yes
C18 . C19 . C22 . 120.24(12) yes
C20 . C19 . C22 . 121.42(12) yes
C19 . C20 . C21 . 121.37(11) yes
C19 . C20 . H201 . 118.6 no
C21 . C20 . H201 . 120.0 no
C20 . C21 . C4 . 119.24(12) yes
C20 . C21 . H211 . 120.0 no
C4 . C21 . H211 . 120.7 no
C19 . C22 . H221 . 111.4 no
C19 . C22 . H222 . 113.4 no
H221 . C22 . H222 . 108.8 no
C19 . C22 . H223 . 109.9 no
H221 . C22 . H223 . 108.9 no
H222 . C22 . H223 . 104.1 no
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_site_symmetry_D
_geom_hbond_atom_site_label_H
_geom_hbond_site_symmetry_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_angle_DHA
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_publ_flag
C21 . H211 . O1 2_656 147.39 0.980 2.529 3.3964(18) yes


_iucr_refine_instructions_details_constraints 
;
#
# Punched on 17/04/15 at 16:26:41
#
#LIST     12                                                                    
BLOCK SCALE X'S, U'S 
RIDE C   (  10,X'S) H   ( 101,X'S) 
RIDE C   (  12,X'S) H   ( 121,X'S) 
RIDE C   (  13,X'S) H   ( 131,X'S) 
RIDE C   (  14,X'S) H   ( 141,X'S) H   ( 142,X'S) H   ( 143,X'S) 
RIDE C   (  15,X'S) H   ( 151,X'S) H   ( 152,X'S) 
RIDE C   (  16,X'S) H   ( 161,X'S) H   ( 162,X'S) 
RIDE C   (  17,X'S) H   ( 171,X'S) H   ( 172,X'S) 
RIDE C   (  18,X'S) H   ( 181,X'S) 
RIDE C   (  20,X'S) H   ( 201,X'S) 
RIDE C   (  21,X'S) H   ( 211,X'S) 
RIDE C   (  22,X'S) H   ( 221,X'S) H   ( 222,X'S) H   ( 223,X'S) 
END                                                                             
;


_iucr_refine_instructions_details_restraints 
;
#
# Punched on 17/04/15 at 16:26:41
#
#LIST     16                                                                    
NO 
REM   HREST   START (DO NOT REMOVE THIS LINE) 
REM   HREST   END (DO NOT REMOVE THIS LINE) 
END                                                                             
;
####################################################################### 
# 
# 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_7a
_database_code_depnum_ccdc_archive 'CCDC 1442063'
_audit_update_record             
;
2015-12-11 deposited with the CCDC.
2016-12-06 downloaded from the CCDC.
;
#============================================================================
_audit_creation_date             2015-04-17
_audit_creation_method           CRYSTALS_ver_14.43

_oxford_structure_analysis_title 045lp14
_chemical_name_systematic        .
_chemical_melting_point          '378-381 K'

_cell_length_a                   7.3292(1)
_cell_length_b                   19.7192(3)
_cell_length_c                   10.6272(2)
_cell_angle_alpha                90
_cell_angle_beta                 97.9329(17)
_cell_angle_gamma                90
_cell_volume                     1521.21(4)

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 21/c '
_symmetry_space_group_name_Hall  '-P 2ybc'
loop_
_symmetry_equiv_pos_as_xyz
x,y,z
-x,-y,-z
x,-y+1/2,z+1/2
-x,y+1/2,-z+1/2

loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_Cromer_Mann_a1
_atom_type_scat_Cromer_Mann_b1
_atom_type_scat_Cromer_Mann_a2
_atom_type_scat_Cromer_Mann_b2
_atom_type_scat_Cromer_Mann_a3
_atom_type_scat_Cromer_Mann_b3
_atom_type_scat_Cromer_Mann_a4
_atom_type_scat_Cromer_Mann_b4
_atom_type_scat_Cromer_Mann_c
_atom_type_scat_source
C 0.0181 0.0091 2.3100 20.8439 1.0200 10.2075 1.5886 0.5687 0.8650 51.6512
0.2156 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
H 0.0000 0.0000 0.4930 10.5109 0.3229 26.1257 0.1402 3.1424 0.0408 57.7998
0.0030 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
N 0.0311 0.0180 12.2126 0.0057 3.1322 9.8933 2.0125 28.9975 1.1663 0.5826
-11.5290 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
O 0.0492 0.0322 3.0485 13.2771 2.2868 5.7011 1.5463 0.3239 0.8670 32.9089
0.2508 'International Tables Vol C 4.2.6.8 and 6.1.1.4'


_cell_formula_units_Z            4

# Given Formula = C18 H18 N2 O1 
# Dc =      1.22 Fooo =    632.00 Mu =      6.00 M =    278.35
# Found Formula = C18 H20 N2 O2 
# Dc =      1.29 FOOO =    632.00 Mu =      6.80 M =    296.37

_chemical_formula_sum            'C18 H20 N2 O2'
_chemical_formula_moiety         'C18 H20 N2 O2'
_chemical_compound_source        .
_chemical_formula_weight         296.37


_cell_measurement_reflns_used    14103
_cell_measurement_theta_min      4
_cell_measurement_theta_max      76
_cell_measurement_temperature    150

_exptl_crystal_description       block
_exptl_crystal_colour            clear_pale_colourless
_exptl_crystal_size_min          0.15
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_max          0.22

_exptl_crystal_density_diffrn    1.294
_exptl_crystal_density_meas      .
_exptl_crystal_density_method    'not measured'
# Non-dispersive F(000): 
_exptl_crystal_F_000             632
_exptl_absorpt_coefficient_mu    0.680

# Sheldrick geometric approximatio 0.88 0.90 
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'CrysAlis, (Oxford Diffraction, 2002)'
_exptl_absorpt_correction_T_min  0.79
_exptl_absorpt_correction_T_max  0.90
_diffrn_measurement_device_type  'Oxford Diffraction SuperNova'
_diffrn_measurement_device       Area
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54180
_diffrn_measurement_method       ω

# If a reference occurs more than once, delete the author 
# and date from subsequent references. 
_computing_data_collection       'SuperNova, (Oxford Diffraction, 2010)'
_computing_cell_refinement       'CrysAlis, (Oxford Diffraction, 2002)'
_computing_data_reduction        'CrysAlis, (Oxford Diffraction, 2002)'
_computing_structure_solution    'Superflip (Palatinus & Chapuis, 2007)'
_computing_structure_refinement  'CRYSTALS (Betteridge et al., 2003)'
_computing_publication_material  'CRYSTALS (Betteridge et al., 2003)'
_computing_molecular_graphics    'CAMERON (Watkin et al., 1996)'

_diffrn_standards_interval_time  .
_diffrn_standards_interval_count .
_diffrn_standards_number         0
_diffrn_standards_decay_%        .

_diffrn_ambient_temperature      150
_diffrn_reflns_number            31065
_reflns_number_total             3194
_diffrn_reflns_av_R_equivalents  0.024
# Number of reflections with Friedels Law is 3194 
# Theoretical number of reflections is about 6397 


_diffrn_reflns_theta_min         4.484
_diffrn_reflns_theta_max         76.540
_diffrn_measured_fraction_theta_max 0.997

_diffrn_reflns_theta_full        76.540
_diffrn_measured_fraction_theta_full 0.997


_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -24
_diffrn_reflns_limit_k_max       24
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       13
_reflns_limit_h_min              -9
_reflns_limit_h_max              9
_reflns_limit_k_min              0
_reflns_limit_k_max              24
_reflns_limit_l_min              0
_reflns_limit_l_max              13

_oxford_diffrn_Wilson_B_factor   2.76
_oxford_diffrn_Wilson_scale      0.02

_atom_sites_solution_primary     Other #heavy,direct,difmap,geom
# _atom_sites_solution_secondary  difmap
_atom_sites_solution_hydrogens   difmap

_refine_diff_density_min         -0.29
_refine_diff_density_max         0.43


# The current dictionary definitions do not cover the 
# situation where the reflections used for refinement were 
# selected by a user-defined sigma threshold 


# The values actually used during refinement 
_oxford_reflns_threshold_expression_ref I>-3.0\s(I)
_refine_ls_number_reflns         3182
_refine_ls_number_restraints     0
_refine_ls_number_parameters     199
_oxford_refine_ls_R_factor_ref   0.0557
_refine_ls_wR_factor_ref         0.1376
_refine_ls_goodness_of_fit_ref   0.9886
_refine_ls_shift/su_max          0.0002511
_refine_ls_shift/su_mean         0.0000383


# The values computed with all filters except I/sigma 
_oxford_reflns_number_all        3182
_refine_ls_R_factor_all          0.0557
_refine_ls_wR_factor_all         0.1376

# The values computed with a 2 sigma cutoff - a la SHELX 
_reflns_threshold_expression     I>2.0σ(I)
_reflns_number_gt                3008
_refine_ls_R_factor_gt           0.0538
_refine_ls_wR_factor_gt          0.1358

# choose from: rm (reference molecule of known chirality), 
# ad (anomolous dispersion - Flack), rmad (rm and ad), 
# syn (from synthesis), unk (unknown) or . (not applicable). 
_chemical_absolute_configuration .


_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_hydrogen_treatment    constr #undef, noref, refall,
# refxyz, refU, constr or mixed
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
;
 Method= Modified Sheldrick 
 w=1/[σ²(F²) + ( 0.06P)² + 1.35P] 
 ,where P=(max(Fo²,0) + 2Fc²)/3 
;

# Uequiv = arithmetic mean of Ui i.e. Ueqiv = (U1+U2+U3)/3

# Replace last . with number of unfound hydrogen atoms attached to an atom.

# ..._refinement_flags_... 
# . no refinement constraints           S special position constraint on site
# G rigid group refinement of site      R riding atom
# D distance or angle restraint on site T thermal displacement constraints
# U Uiso or Uij restraint (rigid bond)  P partial occupancy constraint


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_occupancy
_atom_site_adp_type
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
_atom_site_attached_hydrogens
O1 O 0.67237(15) 0.34598(6) 1.02910(13) 0.0352 1.0000 Uani . . . . . .
C2 C 0.8288(2) 0.36494(8) 1.01028(16) 0.0267 1.0000 Uani . . . . . .
N3 N 0.84613(17) 0.40066(7) 0.90455(13) 0.0272 1.0000 Uani . . . . . .
C4 C 0.6822(2) 0.42253(9) 0.82268(17) 0.0304 1.0000 Uani . . . . . .
C5 C 0.6086(2) 0.38428(9) 0.71851(15) 0.0291 1.0000 Uani . . . . . .
C6 C 0.4627(2) 0.41220(9) 0.63556(17) 0.0329 1.0000 Uani . . . . . .
C7 C 0.3913(2) 0.47533(9) 0.6574(2) 0.0386 1.0000 Uani . . . . . .
C8 C 0.2344(3) 0.50394(12) 0.5644(2) 0.0521 1.0000 Uani . . . . . .
C9 C 0.4605(3) 0.51114(10) 0.7657(2) 0.0507 1.0000 Uani . . . . . .
C10 C 0.6066(3) 0.48490(10) 0.8483(2) 0.0466 1.0000 Uani . . . . . .
C11 C 0.6817(3) 0.31463(10) 0.69783(17) 0.0365 1.0000 Uani . . . . . .
O12 O 0.59151(17) 0.28764(7) 0.58283(13) 0.0406 1.0000 Uani . . . . . .
C13 C 1.0217(2) 0.42324(10) 0.86759(18) 0.0360 1.0000 Uani . . . . . .
C14 C 1.1587(2) 0.36553(11) 0.86566(17) 0.0377 1.0000 Uani . . . . . .
N15 N 1.25599(18) 0.35108(8) 0.98811(14) 0.0347 1.0000 Uani . . . . . .
C16 C 1.1787(2) 0.34430(8) 1.09682(16) 0.0271 1.0000 Uani . . . . . .
C17 C 0.9895(2) 0.35080(8) 1.10989(16) 0.0260 1.0000 Uani . . . . . .
C18 C 0.9384(2) 0.34150(8) 1.23247(17) 0.0299 1.0000 Uani . . . . . .
C19 C 1.0606(2) 0.32681(9) 1.33945(17) 0.0337 1.0000 Uani . . . . . .
C20 C 1.2462(2) 0.31876(9) 1.32371(17) 0.0354 1.0000 Uani . . . . . .
C21 C 1.3017(2) 0.32728(9) 1.20741(17) 0.0330 1.0000 Uani . . . . . .
C22 C 0.9993(3) 0.31990(11) 1.46843(19) 0.0453 1.0000 Uani . . . . . .
H61 H 0.4187 0.3869 0.5623 0.0420 1.0000 Uiso R . . . . .
H83 H 0.2618 0.5504 0.5402 0.0822 1.0000 Uiso R . . . . .
H82 H 0.2252 0.4729 0.4864 0.0810 1.0000 Uiso R . . . . .
H81 H 0.1223 0.5047 0.6023 0.0822 1.0000 Uiso R . . . . .
H91 H 0.4080 0.5554 0.7871 0.0641 1.0000 Uiso R . . . . .
H101 H 0.6537 0.5110 0.9238 0.0573 1.0000 Uiso R . . . . .
H111 H 0.8178 0.3179 0.6958 0.0462 1.0000 Uiso R . . . . .
H112 H 0.6622 0.2844 0.7718 0.0466 1.0000 Uiso R . . . . .
H131 H 1.0751 0.4585 0.9265 0.0473 1.0000 Uiso R . . . . .
H132 H 0.9947 0.4436 0.7817 0.0461 1.0000 Uiso R . . . . .
H142 H 1.2494 0.3791 0.8097 0.0474 1.0000 Uiso R . . . . .
H141 H 1.0891 0.3237 0.8304 0.0472 1.0000 Uiso R . . . . .
H181 H 0.8074 0.3466 1.2418 0.0358 1.0000 Uiso R . . . . .
H201 H 1.3341 0.3063 1.3955 0.0438 1.0000 Uiso R . . . . .
H211 H 1.4308 0.3209 1.1968 0.0406 1.0000 Uiso R . . . . .
H223 H 1.0651 0.2835 1.5178 0.0723 1.0000 Uiso R . . . . .
H222 H 1.0189 0.3629 1.5164 0.0720 1.0000 Uiso R . . . . .
H221 H 0.8677 0.3095 1.4559 0.0722 1.0000 Uiso R . . . . .
H151 H 1.3782 0.3477 0.9952 0.0438 1.0000 Uiso R . . . . .
H121 H 0.6337 0.2456 0.5708 0.0662 1.0000 Uiso R . . . . .

_refine_ls_extinction_method     None
_oxford_refine_ls_scale          6.5(2)
loop_
_geom_bond_atom_site_label_1
_geom_bond_site_symmetry_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
O1 . C2 . 1.2484(19) yes
C2 . N3 . 1.347(2) yes
C2 . C17 . 1.497(2) yes
N3 . C4 . 1.448(2) yes
N3 . C13 . 1.466(2) yes
C4 . C5 . 1.386(2) yes
C4 . C10 . 1.391(3) yes
C5 . C6 . 1.401(2) yes
C5 . C11 . 1.502(2) yes
C6 . C7 . 1.383(3) yes
C6 . H61 . 0.944 no
C7 . C8 . 1.518(3) yes
C7 . C9 . 1.385(3) yes
C8 . H83 . 0.980 no
C8 . H82 . 1.026 no
C8 . H81 . 0.964 no
C9 . C10 . 1.388(3) yes
C9 . H91 . 0.994 no
C10 . H101 . 0.976 no
C11 . O12 . 1.411(2) yes
C11 . H111 . 1.002 no
C11 . H112 . 1.012 no
O12 . H121 . 0.899 no
C13 . C14 . 1.520(3) yes
C13 . H131 . 0.980 no
C13 . H132 . 0.992 no
C14 . N15 . 1.424(2) yes
C14 . H142 . 0.988 no
C14 . H141 . 1.014 no
N15 . C16 . 1.362(2) yes
N15 . H151 . 0.891 no
C16 . C17 . 1.419(2) yes
C16 . C21 . 1.419(2) yes
C17 . C18 . 1.416(2) yes
C18 . C19 . 1.377(2) yes
C18 . H181 . 0.984 no
C19 . C20 . 1.402(3) yes
C19 . C22 . 1.506(3) yes
C20 . C21 . 1.364(3) yes
C20 . H201 . 0.961 no
C21 . H211 . 0.976 no
C22 . H223 . 0.976 no
C22 . H222 . 0.989 no
C22 . H221 . 0.976 no
loop_
_geom_angle_atom_site_label_1
_geom_angle_site_symmetry_1
_geom_angle_atom_site_label_2
_geom_angle_site_symmetry_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
O1 . C2 . N3 . 118.98(14) yes
O1 . C2 . C17 . 118.77(15) yes
N3 . C2 . C17 . 122.14(13) yes
C2 . N3 . C4 . 119.42(13) yes
C2 . N3 . C13 . 124.72(13) yes
C4 . N3 . C13 . 115.77(13) yes
N3 . C4 . C5 . 121.16(15) yes
N3 . C4 . C10 . 117.75(16) yes
C5 . C4 . C10 . 121.01(16) yes
C4 . C5 . C6 . 117.92(16) yes
C4 . C5 . C11 . 120.45(15) yes
C6 . C5 . C11 . 121.62(15) yes
C5 . C6 . C7 . 121.44(17) yes
C5 . C6 . H61 . 117.1 no
C7 . C6 . H61 . 121.4 no
C6 . C7 . C8 . 119.70(19) yes
C6 . C7 . C9 . 119.68(17) yes
C8 . C7 . C9 . 120.60(18) yes
C7 . C8 . H83 . 110.8 no
C7 . C8 . H82 . 105.3 no
H83 . C8 . H82 . 109.8 no
C7 . C8 . H81 . 110.3 no
H83 . C8 . H81 . 108.2 no
H82 . C8 . H81 . 112.5 no
C7 . C9 . C10 . 119.83(18) yes
C7 . C9 . H91 . 122.0 no
C10 . C9 . H91 . 118.2 no
C4 . C10 . C9 . 119.97(19) yes
C4 . C10 . H101 . 121.5 no
C9 . C10 . H101 . 118.5 no
C5 . C11 . O12 . 109.72(14) yes
C5 . C11 . H111 . 108.7 no
O12 . C11 . H111 . 110.7 no
C5 . C11 . H112 . 109.5 no
O12 . C11 . H112 . 110.5 no
H111 . C11 . H112 . 107.6 no
C11 . O12 . H121 . 109.9 no
N3 . C13 . C14 . 112.48(15) yes
N3 . C13 . H131 . 109.4 no
C14 . C13 . H131 . 109.5 no
N3 . C13 . H132 . 107.3 no
C14 . C13 . H132 . 109.8 no
H131 . C13 . H132 . 108.2 no
C13 . C14 . N15 . 112.70(15) yes
C13 . C14 . H142 . 107.8 no
N15 . C14 . H142 . 108.1 no
C13 . C14 . H141 . 108.3 no
N15 . C14 . H141 . 109.7 no
H142 . C14 . H141 . 110.1 no
C14 . N15 . C16 . 125.51(13) yes
C14 . N15 . H151 . 117.6 no
C16 . N15 . H151 . 116.8 no
N15 . C16 . C17 . 126.94(15) yes
N15 . C16 . C21 . 115.78(14) yes
C17 . C16 . C21 . 117.27(15) yes
C2 . C17 . C16 . 129.18(15) yes
C2 . C17 . C18 . 113.11(14) yes
C16 . C17 . C18 . 117.69(15) yes
C17 . C18 . C19 . 124.20(15) yes
C17 . C18 . H181 . 117.7 no
C19 . C18 . H181 . 118.1 no
C18 . C19 . C20 . 117.14(16) yes
C18 . C19 . C22 . 121.90(17) yes
C20 . C19 . C22 . 120.97(17) yes
C19 . C20 . C21 . 120.67(16) yes
C19 . C20 . H201 . 119.3 no
C21 . C20 . H201 . 120.0 no
C16 . C21 . C20 . 122.99(16) yes
C16 . C21 . H211 . 116.7 no
C20 . C21 . H211 . 120.3 no
C19 . C22 . H223 . 111.6 no
C19 . C22 . H222 . 110.6 no
H223 . C22 . H222 . 109.1 no
C19 . C22 . H221 . 107.9 no
H223 . C22 . H221 . 109.0 no
H222 . C22 . H221 . 108.7 no
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_site_symmetry_D
_geom_hbond_atom_site_label_H
_geom_hbond_site_symmetry_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_angle_DHA
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_publ_flag
C20 . H201 . O12 1_656 172.39 0.961 2.573 3.527(3) yes
N15 . H151 . O1 1_655 174.16 0.891 2.137 3.024(3) yes
O12 . H121 . O1 3_554 168.19 0.899 1.891 2.777(3) yes


_iucr_refine_instructions_details_constraints 
;
#
# Punched on 17/04/15 at 16:25:12
#
#LIST     12                                                                    
BLOCK SCALE X'S, U'S 
RIDE C   (   6,X'S) H   (  61,X'S) 
RIDE C   (   8,X'S) H   (  83,X'S) H   (  82,X'S) H   (  81,X'S) 
RIDE C   (   9,X'S) H   (  91,X'S) 
RIDE C   (  10,X'S) H   ( 101,X'S) 
RIDE C   (  11,X'S) H   ( 111,X'S) H   ( 112,X'S) 
RIDE O   (  12,X'S) H   ( 121,X'S) 
RIDE C   (  13,X'S) H   ( 131,X'S) H   ( 132,X'S) 
RIDE C   (  14,X'S) H   ( 142,X'S) H   ( 141,X'S) 
RIDE N   (  15,X'S) H   ( 151,X'S) 
RIDE C   (  18,X'S) H   ( 181,X'S) 
RIDE C   (  20,X'S) H   ( 201,X'S) 
RIDE C   (  21,X'S) H   ( 211,X'S) 
RIDE C   (  22,X'S) H   ( 223,X'S) H   ( 222,X'S) H   ( 221,X'S) 
END                                                                             
;


_iucr_refine_instructions_details_restraints 
;
#
# Punched on 17/04/15 at 16:25:12
#
#LIST     16                                                                    
NO 
REM   HREST   START (DO NOT REMOVE THIS LINE) 
REM   HREST   END (DO NOT REMOVE THIS LINE) 
END                                                                             
;
####################################################################### 
# 
# 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_rp620_1
_database_code_depnum_ccdc_archive 'CCDC 1450259'
_audit_update_record             
;
2016-01-27 deposited with the CCDC.
2016-12-06 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C18 H18 F2 N2'
_chemical_formula_sum            'C18 H18 F2 N2'
_chemical_formula_weight         300.34

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'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   P2(1)/c
_symmetry_int_tables_number      14


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

_cell_length_a                   12.2306(7)
_cell_length_b                   13.6348(8)
_cell_length_c                   8.4844(5)
_cell_angle_alpha                90.00
_cell_angle_beta                 93.6580(10)
_cell_angle_gamma                90.00
_cell_volume                     1411.99(14)
_cell_formula_units_Z            4
_cell_measurement_temperature    99(2)
_cell_measurement_reflns_used    9951
_cell_measurement_theta_min      2.83
_cell_measurement_theta_max      37.48

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.52
_exptl_crystal_size_mid          0.51
_exptl_crystal_size_min          0.34
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.413
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             632
_exptl_absorpt_coefficient_mu    0.102
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9486
_exptl_absorpt_correction_T_max  0.9665
_exptl_absorpt_process_details   SADABS-2004/1

_exptl_special_details           
; 
 ? 
;


_diffrn_ambient_temperature      99(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            20793
_diffrn_reflns_av_R_equivalents  0.0234
_diffrn_reflns_av_sigmaI/netI    0.0163
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_theta_min         1.67
_diffrn_reflns_theta_max         28.70
_reflns_number_total             3657
_reflns_number_gt                3278
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0689P)²+0.5992P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         3657
_refine_ls_number_parameters     201
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0447
_refine_ls_R_factor_gt           0.0406
_refine_ls_wR_factor_ref         0.1174
_refine_ls_wR_factor_gt          0.1138
_refine_ls_goodness_of_fit_ref   1.033
_refine_ls_restrained_S_all      1.033
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
F1 F 0.11788(6) 0.42721(6) 0.58716(9) 0.02348(18) Uani 1 1 d . . .
F2 F 0.37583(6) 0.57926(5) -0.08269(8) 0.02062(17) Uani 1 1 d . . .
N1 N 0.24198(8) 0.57384(7) 0.47708(11) 0.01438(19) Uani 1 1 d . . .
N2 N 0.37500(7) 0.61184(7) 0.23175(11) 0.01451(19) Uani 1 1 d . . .
C1 C 0.26705(8) 0.47461(8) 0.44142(12) 0.0132(2) Uani 1 1 d . . .
C2 C 0.20417(9) 0.40060(8) 0.50326(13) 0.0162(2) Uani 1 1 d . . .
C3 C 0.22523(10) 0.30196(8) 0.48769(13) 0.0193(2) Uani 1 1 d . . .
H3 H 0.1795 0.2546 0.5326 0.023 Uiso 1 1 calc R . .
C4 C 0.31462(10) 0.27252(8) 0.40515(13) 0.0182(2) Uani 1 1 d . . .
C5 C 0.37655(9) 0.34468(8) 0.33735(13) 0.0164(2) Uani 1 1 d . . .
H5 H 0.4363 0.3254 0.2781 0.020 Uiso 1 1 calc R . .
C6 C 0.35435(9) 0.44459(8) 0.35295(12) 0.0138(2) Uani 1 1 d . . .
C7 C 0.42564(8) 0.51741(8) 0.27024(13) 0.0158(2) Uani 1 1 d . . .
H7A H 0.4931 0.5291 0.3386 0.019 Uiso 1 1 calc R . .
H7B H 0.4479 0.4871 0.1713 0.019 Uiso 1 1 calc R . .
C8 C 0.37913(10) 0.68130(8) 0.36227(13) 0.0186(2) Uani 1 1 d . . .
H8A H 0.3347 0.7397 0.3311 0.022 Uiso 1 1 calc R . .
H8B H 0.4558 0.7031 0.3848 0.022 Uiso 1 1 calc R . .
C9 C 0.33636(10) 0.63701(8) 0.51186(13) 0.0189(2) Uani 1 1 d . . .
H9A H 0.3955 0.5985 0.5677 0.023 Uiso 1 1 calc R . .
H9B H 0.3156 0.6905 0.5829 0.023 Uiso 1 1 calc R . .
C10 C 0.15443(9) 0.61909(8) 0.37626(12) 0.0155(2) Uani 1 1 d . . .
H10A H 0.1470 0.6883 0.4090 0.019 Uiso 1 1 calc R . .
H10B H 0.0847 0.5855 0.3955 0.019 Uiso 1 1 calc R . .
C11 C 0.16983(9) 0.61686(8) 0.19953(12) 0.0134(2) Uani 1 1 d . . .
C12 C 0.07683(9) 0.62071(8) 0.09471(13) 0.0157(2) Uani 1 1 d . . .
H12 H 0.0071 0.6300 0.1359 0.019 Uiso 1 1 calc R . .
C13 C 0.08301(9) 0.61144(8) -0.06797(13) 0.0162(2) Uani 1 1 d . . .
C14 C 0.18540(9) 0.59488(8) -0.12702(13) 0.0168(2) Uani 1 1 d . . .
H14 H 0.1921 0.5850 -0.2368 0.020 Uiso 1 1 calc R . .
C15 C 0.27639(9) 0.59310(8) -0.02309(13) 0.0146(2) Uani 1 1 d . . .
C16 C 0.27373(8) 0.60677(7) 0.13965(12) 0.0130(2) Uani 1 1 d . . .
C17 C 0.34292(12) 0.16537(9) 0.39044(16) 0.0255(3) Uani 1 1 d . . .
H17A H 0.3215 0.1427 0.2833 0.038 Uiso 1 1 calc R . .
H17B H 0.3036 0.1273 0.4668 0.038 Uiso 1 1 calc R . .
H17C H 0.4220 0.1565 0.4117 0.038 Uiso 1 1 calc R . .
C18 C -0.01714(10) 0.62014(9) -0.18039(14) 0.0227(2) Uani 1 1 d . . .
H18A H -0.0277 0.6889 -0.2114 0.034 Uiso 1 1 calc R . .
H18B H -0.0816 0.5970 -0.1283 0.034 Uiso 1 1 calc R . .
H18C H -0.0072 0.5802 -0.2745 0.034 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. 

 Least-squares planes (x,y,z in crystal coordinates) and deviations from them
 (* indicates atom used to define plane)

  6.6945 (0.0046) x + 0.2622 (0.0074) y + 6.7879 (0.0023) z = 4.8959 (0.0029) 

 *    0.0126 (0.0007)  C1
 *   -0.0080 (0.0008)  C2
 *    0.0015 (0.0006)  C3
 *    0.0052 (0.0006)  C5
 *   -0.0114 (0.0007)  C6

 Rms deviation of fitted atoms =   0.0087


  1.3146 (0.0054) x + 13.4928 (0.0012) y - 0.8686 (0.0037) z = 8.3963 (0.0010) 

 Angle to previous plane (with approximate esd) = 89.87 ( 0.04 )

 *   -0.0231 (0.0007)  C11
 *   -0.0024 (0.0008)  C12
 *    0.0220 (0.0008)  C13
 *   -0.0155 (0.0008)  C14
 *   -0.0103 (0.0008)  C15
 *    0.0293 (0.0007)  C16

 Rms deviation of fitted atoms =   0.0193
;

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
F1 C2 1.3595(13) . ?
F2 C15 1.3597(12) . ?
N1 C1 1.4241(13) . ?
N1 C9 1.4553(14) . ?
N1 C10 1.4635(13) . ?
N2 C16 1.4234(13) . ?
N2 C8 1.4556(14) . ?
N2 C7 1.4568(14) . ?
C1 C2 1.3916(15) . ?
C1 C6 1.4047(15) . ?
C2 C3 1.3773(16) . ?
C3 C4 1.3945(17) . ?
C4 C5 1.3887(16) . ?
C4 C17 1.5084(16) . ?
C5 C6 1.3970(15) . ?
C6 C7 1.5220(15) . ?
C8 C9 1.5277(16) . ?
C10 C11 1.5234(14) . ?
C11 C12 1.3994(14) . ?
C11 C16 1.4051(14) . ?
C12 C13 1.3929(15) . ?
C13 C14 1.3965(16) . ?
C13 C18 1.5084(15) . ?
C14 C15 1.3752(15) . ?
C15 C16 1.3957(15) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1 N1 C9 115.25(9) . . ?
C1 N1 C10 115.83(9) . . ?
C9 N1 C10 114.23(9) . . ?
C16 N2 C8 115.85(9) . . ?
C16 N2 C7 115.01(8) . . ?
C8 N2 C7 114.26(9) . . ?
C2 C1 C6 116.57(10) . . ?
C2 C1 N1 118.50(10) . . ?
C6 C1 N1 124.87(10) . . ?
F1 C2 C3 117.84(10) . . ?
F1 C2 C1 118.04(10) . . ?
C3 C2 C1 124.11(11) . . ?
C2 C3 C4 119.12(11) . . ?
C5 C4 C3 118.03(10) . . ?
C5 C4 C17 121.19(11) . . ?
C3 C4 C17 120.78(11) . . ?
C4 C5 C6 122.49(11) . . ?
C5 C6 C1 119.59(10) . . ?
C5 C6 C7 118.16(10) . . ?
C1 C6 C7 122.25(9) . . ?
N2 C7 C6 115.60(9) . . ?
N2 C8 C9 112.20(9) . . ?
N1 C9 C8 112.00(9) . . ?
N1 C10 C11 115.79(9) . . ?
C12 C11 C16 119.41(10) . . ?
C12 C11 C10 118.57(9) . . ?
C16 C11 C10 121.96(9) . . ?
C13 C12 C11 122.21(10) . . ?
C12 C13 C14 118.48(10) . . ?
C12 C13 C18 121.75(10) . . ?
C14 C13 C18 119.77(10) . . ?
C15 C14 C13 118.71(10) . . ?
F2 C15 C14 118.06(9) . . ?
F2 C15 C16 117.66(9) . . ?
C14 C15 C16 124.26(10) . . ?
C15 C16 C11 116.71(9) . . ?
C15 C16 N2 118.37(9) . . ?
C11 C16 N2 124.90(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
C9 N1 C1 C2 138.95(10) . . . . ?
C10 N1 C1 C2 -83.96(12) . . . . ?
C9 N1 C1 C6 -38.20(14) . . . . ?
C10 N1 C1 C6 98.89(12) . . . . ?
C6 C1 C2 F1 -178.88(9) . . . . ?
N1 C1 C2 F1 3.74(14) . . . . ?
C6 C1 C2 C3 2.57(16) . . . . ?
N1 C1 C2 C3 -174.82(10) . . . . ?
F1 C2 C3 C4 -178.63(9) . . . . ?
C1 C2 C3 C4 -0.07(17) . . . . ?
C2 C3 C4 C5 -2.16(16) . . . . ?
C2 C3 C4 C17 177.77(11) . . . . ?
C3 C4 C5 C6 1.90(16) . . . . ?
C17 C4 C5 C6 -178.04(10) . . . . ?
C4 C5 C6 C1 0.64(16) . . . . ?
C4 C5 C6 C7 -178.46(10) . . . . ?
C2 C1 C6 C5 -2.78(15) . . . . ?
N1 C1 C6 C5 174.43(9) . . . . ?
C2 C1 C6 C7 176.28(10) . . . . ?
N1 C1 C6 C7 -6.51(16) . . . . ?
C16 N2 C7 C6 -55.30(12) . . . . ?
C8 N2 C7 C6 82.26(12) . . . . ?
C5 C6 C7 N2 154.75(9) . . . . ?
C1 C6 C7 N2 -24.32(14) . . . . ?
C16 N2 C8 C9 85.88(12) . . . . ?
C7 N2 C8 C9 -51.31(13) . . . . ?
C1 N1 C9 C8 86.55(11) . . . . ?
C10 N1 C9 C8 -51.23(12) . . . . ?
N2 C8 C9 N1 -38.76(13) . . . . ?
C1 N1 C10 C11 -55.46(13) . . . . ?
C9 N1 C10 C11 82.06(12) . . . . ?
N1 C10 C11 C12 154.52(10) . . . . ?
N1 C10 C11 C16 -22.63(15) . . . . ?
C16 C11 C12 C13 2.28(16) . . . . ?
C10 C11 C12 C13 -174.95(10) . . . . ?
C11 C12 C13 C14 1.93(16) . . . . ?
C11 C12 C13 C18 -177.27(10) . . . . ?
C12 C13 C14 C15 -3.07(16) . . . . ?
C18 C13 C14 C15 176.14(10) . . . . ?
C13 C14 C15 F2 -178.44(9) . . . . ?
C13 C14 C15 C16 0.06(17) . . . . ?
F2 C15 C16 C11 -177.44(9) . . . . ?
C14 C15 C16 C11 4.05(16) . . . . ?
F2 C15 C16 N2 4.04(14) . . . . ?
C14 C15 C16 N2 -174.47(10) . . . . ?
C12 C11 C16 C15 -5.07(15) . . . . ?
C10 C11 C16 C15 172.06(10) . . . . ?
C12 C11 C16 N2 173.34(10) . . . . ?
C10 C11 C16 N2 -9.54(16) . . . . ?
C8 N2 C16 C15 142.77(10) . . . . ?
C7 N2 C16 C15 -80.37(12) . . . . ?
C8 N2 C16 C11 -35.62(14) . . . . ?
C7 N2 C16 C11 101.25(12) . . . . ?

_diffrn_measured_fraction_theta_max 1.000
_diffrn_reflns_theta_full        28.70
_diffrn_measured_fraction_theta_full 1.000
_refine_diff_density_max         0.605
_refine_diff_density_min         -0.251
_refine_diff_density_rms         0.054
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: Chloroform/Pentane'
####################################################################### 
# 
# 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_4a
_database_code_depnum_ccdc_archive 'CCDC 1442060'
_audit_update_record             
;
2015-12-11 deposited with the CCDC.
2016-12-06 downloaded from the CCDC.
;
#============================================================================
_audit_creation_date             2015-12-11
_audit_creation_method           CRYSTALS_ver_14.43

_oxford_structure_analysis_title 034lp14
_chemical_name_systematic        .
_chemical_melting_point          '593 K'

_cell_length_a                   7.3791(1)
_cell_length_b                   12.5501(2)
_cell_length_c                   7.4981(1)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     694.387(17)

_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_H-M   'P n c 2 '
_symmetry_space_group_name_Hall  'P 2 -2bc'
loop_
_symmetry_equiv_pos_as_xyz
x,y,z
-x,-y,z
-x,y+1/2,z+1/2
x,-y+1/2,z+1/2

loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_Cromer_Mann_a1
_atom_type_scat_Cromer_Mann_b1
_atom_type_scat_Cromer_Mann_a2
_atom_type_scat_Cromer_Mann_b2
_atom_type_scat_Cromer_Mann_a3
_atom_type_scat_Cromer_Mann_b3
_atom_type_scat_Cromer_Mann_a4
_atom_type_scat_Cromer_Mann_b4
_atom_type_scat_Cromer_Mann_c
_atom_type_scat_source
C 0.0181 0.0091 2.3100 20.8439 1.0200 10.2075 1.5886 0.5687 0.8650 51.6512
0.2156 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
H 0.0000 0.0000 0.4930 10.5109 0.3229 26.1257 0.1402 3.1424 0.0408 57.7998
0.0030 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
N 0.0311 0.0180 12.2126 0.0057 3.1322 9.8933 2.0125 28.9975 1.1663 0.5826
-11.5290 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
O 0.0492 0.0322 3.0485 13.2771 2.2868 5.7011 1.5463 0.3239 0.8670 32.9089
0.2508 'International Tables Vol C 4.2.6.8 and 6.1.1.4'


_cell_formula_units_Z            2

# Given Formula = C9 H8 N1 O1 
# Dc =      0.70 Fooo =    308.00 Mu =      3.72 M =     73.08
# Found Formula = C18 H16 N2 O2 
# Dc =      1.40 FOOO =    308.00 Mu =      7.44 M =    146.17

_chemical_formula_sum            'C18 H16 N2 O2'
_chemical_formula_moiety         'C18 H16 N2 O2'
_chemical_compound_source        .
_chemical_formula_weight         292.34


_cell_measurement_reflns_used    10384
_cell_measurement_theta_min      4
_cell_measurement_theta_max      76
_cell_measurement_temperature    150

_exptl_crystal_description       block
_exptl_crystal_colour            clear_pale_colourless
_exptl_crystal_size_min          0.10
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_max          0.15

_exptl_crystal_density_diffrn    1.398
_exptl_crystal_density_meas      .
_exptl_crystal_density_method    'not measured'
# Non-dispersive F(000): 
_exptl_crystal_F_000             308
_exptl_absorpt_coefficient_mu    0.744

# Sheldrick geometric approximatio 0.89 0.93 
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'CrysAlis, (Oxford Diffraction, 2002)'
_exptl_absorpt_correction_T_min  0.76
_exptl_absorpt_correction_T_max  0.93
_diffrn_measurement_device_type  'Oxford Diffraction SuperNova'
_diffrn_measurement_device       Area
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54180
_diffrn_measurement_method       ω

# If a reference occurs more than once, delete the author 
# and date from subsequent references. 
_computing_data_collection       'SuperNova, (Oxford Diffraction, 2010)'
_computing_cell_refinement       'CrysAlis, (Oxford Diffraction, 2002)'
_computing_data_reduction        'CrysAlis, (Oxford Diffraction, 2002)'
_computing_structure_solution    'Superflip (Palatinus & Chapuis, 2007)'
_computing_structure_refinement  'CRYSTALS (Betteridge et al., 2003)'
_computing_publication_material  'CRYSTALS (Betteridge et al., 2003)'
_computing_molecular_graphics    'CAMERON (Watkin et al., 1996)'

_diffrn_standards_interval_time  .
_diffrn_standards_interval_count .
_diffrn_standards_number         0
_diffrn_standards_decay_%        .

_diffrn_ambient_temperature      150
_diffrn_reflns_number            13587
_reflns_number_total             1461
_diffrn_reflns_av_R_equivalents  0.017
# Number of reflections without Friedels Law is 1461 
# Number of reflections with Friedels Law is 792 
# Theoretical number of reflections is about 728 


_diffrn_reflns_theta_min         5.997
_diffrn_reflns_theta_max         76.363
_diffrn_measured_fraction_theta_max 1.000

_diffrn_reflns_theta_full        76.363
_diffrn_measured_fraction_theta_full 1.000


_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_limit_l_max       9
_reflns_limit_h_min              0
_reflns_limit_h_max              9
_reflns_limit_k_min              0
_reflns_limit_k_max              15
_reflns_limit_l_min              -9
_reflns_limit_l_max              9

_oxford_diffrn_Wilson_B_factor   1.84
_oxford_diffrn_Wilson_scale      0.00

_atom_sites_solution_primary     Other #heavy,direct,difmap,geom
# _atom_sites_solution_secondary  difmap
_atom_sites_solution_hydrogens   difmap

_refine_diff_density_min         -0.13
_refine_diff_density_max         0.16


# The current dictionary definitions do not cover the 
# situation where the reflections used for refinement were 
# selected by a user-defined sigma threshold 


# The values actually used during refinement 
_oxford_reflns_threshold_expression_ref I>-3.0\s(I)
_refine_ls_number_reflns         1455
_refine_ls_number_restraints     1
_refine_ls_number_parameters     101
_oxford_refine_ls_R_factor_ref   0.0253
_refine_ls_wR_factor_ref         0.0692
_refine_ls_goodness_of_fit_ref   1.0136
_refine_ls_shift/su_max          0.0001704
_refine_ls_shift/su_mean         0.0000200


# The values computed with all filters except I/sigma 
_oxford_reflns_number_all        1455
_refine_ls_R_factor_all          0.0253
_refine_ls_wR_factor_all         0.0692

# The values computed with a 2 sigma cutoff - a la SHELX 
_reflns_threshold_expression     I>2.0σ(I)
_reflns_number_gt                1451
_refine_ls_R_factor_gt           0.0252
_refine_ls_wR_factor_gt          0.0691

_refine_ls_abs_structure_Flack   0.0(2)
_refine_ls_abs_structure_details 'Flack (1983), 669 Friedel-pairs'
# choose from: rm (reference molecule of known chirality), 
# ad (anomolous dispersion - Flack), rmad (rm and ad), 
# syn (from synthesis), unk (unknown) or . (not applicable). 
_chemical_absolute_configuration ad


_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_hydrogen_treatment    constr #undef, noref, refall,
# refxyz, refU, constr or mixed
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
;
 Method= Modified Sheldrick 
 w=1/[σ²(F²) + ( 0.05P)² + 0.11P] 
 ,where P=(max(Fo²,0) + 2Fc²)/3 
;

# Uequiv = arithmetic mean of Ui i.e. Ueqiv = (U1+U2+U3)/3

# Replace last . with number of unfound hydrogen atoms attached to an atom.

# ..._refinement_flags_... 
# . no refinement constraints           S special position constraint on site
# G rigid group refinement of site      R riding atom
# D distance or angle restraint on site T thermal displacement constraints
# U Uiso or Uij restraint (rigid bond)  P partial occupancy constraint


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_occupancy
_atom_site_adp_type
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
_atom_site_attached_hydrogens
O1 O 0.28594(10) 0.43730(6) 0.33692(17) 0.0251 1.0000 Uani . . . . . .
C2 C 0.31960(12) 0.47647(8) 0.19247(19) 0.0194 1.0000 Uani . . . . . .
N3 N 0.39003(12) 0.41564(6) 0.05205(17) 0.0193 1.0000 Uani . . . . . .
C4 C 0.54757(14) 0.35156(8) 0.09517(19) 0.0194 1.0000 Uani . . . . . .
C5 C 0.70058(13) 0.40585(8) 0.15791(19) 0.0198 1.0000 Uani . . . . . .
C6 C 0.85875(14) 0.34967(9) 0.19589(19) 0.0217 1.0000 Uani . . . . . .
C7 C 0.86791(13) 0.24033(9) 0.16412(19) 0.0234 1.0000 Uani . . . . . .
C8 C 0.71590(15) 0.18884(8) 0.09524(19) 0.0232 1.0000 Uani . . . . . .
C9 C 0.55447(14) 0.24312(9) 0.06158(19) 0.0215 1.0000 Uani . . . . . .
C10 C 1.04012(15) 0.17982(10) 0.2031(2) 0.0314 1.0000 Uani . . . . . .
C11 C 0.41240(13) 0.46668(8) -0.12304(19) 0.0211 1.0000 Uani . . . . . .
H61 H 0.9618 0.3856 0.2468 0.0266 1.0000 Uiso R . . . . .
H81 H 0.7226 0.1135 0.0683 0.0272 1.0000 Uiso R . . . . .
H91 H 0.4526 0.2081 0.0110 0.0273 1.0000 Uiso R . . . . .
H101 H 1.0789 0.1366 0.1045 0.0504 1.0000 Uiso R . . . . .
H103 H 1.1383 0.2276 0.2350 0.0499 1.0000 Uiso R . . . . .
H102 H 1.0223 0.1310 0.2997 0.0509 1.0000 Uiso R . . . . .
H112 H 0.3066 0.5111 -0.1444 0.0235 1.0000 Uiso R . . . . .
H111 H 0.4192 0.4124 -0.2128 0.0221 1.0000 Uiso R . . . . .

_refine_ls_extinction_method     None
_oxford_refine_ls_scale          11.9(6)
loop_
_geom_bond_atom_site_label_1
_geom_bond_site_symmetry_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
O1 . C2 . 1.2151(13) yes
C2 . C5 2_665 1.5068(13) yes
C2 . N3 . 1.4006(13) yes
N3 . C4 . 1.4501(12) yes
N3 . C11 . 1.4701(13) yes
C4 . C5 . 1.4002(14) yes
C4 . C9 . 1.3849(14) yes
C5 . C6 . 1.3930(13) yes
C6 . C7 . 1.3944(16) yes
C6 . H61 . 0.963 no
C7 . C8 . 1.3937(15) yes
C7 . C10 . 1.5089(14) yes
C8 . C9 . 1.3952(15) yes
C8 . H81 . 0.968 no
C9 . H91 . 0.949 no
C10 . H101 . 0.961 no
C10 . H103 . 0.970 no
C10 . H102 . 0.958 no
C11 . C11 2_665 1.5397(19) yes
C11 . H112 . 0.973 no
C11 . H111 . 0.959 no
loop_
_geom_angle_atom_site_label_1
_geom_angle_site_symmetry_1
_geom_angle_atom_site_label_2
_geom_angle_site_symmetry_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C5 2_665 C2 . O1 . 121.98(9) yes
C5 2_665 C2 . N3 . 116.21(9) yes
O1 . C2 . N3 . 121.70(9) yes
C2 . N3 . C4 . 115.60(8) yes
C2 . N3 . C11 . 118.39(8) yes
C4 . N3 . C11 . 110.54(8) yes
N3 . C4 . C5 . 116.84(8) yes
N3 . C4 . C9 . 122.27(9) yes
C5 . C4 . C9 . 120.64(9) yes
C2 2_665 C5 . C4 . 117.07(8) yes
C2 2_665 C5 . C6 . 122.94(9) yes
C4 . C5 . C6 . 119.87(9) yes
C5 . C6 . C7 . 120.25(10) yes
C5 . C6 . H61 . 120.4 no
C7 . C6 . H61 . 119.4 no
C6 . C7 . C8 . 118.72(9) yes
C6 . C7 . C10 . 120.20(10) yes
C8 . C7 . C10 . 121.08(10) yes
C7 . C8 . C9 . 121.86(9) yes
C7 . C8 . H81 . 119.3 no
C9 . C8 . H81 . 118.9 no
C8 . C9 . C4 . 118.57(10) yes
C8 . C9 . H91 . 121.5 no
C4 . C9 . H91 . 119.9 no
C7 . C10 . H101 . 112.7 no
C7 . C10 . H103 . 111.5 no
H101 . C10 . H103 . 108.4 no
C7 . C10 . H102 . 110.6 no
H101 . C10 . H102 . 105.1 no
H103 . C10 . H102 . 108.2 no
C11 2_665 C11 . N3 . 109.33(6) yes
C11 2_665 C11 . H112 . 111.2 no
N3 . C11 . H112 . 107.9 no
C11 2_665 C11 . H111 . 110.0 no
N3 . C11 . H111 . 108.9 no
H112 . C11 . H111 . 109.5 no
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_site_symmetry_D
_geom_hbond_atom_site_label_H
_geom_hbond_site_symmetry_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_angle_DHA
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_publ_flag
C6 . H61 . O1 1_655 163.32 0.963 2.569 3.5021(16) yes
C9 . H91 . O1 4_554 156.06 0.949 2.559 3.4483(16) yes


_iucr_refine_instructions_details_constraints 
;
#
# Punched on 11/12/15 at 11:24:41
#
#LIST     12                                                                    
BLOCK SCALE X'S, U'S 
CONT ENANTIO 
RIDE C   (   6,X'S) H   (  61,X'S) 
RIDE C   (   8,X'S) H   (  81,X'S) 
RIDE C   (   9,X'S) H   (  91,X'S) 
RIDE C   (  10,X'S) H   ( 101,X'S) H   ( 103,X'S) H   ( 102,X'S) 
RIDE C   (  11,X'S) H   ( 112,X'S) H   ( 111,X'S) 
END                                                                             
;


_iucr_refine_instructions_details_restraints 
;
#
# Punched on 11/12/15 at 11:24:41
#
#LIST     16                                                                    
NO 
REM   HREST   START (DO NOT REMOVE THIS LINE) 
REM   HREST   END (DO NOT REMOVE THIS LINE) 
END                                                                             
;

# Manually omitted reflections

loop_
_oxford_refln_omitted_index_h
_oxford_refln_omitted_index_k
_oxford_refln_omitted_index_l
_oxford_refln_omitted_flag
_oxford_refln_omitted_details
0 0 2 x .
