# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 2015

####################################################################### 
# 
# 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_009tjd11
_database_code_depnum_ccdc_archive 'CCDC 1422535'
_audit_update_record             
;
2015-09-06 deposited with the CCDC.
2015-11-20 downloaded from the CCDC.
;

_cell_length_a                   12.0003(5)
_cell_length_b                   5.4759(2)
_cell_length_c                   17.9308(8)
_cell_angle_alpha                90
_cell_angle_beta                 92.310(2)
_cell_angle_gamma                90
_cell_volume                     1177.32(8)

_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 0.0033 0.0016 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 0.0061 0.0033 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 0.0106 0.0060 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'
F 0.0171 0.0103 3.5392 10.2825 2.6412 4.2944 1.5170 0.2615 1.0243 26.1476
0.2776 'International Tables Vol C 4.2.6.8 and 6.1.1.4'


_cell_formula_units_Z            4

# Given Formula = C16 F2 N1 
# Dc =      1.38 Fooo =    528.00 Mu =      1.04 M =    244.18
# Found Formula = C16 H12 F1 N1 O1 
# Dc =      1.43 FOOO =    528.00 Mu =      1.00 M =    253.28

_chemical_formula_sum            'C16 H12 F1 N1 O1'
_chemical_formula_moiety         'C16 H12 F1 N1 O1'
_chemical_compound_source        syn
_chemical_formula_weight         253.28


_cell_measurement_reflns_used    2517
_cell_measurement_theta_min      5
_cell_measurement_theta_max      26
_cell_measurement_temperature    150

_exptl_crystal_description       plate
_exptl_crystal_colour            clear-colourless
_exptl_crystal_size_min          0.030
_exptl_crystal_size_mid          0.240
_exptl_crystal_size_max          0.240

_exptl_crystal_density_diffrn    1.429
_exptl_crystal_density_meas      .
_exptl_crystal_density_method    'not measured'
# Non-dispersive F(000): 
_exptl_crystal_F_000             528
_exptl_absorpt_coefficient_mu    0.100

# Sheldrick geometric approximatio 0.98 1.00 
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'DENZO/SCALEPACK (Otwinowski & Minor, 1997)'
_exptl_absorpt_correction_T_min  0.86
_exptl_absorpt_correction_T_max  1.00
# For a Kappa CCD, set Tmin to 1.0 and 
# Tmax to the ratio of max:min frame scales in scale_all.log 
_diffrn_measurement_device_type  'Nonius KappaCCD'
_diffrn_measurement_device       Area
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_measurement_method       ω

# If a reference occurs more than once, delete the author 
# and date from subsequent references. 
_computing_data_collection       'COLLECT (Nonius, 2001).'
_computing_cell_refinement       'DENZO/SCALEPACK (Otwinowski & Minor, 1997)'
_computing_data_reduction        'DENZO/SCALEPACK (Otwinowski & Minor, 1997)'
_computing_structure_solution    'SIR92 (Altomare et al., 1994)'
_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            30505
_reflns_number_total             2297
_diffrn_reflns_av_R_equivalents  0.028
# Number of reflections without Friedels Law is 4594 
# Number of reflections with Friedels Law is 2297 
# Theoretical number of reflections is about 2323 


_diffrn_reflns_theta_min         5.139
_diffrn_reflns_theta_max         26.035
_diffrn_measured_fraction_theta_max 0.991

_diffrn_reflns_theta_full        25.514
_diffrn_measured_fraction_theta_full 0.991


_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_limit_l_max       22
_reflns_limit_h_min              -14
_reflns_limit_h_max              14
_reflns_limit_k_min              0
_reflns_limit_k_max              6
_reflns_limit_l_min              0
_reflns_limit_l_max              22

_oxford_diffrn_Wilson_B_factor   2.35
_oxford_diffrn_Wilson_scale      3.28

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

_refine_diff_density_min         -0.36
_refine_diff_density_max         0.39


# 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         2296
_refine_ls_number_restraints     0
_refine_ls_number_parameters     172
_oxford_refine_ls_R_factor_ref   0.0756
_refine_ls_wR_factor_ref         0.1498
_refine_ls_goodness_of_fit_ref   1.0312
_refine_ls_shift/su_max          0.0059638
_refine_ls_shift/su_mean         0.0017113


# The values computed from all data 
_oxford_reflns_number_all        2296
_refine_ls_R_factor_all          0.0756
_refine_ls_wR_factor_all         0.1498

# The values computed with a 2 sigma cutoff - a la SHELX 
_reflns_threshold_expression     I>2.0σ(I)
_reflns_number_gt                1621
_refine_ls_R_factor_gt           0.0492
_refine_ls_wR_factor_gt          0.1253

# 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 # none, undef, noref, refall,
# refxyz, refU, constr or mixed
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
;
 Method, part 1, Chebychev polynomial, (Watkin, 1994, Prince, 1982) 
 [weight] = 1.0/[A₀*T₀(x)+A₁*T₁(x) ... +Aₙ₋₁]*Tₙ₋₁(x)] 
 where Ai are the Chebychev coefficients listed below and x= Fcalc/Fmax 
 Method = Robust Weighting (Prince, 1982) 
 W = [weight] * [1-(deltaF/6*sigmaF)²]² 
 Ai are: 
 22.4 34.8 18.3 5.09 
;

# 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
F1 F 0.87532(9) 0.7307(2) 0.67661(6) 0.0351 1.0000 Uani . . . . . .
C2 C 0.82404(15) 0.9113(4) 0.63619(10) 0.0280 1.0000 Uani . . . . . .
C3 C 0.83963(14) 0.9171(3) 0.55917(10) 0.0274 1.0000 Uani . . . . . .
C4 C 0.78691(15) 1.1080(4) 0.51731(10) 0.0277 1.0000 Uani . . . . . .
C5 C 0.80337(15) 1.1123(4) 0.43942(10) 0.0285 1.0000 Uani . . . . . .
C6 C 0.86847(14) 0.9380(3) 0.40686(10) 0.0264 1.0000 Uani . . . . . .
N7 N 0.91895(13) 0.7527(3) 0.44819(9) 0.0286 1.0000 Uani . . . . . .
C8 C 0.90453(15) 0.7462(4) 0.52072(11) 0.0291 1.0000 Uani . . . . . .
C9 C 0.89043(14) 0.9344(3) 0.32612(10) 0.0248 1.0000 Uani . . . . . .
C10 C 0.85159(15) 1.1178(3) 0.27685(11) 0.0288 1.0000 Uani . . . . . .
C11 C 0.87392(15) 1.1111(4) 0.20197(10) 0.0290 1.0000 Uani . . . . . .
C12 C 0.93614(14) 0.9206(3) 0.17373(9) 0.0251 1.0000 Uani . . . . . .
O13 O 0.95433(10) 0.9313(2) 0.09846(7) 0.0299 1.0000 Uani . . . . . .
C14 C 1.01198(17) 0.7300(4) 0.06756(11) 0.0341 1.0000 Uani . . . . . .
C15 C 0.97531(15) 0.7361(3) 0.22074(10) 0.0294 1.0000 Uani . . . . . .
C16 C 0.95207(15) 0.7450(3) 0.29610(11) 0.0288 1.0000 Uani . . . . . .
C17 C 0.72073(15) 1.2807(4) 0.55411(11) 0.0304 1.0000 Uani . . . . . .
C18 C 0.70691(16) 1.2631(4) 0.62906(11) 0.0315 1.0000 Uani . . . . . .
C19 C 0.75928(15) 1.0747(4) 0.67193(10) 0.0309 1.0000 Uani . . . . . .
H51 H 0.7670 1.2420 0.4113 0.0343 1.0000 Uiso R . . . . .
H81 H 0.9414 0.6196 0.5480 0.0354 1.0000 Uiso R . . . . .
H101 H 0.8061 1.2516 0.2945 0.0341 1.0000 Uiso R . . . . .
H111 H 0.8474 1.2341 0.1698 0.0359 1.0000 Uiso R . . . . .
H142 H 1.0157 0.7681 0.0146 0.0492 1.0000 Uiso R . . . . .
H141 H 1.0878 0.7143 0.0896 0.0491 1.0000 Uiso R . . . . .
H143 H 0.9699 0.5825 0.0741 0.0494 1.0000 Uiso R . . . . .
H151 H 1.0166 0.6032 0.2034 0.0359 1.0000 Uiso R . . . . .
H161 H 0.9782 0.6199 0.3283 0.0340 1.0000 Uiso R . . . . .
H171 H 0.6865 1.4107 0.5270 0.0347 1.0000 Uiso R . . . . .
H181 H 0.6595 1.3763 0.6529 0.0373 1.0000 Uiso R . . . . .
H191 H 0.7525 1.0688 0.7243 0.0371 1.0000 Uiso R . . . . .
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
F1 0.0390(6) 0.0379(7) 0.0282(6) 0.0072(5) 0.0009(5) 0.0069(5)
C2 0.0250(8) 0.0316(10) 0.0272(9) 0.0022(8) -0.0014(7) -0.0015(8)
C3 0.0239(8) 0.0292(10) 0.0289(9) -0.0005(7) -0.0014(7) -0.0021(7)
C4 0.0242(8) 0.0303(10) 0.0284(9) -0.0014(8) -0.0022(7) -0.0011(7)
C5 0.0274(9) 0.0297(10) 0.0281(10) 0.0000(8) -0.0018(7) 0.0018(7)
C6 0.0247(8) 0.0270(9) 0.0273(9) 0.0014(7) -0.0002(7) -0.0025(7)
N7 0.0302(8) 0.0294(8) 0.0264(8) 0.0034(6) 0.0024(6) 0.0014(7)
C8 0.0296(9) 0.0284(9) 0.0292(9) 0.0029(8) 0.0012(7) 0.0018(7)
C9 0.0231(8) 0.0261(9) 0.0250(9) -0.0006(7) -0.0014(7) -0.0013(7)
C10 0.0297(9) 0.0284(10) 0.0282(9) -0.0002(8) 0.0015(7) 0.0012(7)
C11 0.0294(9) 0.0298(10) 0.0277(9) 0.0039(8) 0.0006(7) 0.0016(7)
C12 0.0250(9) 0.0290(9) 0.0212(8) -0.0001(7) 0.0005(7) -0.0029(7)
O13 0.0348(7) 0.0325(7) 0.0224(6) -0.0012(5) 0.0017(5) 0.0031(6)
C14 0.0397(10) 0.0359(11) 0.0269(9) -0.0036(8) 0.0031(8) 0.0007(9)
C15 0.0308(9) 0.0295(10) 0.0280(9) -0.0014(8) 0.0023(7) 0.0051(8)
C16 0.0303(9) 0.0279(10) 0.0279(9) 0.0020(8) -0.0009(7) 0.0039(8)
C17 0.0309(9) 0.0301(10) 0.0298(9) -0.0036(8) -0.0035(7) 0.0033(8)
C18 0.0276(9) 0.0339(10) 0.0327(10) -0.0063(8) -0.0014(7) 0.0031(8)
C19 0.0293(9) 0.0382(11) 0.0250(9) -0.0034(8) -0.0015(7) -0.0011(8)

_refine_ls_extinction_coef       0.000
_refine_ls_extinction_method     'Larson (1970), Equation 22'
_oxford_refine_ls_scale          0.565(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
F1 . C2 . 1.359(2) yes
C2 . C3 . 1.401(3) yes
C2 . C19 . 1.362(3) yes
C3 . C4 . 1.421(3) yes
C3 . C8 . 1.415(3) yes
C4 . C5 . 1.419(3) yes
C4 . C17 . 1.415(3) yes
C5 . C6 . 1.378(3) yes
C5 . H51 . 0.965 no
C6 . N7 . 1.382(2) yes
C6 . C9 . 1.482(2) yes
N7 . C8 . 1.319(3) yes
C8 . H81 . 0.948 no
C9 . C10 . 1.405(3) yes
C9 . C16 . 1.395(3) yes
C10 . C11 . 1.380(3) yes
C10 . H101 . 0.974 no
C11 . C12 . 1.390(3) yes
C11 . H111 . 0.934 no
C12 . O13 . 1.377(2) yes
C12 . C15 . 1.386(3) yes
O13 . C14 . 1.425(2) yes
C14 . H142 . 0.975 no
C14 . H141 . 0.981 no
C14 . H143 . 0.962 no
C15 . C16 . 1.392(3) yes
C15 . H151 . 0.941 no
C16 . H161 . 0.941 no
C17 . C18 . 1.364(3) yes
C17 . H171 . 0.946 no
C18 . C19 . 1.418(3) yes
C18 . H181 . 0.954 no
C19 . H191 . 0.946 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
F1 . C2 . C3 . 117.81(16) yes
F1 . C2 . C19 . 118.81(16) yes
C3 . C2 . C19 . 123.38(17) yes
C2 . C3 . C4 . 117.58(17) yes
C2 . C3 . C8 . 124.27(17) yes
C4 . C3 . C8 . 118.15(17) yes
C3 . C4 . C5 . 117.09(17) yes
C3 . C4 . C17 . 119.46(17) yes
C5 . C4 . C17 . 123.44(17) yes
C4 . C5 . C6 . 120.64(17) yes
C4 . C5 . H51 . 116.7 no
C6 . C5 . H51 . 122.7 no
C5 . C6 . N7 . 121.68(17) yes
C5 . C6 . C9 . 123.32(16) yes
N7 . C6 . C9 . 115.00(16) yes
C6 . N7 . C8 . 118.45(16) yes
C3 . C8 . N7 . 123.99(17) yes
C3 . C8 . H81 . 119.1 no
N7 . C8 . H81 . 116.9 no
C6 . C9 . C10 . 122.50(16) yes
C6 . C9 . C16 . 120.33(16) yes
C10 . C9 . C16 . 117.17(17) yes
C9 . C10 . C11 . 121.36(18) yes
C9 . C10 . H101 . 120.6 no
C11 . C10 . H101 . 118.0 no
C10 . C11 . C12 . 120.17(17) yes
C10 . C11 . H111 . 120.4 no
C12 . C11 . H111 . 119.4 no
C11 . C12 . O13 . 115.72(15) yes
C11 . C12 . C15 . 119.96(16) yes
O13 . C12 . C15 . 124.32(16) yes
C12 . O13 . C14 . 116.54(14) yes
O13 . C14 . H142 . 104.8 no
O13 . C14 . H141 . 111.6 no
H142 . C14 . H141 . 109.4 no
O13 . C14 . H143 . 109.7 no
H142 . C14 . H143 . 110.1 no
H141 . C14 . H143 . 111.1 no
C12 . C15 . C16 . 119.27(17) yes
C12 . C15 . H151 . 122.3 no
C16 . C15 . H151 . 118.5 no
C9 . C16 . C15 . 122.07(17) yes
C9 . C16 . H161 . 118.3 no
C15 . C16 . H161 . 119.7 no
C4 . C17 . C18 . 120.32(18) yes
C4 . C17 . H171 . 120.2 no
C18 . C17 . H171 . 119.4 no
C17 . C18 . C19 . 121.11(18) yes
C17 . C18 . H181 . 119.6 no
C19 . C18 . H181 . 119.2 no
C18 . C19 . C2 . 118.13(17) yes
C18 . C19 . H191 . 120.5 no
C2 . C19 . H191 . 121.2 no


_iucr_refine_instruction_details_constraints 
;
#
# Punched on 18/05/12 at 11:48:28
#
#LIST     12                                                                    
BLOCK SCALE X'S, U'S 
RIDE C   (   5,X'S) H   (  51,X'S) 
RIDE C   (   8,X'S) H   (  81,X'S) 
RIDE C   (  10,X'S) H   ( 101,X'S) 
RIDE C   (  11,X'S) H   ( 111,X'S) 
RIDE C   (  14,X'S) H   ( 142,X'S) H   ( 141,X'S) H   ( 143,X'S) 
RIDE C   (  15,X'S) H   ( 151,X'S) 
RIDE C   (  16,X'S) H   ( 161,X'S) 
RIDE C   (  17,X'S) H   ( 171,X'S) 
RIDE C   (  18,X'S) H   ( 181,X'S) 
RIDE C   (  19,X'S) H   ( 191,X'S) 
END                                                                             
;


_iucr_refine_instruction_details_restraints 
;
#
# Punched on 18/05/12 at 11:48:28
#
#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
2 1 1 x .
2 1 1 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_014tjd11
_database_code_depnum_ccdc_archive 'CCDC 1422536'
_audit_update_record             
;
2015-09-06 deposited with the CCDC.
2015-11-20 downloaded from the CCDC.
;

_cell_length_a                   6.54580(10)
_cell_length_b                   8.4459(2)
_cell_length_c                   13.2079(3)
_cell_angle_alpha                90
_cell_angle_beta                 99.9683(9)
_cell_angle_gamma                90
_cell_volume                     719.18(3)

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

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 0.0033 0.0016 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 0.0061 0.0033 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'


_cell_formula_units_Z            2

# Given Formula = C19 H21 
# Dc =      1.15 Fooo =    284.00 Mu =      0.64 M =    249.38
# Found Formula = C19 H21 N1 
# Dc =      1.22 FOOO =    284.00 Mu =      0.70 M =    263.38

_chemical_formula_sum            'C19 H21 N1'
_chemical_formula_moiety         'C19 H21 N1'
_chemical_compound_source        syn
_chemical_formula_weight         263.38


_cell_measurement_reflns_used    1732
_cell_measurement_theta_min      5
_cell_measurement_theta_max      27
_cell_measurement_temperature    150

_exptl_crystal_description       block
_exptl_crystal_colour            clear-colourless
_exptl_crystal_size_min          0.150
_exptl_crystal_size_mid          0.250
_exptl_crystal_size_max          0.350

_exptl_crystal_density_diffrn    1.216
_exptl_crystal_density_meas      .
_exptl_crystal_density_method    'not measured'
# Non-dispersive F(000): 
_exptl_crystal_F_000             284
_exptl_absorpt_coefficient_mu    0.070

# Sheldrick geometric approximatio 0.98 0.99 
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'DENZO/SCALEPACK (Otwinowski & Minor, 1997)'
_exptl_absorpt_correction_T_min  0.95
_exptl_absorpt_correction_T_max  0.99
# For a Kappa CCD, set Tmin to 1.0 and 
# Tmax to the ratio of max:min frame scales in scale_all.log 
_diffrn_measurement_device_type  'Nonius KappaCCD'
_diffrn_measurement_device       Area
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_measurement_method       ω

# If a reference occurs more than once, delete the author 
# and date from subsequent references. 
_computing_data_collection       'COLLECT (Nonius, 2001).'
_computing_cell_refinement       'DENZO/SCALEPACK (Otwinowski & Minor, 1997)'
_computing_data_reduction        'DENZO/SCALEPACK (Otwinowski & Minor, 1997)'
_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            12150
_reflns_number_total             1740
_diffrn_reflns_av_R_equivalents  0.013
# Number of reflections without Friedels Law is 3122 
# Number of reflections with Friedels Law is 1740 
# Theoretical number of reflections is about 1648 


_diffrn_reflns_theta_min         5.193
_diffrn_reflns_theta_max         27.476
_diffrn_measured_fraction_theta_max 0.988

_diffrn_reflns_theta_full        26.926
_diffrn_measured_fraction_theta_full 0.990


_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       17
_reflns_limit_h_min              -8
_reflns_limit_h_max              8
_reflns_limit_k_min              0
_reflns_limit_k_max              10
_reflns_limit_l_min              0
_reflns_limit_l_max              17

_oxford_diffrn_Wilson_B_factor   2.17
_oxford_diffrn_Wilson_scale      0.23

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

_refine_diff_density_min         -0.14
_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         1740
_refine_ls_number_restraints     1
_refine_ls_number_parameters     181
_oxford_refine_ls_R_factor_ref   0.0335
_refine_ls_wR_factor_ref         0.0803
_refine_ls_goodness_of_fit_ref   0.9287
_refine_ls_shift/su_max          0.0069929
_refine_ls_shift/su_mean         0.0013227


# The values computed from all data 
_oxford_reflns_number_all        1740
_refine_ls_R_factor_all          0.0335
_refine_ls_wR_factor_all         0.0803

# The values computed with a 2 sigma cutoff - a la SHELX 
_reflns_threshold_expression     I>2.0σ(I)
_reflns_number_gt                1646
_refine_ls_R_factor_gt           0.0314
_refine_ls_wR_factor_gt          0.0770

# 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 unk


_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_hydrogen_treatment    constr # none, undef, noref, refall,
# refxyz, refU, constr or mixed
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
;
 Method, part 1, Chebychev polynomial, (Watkin, 1994, Prince, 1982) 
 [weight] = 1.0/[A₀*T₀(x)+A₁*T₁(x) ... +Aₙ₋₁]*Tₙ₋₁(x)] 
 where Ai are the Chebychev coefficients listed below and x= Fcalc/Fmax 
 Method = Robust Weighting (Prince, 1982) 
 W = [weight] * [1-(deltaF/6*sigmaF)²]² 
 Ai are: 
 42.7 69.9 42.4 18.6 4.79 
;

# 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
N1 N 0.09272(19) 0.71691(19) 0.65831(10) 0.0281 1.0000 Uani . . . . . .
C2 C 0.2652(2) 0.67917(19) 0.73005(11) 0.0225 1.0000 Uani . . . . . .
C3 C 0.2386(2) 0.53520(19) 0.79532(11) 0.0212 1.0000 Uani . . . . . .
C4 C 0.4390(2) 0.4926(2) 0.86934(11) 0.0230 1.0000 Uani . . . . . .
C5 C 0.4061(2) 0.3470(2) 0.93396(12) 0.0251 1.0000 Uani . . . . . .
C6 C 0.3422(2) 0.2054(2) 0.86279(13) 0.0278 1.0000 Uani . . . . . .
C7 C 0.1403(2) 0.2453(2) 0.78967(12) 0.0265 1.0000 Uani . . . . . .
C8 C 0.1734(2) 0.3907(2) 0.72506(11) 0.0249 1.0000 Uani . . . . . .
C9 C -0.0315(2) 0.2804(2) 0.85236(13) 0.0281 1.0000 Uani . . . . . .
C10 C 0.0327(2) 0.4220(2) 0.92384(11) 0.0263 1.0000 Uani . . . . . .
C11 C 0.2351(2) 0.3823(2) 0.99696(12) 0.0276 1.0000 Uani . . . . . .
C12 C 0.0665(2) 0.5677(2) 0.85926(11) 0.0244 1.0000 Uani . . . . . .
C13 C 0.4440(2) 0.76706(19) 0.73966(11) 0.0232 1.0000 Uani . . . . . .
C14 C 0.4575(2) 0.8983(2) 0.67438(10) 0.0228 1.0000 Uani . . . . . .
C15 C 0.6397(3) 0.9903(2) 0.67754(12) 0.0299 1.0000 Uani . . . . . .
C16 C 0.6425(3) 1.1123(2) 0.60943(13) 0.0357 1.0000 Uani . . . . . .
C17 C 0.4658(3) 1.1481(2) 0.53586(14) 0.0370 1.0000 Uani . . . . . .
C18 C 0.2882(3) 1.0622(2) 0.53047(12) 0.0312 1.0000 Uani . . . . . .
C19 C 0.2809(2) 0.9356(2) 0.60025(11) 0.0242 1.0000 Uani . . . . . .
C20 C 0.1039(2) 0.8385(2) 0.59757(12) 0.0288 1.0000 Uani . . . . . .
H41 H 0.4810 0.5847 0.9155 0.0281 1.0000 Uiso R . . . . .
H42 H 0.5500 0.4701 0.8293 0.0273 1.0000 Uiso R . . . . .
H51 H 0.5381 0.3225 0.9810 0.0297 1.0000 Uiso R . . . . .
H62 H 0.3204 0.1137 0.9035 0.0342 1.0000 Uiso R . . . . .
H61 H 0.4520 0.1843 0.8214 0.0347 1.0000 Uiso R . . . . .
H71 H 0.0970 0.1534 0.7426 0.0316 1.0000 Uiso R . . . . .
H82 H 0.0398 0.4154 0.6777 0.0299 1.0000 Uiso R . . . . .
H81 H 0.2845 0.3704 0.6859 0.0301 1.0000 Uiso R . . . . .
H92 H -0.0494 0.1857 0.8941 0.0349 1.0000 Uiso R . . . . .
H91 H -0.1637 0.3052 0.8055 0.0332 1.0000 Uiso R . . . . .
H101 H -0.0793 0.4438 0.9656 0.0306 1.0000 Uiso R . . . . .
H112 H 0.2772 0.4730 1.0432 0.0338 1.0000 Uiso R . . . . .
H111 H 0.2143 0.2887 1.0392 0.0330 1.0000 Uiso R . . . . .
H122 H 0.1042 0.6572 0.9058 0.0299 1.0000 Uiso R . . . . .
H121 H -0.0661 0.5937 0.8115 0.0296 1.0000 Uiso R . . . . .
H131 H 0.5649 0.7408 0.7898 0.0278 1.0000 Uiso R . . . . .
H151 H 0.7589 0.9684 0.7281 0.0360 1.0000 Uiso R . . . . .
H161 H 0.7664 1.1748 0.6114 0.0435 1.0000 Uiso R . . . . .
H171 H 0.4680 1.2335 0.4888 0.0464 1.0000 Uiso R . . . . .
H181 H 0.1705 1.0856 0.4787 0.0370 1.0000 Uiso R . . . . .
H201 H -0.0177 0.8628 0.5474 0.0340 1.0000 Uiso R . . . . .
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
N1 0.0224(6) 0.0290(7) 0.0305(6) 0.0033(6) -0.0025(5) 0.0004(6)
C2 0.0212(6) 0.0226(7) 0.0231(7) -0.0002(6) 0.0018(5) 0.0016(6)
C3 0.0192(6) 0.0212(7) 0.0226(6) -0.0003(6) 0.0016(5) 0.0007(5)
C4 0.0187(6) 0.0240(7) 0.0251(7) 0.0023(6) 0.0006(5) 0.0001(5)
C5 0.0211(7) 0.0251(8) 0.0278(7) 0.0034(6) 0.0007(5) 0.0008(6)
C6 0.0262(7) 0.0232(8) 0.0339(8) 0.0027(7) 0.0050(6) 0.0037(6)
C7 0.0268(7) 0.0229(8) 0.0287(7) -0.0036(6) 0.0021(6) -0.0017(6)
C8 0.0252(7) 0.0243(7) 0.0245(7) -0.0031(6) 0.0025(6) -0.0016(6)
C9 0.0224(7) 0.0285(8) 0.0328(8) 0.0016(7) 0.0028(6) -0.0042(6)
C10 0.0238(7) 0.0288(8) 0.0269(7) -0.0006(6) 0.0064(6) 0.0004(6)
C11 0.0271(7) 0.0316(8) 0.0239(6) 0.0019(6) 0.0042(6) -0.0012(6)
C12 0.0208(7) 0.0252(7) 0.0272(7) -0.0012(6) 0.0042(5) 0.0022(6)
C13 0.0210(6) 0.0259(8) 0.0217(6) -0.0010(6) 0.0005(5) -0.0001(6)
C14 0.0236(7) 0.0235(8) 0.0215(6) -0.0030(6) 0.0041(5) 0.0001(6)
C15 0.0288(8) 0.0339(9) 0.0266(7) -0.0004(7) 0.0034(6) -0.0049(7)
C16 0.0374(9) 0.0365(10) 0.0337(8) 0.0036(8) 0.0073(7) -0.0100(8)
C17 0.0451(10) 0.0338(9) 0.0321(8) 0.0086(7) 0.0070(7) -0.0042(8)
C18 0.0360(8) 0.0284(8) 0.0278(7) 0.0041(7) 0.0015(6) 0.0029(7)
C19 0.0255(7) 0.0237(7) 0.0230(7) -0.0010(6) 0.0027(5) 0.0027(6)
C20 0.0257(7) 0.0284(8) 0.0297(8) 0.0036(7) -0.0025(6) 0.0021(6)

_refine_ls_extinction_method     None
_oxford_refine_ls_scale          2.017(18)
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
N1 . C2 . 1.3796(18) yes
N1 . C20 . 1.313(2) yes
C2 . C3 . 1.518(2) yes
C2 . C13 . 1.373(2) yes
C3 . C4 . 1.5365(19) yes
C3 . C8 . 1.548(2) yes
C3 . C12 . 1.5453(19) yes
C4 . C5 . 1.533(2) yes
C4 . H41 . 0.997 no
C4 . H42 . 0.989 no
C5 . C6 . 1.534(2) yes
C5 . C11 . 1.535(2) yes
C5 . H51 . 0.995 no
C6 . C7 . 1.533(2) yes
C6 . H62 . 0.968 no
C6 . H61 . 0.992 no
C7 . C8 . 1.532(2) yes
C7 . C9 . 1.536(2) yes
C7 . H71 . 1.004 no
C8 . H82 . 1.005 no
C8 . H81 . 0.978 no
C9 . C10 . 1.536(2) yes
C9 . H92 . 0.990 no
C9 . H91 . 0.995 no
C10 . C11 . 1.535(2) yes
C10 . C12 . 1.535(2) yes
C10 . H101 . 1.008 no
C11 . H112 . 0.988 no
C11 . H111 . 0.991 no
C12 . H122 . 0.978 no
C12 . H121 . 1.005 no
C13 . C14 . 1.416(2) yes
C13 . H131 . 0.966 no
C14 . C15 . 1.418(2) yes
C14 . C19 . 1.4153(19) yes
C15 . C16 . 1.370(2) yes
C15 . H151 . 0.953 no
C16 . C17 . 1.409(3) yes
C16 . H161 . 0.964 no
C17 . C18 . 1.362(2) yes
C17 . H171 . 0.954 no
C18 . C19 . 1.418(2) yes
C18 . H181 . 0.958 no
C19 . C20 . 1.415(2) yes
C20 . H201 . 0.965 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
C2 . N1 . C20 . 118.35(13) yes
N1 . C2 . C3 . 114.50(13) yes
N1 . C2 . C13 . 121.43(14) yes
C3 . C2 . C13 . 124.06(13) yes
C2 . C3 . C4 . 112.33(12) yes
C2 . C3 . C8 . 109.76(11) yes
C4 . C3 . C8 . 108.27(12) yes
C2 . C3 . C12 . 109.51(12) yes
C4 . C3 . C12 . 108.46(11) yes
C8 . C3 . C12 . 108.42(12) yes
C3 . C4 . C5 . 110.82(12) yes
C3 . C4 . H41 . 108.8 no
C5 . C4 . H41 . 109.6 no
C3 . C4 . H42 . 109.3 no
C5 . C4 . H42 . 109.3 no
H41 . C4 . H42 . 109.1 no
C4 . C5 . C6 . 109.50(12) yes
C4 . C5 . C11 . 109.37(13) yes
C6 . C5 . C11 . 109.65(13) yes
C4 . C5 . H51 . 108.9 no
C6 . C5 . H51 . 109.6 no
C11 . C5 . H51 . 109.7 no
C5 . C6 . C7 . 109.18(13) yes
C5 . C6 . H62 . 109.5 no
C7 . C6 . H62 . 109.4 no
C5 . C6 . H61 . 109.3 no
C7 . C6 . H61 . 108.7 no
H62 . C6 . H61 . 110.7 no
C6 . C7 . C8 . 109.75(12) yes
C6 . C7 . C9 . 109.53(13) yes
C8 . C7 . C9 . 109.43(13) yes
C6 . C7 . H71 . 109.9 no
C8 . C7 . H71 . 109.1 no
C9 . C7 . H71 . 109.2 no
C3 . C8 . C7 . 110.42(11) yes
C3 . C8 . H82 . 109.2 no
C7 . C8 . H82 . 108.8 no
C3 . C8 . H81 . 107.5 no
C7 . C8 . H81 . 110.1 no
H82 . C8 . H81 . 110.7 no
C7 . C9 . C10 . 109.50(13) yes
C7 . C9 . H92 . 108.2 no
C10 . C9 . H92 . 109.5 no
C7 . C9 . H91 . 110.1 no
C10 . C9 . H91 . 109.6 no
H92 . C9 . H91 . 110.0 no
C9 . C10 . C11 . 109.33(14) yes
C9 . C10 . C12 . 109.44(12) yes
C11 . C10 . C12 . 109.44(13) yes
C9 . C10 . H101 . 109.4 no
C11 . C10 . H101 . 109.0 no
C12 . C10 . H101 . 110.2 no
C10 . C11 . C5 . 109.40(12) yes
C10 . C11 . H112 . 109.7 no
C5 . C11 . H112 . 109.5 no
C10 . C11 . H111 . 109.9 no
C5 . C11 . H111 . 109.6 no
H112 . C11 . H111 . 108.7 no
C10 . C12 . C3 . 110.49(12) yes
C10 . C12 . H122 . 108.4 no
C3 . C12 . H122 . 110.6 no
C10 . C12 . H121 . 109.4 no
C3 . C12 . H121 . 109.1 no
H122 . C12 . H121 . 108.8 no
C2 . C13 . C14 . 120.59(13) yes
C2 . C13 . H131 . 121.5 no
C14 . C13 . H131 . 117.9 no
C13 . C14 . C15 . 123.49(13) yes
C13 . C14 . C19 . 117.78(13) yes
C15 . C14 . C19 . 118.70(14) yes
C14 . C15 . C16 . 119.98(15) yes
C14 . C15 . H151 . 119.8 no
C16 . C15 . H151 . 120.2 no
C15 . C16 . C17 . 120.77(16) yes
C15 . C16 . H161 . 120.0 no
C17 . C16 . H161 . 119.2 no
C16 . C17 . C18 . 120.89(16) yes
C16 . C17 . H171 . 120.6 no
C18 . C17 . H171 . 118.5 no
C17 . C18 . C19 . 119.48(15) yes
C17 . C18 . H181 . 120.1 no
C19 . C18 . H181 . 120.4 no
C18 . C19 . C14 . 120.17(14) yes
C18 . C19 . C20 . 122.72(14) yes
C14 . C19 . C20 . 117.07(13) yes
C19 . C20 . N1 . 124.77(14) yes
C19 . C20 . H201 . 117.9 no
N1 . C20 . H201 . 117.3 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
C18 . H181 . N1 2_556 164.90(5) 0.958 2.529 3.462(2) yes


_iucr_refine_instruction_details_constraints 
;
#
# Punched on 18/05/12 at 11:59:30
#
#LIST     12                                                                    
BLOCK SCALE X'S, U'S 
RIDE C   (   4,X'S) H   (  41,X'S) H   (  42,X'S) 
RIDE C   (   5,X'S) H   (  51,X'S) 
RIDE C   (   6,X'S) H   (  62,X'S) H   (  61,X'S) 
RIDE C   (   7,X'S) H   (  71,X'S) 
RIDE C   (   8,X'S) H   (  82,X'S) H   (  81,X'S) 
RIDE C   (   9,X'S) H   (  92,X'S) H   (  91,X'S) 
RIDE C   (  10,X'S) H   ( 101,X'S) 
RIDE C   (  11,X'S) H   ( 112,X'S) H   ( 111,X'S) 
RIDE C   (  12,X'S) H   ( 122,X'S) H   ( 121,X'S) 
RIDE C   (  13,X'S) H   ( 131,X'S) 
RIDE C   (  15,X'S) H   ( 151,X'S) 
RIDE C   (  16,X'S) H   ( 161,X'S) 
RIDE C   (  17,X'S) H   ( 171,X'S) 
RIDE C   (  18,X'S) H   ( 181,X'S) 
RIDE C   (  20,X'S) H   ( 201,X'S) 
END                                                                             
;


_iucr_refine_instruction_details_restraints 
;
#
# Punched on 18/05/12 at 11:59:30
#
#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_016tjd11
_database_code_depnum_ccdc_archive 'CCDC 1422537'
_audit_update_record             
;
2015-09-06 deposited with the CCDC.
2015-11-20 downloaded from the CCDC.
;

_cell_length_a                   9.45540(10)
_cell_length_b                   10.6808(2)
_cell_length_c                   12.7524(2)
_cell_angle_alpha                90
_cell_angle_beta                 92.8615(7)
_cell_angle_gamma                90
_cell_volume                     1286.28(3)

_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 0.0033 0.0016 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 0.0061 0.0033 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 0.0106 0.0060 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 = C17 H15 N1 
# Dc =      1.20 Fooo =    528.00 Mu =      0.70 M =    233.31
# Found Formula = C17 H15 N1 O1 
# Dc =      1.29 FOOO =    528.00 Mu =      0.80 M =    249.31

_chemical_formula_sum            'C17 H15 N1 O1'
_chemical_formula_moiety         'C17 H15 N1 O1'
_chemical_compound_source        syn
_chemical_formula_weight         249.31


_cell_measurement_reflns_used    3111
_cell_measurement_theta_min      1
_cell_measurement_theta_max      27
_cell_measurement_temperature    150

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_size_min          0.250
_exptl_crystal_size_mid          0.400
_exptl_crystal_size_max          0.400

_exptl_crystal_density_diffrn    1.287
_exptl_crystal_density_meas      .
_exptl_crystal_density_method    'not measured'
# Non-dispersive F(000): 
_exptl_crystal_F_000             528
_exptl_absorpt_coefficient_mu    0.080

# Sheldrick geometric approximatio 0.97 0.98 
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'DENZO/SCALEPACK (Otwinowski & Minor, 1997)'
_exptl_absorpt_correction_T_min  0.88
_exptl_absorpt_correction_T_max  0.98
# For a Kappa CCD, set Tmin to 1.0 and 
# Tmax to the ratio of max:min frame scales in scale_all.log 
_diffrn_measurement_device_type  'Nonius KappaCCD'
_diffrn_measurement_device       Area
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_measurement_method       ω

# If a reference occurs more than once, delete the author 
# and date from subsequent references. 
_computing_data_collection       'COLLECT (Nonius, 2001).'
_computing_cell_refinement       'DENZO/SCALEPACK (Otwinowski & Minor, 1997)'
_computing_data_reduction        'DENZO/SCALEPACK (Otwinowski & Minor, 1997)'
_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            46617
_reflns_number_total             2960
_diffrn_reflns_av_R_equivalents  0.014
# Number of reflections without Friedels Law is 5741 
# Number of reflections with Friedels Law is 2960 
# Theoretical number of reflections is about 2952 


_diffrn_reflns_theta_min         2.157
_diffrn_reflns_theta_max         27.492
_diffrn_measured_fraction_theta_max 0.998

_diffrn_reflns_theta_full        27.492
_diffrn_measured_fraction_theta_full 0.998


_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       16
_reflns_limit_h_min              -12
_reflns_limit_h_max              12
_reflns_limit_k_min              0
_reflns_limit_k_max              13
_reflns_limit_l_min              0
_reflns_limit_l_max              16

_oxford_diffrn_Wilson_B_factor   2.50
_oxford_diffrn_Wilson_scale      0.75

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

_refine_diff_density_min         -0.18
_refine_diff_density_max         0.19


# 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         2314
_refine_ls_number_restraints     0
_refine_ls_number_parameters     172
_oxford_refine_ls_R_factor_ref   0.0377
_refine_ls_wR_factor_ref         0.0937
_refine_ls_goodness_of_fit_ref   0.8803
_refine_ls_shift/su_max          0.0003855
_refine_ls_shift/su_mean         0.0000360


# The values computed from all data 
_oxford_reflns_number_all        2950
_refine_ls_R_factor_all          0.0496
_refine_ls_wR_factor_all         0.1138

# The values computed with a 2 sigma cutoff - a la SHELX 
_reflns_threshold_expression     I>2.0σ(I)
_reflns_number_gt                2448
_refine_ls_R_factor_gt           0.0400
_refine_ls_wR_factor_gt          0.0982

# 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 # none, undef, noref, refall,
# refxyz, refU, constr or mixed
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
;
 Method, part 1, Chebychev polynomial, (Watkin, 1994, Prince, 1982) 
 [weight] = 1.0/[A₀*T₀(x)+A₁*T₁(x) ... +Aₙ₋₁]*Tₙ₋₁(x)] 
 where Ai are the Chebychev coefficients listed below and x= Fcalc/Fmax 
 Method = Robust Weighting (Prince, 1982) 
 W = [weight] * [1-(deltaF/6*sigmaF)²]² 
 Ai are: 
 57.6 95.1 57.4 24.1 6.40 
;

# 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 0.82538(9) 0.77550(8) 0.23630(7) 0.0339 1.0000 Uani . . . . . .
N2 N 0.81097(9) 0.85285(9) 0.31464(7) 0.0247 1.0000 Uani . . . . . .
C3 C 0.71840(11) 0.81786(10) 0.39242(9) 0.0234 1.0000 Uani . . . . . .
C4 C 0.70010(11) 0.89363(10) 0.47674(9) 0.0241 1.0000 Uani . . . . . .
C5 C 0.77677(11) 1.00917(11) 0.48560(9) 0.0246 1.0000 Uani . . . . . .
C6 C 0.86624(11) 1.04380(10) 0.40430(9) 0.0247 1.0000 Uani . . . . . .
C7 C 0.88179(11) 0.96212(11) 0.31799(9) 0.0253 1.0000 Uani . . . . . .
C8 C 0.97067(13) 0.98702(12) 0.22659(10) 0.0340 1.0000 Uani . . . . . .
C9 C 0.93946(12) 1.16013(11) 0.41211(10) 0.0310 1.0000 Uani . . . . . .
C10 C 0.92432(14) 1.23596(12) 0.49730(11) 0.0364 1.0000 Uani . . . . . .
C11 C 0.83870(14) 1.20042(13) 0.57864(11) 0.0384 1.0000 Uani . . . . . .
C12 C 0.76605(13) 1.08934(12) 0.57281(10) 0.0329 1.0000 Uani . . . . . .
C13 C 0.60234(12) 0.85645(12) 0.56078(9) 0.0297 1.0000 Uani . . . . . .
C14 C 0.64286(12) 0.69679(11) 0.37363(9) 0.0256 1.0000 Uani . . . . . .
C15 C 0.50719(13) 0.69722(12) 0.32671(10) 0.0326 1.0000 Uani . . . . . .
C16 C 0.43267(14) 0.58647(13) 0.31187(11) 0.0390 1.0000 Uani . . . . . .
C17 C 0.49170(15) 0.47404(12) 0.34453(11) 0.0388 1.0000 Uani . . . . . .
C18 C 0.62713(17) 0.47255(13) 0.39028(14) 0.0474 1.0000 Uani . . . . . .
C19 C 0.70229(15) 0.58341(12) 0.40487(12) 0.0412 1.0000 Uani . . . . . .
H81 H 1.0204 1.0679 0.2362 0.0513 1.0000 Uiso R . . . . .
H83 H 1.0390 0.9180 0.2225 0.0510 1.0000 Uiso R . . . . .
H82 H 0.9075 0.9876 0.1629 0.0513 1.0000 Uiso R . . . . .
H91 H 1.0016 1.1851 0.3567 0.0361 1.0000 Uiso R . . . . .
H101 H 0.9744 1.3170 0.5010 0.0427 1.0000 Uiso R . . . . .
H111 H 0.8305 1.2551 0.6394 0.0470 1.0000 Uiso R . . . . .
H121 H 0.7070 1.0644 0.6307 0.0395 1.0000 Uiso R . . . . .
H131 H 0.5353 0.9259 0.5732 0.0453 1.0000 Uiso R . . . . .
H133 H 0.6584 0.8376 0.6253 0.0453 1.0000 Uiso R . . . . .
H132 H 0.5474 0.7809 0.5381 0.0453 1.0000 Uiso R . . . . .
H151 H 0.4650 0.7773 0.3030 0.0401 1.0000 Uiso R . . . . .
H161 H 0.3363 0.5874 0.2769 0.0473 1.0000 Uiso R . . . . .
H171 H 0.4393 0.3953 0.3348 0.0468 1.0000 Uiso R . . . . .
H181 H 0.6677 0.3930 0.4123 0.0567 1.0000 Uiso R . . . . .
H191 H 0.7983 0.5833 0.4362 0.0493 1.0000 Uiso R . . . . .
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
O1 0.0359(5) 0.0342(5) 0.0322(5) -0.0109(4) 0.0088(4) -0.0051(4)
N2 0.0222(4) 0.0248(5) 0.0270(5) -0.0012(4) 0.0017(4) 0.0004(4)
C3 0.0192(5) 0.0226(5) 0.0284(6) 0.0015(4) 0.0004(4) 0.0001(4)
C4 0.0196(5) 0.0249(5) 0.0274(5) 0.0023(4) -0.0006(4) 0.0020(4)
C5 0.0201(5) 0.0242(5) 0.0293(6) -0.0005(4) -0.0023(4) 0.0020(4)
C6 0.0201(5) 0.0220(5) 0.0316(6) 0.0024(4) -0.0027(4) 0.0012(4)
C7 0.0215(5) 0.0247(5) 0.0295(6) 0.0039(5) 0.0003(4) -0.0008(4)
C8 0.0334(6) 0.0342(7) 0.0350(7) 0.0034(5) 0.0079(5) -0.0039(5)
C9 0.0260(5) 0.0243(6) 0.0424(7) 0.0039(5) -0.0023(5) -0.0017(4)
C10 0.0316(6) 0.0242(6) 0.0527(8) -0.0033(5) -0.0056(5) -0.0032(5)
C11 0.0373(7) 0.0320(7) 0.0457(7) -0.0127(6) -0.0016(6) 0.0005(5)
C12 0.0307(6) 0.0326(6) 0.0354(6) -0.0063(5) 0.0009(5) 0.0011(5)
C13 0.0292(6) 0.0309(6) 0.0294(6) 0.0015(5) 0.0044(5) -0.0009(5)
C14 0.0246(5) 0.0237(6) 0.0286(5) -0.0014(4) 0.0042(4) -0.0024(4)
C15 0.0286(6) 0.0291(6) 0.0398(7) 0.0009(5) -0.0014(5) -0.0032(5)
C16 0.0334(7) 0.0380(7) 0.0453(8) -0.0032(6) -0.0012(5) -0.0110(5)
C17 0.0455(7) 0.0290(7) 0.0425(7) -0.0062(5) 0.0091(6) -0.0126(6)
C18 0.0507(8) 0.0237(7) 0.0677(10) 0.0032(6) 0.0010(7) -0.0005(6)
C19 0.0337(7) 0.0290(7) 0.0600(9) 0.0037(6) -0.0064(6) -0.0007(5)

_refine_ls_extinction_method     None
_oxford_refine_ls_scale          1.104(5)
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 . N2 . 1.3087(12) yes
N2 . C3 . 1.4058(14) yes
N2 . C7 . 1.3451(14) yes
C3 . C4 . 1.3638(16) yes
C3 . C14 . 1.4907(15) yes
C4 . C5 . 1.4328(16) yes
C4 . C13 . 1.5032(15) yes
C5 . C6 . 1.4195(16) yes
C5 . C12 . 1.4112(17) yes
C6 . C7 . 1.4179(17) yes
C6 . C9 . 1.4235(16) yes
C7 . C8 . 1.4944(16) yes
C8 . H81 . 0.988 no
C8 . H83 . 0.983 no
C8 . H82 . 0.984 no
C9 . C10 . 1.3683(19) yes
C9 . H91 . 0.979 no
C10 . C11 . 1.400(2) yes
C10 . H101 . 0.986 no
C11 . C12 . 1.3711(18) yes
C11 . H111 . 0.977 no
C12 . H121 . 0.985 no
C13 . H131 . 0.994 no
C13 . H133 . 0.977 no
C13 . H132 . 0.995 no
C14 . C15 . 1.3882(16) yes
C14 . C19 . 1.3852(17) yes
C15 . C16 . 1.3851(17) yes
C15 . H151 . 0.985 no
C16 . C17 . 1.380(2) yes
C16 . H161 . 0.995 no
C17 . C18 . 1.380(2) yes
C17 . H171 . 0.981 no
C18 . C19 . 1.3887(19) yes
C18 . H181 . 0.968 no
C19 . H191 . 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
O1 . N2 . C3 . 117.58(9) yes
O1 . N2 . C7 . 120.09(9) yes
C3 . N2 . C7 . 122.33(9) yes
N2 . C3 . C4 . 120.43(10) yes
N2 . C3 . C14 . 115.30(9) yes
C4 . C3 . C14 . 124.25(10) yes
C3 . C4 . C5 . 119.32(10) yes
C3 . C4 . C13 . 120.80(10) yes
C5 . C4 . C13 . 119.87(10) yes
C4 . C5 . C6 . 118.98(10) yes
C4 . C5 . C12 . 121.92(11) yes
C6 . C5 . C12 . 119.10(11) yes
C5 . C6 . C7 . 119.69(10) yes
C5 . C6 . C9 . 118.81(11) yes
C7 . C6 . C9 . 121.50(11) yes
C6 . C7 . N2 . 119.19(10) yes
C6 . C7 . C8 . 125.46(10) yes
N2 . C7 . C8 . 115.35(10) yes
C7 . C8 . H81 . 110.0 no
C7 . C8 . H83 . 107.8 no
H81 . C8 . H83 . 110.6 no
C7 . C8 . H82 . 107.6 no
H81 . C8 . H82 . 111.2 no
H83 . C8 . H82 . 109.5 no
C6 . C9 . C10 . 120.16(12) yes
C6 . C9 . H91 . 119.6 no
C10 . C9 . H91 . 120.2 no
C9 . C10 . C11 . 121.00(12) yes
C9 . C10 . H101 . 119.2 no
C11 . C10 . H101 . 119.8 no
C10 . C11 . C12 . 120.08(12) yes
C10 . C11 . H111 . 119.9 no
C12 . C11 . H111 . 120.1 no
C5 . C12 . C11 . 120.82(12) yes
C5 . C12 . H121 . 119.5 no
C11 . C12 . H121 . 119.7 no
C4 . C13 . H131 . 109.6 no
C4 . C13 . H133 . 109.1 no
H131 . C13 . H133 . 110.1 no
C4 . C13 . H132 . 109.7 no
H131 . C13 . H132 . 108.9 no
H133 . C13 . H132 . 109.4 no
C3 . C14 . C15 . 119.43(10) yes
C3 . C14 . C19 . 121.86(10) yes
C15 . C14 . C19 . 118.67(11) yes
C14 . C15 . C16 . 120.60(12) yes
C14 . C15 . H151 . 119.1 no
C16 . C15 . H151 . 120.3 no
C15 . C16 . C17 . 120.44(12) yes
C15 . C16 . H161 . 120.1 no
C17 . C16 . H161 . 119.5 no
C16 . C17 . C18 . 119.37(12) yes
C16 . C17 . H171 . 120.9 no
C18 . C17 . H171 . 119.7 no
C17 . C18 . C19 . 120.30(13) yes
C17 . C18 . H181 . 118.6 no
C19 . C18 . H181 . 121.1 no
C18 . C19 . C14 . 120.62(12) yes
C18 . C19 . H191 . 121.0 no
C14 . C19 . H191 . 118.4 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
C9 . H91 . O1 4_755 164.23(4) 0.979 2.282 3.2349(18) yes
C13 . H133 . O1 3_565 156.32(4) 0.977 2.394 3.3125(18) yes


_iucr_refine_instruction_details_constraints 
;
#
# Punched on 18/05/12 at 13:36:55
#
#LIST     12                                                                    
BLOCK SCALE X'S, U'S 
RIDE C   (   8,X'S) H   (  81,X'S) H   (  83,X'S) H   (  82,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) 
RIDE C   (  12,X'S) H   ( 121,X'S) 
RIDE C   (  13,X'S) H   ( 131,X'S) H   ( 133,X'S) H   ( 132,X'S) 
RIDE C   (  15,X'S) H   ( 151,X'S) 
RIDE C   (  16,X'S) H   ( 161,X'S) 
RIDE C   (  17,X'S) H   ( 171,X'S) 
RIDE C   (  18,X'S) H   ( 181,X'S) 
RIDE C   (  19,X'S) H   ( 191,X'S) 
END                                                                             
;


_iucr_refine_instruction_details_restraints 
;
#
# Punched on 18/05/12 at 13:36:55
#
#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_017tjd11
_database_code_depnum_ccdc_archive 'CCDC 1422538'
_audit_update_record             
;
2015-09-06 deposited with the CCDC.
2015-11-20 downloaded from the CCDC.
;

_cell_length_a                   6.01900(10)
_cell_length_b                   8.0659(2)
_cell_length_c                   23.9029(5)
_cell_angle_alpha                90
_cell_angle_beta                 91.3683(11)
_cell_angle_gamma                90
_cell_volume                     1160.12(4)

_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 0.0033 0.0016 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 0.0061 0.0033 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 0.0106 0.0060 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 H13 N1 
# Dc =      1.26 Fooo =    496.00 Mu =      0.73 M =    219.29
# Found Formula = C16 H13 N1 O1 
# Dc =      1.35 FOOO =    496.00 Mu =      0.84 M =    235.29

_chemical_formula_sum            'C16 H13 N1 O1'
_chemical_formula_moiety         'C16 H13 N1 O1'
_chemical_compound_source        Syn
_chemical_formula_weight         235.29


_cell_measurement_reflns_used    2550
_cell_measurement_theta_min      5
_cell_measurement_theta_max      27
_cell_measurement_temperature    150

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_size_min          0.250
_exptl_crystal_size_mid          0.250
_exptl_crystal_size_max          0.600

_exptl_crystal_density_diffrn    1.347
_exptl_crystal_density_meas      .
_exptl_crystal_density_method    'not measured'
# Non-dispersive F(000): 
_exptl_crystal_F_000             496
_exptl_absorpt_coefficient_mu    0.084

# Sheldrick geometric approximatio 0.98 0.98 
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'DENZO/SCALEPACK (Otwinowski & Minor, 1997)'
_exptl_absorpt_correction_T_min  0.77
_exptl_absorpt_correction_T_max  0.98
# For a Kappa CCD, set Tmin to 1.0 and 
# Tmax to the ratio of max:min frame scales in scale_all.log 
_diffrn_measurement_device_type  'Nonius KappaCCD'
_diffrn_measurement_device       Area
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_measurement_method       ω

# If a reference occurs more than once, delete the author 
# and date from subsequent references. 
_computing_data_collection       'COLLECT (Nonius, 2001).'
_computing_cell_refinement       'DENZO/SCALEPACK (Otwinowski & Minor, 1997)'
_computing_data_reduction        'DENZO/SCALEPACK (Otwinowski & Minor, 1997)'
_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            17757
_reflns_number_total             2619
_diffrn_reflns_av_R_equivalents  0.027
# Number of reflections without Friedels Law is 4806 
# Number of reflections with Friedels Law is 2619 
# Theoretical number of reflections is about 2662 


_diffrn_reflns_theta_min         5.127
_diffrn_reflns_theta_max         27.487
_diffrn_measured_fraction_theta_max 0.985

_diffrn_reflns_theta_full        25.014
_diffrn_measured_fraction_theta_full 0.985


_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -30
_diffrn_reflns_limit_l_max       30
_reflns_limit_h_min              -7
_reflns_limit_h_max              7
_reflns_limit_k_min              0
_reflns_limit_k_max              10
_reflns_limit_l_min              0
_reflns_limit_l_max              30

_oxford_diffrn_Wilson_B_factor   2.30
_oxford_diffrn_Wilson_scale      0.59

_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         0.33


# 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         2618
_refine_ls_number_restraints     0
_refine_ls_number_parameters     163
_oxford_refine_ls_R_factor_ref   0.0608
_refine_ls_wR_factor_ref         0.1160
_refine_ls_goodness_of_fit_ref   0.9517
_refine_ls_shift/su_max          0.0005627
_refine_ls_shift/su_mean         0.0000608


# The values computed from all data 
_oxford_reflns_number_all        2618
_refine_ls_R_factor_all          0.0608
_refine_ls_wR_factor_all         0.1160

# The values computed with a 2 sigma cutoff - a la SHELX 
_reflns_threshold_expression     I>2.0σ(I)
_reflns_number_gt                2075
_refine_ls_R_factor_gt           0.0452
_refine_ls_wR_factor_gt          0.1052

# 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 # none, undef, noref, refall,
# refxyz, refU, constr or mixed
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
;
 Method, part 1, Chebychev polynomial, (Watkin, 1994, Prince, 1982) 
 [weight] = 1.0/[A₀*T₀(x)+A₁*T₁(x) ... +Aₙ₋₁]*Tₙ₋₁(x)] 
 where Ai are the Chebychev coefficients listed below and x= Fcalc/Fmax 
 Method = Robust Weighting (Prince, 1982) 
 W = [weight] * [1-(deltaF/6*sigmaF)²]² 
 Ai are: 
 53.0 83.8 48.2 19.1 4.04 
;

# 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 0.62777(18) 0.59686(15) 0.62455(5) 0.0324 1.0000 Uani . . . . . .
N2 N 0.7662(2) 0.65751(16) 0.58910(5) 0.0244 1.0000 Uani . . . . . .
C3 C 0.9505(2) 0.74904(18) 0.60892(6) 0.0221 1.0000 Uani . . . . . .
C4 C 0.9725(3) 0.76682(19) 0.67065(6) 0.0244 1.0000 Uani . . . . . .
C5 C 0.8201(3) 0.8597(2) 0.70072(6) 0.0306 1.0000 Uani . . . . . .
C6 C 0.8502(3) 0.8806(2) 0.75800(7) 0.0355 1.0000 Uani . . . . . .
C7 C 1.0283(3) 0.8064(2) 0.78565(7) 0.0360 1.0000 Uani . . . . . .
C8 C 1.1785(3) 0.7126(2) 0.75633(7) 0.0353 1.0000 Uani . . . . . .
C9 C 1.1525(3) 0.6941(2) 0.69872(6) 0.0294 1.0000 Uani . . . . . .
C10 C 1.0993(2) 0.81224(18) 0.57175(6) 0.0225 1.0000 Uani . . . . . .
C11 C 1.2896(3) 0.9175(2) 0.59248(7) 0.0298 1.0000 Uani . . . . . .
C12 C 1.0723(2) 0.77952(18) 0.51305(6) 0.0237 1.0000 Uani . . . . . .
C13 C 0.8839(3) 0.68766(19) 0.49464(6) 0.0258 1.0000 Uani . . . . . .
C14 C 0.7341(3) 0.6325(2) 0.53448(6) 0.0287 1.0000 Uani . . . . . .
C15 C 0.8525(3) 0.6491(2) 0.43694(6) 0.0315 1.0000 Uani . . . . . .
C16 C 1.0057(3) 0.7002(2) 0.39936(6) 0.0340 1.0000 Uani . . . . . .
C17 C 1.1927(3) 0.7921(2) 0.41728(7) 0.0340 1.0000 Uani . . . . . .
C18 C 1.2252(3) 0.8315(2) 0.47256(7) 0.0301 1.0000 Uani . . . . . .
H51 H 0.6914 0.9099 0.6811 0.0380 1.0000 Uiso R . . . . .
H61 H 0.7483 0.9466 0.7777 0.0427 1.0000 Uiso R . . . . .
H71 H 1.0473 0.8188 0.8252 0.0431 1.0000 Uiso R . . . . .
H81 H 1.3024 0.6601 0.7750 0.0422 1.0000 Uiso R . . . . .
H91 H 1.2593 0.6331 0.6780 0.0356 1.0000 Uiso R . . . . .
H111 H 1.3050 1.0152 0.5689 0.0449 1.0000 Uiso R . . . . .
H112 H 1.2739 0.9514 0.6313 0.0444 1.0000 Uiso R . . . . .
H113 H 1.4310 0.8550 0.5909 0.0459 1.0000 Uiso R . . . . .
H141 H 0.6005 0.5752 0.5239 0.0356 1.0000 Uiso R . . . . .
H151 H 0.7239 0.5910 0.4253 0.0389 1.0000 Uiso R . . . . .
H161 H 0.9856 0.6750 0.3605 0.0389 1.0000 Uiso R . . . . .
H171 H 1.2984 0.8299 0.3909 0.0411 1.0000 Uiso R . . . . .
H181 H 1.3559 0.8921 0.4841 0.0366 1.0000 Uiso R . . . . .
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
O1 0.0313(6) 0.0395(7) 0.0268(6) 0.0016(5) 0.0081(4) -0.0072(5)
N2 0.0245(6) 0.0266(6) 0.0222(6) 0.0010(5) 0.0024(5) -0.0001(5)
C3 0.0233(7) 0.0213(7) 0.0217(7) 0.0002(5) 0.0006(5) 0.0039(5)
C4 0.0280(7) 0.0248(7) 0.0204(7) -0.0002(5) 0.0021(5) -0.0002(6)
C5 0.0314(8) 0.0351(9) 0.0256(8) -0.0026(6) 0.0035(6) 0.0032(7)
C6 0.0392(9) 0.0406(9) 0.0271(8) -0.0084(7) 0.0095(7) -0.0020(8)
C7 0.0442(10) 0.0454(10) 0.0184(7) -0.0024(7) 0.0020(6) -0.0098(8)
C8 0.0372(9) 0.0428(10) 0.0258(8) 0.0023(7) -0.0046(7) 0.0007(8)
C9 0.0317(8) 0.0311(8) 0.0253(7) -0.0004(6) 0.0002(6) 0.0046(7)
C10 0.0241(7) 0.0196(7) 0.0239(7) 0.0007(5) 0.0011(5) 0.0033(5)
C11 0.0300(8) 0.0293(8) 0.0302(8) -0.0020(6) 0.0035(6) -0.0021(7)
C12 0.0276(7) 0.0199(7) 0.0236(7) 0.0025(5) 0.0028(5) 0.0061(6)
C13 0.0295(8) 0.0266(7) 0.0213(7) 0.0017(6) 0.0007(6) 0.0054(6)
C14 0.0276(8) 0.0335(8) 0.0249(8) -0.0016(6) -0.0015(6) -0.0037(7)
C15 0.0370(9) 0.0340(9) 0.0233(8) -0.0007(6) -0.0029(6) 0.0061(7)
C16 0.0463(10) 0.0369(9) 0.0191(7) 0.0014(6) 0.0020(6) 0.0124(8)
C17 0.0403(9) 0.0355(9) 0.0268(8) 0.0060(7) 0.0112(7) 0.0085(7)
C18 0.0326(8) 0.0289(8) 0.0291(8) 0.0029(6) 0.0076(6) 0.0022(6)

_refine_ls_extinction_method     None
_oxford_refine_ls_scale          1.259(8)
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 . N2 . 1.2982(16) yes
N2 . C3 . 1.4056(19) yes
N2 . C14 . 1.3304(19) yes
C3 . C4 . 1.4851(19) yes
C3 . C10 . 1.374(2) yes
C4 . C5 . 1.397(2) yes
C4 . C9 . 1.391(2) yes
C5 . C6 . 1.387(2) yes
C5 . H51 . 0.983 no
C6 . C7 . 1.382(3) yes
C6 . H61 . 0.946 no
C7 . C8 . 1.382(3) yes
C7 . H71 . 0.954 no
C8 . C9 . 1.390(2) yes
C8 . H81 . 0.958 no
C9 . H91 . 0.957 no
C10 . C11 . 1.501(2) yes
C10 . C12 . 1.433(2) yes
C11 . H111 . 0.975 no
C11 . H112 . 0.975 no
C11 . H113 . 0.990 no
C12 . C13 . 1.416(2) yes
C12 . C18 . 1.415(2) yes
C13 . C14 . 1.400(2) yes
C13 . C15 . 1.422(2) yes
C14 . H141 . 0.957 no
C15 . C16 . 1.366(2) yes
C15 . H151 . 0.941 no
C16 . C17 . 1.406(3) yes
C16 . H161 . 0.957 no
C17 . C18 . 1.368(2) yes
C17 . H171 . 0.956 no
C18 . H181 . 0.961 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 . N2 . C3 . 119.44(12) yes
O1 . N2 . C14 . 120.22(13) yes
C3 . N2 . C14 . 120.34(13) yes
N2 . C3 . C4 . 115.89(12) yes
N2 . C3 . C10 . 119.87(13) yes
C4 . C3 . C10 . 124.22(13) yes
C3 . C4 . C5 . 121.26(14) yes
C3 . C4 . C9 . 119.25(13) yes
C5 . C4 . C9 . 119.45(14) yes
C4 . C5 . C6 . 120.07(15) yes
C4 . C5 . H51 . 119.7 no
C6 . C5 . H51 . 120.2 no
C5 . C6 . C7 . 120.07(16) yes
C5 . C6 . H61 . 119.2 no
C7 . C6 . H61 . 120.7 no
C6 . C7 . C8 . 120.24(15) yes
C6 . C7 . H71 . 120.1 no
C8 . C7 . H71 . 119.7 no
C7 . C8 . C9 . 120.10(16) yes
C7 . C8 . H81 . 121.2 no
C9 . C8 . H81 . 118.7 no
C4 . C9 . C8 . 120.04(15) yes
C4 . C9 . H91 . 119.4 no
C8 . C9 . H91 . 120.5 no
C3 . C10 . C11 . 120.03(13) yes
C3 . C10 . C12 . 120.28(14) yes
C11 . C10 . C12 . 119.69(13) yes
C10 . C11 . H111 . 110.4 no
C10 . C11 . H112 . 112.5 no
H111 . C11 . H112 . 109.7 no
C10 . C11 . H113 . 110.4 no
H111 . C11 . H113 . 107.2 no
H112 . C11 . H113 . 106.5 no
C10 . C12 . C13 . 118.17(13) yes
C10 . C12 . C18 . 123.69(14) yes
C13 . C12 . C18 . 118.13(14) yes
C12 . C13 . C14 . 118.60(13) yes
C12 . C13 . C15 . 120.21(14) yes
C14 . C13 . C15 . 121.17(15) yes
C13 . C14 . N2 . 122.62(14) yes
C13 . C14 . H141 . 121.7 no
N2 . C14 . H141 . 115.7 no
C13 . C15 . C16 . 119.71(16) yes
C13 . C15 . H151 . 119.0 no
C16 . C15 . H151 . 121.2 no
C15 . C16 . C17 . 120.44(15) yes
C15 . C16 . H161 . 120.2 no
C17 . C16 . H161 . 119.3 no
C16 . C17 . C18 . 120.76(15) yes
C16 . C17 . H171 . 120.5 no
C18 . C17 . H171 . 118.7 no
C12 . C18 . C17 . 120.75(16) yes
C12 . C18 . H181 . 119.7 no
C17 . C18 . H181 . 119.5 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
C11 . H113 . O1 1_655 143.74(4) 0.990 2.518 3.368(2) yes
C11 . H113 . N2 1_655 172.25(5) 0.990 2.572 3.556(2) yes


_iucr_refine_instruction_details_constraints 
;
#
# Punched on 18/05/12 at 13:24:16
#
#LIST     12                                                                    
BLOCK SCALE X'S, U'S 
RIDE C   (   5,X'S) H   (  51,X'S) 
RIDE C   (   6,X'S) H   (  61,X'S) 
RIDE C   (   7,X'S) H   (  71,X'S) 
RIDE C   (   8,X'S) H   (  81,X'S) 
RIDE C   (   9,X'S) H   (  91,X'S) 
RIDE C   (  11,X'S) H   ( 111,X'S) H   ( 112,X'S) H   ( 113,X'S) 
RIDE C   (  14,X'S) H   ( 141,X'S) 
RIDE C   (  15,X'S) H   ( 151,X'S) 
RIDE C   (  16,X'S) H   ( 161,X'S) 
RIDE C   (  17,X'S) H   ( 171,X'S) 
RIDE C   (  18,X'S) H   ( 181,X'S) 
END                                                                             
;


_iucr_refine_instruction_details_restraints 
;
#
# Punched on 18/05/12 at 13:24:16
#
#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
-1 0 11 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_035tjd13
_database_code_depnum_ccdc_archive 'CCDC 1422539'
_audit_update_record             
;
2015-09-06 deposited with the CCDC.
2015-11-20 downloaded from the CCDC.
;

_cell_length_a                   8.80660(10)
_cell_length_b                   13.3703(2)
_cell_length_c                   12.5739(2)
_cell_angle_alpha                90
_cell_angle_beta                 105.1056(5)
_cell_angle_gamma                90
_cell_volume                     1429.38(4)

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

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 0.0033 0.0016 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'
Br -0.2901 2.4595 17.1789 2.1723 5.2358 16.5796 5.6377 0.2609 3.9851 41.4328
2.9557 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
N 0.0061 0.0033 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'


_cell_formula_units_Z            4

# Given Formula = C18 H14 Br1 N1 
# Dc =      1.51 Fooo =    656.00 Mu =     28.64 M =    324.22
# Found Formula = C18 H14 Br1 N1 
# Dc =      1.51 FOOO =    656.00 Mu =     28.64 M =    324.22

_chemical_formula_sum            'C18 H14 Br1 N1'
_chemical_formula_moiety         'C18 H14 Br1 N1'
_chemical_compound_source        syn
_chemical_formula_weight         324.22


_cell_measurement_reflns_used    3388
_cell_measurement_theta_min      5
_cell_measurement_theta_max      27
_cell_measurement_temperature    150

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_size_min          0.200
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_max          0.400

_exptl_crystal_density_diffrn    1.507
_exptl_crystal_density_meas      .
_exptl_crystal_density_method    'not measured'
# Non-dispersive F(000): 
_exptl_crystal_F_000             656
_exptl_absorpt_coefficient_mu    2.864

# Sheldrick geometric approximatio 0.56 0.32 
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'DENZO/SCALEPACK (Otwinowski & Minor, 1997)'
_exptl_absorpt_correction_T_min  0.32
_exptl_absorpt_correction_T_max  0.38
# For a Kappa CCD, set Tmin to 1.0 and 
# Tmax to the ratio of max:min frame scales in scale_all.log 
_diffrn_measurement_device_type  'Nonius KappaCCD'
_diffrn_measurement_device       Area
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_measurement_method       ω

# If a reference occurs more than once, delete the author 
# and date from subsequent references. 
_computing_data_collection       'COLLECT (Nonius, 2001).'
_computing_cell_refinement       'DENZO/SCALEPACK (Otwinowski & Minor, 1997)'
_computing_data_reduction        'DENZO/SCALEPACK (Otwinowski & Minor, 1997)'
_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            44305
_reflns_number_total             6127
_diffrn_reflns_av_R_equivalents  0.013
# Number of reflections without Friedels Law is 0 
# Number of reflections with Friedels Law is 6127 
# Theoretical number of reflections is about 6551 


_diffrn_reflns_theta_min         5.165
_diffrn_reflns_theta_max         27.475
_diffrn_measured_fraction_theta_max 0.992

_diffrn_reflns_theta_full        27.475
_diffrn_measured_fraction_theta_full 0.992


_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       16
_reflns_limit_h_min              -11
_reflns_limit_h_max              11
_reflns_limit_k_min              0
_reflns_limit_k_max              17
_reflns_limit_l_min              0
_reflns_limit_l_max              16

_oxford_diffrn_Wilson_B_factor   2.90
_oxford_diffrn_Wilson_scale      1.52

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

_refine_diff_density_min         -0.68
_refine_diff_density_max         0.60


# 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>0.0\s(I)
_refine_ls_number_reflns         3256
_refine_ls_number_restraints     0
_refine_ls_number_parameters     181
_oxford_refine_ls_R_factor_ref   0.0371
_refine_ls_wR_factor_ref         0.0772
_refine_ls_goodness_of_fit_ref   0.8809
_refine_ls_shift/su_max          0.0002896
_refine_ls_shift/su_mean         0.0000161


# The values computed with all filters except I/sigma 
_oxford_reflns_number_all        3256
_refine_ls_R_factor_all          0.0371
_refine_ls_wR_factor_all         0.0772

# The values computed with a 2 sigma cutoff - a la SHELX 
_reflns_threshold_expression     I>2.0σ(I)
_reflns_number_gt                2943
_refine_ls_R_factor_gt           0.0326
_refine_ls_wR_factor_gt          0.0730

# 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, part 1, Chebychev polynomial, (Watkin, 1994, Prince, 1982) 
 [weight] = 1.0/[A₀*T₀(x)+A₁*T₁(x) ... +Aₙ₋₁]*Tₙ₋₁(x)] 
 where Ai are the Chebychev coefficients listed below and x= Fcalc/Fmax 
 Method = Robust Weighting (Prince, 1982) 
 W = [weight] * [1-(deltaF/6*sigmaF)²]² 
 Ai are: 
 50.8 80.5 47.1 19.4 4.95 
;

# 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
Br1 Br 0.42787(3) 0.359538(17) 0.371865(19) 0.0384 1.0000 Uani . . . . . .
C2 C 0.3704(2) 0.47635(15) 0.28221(16) 0.0277 1.0000 Uani . . . . . .
C3 C 0.1991(2) 0.47662(15) 0.22107(17) 0.0280 1.0000 Uani . . . . . .
C4 C 0.1449(2) 0.57205(15) 0.15820(16) 0.0271 1.0000 Uani . . . . . .
C5 C 0.1705(2) 0.58607(17) 0.05149(16) 0.0320 1.0000 Uani . . . . . .
C6 C 0.2524(3) 0.5164(2) 0.00142(19) 0.0398 1.0000 Uani . . . . . .
C7 C 0.2714(3) 0.5350(3) -0.1019(2) 0.0528 1.0000 Uani . . . . . .
C8 C 0.2111(3) 0.6226(3) -0.1595(2) 0.0568 1.0000 Uani . . . . . .
C9 C 0.1325(3) 0.6911(2) -0.11380(19) 0.0495 1.0000 Uani . . . . . .
C10 C 0.1102(3) 0.6740(2) -0.00728(18) 0.0383 1.0000 Uani . . . . . .
C11 C 0.0285(3) 0.74200(19) 0.04279(19) 0.0405 1.0000 Uani . . . . . .
N12 N 0.0047(2) 0.72991(15) 0.14097(16) 0.0361 1.0000 Uani . . . . . .
C13 C 0.0650(2) 0.64542(15) 0.19939(16) 0.0273 1.0000 Uani . . . . . .
C14 C 0.0315(2) 0.64095(14) 0.30970(17) 0.0274 1.0000 Uani . . . . . .
C15 C 0.1464(2) 0.61574(16) 0.40517(17) 0.0292 1.0000 Uani . . . . . .
C16 C 0.1115(3) 0.61492(17) 0.50681(18) 0.0340 1.0000 Uani . . . . . .
C17 C -0.0385(3) 0.63846(16) 0.51452(19) 0.0352 1.0000 Uani . . . . . .
C18 C -0.1529(3) 0.66455(17) 0.4207(2) 0.0377 1.0000 Uani . . . . . .
C19 C -0.1186(2) 0.66622(16) 0.31908(19) 0.0336 1.0000 Uani . . . . . .
C20 C 0.4777(2) 0.54510(17) 0.28264(18) 0.0340 1.0000 Uani . . . . . .
H31 H 0.1386 0.4657 0.2763 0.0340 1.0000 Uiso R . . . . .
H32 H 0.1822 0.4198 0.1701 0.0337 1.0000 Uiso R . . . . .
H61 H 0.2953 0.4566 0.0397 0.0497 1.0000 Uiso R . . . . .
H71 H 0.3264 0.4884 -0.1341 0.0628 1.0000 Uiso R . . . . .
H81 H 0.2256 0.6344 -0.2305 0.0660 1.0000 Uiso R . . . . .
H91 H 0.0930 0.7501 -0.1531 0.0604 1.0000 Uiso R . . . . .
H111 H -0.0129 0.8005 0.0027 0.0497 1.0000 Uiso R . . . . .
H151 H 0.2493 0.5997 0.4007 0.0352 1.0000 Uiso R . . . . .
H161 H 0.1921 0.5981 0.5716 0.0410 1.0000 Uiso R . . . . .
H171 H -0.0642 0.6372 0.5848 0.0423 1.0000 Uiso R . . . . .
H181 H -0.2571 0.6811 0.4254 0.0452 1.0000 Uiso R . . . . .
H191 H -0.1984 0.6851 0.2550 0.0416 1.0000 Uiso R . . . . .
H201 H 0.4504 0.6044 0.2404 0.0413 1.0000 Uiso R . . . . .
H202 H 0.5818 0.5350 0.3263 0.0413 1.0000 Uiso R . . . . .
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
Br1 0.04102(13) 0.03410(13) 0.04063(13) 0.00709(9) 0.01147(9) 0.00645(9)
C2 0.0281(9) 0.0284(10) 0.0282(9) -0.0021(7) 0.0099(7) 0.0040(8)
C3 0.0265(9) 0.0268(9) 0.0318(10) -0.0044(8) 0.0096(8) -0.0011(7)
C4 0.0213(8) 0.0314(9) 0.0271(9) -0.0033(8) 0.0039(7) -0.0048(7)
C5 0.0254(9) 0.0436(12) 0.0255(9) -0.0058(8) 0.0040(7) -0.0092(9)
C6 0.0345(11) 0.0531(14) 0.0327(10) -0.0124(10) 0.0106(8) -0.0101(10)
C7 0.0446(13) 0.083(2) 0.0344(12) -0.0214(13) 0.0172(11) -0.0191(14)
C8 0.0457(14) 0.102(2) 0.0226(10) -0.0047(13) 0.0082(10) -0.0266(15)
C9 0.0393(12) 0.0777(19) 0.0264(11) 0.0095(11) -0.0007(9) -0.0184(13)
C10 0.0283(10) 0.0551(14) 0.0275(10) 0.0023(9) 0.0000(8) -0.0104(10)
C11 0.0339(11) 0.0448(13) 0.0367(11) 0.0117(10) -0.0020(9) 0.0000(10)
N12 0.0319(9) 0.0385(10) 0.0343(9) 0.0046(8) 0.0019(7) 0.0031(8)
C13 0.0227(8) 0.0305(10) 0.0264(9) -0.0014(7) 0.0023(7) -0.0015(7)
C14 0.0264(9) 0.0247(9) 0.0311(10) -0.0038(7) 0.0076(7) -0.0014(7)
C15 0.0277(9) 0.0313(10) 0.0295(9) -0.0045(8) 0.0091(8) 0.0005(8)
C16 0.0401(11) 0.0330(10) 0.0302(10) -0.0041(8) 0.0116(9) -0.0023(9)
C17 0.0448(12) 0.0286(10) 0.0382(11) -0.0071(8) 0.0214(9) -0.0075(9)
C18 0.0341(11) 0.0316(10) 0.0534(14) -0.0097(10) 0.0218(10) -0.0021(9)
C19 0.0252(9) 0.0322(10) 0.0425(12) -0.0052(9) 0.0074(8) 0.0014(8)
C20 0.0277(10) 0.0372(11) 0.0373(11) 0.0015(9) 0.0087(8) 0.0010(8)

_refine_ls_extinction_method     None
_oxford_refine_ls_scale          0.8281(19)
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
Br1 . C2 . 1.915(2) yes
C2 . C3 . 1.504(3) yes
C2 . C20 . 1.317(3) yes
C3 . C4 . 1.511(3) yes
C3 . H31 . 0.990 no
C3 . H32 . 0.980 no
C4 . C5 . 1.430(3) yes
C4 . C13 . 1.384(3) yes
C5 . C6 . 1.422(3) yes
C5 . C10 . 1.416(3) yes
C6 . C7 . 1.376(3) yes
C6 . H61 . 0.958 no
C7 . C8 . 1.406(5) yes
C7 . H71 . 0.942 no
C8 . C9 . 1.363(5) yes
C8 . H81 . 0.947 no
C9 . C10 . 1.422(3) yes
C9 . H91 . 0.947 no
C10 . C11 . 1.406(4) yes
C11 . N12 . 1.315(3) yes
C11 . H111 . 0.951 no
N12 . C13 . 1.376(3) yes
C13 . C14 . 1.493(3) yes
C14 . C15 . 1.395(3) yes
C14 . C19 . 1.399(3) yes
C15 . C16 . 1.390(3) yes
C15 . H151 . 0.947 no
C16 . C17 . 1.386(3) yes
C16 . H161 . 0.958 no
C17 . C18 . 1.382(4) yes
C17 . H171 . 0.968 no
C18 . C19 . 1.387(3) yes
C18 . H181 . 0.960 no
C19 . H191 . 0.955 no
C20 . H201 . 0.950 no
C20 . H202 . 0.948 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
Br1 . C2 . C3 . 112.26(14) yes
Br1 . C2 . C20 . 119.16(16) yes
C3 . C2 . C20 . 128.55(19) yes
C2 . C3 . C4 . 114.04(16) yes
C2 . C3 . H31 . 107.0 no
C4 . C3 . H31 . 109.7 no
C2 . C3 . H32 . 107.1 no
C4 . C3 . H32 . 109.8 no
H31 . C3 . H32 . 109.1 no
C3 . C4 . C5 . 119.74(18) yes
C3 . C4 . C13 . 121.65(18) yes
C5 . C4 . C13 . 118.57(19) yes
C4 . C5 . C6 . 123.5(2) yes
C4 . C5 . C10 . 118.0(2) yes
C6 . C5 . C10 . 118.5(2) yes
C5 . C6 . C7 . 120.0(3) yes
C5 . C6 . H61 . 120.2 no
C7 . C6 . H61 . 119.8 no
C6 . C7 . C8 . 121.0(3) yes
C6 . C7 . H71 . 119.2 no
C8 . C7 . H71 . 119.8 no
C7 . C8 . C9 . 120.5(2) yes
C7 . C8 . H81 . 119.9 no
C9 . C8 . H81 . 119.6 no
C8 . C9 . C10 . 119.9(3) yes
C8 . C9 . H91 . 119.9 no
C10 . C9 . H91 . 120.2 no
C9 . C10 . C5 . 120.0(2) yes
C9 . C10 . C11 . 122.0(2) yes
C5 . C10 . C11 . 118.0(2) yes
C10 . C11 . N12 . 124.5(2) yes
C10 . C11 . H111 . 117.7 no
N12 . C11 . H111 . 117.8 no
C11 . N12 . C13 . 117.9(2) yes
C4 . C13 . N12 . 123.02(19) yes
C4 . C13 . C14 . 124.21(18) yes
N12 . C13 . C14 . 112.75(18) yes
C13 . C14 . C15 . 122.33(18) yes
C13 . C14 . C19 . 119.26(19) yes
C15 . C14 . C19 . 118.38(19) yes
C14 . C15 . C16 . 120.58(19) yes
C14 . C15 . H151 . 119.6 no
C16 . C15 . H151 . 119.8 no
C15 . C16 . C17 . 120.4(2) yes
C15 . C16 . H161 . 119.5 no
C17 . C16 . H161 . 120.2 no
C16 . C17 . C18 . 119.6(2) yes
C16 . C17 . H171 . 120.9 no
C18 . C17 . H171 . 119.5 no
C17 . C18 . C19 . 120.4(2) yes
C17 . C18 . H181 . 120.1 no
C19 . C18 . H181 . 119.6 no
C14 . C19 . C18 . 120.7(2) yes
C14 . C19 . H191 . 119.8 no
C18 . C19 . H191 . 119.5 no
C2 . C20 . H201 . 120.3 no
C2 . C20 . H202 . 119.2 no
H201 . C20 . H202 . 120.5 no


_iucr_refine_instruction_details_constraints 
;
#
# Punched on 20/08/13 at 16:35:59
#
#LIST     12                                                                    
BLOCK SCALE X'S, U'S 
RIDE C   (   3,X'S) H   (  31,X'S) H   (  32,X'S) 
RIDE C   (   6,X'S) H   (  61,X'S) 
RIDE C   (   7,X'S) H   (  71,X'S) 
RIDE C   (   8,X'S) H   (  81,X'S) 
RIDE C   (   9,X'S) H   (  91,X'S) 
RIDE C   (  11,X'S) H   ( 111,X'S) 
RIDE C   (  15,X'S) H   ( 151,X'S) 
RIDE C   (  16,X'S) H   ( 161,X'S) 
RIDE C   (  17,X'S) H   ( 171,X'S) 
RIDE C   (  18,X'S) H   ( 181,X'S) 
RIDE C   (  19,X'S) H   ( 191,X'S) 
RIDE C   (  20,X'S) H   ( 201,X'S) H   ( 202,X'S) 
END                                                                             
;


_iucr_refine_instruction_details_restraints 
;
#
# Punched on 20/08/13 at 16:35:59
#
#LIST     16                                                                    
NO 
REM   HREST   START (DO NOT REMOVE THIS LINE) 
REM   HREST   END (DO NOT REMOVE THIS LINE) 
END                                                                             
;
