# Electronic Supplementary Material (ESI) for CrystEngComm.
# This journal is © The Royal Society of Chemistry 2014

#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_ethylamine_phase1
_audit_creation_date             11-02-08
_audit_creation_method           CRYSTALS_ver_14.11

_oxford_structure_analysis_title 'ethylamine in P2(1)/c'
_chemical_name_systematic        ethylamine
_chemical_melting_point          192



#end of refcif 
_cell_length_a                   8.2633(3)
_cell_length_b                   7.3098(3)
_cell_length_c                   5.5317(2)
_cell_angle_alpha                90
_cell_angle_beta                 99.088(3)
_cell_angle_gamma                90
_cell_volume                     329.94(2)

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   'P 1 21/c 1 '
_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'


_cell_formula_units_Z            4

# Given Formula = C2 H5 N1 
# Dc =      0.87 Fooo =    104.00 Mu =      0.55 M =     43.07
# Found Formula = C2 H7 N1 
# Dc =      0.91 FOOO =    104.00 Mu =      0.57 M =     45.08

_chemical_formula_sum            'C2 H7 N1'
_chemical_formula_moiety         'C2 H7 N1'
_chemical_compound_source        ?
_chemical_formula_weight         45.08


_cell_measurement_reflns_used    1705
_cell_measurement_theta_min      2
_cell_measurement_theta_max      26
_cell_measurement_temperature    180

_exptl_crystal_description       cylinder
_exptl_crystal_colour            colourless
_exptl_crystal_size_min          0.200
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_max          2.000

_exptl_crystal_density_diffrn    0.908
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
# Non-dispersive F(000): 
_exptl_crystal_F_000             104
_exptl_absorpt_coefficient_mu    0.057

# Sheldrick geometric approximatio 0.99 0.99 
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Siemens, 1996)'
_exptl_absorpt_correction_T_min  0.79
_exptl_absorpt_correction_T_max  0.99
_diffrn_measurement_device_type  'Bruker Kappa Apex2'
_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       'Apex2 (Bruker AXS, 2006)'
_computing_cell_refinement       'Apex2 (Bruker AXS, 2006)'
_computing_data_reduction        'Apex2 (Bruker AXS, 2006)'
_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      180
_diffrn_reflns_number            3375
_reflns_number_total             679
_diffrn_reflns_av_R_equivalents  0.027
# Number of reflections without Friedels Law is 0 
# Number of reflections with Friedels Law is 679 
# Theoretical number of reflections is about 1351 


_diffrn_reflns_theta_min         2.496
_diffrn_reflns_theta_max         26.384
_diffrn_measured_fraction_theta_max 0.999

_diffrn_reflns_theta_full        26.384
_diffrn_measured_fraction_theta_full 0.999


_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -6
_diffrn_reflns_limit_l_max       6
_reflns_limit_h_min              -10
_reflns_limit_h_max              10
_reflns_limit_k_min              0
_reflns_limit_k_max              9
_reflns_limit_l_min              0
_reflns_limit_l_max              6

_oxford_diffrn_Wilson_B_factor   0.00
_oxford_diffrn_Wilson_scale      0.00

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

_refine_diff_density_min         -0.12
_refine_diff_density_max         0.18


# 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>-10.0\s(I)
_refine_ls_number_reflns         679
_refine_ls_number_restraints     27
_refine_ls_number_parameters     56
_oxford_refine_ls_R_factor_ref   0.0424
_refine_ls_wR_factor_ref         0.0854
_refine_ls_goodness_of_fit_ref   0.9250
_refine_ls_shift/su_max          0.0001792
_refine_ls_shift/su_mean         0.0000164


# The values computed from all data 
_oxford_reflns_number_all        679
_refine_ls_R_factor_all          0.0424
_refine_ls_wR_factor_all         0.0854

# The values computed with a 2 sigma cutoff - a la SHELX 
_reflns_threshold_expression     I>2.0σ(I)
_reflns_number_gt                614
_refine_ls_R_factor_gt           0.0375
_refine_ls_wR_factor_gt          0.0834

# 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    'restrained refall'

_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: 
 3.12 4.17 1.15 
;

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

# Replace last . with number of unfound hydrogen atomsattached 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 0.41088(10) 0.63357(12) 0.70604(15) 0.0445 1.0000 Uani D . . . . .
C2 C 0.24363(11) 0.56621(14) 0.64734(16) 0.0435 1.0000 Uani D . . . . .
C3 C 0.19329(13) 0.43052(17) 0.8279(2) 0.0531 1.0000 Uani D . . . . .
H32 H 0.1990(17) 0.486(2) 0.991(2) 0.0787(18) 1.0000 Uiso D . . . . .
H33 H 0.0850(17) 0.390(2) 0.772(2) 0.0826(19) 1.0000 Uiso D . . . . .
H31 H 0.2642(17) 0.3255(18) 0.835(2) 0.0798(19) 1.0000 Uiso D . . . . .
H22 H 0.1719(15) 0.6717(15) 0.636(2) 0.0542(17) 1.0000 Uiso D . . . . .
H21 H 0.2312(14) 0.5101(16) 0.487(2) 0.0555(17) 1.0000 Uiso D . . . . .
H11 H 0.4798(15) 0.5477(16) 0.721(2) 0.0549(17) 1.0000 Uiso D . . . . .
H12 H 0.4255(15) 0.6855(17) 0.851(2) 0.0529(17) 1.0000 Uiso D . . . . .
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 0.0467(4) 0.0496(5) 0.0385(4) 0.0042(3) 0.0105(3) 0.0015(3)
C2 0.0476(5) 0.0445(5) 0.0370(4) 0.0003(4) 0.0027(3) 0.0046(4)
C3 0.0514(5) 0.0533(6) 0.0557(6) 0.0017(4) 0.0120(4) -0.0082(4)

_refine_ls_extinction_method     None
_oxford_refine_ls_scale          0.754(4)
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 . 1.4547(13) yes
N1 . H11 . 0.843(12) no
N1 . H12 . 0.879(12) no
C2 . C3 . 1.5118(15) yes
C2 . H22 . 0.969(11) no
C2 . H21 . 0.966(11) no
C3 . H32 . 0.985(13) no
C3 . H33 . 0.947(13) no
C3 . H31 . 0.963(13) 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 . H11 . 111.9(8) no
C2 . N1 . H12 . 109.8(8) no
H11 . N1 . H12 . 103.7(11) no
N1 . C2 . C3 . 115.18(8) yes
N1 . C2 . H22 . 107.2(7) no
C3 . C2 . H22 . 109.7(7) no
N1 . C2 . H21 . 107.9(7) no
C3 . C2 . H21 . 109.0(7) no
H22 . C2 . H21 . 107.6(9) no
C2 . C3 . H32 . 110.8(8) no
C2 . C3 . H33 . 109.4(9) no
H32 . C3 . H33 . 109.6(11) no
C2 . C3 . H31 . 108.8(8) no
H32 . C3 . H31 . 110.6(10) no
H33 . C3 . H31 . 107.6(11) no


_iucr_refine_instruction_details_constraints 
;
#
# Punched on 08/02/11 at 16:27:05
#
#LIST     12                                                                    
BLOCK 
CONT SCALE 
CONT N    (    1 ,X'S,U'S)  UNTIL C    (    3 ) 
CONT H    (   32 ,X'S,U[ISO])  UNTIL H    (   12 ) 
END                                                                             
;


_iucr_refine_instruction_details_restraints 
;
#
# Punched on 08/02/11 at 16:27:05
#
#LIST     16                                                                    
NO 
REM   HREST   START (DO NOT REMOVE THIS LINE) 
REM NO H   NO #H U MULT DIST 
REM C-H 
REM >4           1.5    .96 DISORDER 
REM 1      1     1.2    .93 C C-H (ACETYLENE) 
REM 1      2     1.2    .93 C-C(H)-C 
REM 1      3     1.2    .98 (C)3-C-H 
REM 2      1     1.2    .93 C=C-H(2) 
REM 2      2     1.2    .97 (C)2-C-(H)2 
REM 3      1     1.5    .96 C-C-(H)3 
REM N-H 
REM >4           1.5    .89 DISORDER 
REM 1      1     1.2    .86 N-N/H 
REM 1      2     1.2    .86 (C)2-N-H 
REM 1      3     1.2    .89 (C)3-N-H 
REM 2      1     1.2    .86 C-N-(H)2 
REM 2      2     1.2    .89 (C)2-N-(H)2 
REM 3      1     1.2    .89 C-H-(H)3 
REM O-H 
REM 1      1     1.5    .82 O-H 
REM 
REM DIST      ESD = 0.02 
REM VIB       ESD = 0.002 
REM ANGLE     ESD = 2.0 
REM            H2-N-R 
DIST 0.86, 0.02 = 
CONT N ( 1) TO H(11) 
CONT N ( 1) TO H(12) 
REST 0.055, 0.002 = H(11,U[ISO]) 
REST 0.055, 0.002 = H(12,U[ISO]) 
ANGLE 120.0, 2.0 = 
CONT C(2) TO N ( 1) TO H(11) 
CONT C(2) TO N ( 1) TO H(12) 
REM            2 H ON SP 3 
DIST 0.97, 0.02 = 
CONT C ( 2) TO H(22) 
CONT C ( 2) TO H(21) 
REST 0.053, 0.002 = H(22,U[ISO]) 
REST 0.053, 0.002 = H(21,U[ISO]) 
ANGLE 0.0, 2.0 = MEAN 
CONT H(22) TO C ( 2) TO N(1) 
CONT H(22) TO C ( 2) TO C(3) 
CONT H(21) TO C ( 2) TO N(1) 
CONT H(21) TO C ( 2) TO C(3) 
ANGLE 109.54, 2.0 = 
CONT H(22) TO C ( 2) TO H(21) 
REM            3 H ON SP 3 
DIST 0.96, 0.02 = 
CONT C ( 3) TO H(32) 
CONT C ( 3) TO H(33) 
CONT C ( 3) TO H(31) 
REST 0.082, 0.002 = H(32,U[ISO]) 
REST 0.082, 0.002 = H(33,U[ISO]) 
REST 0.082, 0.002 = H(31,U[ISO]) 
ANGLE 109.54, 2.0 = 
CONT C(2) TO C ( 3) TO H(32) 
CONT C(2) TO C ( 3) TO H(33) 
CONT C(2) TO C ( 3) TO H(31) 
ANGLE 0.0, 2.0 = MEAN H(32) TO C ( 3) TO H(33) 
CONT H(32) TO C ( 3) TO H(31) 
CONT H(33) TO C ( 3) TO H(31) 
REM   HREST   END (DO NOT REMOVE THIS LINE) 
END                                                                             
;
_database_code_depnum_ccdc_archive 'CCDC 978652'
#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_ethylamine_phase2_150K

loop_
_audit_conform.dict_name
_audit_conform.dict_version
_audit_conform.dict_location
cif_core.dic . ftp://ftp.iucr.org/pub/cif_core.dic
cif_pd.dic . ftp://ftp.iucr.org/pub/cif_pd.dic

_chemical_name_systematic        
; 
ethylamine
;
_chemical_name_common            ethylamine
_chemical_formula_moiety         'C2 H7 N'
_chemical_formula_structural     ?
_chemical_formula_analytical     ?
_chemical_formula_sum            'C2 H7 N'
_chemical_formula_weight         45.09
_chemical_melting_point          ?
_chemical_compound_source        Aldrich


_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   P21/c
_symmetry_Int_Tables_number      14

loop_
_symmetry_equiv_pos_site_id
_symmetry_equiv_pos_as_xyz
1 x,y,z
2 -x,1/2+y,1/2-z
3 -x,-y,-z
4 x,1/2-y,1/2+z

_cell_length_a                   8.97420(18)
_cell_length_b                   5.21927(8)
_cell_length_c                   7.40243(16)
_cell_angle_alpha                90
_cell_angle_beta                 112.9722(13)
_cell_angle_gamma                90
_cell_volume                     319.224(11)
_cell_formula_units_Z            4
_exptl_crystal_density_diffrn    0.938
_cell_measurement_temperature    150

_cell_special_details            
; ?
;

_pd_spec_size_axial              2
_pd_spec_size_equat              0.2
_pd_spec_size_thick              0.2
_pd_spec_mounting                Capillary
_pd_spec_mount_mode              transmission
_pd_spec_shape                   cylinder
_pd_char_particle_morphology     ?
_pd_char_colour                  colourless


# The following three fields describe the preparation of the specimen.   
# The cooling rate is in K/min.  The pressure at which the sample was  
# prepared is in kPa.  The temperature of preparation is in K.

_pd_prep_cool_rate               ?
_pd_prep_pressure                ?
_pd_prep_temperature             150

# The next four fields are normally only needed for transmission experiments.
_exptl_absorpt_coefficient_mu    0.446861 #mm-1
_exptl_absorpt_correction_type   ? # include if applicable
_exptl_absorpt_process_details   ? # include if applicable
_exptl_absorpt_correction_T_min  ? # include if applicable
_exptl_absorpt_correction_T_max  ? # include if applicable


_exptl_special_details           
; ?
;

# The following item is used to identify the equipment used to record 
# the powder pattern when the diffractogram was measured at a laboratory 
# other than the authors' home institution, e.g. when neutron or synchrotron
# radiation is used.

_pd_instr_location               
; 
University of Edinburgh, School of Chemistry
;
_pd_calibration_special_details  
# description of the method used
# to calibrate the instrument
; ?
;

_diffrn_ambient_temperature      150
_diffrn_source                   Sealed-tube
_diffrn_source_target            Cu
_diffrn_source_type              ?
_diffrn_radiation_type           CuK\a1
_diffrn_measurement_device_type  'Bruker D8 Advance'
_diffrn_detector                 psd
_diffrn_detector_type            Lynxeye

_pd_meas_scan_method             step

_pd_meas_special_details         
;  ?
;

# The following six items are used for angular dispersive measurements only.

_diffrn_radiation_wavelength     1.540596
_diffrn_radiation_monochromator  'Johansson monochromator'

#  The following four items give details of the measured (not processed)
#  powder pattern.  Angles are in degrees.

_pd_meas_number_of_points        6694
_pd_meas_2theta_range_min        4
_pd_meas_2theta_range_max        65
_pd_meas_2theta_range_inc        ?

# The following three items are used for time-of-flight measurements only.

_pd_instr_dist_src/spec          ?
_pd_instr_dist_spec/detc         ?
_pd_meas_2theta_fixed            ?


#==============================================================================

# 8. REFINEMENT DATA

# Use the next field to give any special details about the fitting of the
# powder pattern.

_pd_proc_ls_special_details      
; 

Details of Topas refinement:

Line shape: Fundamental parameters with crystal size and strain convolutions

Background: 9-term Chebychev

          prm !dnc      1.43425      
          prm !dcc      1.53088      
          prm !dnh      0.87404      
          prm !dch      0.99168      
                                     
          prm !accn     114.72629    
          prm !ahnc     108.11632    
          prm !ahcc2    111.30928    
          prm !ahcc3    109.71221    
                                     
          prm !nh2_tor -1.61484      
          prm !ch2_tor -1.42183      
          prm !ch3_tor -1.98402      
          
          
          rigid                             
          load z_matrix                     
          {                                 
          N1
          C2   N1   =dnc;
          C3   C2   =dcc;    N1    =accn;
          H11  N1   =dnh;    C2    =ahnc;   C3   = 60+nh2_tor;    
          H12  N1   =dnh;    C2    =ahnc;   C3   =-60+nh2_tor;    
          H31  C3   =dch;    C2    =ahcc2;   N1  =-60 + ch3_tor;
          H32  C3   =dch;    C2    =ahcc2;   N1  = 60 + ch3_tor;
          H33  C3   =dch;    C2    =ahcc2;   N1  = 180+ ch3_tor;
          H21  C2   =dch;    C3    =ahcc3;   H31 =60  + ch2_tor;
          H22  C2   =dch;    C3    =ahcc3;   H31 =180 + ch2_tor;
          }
  
          rotate rot_x -130.05154`_0.73493 qx 1    
          rotate rot_y -41.83072`_0.50842 qy 1    
          rotate rot_z -260.94781`_0.60071 qz 1   
                                       
          translate                    
             ta  trans_x   0.40457`_0.00035
             tb  trans_y   0.29060`_0.00091
             tc  trans_z   0.77455`_0.00102

          'restraint =  (1.47318 -  dnc)/0.01;:3.89301505
          'restraint =  (1.53263 -  dcc)/0.01;:0.175413411
          'restraint =  (0.87404 -  dnh)/0.01;:0  
          'restraint =  (0.99168 -  dch)/0.01;:0  
                         
          'restraint =  (115.83300 -  accn )/1.0;:1.10670703
          'restraint =  (108.11632 -  ahnc )/1.0;:0  
          'restraint =  (111.30928 -  ahcc2)/1.0;:0  
          'restraint =  (109.71221 -  ahcc3)/1.0;:0  
                         
          'restraint =  (-1.61484 - nh2_tor)/2.0;:0 
          'restraint =  (-1.42183 - ch2_tor)/2.0;:0 
          'restraint =  (-1.98402 - ch3_tor)/2.0;:0 

          restraint =  (-128.21262 -  rot_x)/2.0;:0.91946`
          restraint =  (-41.88491  -  rot_y)/2.0;:-0.027095`
          restraint =  (-261.07865 -  rot_z)/2.0;:-0.06542`

          restraint =  (0.41138  -  trans_x)/0.01;:0.681`
          restraint =  (0.30725  -  trans_y)/0.01;:1.665`
          restraint =  (0.78341  -  trans_z)/0.01;:0.886`



;

# The next three items are given as text.

_pd_proc_ls_profile_function     FP
_pd_proc_ls_background_function  '9-term Chebychev'
_pd_proc_ls_pref_orient_corr     
; 
8-order spherical harmonics
;

_pd_proc_ls_prof_R_factor        3.211
_pd_proc_ls_prof_wR_factor       4.943
_pd_proc_ls_prof_wR_expected     2.370
_refine_ls_R_I_factor            ?
_refine_ls_R_Fsqd_factor         ?
_refine_ls_R_factor_all          ?

_refine_special_details          
; 


Checkcif output:

086_ALERT_2_A Unsatisfactory S Value (Too Low or Not Given) ..       0.00

see _refine_ls_restrained_S_all       2.085  

049_ALERT_1_B Calculated Density less than 1.0 gcm-3 .........     0.9381

Checked - OK

340_ALERT_3_B Low Bond Precision on  C-C Bonds ...............     0.0300 Ang.

Powder data


125_ALERT_4_C No '_symmetry_space_group_name_Hall' Given .....     Please Do !

No action

420_ALERT_2_C D-H Without Acceptor       N1     -   H11    ...     Please Check

See text

761_ALERT_1_C CIF Contains no X-H Bonds ......................     Please Check
762_ALERT_1_C CIF Contains no X-Y-H or H-Y-H Angles ..........     Please Check

No action

201_ALERT_2_G Isotropic non-H Atoms in Main Residue(s) .......          3 Why ?
210_ALERT_3_G No Anisotropic ADP's Found in CIF ..............     Please Check

Powder data

760_ALERT_1_G CIF Contains no Torsion Angles .................          ? Info

No action



;

_refine_ls_matrix_type           Full
_refine_ls_weighting_scheme      sigma

_refine_ls_weighting_details     statistical
_refine_ls_hydrogen_treatment    'rigid body'
_refine_ls_extinction_method     ?
_refine_ls_extinction_coef       ?
_refine_ls_number_parameters     60
_refine_ls_number_restraints     ?
_refine_ls_number_constraints    ?

# The following item is the same as CHI, the square root of 'CHI squared'
_refine_ls_goodness_of_fit_all   ?

_refine_ls_restrained_S_all      2.085
_refine_ls_shift/su_max          <0.001
_refine_ls_shift/su_mean         ?

# The following items are used to identify the programs used.

_computing_data_collection       Diffrac
_computing_cell_refinement       Topas
_computing_data_reduction        ?
_computing_structure_solution    Topas
_computing_structure_refinement  Topas
_computing_molecular_graphics    ?
_computing_publication_material  ?


loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_symmetry_multiplicity
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_occupancy
_atom_site_B_iso_or_equiv
N1 N 0 0.4046(3) 0.2906(9) 0.7745(10) 1 3.7(2)
C2 C 0 0.2405(9) 0.374(4) 0.674(2) 1 3.7(2)
C3 C 0 0.193(2) 0.607(5) 0.765(4) 1 3.7(2)
H11 H 0 0.4190(12) 0.2541(17) 0.8955(11) 1 5.6(4)
H12 H 0 0.4685(13) 0.4153(18) 0.7712(16) 1 5.6(4)
H21 H 0 0.1698(7) 0.227(5) 0.671(3) 1 4.5(3)
H22 H 0 0.228(2) 0.414(4) 0.5376(18) 1 4.5(3)
H31 H 0 0.202(2) 0.570(6) 0.900(4) 1 5.6(4)
H32 H 0 0.264(4) 0.756(3) 0.772(4) 1 5.6(4)
H33 H 0 0.080(3) 0.660(7) 0.687(5) 1 5.6(4)
_database_code_depnum_ccdc_archive 'CCDC 978653'
#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_propylamine
_audit_creation_date             11-02-01
_audit_creation_method           CRYSTALS_ver_14.11

_oxford_structure_analysis_title 'Propylamine in Pbcn'
_chemical_name_systematic        propylamine
_chemical_melting_point          190

#end of refcif 
_cell_length_a                   23.2870(13)
_cell_length_b                   6.2354(4)
_cell_length_c                   5.9794(4)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     868.23(9)

_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
x+1/2,-y+1/2,-z
x,-y,z+1/2
-x,y,-z+1/2
-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'


_cell_formula_units_Z            8

# Given Formula = C3 H9 N1 
# Dc =      0.90 Fooo =    272.00 Mu =      0.55 M =     59.11
# Found Formula = C3 H9 N1 
# Dc =      0.90 FOOO =    272.00 Mu =      0.55 M =     59.11

_chemical_formula_sum            'C3 H9 N1'
_chemical_formula_moiety         'C3 H9 N1'
_chemical_compound_source        Aldrich
_chemical_formula_weight         59.11


_cell_measurement_reflns_used    2006
_cell_measurement_theta_min      4
_cell_measurement_theta_max      26
_cell_measurement_temperature    150

_exptl_crystal_description       cylinder
_exptl_crystal_colour            colourless
_exptl_crystal_size_min          0.300
_exptl_crystal_size_mid          0.300
_exptl_crystal_size_max          2.000

_exptl_crystal_density_diffrn    0.904
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
# Non-dispersive F(000): 
_exptl_crystal_F_000             272
_exptl_absorpt_coefficient_mu    0.055

# Sheldrick geometric approximatio 0.98 0.98 
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Siemens, 1996)'
_exptl_absorpt_correction_T_min  0.80
_exptl_absorpt_correction_T_max  0.98
_diffrn_measurement_device_type  'Bruker Kappa Apex2'
_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       'Apex2 (Bruker AXS, 2006)'
_computing_cell_refinement       'Apex2 (Bruker AXS, 2006)'
_computing_data_reduction        'Apex2 (Bruker AXS, 2006)'
_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            9836
_reflns_number_total             890
_diffrn_reflns_av_R_equivalents  0.059
# Number of reflections without Friedels Law is 0 
# Number of reflections with Friedels Law is 890 
# Theoretical number of reflections is about 1781 


_diffrn_reflns_theta_min         1.749
_diffrn_reflns_theta_max         26.400
_diffrn_measured_fraction_theta_max 0.998

_diffrn_reflns_theta_full        26.400
_diffrn_measured_fraction_theta_full 0.998


_diffrn_reflns_limit_h_min       -29
_diffrn_reflns_limit_h_max       28
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_l_min       -7
_diffrn_reflns_limit_l_max       7
_reflns_limit_h_min              0
_reflns_limit_h_max              28
_reflns_limit_k_min              0
_reflns_limit_k_max              7
_reflns_limit_l_min              0
_reflns_limit_l_max              7

_oxford_diffrn_Wilson_B_factor   3.01
_oxford_diffrn_Wilson_scale      14.44

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

_refine_diff_density_min         -0.29
_refine_diff_density_max         0.29


# 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>-10.0\s(I)
_refine_ls_number_reflns         883
_refine_ls_number_restraints     36
_refine_ls_number_parameters     73
_oxford_refine_ls_R_factor_ref   0.0777
_refine_ls_wR_factor_ref         0.1494
_refine_ls_goodness_of_fit_ref   0.9898
_refine_ls_shift/su_max          0.0004408
_refine_ls_shift/su_mean         0.0000219


# The values computed from all data 
_oxford_reflns_number_all        883
_refine_ls_R_factor_all          0.0777
_refine_ls_wR_factor_all         0.1494

# The values computed with a 2 sigma cutoff - a la SHELX 
_reflns_threshold_expression     I>2.0σ(I)
_reflns_number_gt                690
_refine_ls_R_factor_gt           0.0598
_refine_ls_wR_factor_gt          0.1337

# 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    'restrained refall'

_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: 
 9.53 14.0 5.18 0.123 -0.495 
;

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

# Replace last . with number of unfound hydrogen atomsattached 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 0.72466(5) 0.7067(2) 0.5121(2) 0.0338 1.0000 Uani D . . . . .
C2 C 0.66843(5) 0.7878(2) 0.4443(2) 0.0308 1.0000 Uani D . . . . .
C3 C 0.61693(6) 0.6954(2) 0.5682(2) 0.0375 1.0000 Uani D . . . . .
C4 C 0.56034(7) 0.7791(4) 0.4763(4) 0.0602 1.0000 Uani D . . . . .
H22 H 0.6701(5) 0.945(2) 0.461(2) 0.0371(18) 1.0000 Uiso D . . . . .
H11 H 0.7278(5) 0.569(2) 0.495(3) 0.0401(18) 1.0000 Uiso D . . . . .
H21 H 0.6651(5) 0.758(2) 0.286(2) 0.0364(18) 1.0000 Uiso D . . . . .
H32 H 0.6207(6) 0.730(2) 0.724(2) 0.0456(18) 1.0000 Uiso D . . . . .
H31 H 0.6178(5) 0.540(2) 0.557(2) 0.0451(18) 1.0000 Uiso D . . . . .
H12 H 0.7299(6) 0.728(2) 0.655(2) 0.0413(18) 1.0000 Uiso D . . . . .
H41 H 0.5568(8) 0.739(3) 0.320(3) 0.089(2) 1.0000 Uiso D . . . . .
H43 H 0.5285(7) 0.720(3) 0.561(3) 0.0898(19) 1.0000 Uiso D . . . . .
H42 H 0.5599(7) 0.934(3) 0.490(3) 0.0889(19) 1.0000 Uiso D . . . . .
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 0.0300(6) 0.0352(7) 0.0361(7) 0.0020(5) -0.0019(4) 0.0018(4)
C2 0.0291(8) 0.0332(8) 0.0301(7) 0.0012(5) -0.0007(4) 0.0014(5)
C3 0.0326(8) 0.0429(9) 0.0369(8) 0.0005(6) 0.0039(5) -0.0013(6)
C4 0.0285(9) 0.0845(14) 0.0677(12) 0.0013(10) 0.0027(7) 0.0054(8)

_refine_ls_extinction_method     None
_oxford_refine_ls_scale          0.2689(9)
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 . 1.4610(16) yes
N1 . H11 . 0.866(13) no
N1 . H12 . 0.871(14) no
C2 . C3 . 1.5229(18) yes
C2 . H22 . 0.984(13) no
C2 . H21 . 0.970(13) no
C3 . C4 . 1.520(2) yes
C3 . H32 . 0.961(14) no
C3 . H31 . 0.969(13) no
C4 . H41 . 0.972(17) no
C4 . H43 . 0.972(16) no
C4 . H42 . 0.968(16) 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 . H11 . 112.6(8) no
C2 . N1 . H12 . 110.2(9) no
H11 . N1 . H12 . 104.6(14) no
N1 . C2 . C3 . 116.09(13) yes
N1 . C2 . H22 . 106.2(7) no
C3 . C2 . H22 . 111.0(7) no
N1 . C2 . H21 . 106.2(7) no
C3 . C2 . H21 . 109.9(7) no
H22 . C2 . H21 . 107.0(10) no
C2 . C3 . C4 . 112.14(15) yes
C2 . C3 . H32 . 108.4(8) no
C4 . C3 . H32 . 110.7(8) no
C2 . C3 . H31 . 109.2(8) no
C4 . C3 . H31 . 109.7(7) no
H32 . C3 . H31 . 106.7(11) no
C3 . C4 . H41 . 109.4(11) no
C3 . C4 . H43 . 110.0(11) no
H41 . C4 . H43 . 110.0(13) no
C3 . C4 . H42 . 108.7(10) no
H41 . C4 . H42 . 109.6(13) no
H43 . C4 . H42 . 109.1(13) 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
N1 . H11 . N1 3_645 156.9(11) 0.866(13) 2.520(13) 3.334(2) yes
N1 . H12 . N1 7_665 162.0(12) 0.871(14) 2.419(14) 3.259(2) yes


_iucr_refine_instruction_details_constraints 
;
#
# Punched on 01/02/11 at 15:25:08
#
#LIST     12                                                                    
BLOCK 
CONT SCALE 
CONT N    (    1 ,X'S,U'S)  UNTIL C    (    4 ) 
CONT H    (   22 ,X'S,U[ISO])  UNTIL H    (   42 ) 
END                                                                             
;


_iucr_refine_instruction_details_restraints 
;
#
# Punched on 01/02/11 at 15:25:08
#
#LIST     16                                                                    
NO 
REM   HREST   START (DO NOT REMOVE THIS LINE) 
REM NO H   NO #H U MULT DIST 
REM C-H 
REM >4           1.5    .96 DISORDER 
REM 1      1     1.2    .93 C C-H (ACETYLENE) 
REM 1      2     1.2    .93 C-C(H)-C 
REM 1      3     1.2    .98 (C)3-C-H 
REM 2      1     1.2    .93 C=C-H(2) 
REM 2      2     1.2    .97 (C)2-C-(H)2 
REM 3      1     1.5    .96 C-C-(H)3 
REM N-H 
REM >4           1.5    .89 DISORDER 
REM 1      1     1.2    .86 N-N/H 
REM 1      2     1.2    .86 (C)2-N-H 
REM 1      3     1.2    .89 (C)3-N-H 
REM 2      1     1.2    .86 C-N-(H)2 
REM 2      2     1.2    .89 (C)2-N-(H)2 
REM 3      1     1.2    .89 C-H-(H)3 
REM O-H 
REM 1      1     1.5    .82 O-H 
REM 
REM DIST      ESD = 0.02 
REM VIB       ESD = 0.002 
REM ANGLE     ESD = 2.0 
REM            H2-N-R 
DIST 0.86, 0.02 = 
CONT N ( 1) TO H(11) 
CONT N ( 1) TO H(12) 
REST 0.041, 0.002 = H(11,U[ISO]) 
REST 0.041, 0.002 = H(12,U[ISO]) 
ANGLE 120.0, 2.0 = 
CONT C(2) TO N ( 1) TO H(11) 
CONT C(2) TO N ( 1) TO H(12) 
REM            2 H ON SP 3 
DIST 0.97, 0.02 = 
CONT C ( 2) TO H(22) 
CONT C ( 2) TO H(21) 
REST 0.037, 0.002 = H(22,U[ISO]) 
REST 0.037, 0.002 = H(21,U[ISO]) 
ANGLE 0.0, 2.0 = MEAN 
CONT H(22) TO C ( 2) TO N(1) 
CONT H(22) TO C ( 2) TO C(3) 
CONT H(21) TO C ( 2) TO N(1) 
CONT H(21) TO C ( 2) TO C(3) 
ANGLE 109.54, 2.0 = 
CONT H(22) TO C ( 2) TO H(21) 
REM            2 H ON SP 3 
DIST 0.97, 0.02 = 
CONT C ( 3) TO H(32) 
CONT C ( 3) TO H(31) 
REST 0.045, 0.002 = H(32,U[ISO]) 
REST 0.045, 0.002 = H(31,U[ISO]) 
ANGLE 0.0, 2.0 = MEAN 
CONT H(32) TO C ( 3) TO C(2) 
CONT H(32) TO C ( 3) TO C(4) 
CONT H(31) TO C ( 3) TO C(2) 
CONT H(31) TO C ( 3) TO C(4) 
ANGLE 109.54, 2.0 = 
CONT H(32) TO C ( 3) TO H(31) 
REM            3 H ON SP 3 
DIST 0.96, 0.02 = 
CONT C ( 4) TO H(41) 
CONT C ( 4) TO H(43) 
CONT C ( 4) TO H(42) 
REST 0.090, 0.002 = H(41,U[ISO]) 
REST 0.090, 0.002 = H(43,U[ISO]) 
REST 0.090, 0.002 = H(42,U[ISO]) 
ANGLE 109.54, 2.0 = 
CONT C(3) TO C ( 4) TO H(41) 
CONT C(3) TO C ( 4) TO H(43) 
CONT C(3) TO C ( 4) TO H(42) 
ANGLE 0.0, 2.0 = MEAN H(41) TO C ( 4) TO H(43) 
CONT H(41) TO C ( 4) TO H(42) 
CONT H(43) TO C ( 4) TO H(42) 
REM   HREST   END (DO NOT REMOVE THIS LINE) 
END                                                                             
;
_database_code_depnum_ccdc_archive 'CCDC 978654'
#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_butylamine
_audit_creation_date             10-11-04
_audit_creation_method           CRYSTALS_ver_14.09

_oxford_structure_analysis_title 'Butylamine in Pbcn'
_chemical_name_systematic        Butylamine
_chemical_melting_point          224

#end of refcif 
_cell_length_a                   26.7852(8)
_cell_length_b                   6.8166(2)
_cell_length_c                   5.6703(2)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1035.31(6)

_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
x+1/2,-y+1/2,-z
x,-y,z+1/2
-x,y,-z+1/2
-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'


_cell_formula_units_Z            8

# Given Formula = C4 H11 N1 
# Dc =      0.94 Fooo =    336.00 Mu =      0.56 M =     73.14
# Found Formula = C4 H11 N1 
# Dc =      0.94 FOOO =    336.00 Mu =      0.56 M =     73.14

_chemical_formula_sum            'C4 H11 N1'
_chemical_formula_moiety         'C4 H11 N1'
_chemical_compound_source        Aldrich
_chemical_formula_weight         73.14


_cell_measurement_reflns_used    3283
_cell_measurement_theta_min      3
_cell_measurement_theta_max      31
_cell_measurement_temperature    150

_exptl_crystal_description       cylinder
_exptl_crystal_colour            colourless
_exptl_crystal_size_min          0.450
_exptl_crystal_size_mid          0.450
_exptl_crystal_size_max          2.000

_exptl_crystal_density_diffrn    0.938
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
# Non-dispersive F(000): 
_exptl_crystal_F_000             336
_exptl_absorpt_coefficient_mu    0.056

# Sheldrick geometric approximatio 0.98 0.98 
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Siemens, 1996)'
_exptl_absorpt_correction_T_min  0.82
_exptl_absorpt_correction_T_max  0.98
_diffrn_measurement_device_type  'Bruker Apex2'
_diffrn_measurement_device       Area
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_measurement_method       'φ & ω scans'

# If a reference occurs more than once, delete the author 
# and date from subsequent references. 
_computing_data_collection       'Apex2 (Bruker AXS, 2006)'
_computing_cell_refinement       'Apex2 (Bruker AXS, 2006)'
_computing_data_reduction        'Apex2 (Bruker AXS, 2006)'
_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            7989
_reflns_number_total             1572
_diffrn_reflns_av_R_equivalents  0.026
# Number of reflections without Friedels Law is 0 
# Number of reflections with Friedels Law is 1572 
# Theoretical number of reflections is about 3161 


_diffrn_reflns_theta_min         1.520
_diffrn_reflns_theta_max         30.507
_diffrn_measured_fraction_theta_max 0.996

_diffrn_reflns_theta_full        30.507
_diffrn_measured_fraction_theta_full 0.996


_diffrn_reflns_limit_h_min       -38
_diffrn_reflns_limit_h_max       37
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_limit_l_max       8
_reflns_limit_h_min              0
_reflns_limit_h_max              38
_reflns_limit_k_min              0
_reflns_limit_k_max              9
_reflns_limit_l_min              0
_reflns_limit_l_max              8

_oxford_diffrn_Wilson_B_factor   2.40
_oxford_diffrn_Wilson_scale      8.14

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

_refine_diff_density_min         -0.11
_refine_diff_density_max         0.26


# 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>-10.0\s(I)
_refine_ls_number_reflns         1572
_refine_ls_number_restraints     45
_refine_ls_number_parameters     90
_oxford_refine_ls_R_factor_ref   0.0562
_refine_ls_wR_factor_ref         0.1423
_refine_ls_goodness_of_fit_ref   1.1050
_refine_ls_shift/su_max          0.0007843
_refine_ls_shift/su_mean         0.0000358


# The values computed from all data 
_oxford_reflns_number_all        1572
_refine_ls_R_factor_all          0.0562
_refine_ls_wR_factor_all         0.1423

# The values computed with a 2 sigma cutoff - a la SHELX 
_reflns_threshold_expression     I>2.0σ(I)
_reflns_number_gt                1327
_refine_ls_R_factor_gt           0.0471
_refine_ls_wR_factor_gt          0.1219

# 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    'restrained refall'

_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
;
 Method= Modified Sheldrick 
 w=1/[σ²(F²) + ( 0.06P)² + 0.18P] 
 ,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 atomsattached 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 0.72790(3) 0.30818(15) 0.19230(16) 0.0355 1.0000 Uani D . . . . .
C2 C 0.67812(3) 0.22006(15) 0.17765(16) 0.0299 1.0000 Uani D . . . . .
C3 C 0.63984(3) 0.29726(14) 0.35336(16) 0.0294 1.0000 Uani D . . . . .
C4 C 0.58898(4) 0.20079(17) 0.32972(19) 0.0365 1.0000 Uani D . . . . .
C5 C 0.55075(4) 0.2783(2) 0.5053(2) 0.0476 1.0000 Uani D . . . . .
H11 H 0.7399(5) 0.2924(19) 0.337(2) 0.0441(18) 1.0000 Uiso D . . . . .
H12 H 0.7264(4) 0.4349(18) 0.173(2) 0.0455(18) 1.0000 Uiso D . . . . .
H21 H 0.6815(4) 0.0780(16) 0.1987(18) 0.0361(17) 1.0000 Uiso D . . . . .
H22 H 0.6655(4) 0.2403(16) 0.0170(19) 0.0366(17) 1.0000 Uiso D . . . . .
H31 H 0.6528(4) 0.2764(15) 0.5166(19) 0.0359(17) 1.0000 Uiso D . . . . .
H32 H 0.6364(4) 0.4389(16) 0.3290(18) 0.0370(17) 1.0000 Uiso D . . . . .
H41 H 0.5928(4) 0.0603(17) 0.347(2) 0.0452(17) 1.0000 Uiso D . . . . .
H42 H 0.5767(5) 0.2209(17) 0.169(2) 0.0448(17) 1.0000 Uiso D . . . . .
H51 H 0.5635(5) 0.261(2) 0.668(2) 0.0688(19) 1.0000 Uiso D . . . . .
H52 H 0.5451(5) 0.416(2) 0.481(3) 0.0708(19) 1.0000 Uiso D . . . . .
H53 H 0.5185(5) 0.2098(19) 0.488(3) 0.0725(19) 1.0000 Uiso D . . . . .
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 0.0312(4) 0.0425(5) 0.0327(4) -0.0017(4) 0.0016(3) -0.0019(3)
C2 0.0301(4) 0.0321(5) 0.0275(4) -0.0026(4) 0.0004(3) 0.0019(3)
C3 0.0310(4) 0.0294(5) 0.0279(4) -0.0016(3) 0.0004(3) 0.0025(3)
C4 0.0314(5) 0.0395(5) 0.0385(5) -0.0030(4) 0.0020(4) 0.0002(4)
C5 0.0351(5) 0.0555(8) 0.0523(7) 0.0019(6) 0.0099(5) 0.0067(5)

_refine_ls_extinction_method     None
_oxford_refine_ls_scale          0.3852(11)
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 . 1.4647(13) yes
N1 . H11 . 0.886(12) no
N1 . H12 . 0.871(12) no
C2 . C3 . 1.5234(13) yes
C2 . H21 . 0.980(11) no
C2 . H22 . 0.982(11) no
C3 . C4 . 1.5187(14) yes
C3 . H31 . 0.999(10) no
C3 . H32 . 0.979(11) no
C4 . C5 . 1.5228(15) yes
C4 . H41 . 0.969(11) no
C4 . H42 . 0.981(12) no
C5 . H51 . 0.991(13) no
C5 . H52 . 0.958(13) no
C5 . H53 . 0.986(13) 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 . H11 . 109.5(8) no
C2 . N1 . H12 . 110.9(8) no
H11 . N1 . H12 . 104.7(12) no
N1 . C2 . C3 . 115.71(8) yes
N1 . C2 . H21 . 108.3(6) no
C3 . C2 . H21 . 108.9(6) no
N1 . C2 . H22 . 108.0(6) no
C3 . C2 . H22 . 109.0(7) no
H21 . C2 . H22 . 106.5(8) no
C2 . C3 . C4 . 113.36(8) yes
C2 . C3 . H31 . 108.8(6) no
C4 . C3 . H31 . 109.4(6) no
C2 . C3 . H32 . 108.1(6) no
C4 . C3 . H32 . 109.3(6) no
H31 . C3 . H32 . 107.7(8) no
C3 . C4 . C5 . 113.29(9) yes
C3 . C4 . H41 . 108.9(7) no
C5 . C4 . H41 . 110.3(7) no
C3 . C4 . H42 . 108.8(7) no
C5 . C4 . H42 . 109.6(7) no
H41 . C4 . H42 . 105.6(9) no
C4 . C5 . H51 . 109.6(8) no
C4 . C5 . H52 . 110.5(8) no
H51 . C5 . H52 . 108.0(11) no
C4 . C5 . H53 . 111.1(8) no
H51 . C5 . H53 . 109.6(11) no
H52 . C5 . H53 . 108.0(10) no
_database_code_depnum_ccdc_archive 'CCDC 978655'
#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_pentylamine
_audit_creation_date             11-02-01
_audit_creation_method           CRYSTALS_ver_14.11

_oxford_structure_analysis_title 'Pentylamine in Pbcn'
_chemical_name_systematic        pentylamine
_chemical_melting_point          223

#end of refcif 
_cell_length_a                   33.546(4)
_cell_length_b                   6.4878(8)
_cell_length_c                   5.7295(7)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1247.0(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
x+1/2,-y+1/2,-z
x,-y,z+1/2
-x,y,-z+1/2
-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'


_cell_formula_units_Z            8

# Given Formula = C5 H13 N1 
# Dc =      0.93 Fooo =    400.00 Mu =      0.55 M =     87.16
# Found Formula = C5 H13 N1 
# Dc =      0.93 FOOO =    400.00 Mu =      0.55 M =     87.16

_chemical_formula_sum            'C5 H13 N1'
_chemical_formula_moiety         'C5 H13 N1'
_chemical_compound_source        Aldrich
_chemical_formula_weight         87.16


_cell_measurement_reflns_used    1184
_cell_measurement_theta_min      2
_cell_measurement_theta_max      24
_cell_measurement_temperature    150

_exptl_crystal_description       cylinder
_exptl_crystal_colour            colourless
_exptl_crystal_size_min          0.300
_exptl_crystal_size_mid          0.300
_exptl_crystal_size_max          2.000

_exptl_crystal_density_diffrn    0.929
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
# Non-dispersive F(000): 
_exptl_crystal_F_000             400
_exptl_absorpt_coefficient_mu    0.055

# Sheldrick geometric approximatio 0.98 0.98 
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Siemens, 1996)'
_exptl_absorpt_correction_T_min  0.75
_exptl_absorpt_correction_T_max  0.98
_diffrn_measurement_device_type  'Bruker Kappa Apex2'
_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       'Apex2 (Bruker AXS, 2006)'
_computing_cell_refinement       'Apex2 (Bruker AXS, 2006)'
_computing_data_reduction        'Apex2 (Bruker AXS, 2006)'
_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            7311
_reflns_number_total             1275
_diffrn_reflns_av_R_equivalents  0.075
# Number of reflections without Friedels Law is 0 
# Number of reflections with Friedels Law is 1275 
# Theoretical number of reflections is about 2557 


_diffrn_reflns_theta_min         1.214
_diffrn_reflns_theta_max         26.397
_diffrn_measured_fraction_theta_max 0.998

_diffrn_reflns_theta_full        26.397
_diffrn_measured_fraction_theta_full 0.998


_diffrn_reflns_limit_h_min       -38
_diffrn_reflns_limit_h_max       41
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -5
_diffrn_reflns_limit_l_max       7
_reflns_limit_h_min              0
_reflns_limit_h_max              41
_reflns_limit_k_min              0
_reflns_limit_k_max              8
_reflns_limit_l_min              0
_reflns_limit_l_max              7

_oxford_diffrn_Wilson_B_factor   2.15
_oxford_diffrn_Wilson_scale      41.58

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

_refine_diff_density_min         -0.199
_refine_diff_density_max         0.181


# 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>-10.0\s(I)
_refine_ls_number_reflns         1274
_refine_ls_number_restraints     54
_refine_ls_number_parameters     107
_oxford_refine_ls_R_factor_ref   0.1555
_refine_ls_wR_factor_ref         0.1959
_refine_ls_goodness_of_fit_ref   0.9616
_refine_ls_shift/su_max          0.0004202
_refine_ls_shift/su_mean         0.0000555


# The values computed from all data 
_oxford_reflns_number_all        1274
_refine_ls_R_factor_all          0.1555
_refine_ls_wR_factor_all         0.1959

# The values computed with a 2 sigma cutoff - a la SHELX 
_reflns_threshold_expression     I>2.0σ(I)
_reflns_number_gt                547
_refine_ls_R_factor_gt           0.0612
_refine_ls_wR_factor_gt          0.1373

# 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    'restrained refall'

_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: 
 6.39 9.50 4.21 0.885 0.147E-01 
;

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

# Replace last . with number of unfound hydrogen atomsattached 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 0.73190(7) 0.3015(5) 0.5518(4) 0.0320 1.0000 Uani D . . . . .
C2 C 0.69327(8) 0.2164(5) 0.6129(5) 0.0291 1.0000 Uani D . . . . .
C3 C 0.65776(8) 0.2963(5) 0.4783(5) 0.0293 1.0000 Uani D . . . . .
C4 C 0.61822(8) 0.2104(5) 0.5607(5) 0.0361 1.0000 Uani D . . . . .
C5 C 0.58237(9) 0.2954(6) 0.4318(6) 0.0481 1.0000 Uani D . . . . .
C6 C 0.54278(10) 0.2194(8) 0.5305(8) 0.0702 1.0000 Uani D . . . . .
H21 H 0.6890(6) 0.245(3) 0.776(3) 0.0346(19) 1.0000 Uiso D . . . . .
H22 H 0.6948(6) 0.067(3) 0.591(4) 0.0344(19) 1.0000 Uiso D . . . . .
H31 H 0.6572(6) 0.447(3) 0.491(4) 0.0341(19) 1.0000 Uiso D . . . . .
H42 H 0.6186(6) 0.060(3) 0.544(4) 0.0428(19) 1.0000 Uiso D . . . . .
H32 H 0.6615(5) 0.259(3) 0.315(3) 0.0348(19) 1.0000 Uiso D . . . . .
H41 H 0.6156(6) 0.241(3) 0.727(3) 0.0421(19) 1.0000 Uiso D . . . . .
H12 H 0.7399(7) 0.280(4) 0.414(3) 0.0387(19) 1.0000 Uiso D . . . . .
H52 H 0.5847(6) 0.255(4) 0.268(3) 0.0573(19) 1.0000 Uiso D . . . . .
H63 H 0.5215(6) 0.286(4) 0.449(5) 0.106(2) 1.0000 Uiso D . . . . .
H61 H 0.5409(7) 0.253(5) 0.695(4) 0.105(2) 1.0000 Uiso D . . . . .
H62 H 0.5409(7) 0.073(3) 0.509(6) 0.106(2) 1.0000 Uiso D . . . . .
H11 H 0.7335(6) 0.433(3) 0.560(6) 0.0386(19) 1.0000 Uiso D . . . . .
H51 H 0.5832(6) 0.447(3) 0.441(4) 0.0577(19) 1.0000 Uiso D . . . . .
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 0.0281(12) 0.0372(13) 0.0308(12) 0.0015(15) 0.0010(10) -0.0026(13)
C2 0.0331(16) 0.0258(14) 0.0283(13) -0.0020(14) 0.0010(11) 0.0021(14)
C3 0.0335(16) 0.0290(15) 0.0255(13) -0.0023(14) 0.0010(10) 0.0001(15)
C4 0.0334(16) 0.0374(17) 0.0374(16) 0.0013(17) -0.0011(14) -0.0018(15)
C5 0.0326(16) 0.059(2) 0.053(2) -0.004(2) -0.0031(17) -0.0006(19)
C6 0.0314(19) 0.102(4) 0.077(3) -0.003(3) -0.0061(18) -0.004(2)

_refine_ls_extinction_method     None
_oxford_refine_ls_scale          0.1778(3)
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 . 1.451(3) yes
N1 . H12 . 0.848(17) no
N1 . H11 . 0.854(16) no
C2 . C3 . 1.511(4) yes
C2 . H21 . 0.964(17) no
C2 . H22 . 0.980(16) no
C3 . C4 . 1.514(4) yes
C3 . H31 . 0.977(16) no
C3 . H32 . 0.975(17) no
C4 . C5 . 1.515(4) yes
C4 . H42 . 0.978(17) no
C4 . H41 . 0.975(17) no
C5 . C6 . 1.525(5) yes
C5 . H52 . 0.976(17) no
C5 . H51 . 0.984(17) no
C6 . H63 . 0.956(18) no
C6 . H61 . 0.970(18) no
C6 . H62 . 0.960(18) 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 . H12 . 116.3(14) no
C2 . N1 . H11 . 115.0(14) no
H12 . N1 . H11 . 101(3) no
N1 . C2 . C3 . 116.8(2) yes
N1 . C2 . H21 . 107.1(12) no
C3 . C2 . H21 . 108.1(12) no
N1 . C2 . H22 . 107.4(12) no
C3 . C2 . H22 . 108.5(12) no
H21 . C2 . H22 . 108.8(14) no
C2 . C3 . C4 . 113.9(2) yes
C2 . C3 . H31 . 108.7(12) no
C4 . C3 . H31 . 109.1(12) no
C2 . C3 . H32 . 107.6(12) no
C4 . C3 . H32 . 108.5(11) no
H31 . C3 . H32 . 108.8(14) no
C3 . C4 . C5 . 114.2(3) yes
C3 . C4 . H42 . 108.9(12) no
C5 . C4 . H42 . 108.9(12) no
C3 . C4 . H41 . 107.9(12) no
C5 . C4 . H41 . 109.3(12) no
H42 . C4 . H41 . 107.5(15) no
C4 . C5 . C6 . 113.1(3) yes
C4 . C5 . H52 . 107.9(13) no
C6 . C5 . H52 . 109.8(13) no
C4 . C5 . H51 . 108.2(13) no
C6 . C5 . H51 . 109.1(13) no
H52 . C5 . H51 . 108.6(16) no
C5 . C6 . H63 . 108.9(15) no
C5 . C6 . H61 . 110.1(15) no
H63 . C6 . H61 . 108.9(16) no
C5 . C6 . H62 . 109.3(15) no
H63 . C6 . H62 . 109.7(16) no
H61 . C6 . H62 . 110.0(17) 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
N1 . H12 . N1 7_654 173(3) 0.848(17) 2.339(17) 3.182(5) yes


_iucr_refine_instruction_details_constraints 
;
#
# Punched on 01/02/11 at 15:57:56
#
#LIST     12                                                                    
BLOCK 
CONT SCALE 
CONT N    (    1 ,X'S,U'S)  UNTIL C    (    6 ) 
CONT H    (   21 ,X'S,U[ISO])  UNTIL H    (   51 ) 
END                                                                             
;


_iucr_refine_instruction_details_restraints 
;
#
# Punched on 01/02/11 at 15:57:56
#
#LIST     16                                                                    
NO 
REM   HREST   START (DO NOT REMOVE THIS LINE) 
REM NO H   NO #H U MULT DIST 
REM C-H 
REM >4           1.5    .96 DISORDER 
REM 1      1     1.2    .93 C C-H (ACETYLENE) 
REM 1      2     1.2    .93 C-C(H)-C 
REM 1      3     1.2    .98 (C)3-C-H 
REM 2      1     1.2    .93 C=C-H(2) 
REM 2      2     1.2    .97 (C)2-C-(H)2 
REM 3      1     1.5    .96 C-C-(H)3 
REM N-H 
REM >4           1.5    .89 DISORDER 
REM 1      1     1.2    .86 N-N/H 
REM 1      2     1.2    .86 (C)2-N-H 
REM 1      3     1.2    .89 (C)3-N-H 
REM 2      1     1.2    .86 C-N-(H)2 
REM 2      2     1.2    .89 (C)2-N-(H)2 
REM 3      1     1.2    .89 C-H-(H)3 
REM O-H 
REM 1      1     1.5    .82 O-H 
REM 
REM DIST      ESD = 0.02 
REM VIB       ESD = 0.002 
REM ANGLE     ESD = 2.0 
REM            H2-N-R 
DIST 0.86, 0.02 = 
CONT N ( 1) TO H(12) 
CONT N ( 1) TO H(11) 
REST 0.038, 0.002 = H(12,U[ISO]) 
REST 0.038, 0.002 = H(11,U[ISO]) 
ANGLE 120.0, 2.0 = 
CONT C(2) TO N ( 1) TO H(12) 
CONT C(2) TO N ( 1) TO H(11) 
REM            2 H ON SP 3 
DIST 0.97, 0.02 = 
CONT C ( 2) TO H(21) 
CONT C ( 2) TO H(22) 
REST 0.035, 0.002 = H(21,U[ISO]) 
REST 0.035, 0.002 = H(22,U[ISO]) 
ANGLE 0.0, 2.0 = MEAN 
CONT H(21) TO C ( 2) TO N(1) 
CONT H(21) TO C ( 2) TO C(3) 
CONT H(22) TO C ( 2) TO N(1) 
CONT H(22) TO C ( 2) TO C(3) 
ANGLE 109.54, 2.0 = 
CONT H(21) TO C ( 2) TO H(22) 
REM            2 H ON SP 3 
DIST 0.97, 0.02 = 
CONT C ( 3) TO H(31) 
CONT C ( 3) TO H(32) 
REST 0.035, 0.002 = H(31,U[ISO]) 
REST 0.035, 0.002 = H(32,U[ISO]) 
ANGLE 0.0, 2.0 = MEAN 
CONT H(31) TO C ( 3) TO C(2) 
CONT H(31) TO C ( 3) TO C(4) 
CONT H(32) TO C ( 3) TO C(2) 
CONT H(32) TO C ( 3) TO C(4) 
ANGLE 109.54, 2.0 = 
CONT H(31) TO C ( 3) TO H(32) 
REM            2 H ON SP 3 
DIST 0.97, 0.02 = 
CONT C ( 4) TO H(42) 
CONT C ( 4) TO H(41) 
REST 0.043, 0.002 = H(42,U[ISO]) 
REST 0.043, 0.002 = H(41,U[ISO]) 
ANGLE 0.0, 2.0 = MEAN 
CONT H(42) TO C ( 4) TO C(3) 
CONT H(42) TO C ( 4) TO C(5) 
CONT H(41) TO C ( 4) TO C(3) 
CONT H(41) TO C ( 4) TO C(5) 
ANGLE 109.54, 2.0 = 
CONT H(42) TO C ( 4) TO H(41) 
REM            2 H ON SP 3 
DIST 0.97, 0.02 = 
CONT C ( 5) TO H(52) 
CONT C ( 5) TO H(51) 
REST 0.058, 0.002 = H(52,U[ISO]) 
REST 0.058, 0.002 = H(51,U[ISO]) 
ANGLE 0.0, 2.0 = MEAN 
CONT H(52) TO C ( 5) TO C(4) 
CONT H(52) TO C ( 5) TO C(6) 
CONT H(51) TO C ( 5) TO C(4) 
CONT H(51) TO C ( 5) TO C(6) 
ANGLE 109.54, 2.0 = 
CONT H(52) TO C ( 5) TO H(51) 
REM            3 H ON SP 3 
DIST 0.96, 0.02 = 
CONT C ( 6) TO H(63) 
CONT C ( 6) TO H(61) 
CONT C ( 6) TO H(62) 
REST 0.106, 0.002 = H(63,U[ISO]) 
REST 0.106, 0.002 = H(61,U[ISO]) 
REST 0.106, 0.002 = H(62,U[ISO]) 
ANGLE 109.54, 2.0 = 
CONT C(5) TO C ( 6) TO H(63) 
CONT C(5) TO C ( 6) TO H(61) 
CONT C(5) TO C ( 6) TO H(62) 
ANGLE 0.0, 2.0 = MEAN H(63) TO C ( 6) TO H(61) 
CONT H(63) TO C ( 6) TO H(62) 
CONT H(61) TO C ( 6) TO H(62) 
REM   HREST   END (DO NOT REMOVE THIS LINE) 
END                                                                             
;
_database_code_depnum_ccdc_archive 'CCDC 978656'
#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_hexylamine
_audit_creation_date             11-02-01
_audit_creation_method           CRYSTALS_ver_14.11

_oxford_structure_analysis_title 'Hexylamine in Pca2(1)'
_chemical_name_systematic        hexylamine
_chemical_melting_point          250

#end of refcif 
_cell_length_a                   6.9725(3)
_cell_length_b                   17.7977(6)
_cell_length_c                   5.6105(2)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     696.23(5)

_symmetry_cell_setting           Orthorhombic
_symmetry_space_group_name_H-M   'P c a 21 '
_symmetry_space_group_name_Hall  'P 2c -2ac'

loop_
_symmetry_equiv_pos_as_xyz
x,y,z
-x+1/2,y,z+1/2
x+1/2,-y,z
-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 0.0033 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            4

# Given Formula = C6 H15 N1 
# Dc =      0.97 Fooo =    232.00 Mu =      0.56 M =    101.19
# Found Formula = C6 H15 N1 
# Dc =      0.97 FOOO =    232.00 Mu =      0.56 M =    101.19

_chemical_formula_sum            'C6 H15 N1'
_chemical_formula_moiety         'C6 H15 N1'
_chemical_compound_source        Aldrich
_chemical_formula_weight         101.19


_cell_measurement_reflns_used    3014
_cell_measurement_theta_min      2
_cell_measurement_theta_max      28
_cell_measurement_temperature    150

_exptl_crystal_description       cylinder
_exptl_crystal_colour            colourless
_exptl_crystal_size_min          0.410
_exptl_crystal_size_mid          0.410
_exptl_crystal_size_max          1.000

_exptl_crystal_density_diffrn    0.965
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
# Non-dispersive F(000): 
_exptl_crystal_F_000             232
_exptl_absorpt_coefficient_mu    0.056

# Sheldrick geometric approximatio 0.98 0.98 
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Siemens, 1996)'
_exptl_absorpt_correction_T_min  0.83
_exptl_absorpt_correction_T_max  0.98
_diffrn_measurement_device_type  'Bruker Kappa Apex2'
_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       'Apex2 (Bruker AXS, 2006)'
_computing_cell_refinement       'Apex2 (Bruker AXS, 2006)'
_computing_data_reduction        'Apex2 (Bruker AXS, 2006)'
_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            8013
_reflns_number_total             913
_diffrn_reflns_av_R_equivalents  0.033
# Number of reflections without Friedels Law is 0 
# Number of reflections with Friedels Law is 913 
# Theoretical number of reflections is about 1791 


_diffrn_reflns_theta_min         1.144
_diffrn_reflns_theta_max         28.653
_diffrn_measured_fraction_theta_max 0.927

_diffrn_reflns_theta_full        25.215
_diffrn_measured_fraction_theta_full 0.990


_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_l_min       -7
_diffrn_reflns_limit_l_max       7
_reflns_limit_h_min              0
_reflns_limit_h_max              9
_reflns_limit_k_min              0
_reflns_limit_k_max              23
_reflns_limit_l_min              0
_reflns_limit_l_max              7

_oxford_diffrn_Wilson_B_factor   2.21
_oxford_diffrn_Wilson_scale      13.55

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

_refine_diff_density_min         -0.13
_refine_diff_density_max         0.26


# 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>-10.0\s(I)
_refine_ls_number_reflns         910
_refine_ls_number_restraints     64
_refine_ls_number_parameters     124
_oxford_refine_ls_R_factor_ref   0.0504
_refine_ls_wR_factor_ref         0.1078
_refine_ls_goodness_of_fit_ref   1.0087
_refine_ls_shift/su_max          0.0001408
_refine_ls_shift/su_mean         0.0000095


# The values computed from all data 
_oxford_reflns_number_all        910
_refine_ls_R_factor_all          0.0504
_refine_ls_wR_factor_all         0.1078

# The values computed with a 2 sigma cutoff - a la SHELX 
_reflns_threshold_expression     I>2.0σ(I)
_reflns_number_gt                794
_refine_ls_R_factor_gt           0.0418
_refine_ls_wR_factor_gt          0.0969

# 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    'restrained refall'

_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: 
 9.31 15.1 8.32 2.97 0.519 
;

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

# Replace last . with number of unfound hydrogen atomsattached 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 0.5545(2) 0.03498(8) 0.9040(5) 0.0317 1.0000 Uani D . . . . .
C2 C 0.4689(2) 0.10995(9) 0.8954(5) 0.0275 1.0000 Uani D . . . . .
C3 C 0.5482(3) 0.16201(9) 0.7044(5) 0.0250 1.0000 Uani D . . . . .
C4 C 0.4592(3) 0.24017(9) 0.7063(5) 0.0262 1.0000 Uani D . . . . .
C5 C 0.5409(3) 0.29211(9) 0.5160(5) 0.0265 1.0000 Uani D . . . . .
C6 C 0.4525(3) 0.37048(9) 0.5178(5) 0.0318 1.0000 Uani D . . . . .
C7 C 0.5366(3) 0.42212(11) 0.3292(5) 0.0397 1.0000 Uani D . . . . .
H31 H 0.686(2) 0.1669(8) 0.729(3) 0.0295(19) 1.0000 Uiso D . . . . .
H42 H 0.321(2) 0.2360(9) 0.684(3) 0.0316(18) 1.0000 Uiso D . . . . .
H11 H 0.676(2) 0.0364(10) 0.928(5) 0.0381(19) 1.0000 Uiso D . . . . .
H51 H 0.680(2) 0.2953(8) 0.541(3) 0.0321(19) 1.0000 Uiso D . . . . .
H62 H 0.314(2) 0.3664(9) 0.493(3) 0.0376(19) 1.0000 Uiso D . . . . .
H12 H 0.542(3) 0.0106(11) 0.769(3) 0.0381(19) 1.0000 Uiso D . . . . .
H22 H 0.331(2) 0.1037(9) 0.867(3) 0.0327(19) 1.0000 Uiso D . . . . .
H21 H 0.489(2) 0.1330(9) 1.051(3) 0.0322(19) 1.0000 Uiso D . . . . .
H52 H 0.515(2) 0.2699(9) 0.361(3) 0.0315(19) 1.0000 Uiso D . . . . .
H71 H 0.673(2) 0.4281(11) 0.354(4) 0.0601(19) 1.0000 Uiso D . . . . .
H32 H 0.523(2) 0.1395(9) 0.551(3) 0.0296(18) 1.0000 Uiso D . . . . .
H41 H 0.482(2) 0.2636(9) 0.860(3) 0.0321(19) 1.0000 Uiso D . . . . .
H61 H 0.475(3) 0.3919(10) 0.676(3) 0.0380(19) 1.0000 Uiso D . . . . .
H73 H 0.480(3) 0.4714(9) 0.333(4) 0.0594(19) 1.0000 Uiso D . . . . .
H72 H 0.517(3) 0.4006(12) 0.173(3) 0.0590(19) 1.0000 Uiso D . . . . .
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 0.0397(9) 0.0261(7) 0.0292(8) 0.0026(7) -0.0008(10) 0.0000(7)
C2 0.0309(9) 0.0286(8) 0.0230(9) -0.0003(8) 0.0024(11) -0.0020(7)
C3 0.0255(8) 0.0246(7) 0.0249(8) 0.0011(7) 0.0007(10) -0.0013(7)
C4 0.0262(9) 0.0250(7) 0.0273(8) 0.0003(7) 0.0025(11) 0.0008(7)
C5 0.0268(8) 0.0249(7) 0.0279(10) 0.0015(7) 0.0006(10) -0.0008(7)
C6 0.0356(10) 0.0253(8) 0.0345(11) 0.0018(8) 0.0018(11) 0.0010(8)
C7 0.0461(12) 0.0294(8) 0.0436(12) 0.0085(9) 0.0003(13) 0.0001(9)

_refine_ls_extinction_method     None
_oxford_refine_ls_scale          0.2841(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
N1 . C2 . 1.463(2) yes
N1 . H11 . 0.854(14) no
N1 . H12 . 0.879(16) no
C2 . C3 . 1.521(3) yes
C2 . H22 . 0.978(14) no
C2 . H21 . 0.973(16) no
C3 . C4 . 1.523(2) yes
C3 . H31 . 0.973(14) no
C3 . H32 . 0.964(16) no
C4 . C5 . 1.523(2) yes
C4 . H42 . 0.976(13) no
C4 . H41 . 0.970(16) no
C5 . C6 . 1.525(2) yes
C5 . H51 . 0.978(14) no
C5 . H52 . 0.973(16) no
C6 . C7 . 1.520(3) yes
C6 . H62 . 0.975(14) no
C6 . H61 . 0.977(16) no
C7 . H71 . 0.965(15) no
C7 . H73 . 0.962(16) no
C7 . H72 . 0.968(17) 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 . H11 . 112.4(12) no
C2 . N1 . H12 . 112.5(13) no
H11 . N1 . H12 . 104(2) no
N1 . C2 . C3 . 115.49(16) yes
N1 . C2 . H22 . 107.6(9) no
C3 . C2 . H22 . 108.2(10) no
N1 . C2 . H21 . 107.2(10) no
C3 . C2 . H21 . 108.8(10) no
H22 . C2 . H21 . 109.6(13) no
C2 . C3 . C4 . 113.79(14) yes
C2 . C3 . H31 . 108.4(10) no
C4 . C3 . H31 . 108.6(9) no
C2 . C3 . H32 . 108.1(10) no
C4 . C3 . H32 . 108.1(10) no
H31 . C3 . H32 . 109.9(13) no
C3 . C4 . C5 . 113.39(14) yes
C3 . C4 . H42 . 109.4(9) no
C5 . C4 . H42 . 109.1(11) no
C3 . C4 . H41 . 109.5(10) no
C5 . C4 . H41 . 107.5(10) no
H42 . C4 . H41 . 107.8(13) no
C4 . C5 . C6 . 113.52(15) yes
C4 . C5 . H51 . 107.8(11) no
C6 . C5 . H51 . 110.2(9) no
C4 . C5 . H52 . 108.2(10) no
C6 . C5 . H52 . 107.6(10) no
H51 . C5 . H52 . 109.5(13) no
C5 . C6 . C7 . 113.10(17) yes
C5 . C6 . H62 . 109.3(10) no
C7 . C6 . H62 . 109.1(11) no
C5 . C6 . H61 . 107.3(11) no
C7 . C6 . H61 . 109.4(11) no
H62 . C6 . H61 . 108.6(13) no
C6 . C7 . H71 . 110.3(12) no
C6 . C7 . H73 . 112.3(13) no
H71 . C7 . H73 . 107.5(13) no
C6 . C7 . H72 . 109.7(12) no
H71 . C7 . H72 . 108.2(14) no
H73 . C7 . H72 . 108.8(15) no


_iucr_refine_instruction_details_constraints 
;
#
# Punched on 01/02/11 at 16:25:26
#
#LIST     12                                                                    
BLOCK 
CONT SCALE 
CONT N    (    1 ,X'S,U'S)  UNTIL C    (    7 ) 
CONT H    (   31 ,X'S,U[ISO])  UNTIL H    (   72 ) 
END                                                                             
;


_iucr_refine_instruction_details_restraints 
;
#
# Punched on 01/02/11 at 16:25:26
#
#LIST     16                                                                    
NO 
REM   HREST   START (DO NOT REMOVE THIS LINE) 
REM NO H   NO #H U MULT DIST 
REM C-H 
REM >4           1.5    .96 DISORDER 
REM 1      1     1.2    .93 C C-H (ACETYLENE) 
REM 1      2     1.2    .93 C-C(H)-C 
REM 1      3     1.2    .98 (C)3-C-H 
REM 2      1     1.2    .93 C=C-H(2) 
REM 2      2     1.2    .97 (C)2-C-(H)2 
REM 3      1     1.5    .96 C-C-(H)3 
REM N-H 
REM >4           1.5    .89 DISORDER 
REM 1      1     1.2    .86 N-N/H 
REM 1      2     1.2    .86 (C)2-N-H 
REM 1      3     1.2    .89 (C)3-N-H 
REM 2      1     1.2    .86 C-N-(H)2 
REM 2      2     1.2    .89 (C)2-N-(H)2 
REM 3      1     1.2    .89 C-H-(H)3 
REM O-H 
REM 1      1     1.5    .82 O-H 
REM 
REM DIST      ESD = 0.02 
REM VIB       ESD = 0.002 
REM ANGLE     ESD = 2.0 
REM            H2-N-R 
DIST 0.86, 0.02 = 
CONT N ( 1) TO H(11) 
CONT N ( 1) TO H(12) 
REST 0.038, 0.002 = H(11,U[ISO]) 
REST 0.038, 0.002 = H(12,U[ISO]) 
ANGLE 120.0, 2.0 = 
CONT C(2) TO N ( 1) TO H(11) 
CONT C(2) TO N ( 1) TO H(12) 
REM            2 H ON SP 3 
DIST 0.97, 0.02 = 
CONT C ( 2) TO H(22) 
CONT C ( 2) TO H(21) 
REST 0.033, 0.002 = H(22,U[ISO]) 
REST 0.033, 0.002 = H(21,U[ISO]) 
ANGLE 0.0, 2.0 = MEAN 
CONT H(22) TO C ( 2) TO N(1) 
CONT H(22) TO C ( 2) TO C(3) 
CONT H(21) TO C ( 2) TO N(1) 
CONT H(21) TO C ( 2) TO C(3) 
ANGLE 109.54, 2.0 = 
CONT H(22) TO C ( 2) TO H(21) 
REM            2 H ON SP 3 
DIST 0.97, 0.02 = 
CONT C ( 3) TO H(31) 
CONT C ( 3) TO H(32) 
REST 0.030, 0.002 = H(31,U[ISO]) 
REST 0.030, 0.002 = H(32,U[ISO]) 
ANGLE 0.0, 2.0 = MEAN 
CONT H(31) TO C ( 3) TO C(2) 
CONT H(31) TO C ( 3) TO C(4) 
CONT H(32) TO C ( 3) TO C(2) 
CONT H(32) TO C ( 3) TO C(4) 
ANGLE 109.54, 2.0 = 
CONT H(31) TO C ( 3) TO H(32) 
REM            2 H ON SP 3 
DIST 0.97, 0.02 = 
CONT C ( 4) TO H(42) 
CONT C ( 4) TO H(41) 
REST 0.032, 0.002 = H(42,U[ISO]) 
REST 0.032, 0.002 = H(41,U[ISO]) 
ANGLE 0.0, 2.0 = MEAN 
CONT H(42) TO C ( 4) TO C(3) 
CONT H(42) TO C ( 4) TO C(5) 
CONT H(41) TO C ( 4) TO C(3) 
CONT H(41) TO C ( 4) TO C(5) 
ANGLE 109.54, 2.0 = 
CONT H(42) TO C ( 4) TO H(41) 
REM            2 H ON SP 3 
DIST 0.97, 0.02 = 
CONT C ( 5) TO H(51) 
CONT C ( 5) TO H(52) 
REST 0.032, 0.002 = H(51,U[ISO]) 
REST 0.032, 0.002 = H(52,U[ISO]) 
ANGLE 0.0, 2.0 = MEAN 
CONT H(51) TO C ( 5) TO C(4) 
CONT H(51) TO C ( 5) TO C(6) 
CONT H(52) TO C ( 5) TO C(4) 
CONT H(52) TO C ( 5) TO C(6) 
ANGLE 109.54, 2.0 = 
CONT H(51) TO C ( 5) TO H(52) 
REM            2 H ON SP 3 
DIST 0.97, 0.02 = 
CONT C ( 6) TO H(6) 
CONT C ( 6) TO H(61) 
REST 0.038, 0.002 = H(6,U[ISO]) 
REST 0.038, 0.002 = H(61,U[ISO]) 
ANGLE 0.0, 2.0 = MEAN 
CONT H(6) TO C ( 6) TO C(5) 
CONT H(6) TO C ( 6) TO C(7) 
CONT H(61) TO C ( 6) TO C(5) 
CONT H(61) TO C ( 6) TO C(7) 
ANGLE 109.54, 2.0 = 
CONT H(6) TO C ( 6) TO H(61) 
REM            3 H ON SP 3 
DIST 0.96, 0.02 = 
CONT C ( 7) TO H(71) 
CONT C ( 7) TO H(73) 
CONT C ( 7) TO H(72) 
REST 0.060, 0.002 = H(71,U[ISO]) 
REST 0.060, 0.002 = H(73,U[ISO]) 
REST 0.060, 0.002 = H(72,U[ISO]) 
ANGLE 109.54, 2.0 = 
CONT C(6) TO C ( 7) TO H(71) 
CONT C(6) TO C ( 7) TO H(73) 
CONT C(6) TO C ( 7) TO H(72) 
ANGLE 0.0, 2.0 = MEAN H(71) TO C ( 7) TO H(73) 
CONT H(71) TO C ( 7) TO H(72) 
CONT H(73) TO C ( 7) TO H(72) 
REM   HREST   END (DO NOT REMOVE THIS LINE) 
END                                                                             
;
_database_code_depnum_ccdc_archive 'CCDC 978657'
#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_heptylamine
_audit_creation_date             13-02-07
_audit_creation_method           CRYSTALS_ver_14.40

_oxford_structure_analysis_title 'Heptylamine in P2(1)/c'
_chemical_name_systematic        heptylamine
_chemical_melting_point          250


#end of refcif 
_cell_length_a                   5.5669(5)
_cell_length_b                   41.700(4)
_cell_length_c                   6.9982(7)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1624.6(3)

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 1 21/c 1 '
_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'


_cell_formula_units_Z            8

# Given Formula = C7 H17 N1 
# Dc =      0.94 Fooo =    528.00 Mu =      0.55 M =    230.44
# Found Formula = C7 H17 N1 
# Dc =      0.94 FOOO =    528.00 Mu =      0.55 M =    230.44

_chemical_formula_sum            'C7 H17 N1'
_chemical_formula_moiety         'C7 H17 N1'
_chemical_compound_source        ?
_chemical_formula_weight         115.22


_cell_measurement_reflns_used    1338
_cell_measurement_theta_min      3
_cell_measurement_theta_max      25
_cell_measurement_temperature    150

_exptl_crystal_description       cylinder
_exptl_crystal_colour            colourless
_exptl_crystal_size_min          0.450
_exptl_crystal_size_mid          0.450
_exptl_crystal_size_max          2.000

_exptl_crystal_density_diffrn    0.942
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
# Non-dispersive F(000): 
_exptl_crystal_F_000             528
_exptl_absorpt_coefficient_mu    0.055

# Sheldrick geometric approximatio 0.98 0.98 
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Siemens, 1996)'
_exptl_absorpt_correction_T_min  0.67
_exptl_absorpt_correction_T_max  0.98
_diffrn_measurement_device_type  'Bruker Kappa Apex2'
_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       'Apex2 (Bruker AXS, 2006)'
_computing_cell_refinement       'Apex2 (Bruker AXS, 2006)'
_computing_data_reduction        'Apex2 (Bruker AXS, 2006)'
_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            2893
_reflns_number_total             2893
_diffrn_reflns_av_R_equivalents  0.097
# Number of reflections without Friedels Law is 0 
# Number of reflections with Friedels Law is 2893 
# Theoretical number of reflections is about 6664 


_diffrn_reflns_theta_min         1.953
_diffrn_reflns_theta_max         26.400
_diffrn_measured_fraction_theta_max 0.871

_diffrn_reflns_theta_full        25.080
_diffrn_measured_fraction_theta_full 0.888


_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_k_max       52
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_limit_l_max       8
_reflns_limit_h_min              -6
_reflns_limit_h_max              6
_reflns_limit_k_min              0
_reflns_limit_k_max              52
_reflns_limit_l_min              0
_reflns_limit_l_max              8

_oxford_diffrn_Wilson_B_factor   0.00
_oxford_diffrn_Wilson_scale      0.00

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

_refine_diff_density_min         -0.50
_refine_diff_density_max         0.54


# 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>-10.0\s(I)
_refine_ls_number_reflns         2893
_refine_ls_number_restraints     144
_refine_ls_number_parameters     282
_oxford_refine_ls_R_factor_ref   0.1758
_refine_ls_wR_factor_ref         0.3126
_refine_ls_goodness_of_fit_ref   1.0880
_refine_ls_shift/su_max          0.0001068
_refine_ls_shift/su_mean         0.0000085


# The values computed with all filters except I/sigma 
_oxford_reflns_number_all        2893
_refine_ls_R_factor_all          0.1758
_refine_ls_wR_factor_all         0.3126

# The values computed with a 2 sigma cutoff - a la SHELX 
_reflns_threshold_expression     I>2.0σ(I)
_reflns_number_gt                1116
_refine_ls_R_factor_gt           0.0745
_refine_ls_wR_factor_gt          0.2017

# 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    mixed #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: 
 15.2 24.3 13.3 4.86 0.893 
;

# 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 1.1045(10) 0.26549(13) 0.3714(7) 0.0323 1.0000 Uani D . . . . .
C2 C 1.0908(11) 0.29765(15) 0.2870(8) 0.0286 1.0000 Uani D . . . . .
C3 C 0.8942(11) 0.31941(14) 0.3650(8) 0.0278 1.0000 Uani D . . . . .
C4 C 0.8907(12) 0.35278(13) 0.2777(8) 0.0262 1.0000 Uani D . . . . .
C5 C 0.6969(12) 0.37445(13) 0.3610(8) 0.0271 1.0000 Uani D . . . . .
C6 C 0.6969(13) 0.40833(15) 0.2836(8) 0.0331 1.0000 Uani D . . . . .
C7 C 0.5009(14) 0.42941(16) 0.3698(9) 0.0394 1.0000 Uani D . . . . .
C8 C 0.503(2) 0.46386(18) 0.2992(12) 0.0641 1.0000 Uani D . . . . .
N11 N 0.6030(10) 0.26540(13) 0.7649(8) 0.0340 1.0000 Uani D . . . . .
C12 C 0.5892(11) 0.29710(14) 0.8529(8) 0.0291 1.0000 Uani D . . . . .
C13 C 0.3944(12) 0.31879(14) 0.7729(8) 0.0280 1.0000 Uani D . . . . .
C14 C 0.3935(13) 0.35218(15) 0.8624(8) 0.0310 1.0000 Uani D . . . . .
C15 C 0.1977(12) 0.37393(15) 0.7814(8) 0.0307 1.0000 Uani D . . . . .
C16 C 0.1946(13) 0.40762(14) 0.8635(8) 0.0312 1.0000 Uani D . . . . .
C17 C 0.0033(15) 0.42874(15) 0.7796(9) 0.0371 1.0000 Uani D . . . . .
C18 C 0.0062(18) 0.46260(17) 0.8569(12) 0.0584 1.0000 Uani D . . . . .
H22 H 1.243(4) 0.3081(6) 0.313(4) 0.0339(19) 1.0000 Uiso D . . . . .
H21 H 1.069(6) 0.2954(6) 0.150(3) 0.0337(19) 1.0000 Uiso D . . . . .
H32 H 0.920(5) 0.3217(6) 0.502(3) 0.0328(19) 1.0000 Uiso D . . . . .
H31 H 0.740(4) 0.3092(6) 0.344(4) 0.0326(19) 1.0000 Uiso D . . . . .
H42 H 1.045(4) 0.3629(6) 0.303(4) 0.0309(19) 1.0000 Uiso D . . . . .
H41 H 0.866(6) 0.3509(6) 0.139(3) 0.0307(19) 1.0000 Uiso D . . . . .
H52 H 0.720(6) 0.3756(6) 0.499(3) 0.0326(19) 1.0000 Uiso D . . . . .
H51 H 0.542(4) 0.3647(6) 0.335(4) 0.0332(19) 1.0000 Uiso D . . . . .
H62 H 0.853(4) 0.4180(6) 0.313(5) 0.0398(19) 1.0000 Uiso D . . . . .
H61 H 0.673(6) 0.4075(6) 0.146(3) 0.0397(19) 1.0000 Uiso D . . . . .
H72 H 0.521(6) 0.4296(7) 0.507(3) 0.0467(19) 1.0000 Uiso D . . . . .
H71 H 0.347(4) 0.4200(6) 0.339(5) 0.0471(19) 1.0000 Uiso D . . . . .
H83 H 0.378(8) 0.4758(7) 0.361(8) 0.0958(19) 1.0000 Uiso D . . . . .
H82 H 0.656(6) 0.4733(8) 0.329(9) 0.0960(19) 1.0000 Uiso D . . . . .
H81 H 0.480(13) 0.4642(7) 0.162(3) 0.0958(19) 1.0000 Uiso D . . . . .
H121 H 0.743(4) 0.3075(6) 0.832(4) 0.0350(19) 1.0000 Uiso D . . . . .
H122 H 0.563(5) 0.2942(6) 0.990(3) 0.0349(19) 1.0000 Uiso D . . . . .
H131 H 0.420(6) 0.3209(6) 0.636(3) 0.0338(19) 1.0000 Uiso D . . . . .
H132 H 0.239(4) 0.3090(6) 0.796(4) 0.0340(19) 1.0000 Uiso D . . . . .
H141 H 0.549(4) 0.3622(6) 0.843(5) 0.0369(19) 1.0000 Uiso D . . . . .
H142 H 0.368(6) 0.3498(6) 0.999(3) 0.0369(19) 1.0000 Uiso D . . . . .
H151 H 0.223(6) 0.3755(6) 0.644(3) 0.0366(19) 1.0000 Uiso D . . . . .
H152 H 0.042(4) 0.3639(6) 0.804(5) 0.0369(19) 1.0000 Uiso D . . . . .
H161 H 0.350(4) 0.4173(6) 0.841(5) 0.0369(19) 1.0000 Uiso D . . . . .
H162 H 0.169(6) 0.4060(6) 1.001(3) 0.0370(19) 1.0000 Uiso D . . . . .
H171 H 0.029(6) 0.4298(6) 0.642(3) 0.0437(19) 1.0000 Uiso D . . . . .
H172 H -0.152(4) 0.4191(6) 0.802(5) 0.0441(19) 1.0000 Uiso D . . . . .
H183 H -0.113(8) 0.4754(7) 0.793(7) 0.0879(19) 1.0000 Uiso D . . . . .
H181 H 0.162(5) 0.4718(8) 0.835(9) 0.0879(19) 1.0000 Uiso D . . . . .
H182 H -0.026(12) 0.4624(7) 0.993(4) 0.0879(19) 1.0000 Uiso D . . . . .
H111 H 0.637(13) 0.2645(7) 0.644(4) 0.0411(19) 1.0000 Uiso D . . . . .
H12 H 1.139(13) 0.2640(7) 0.491(4) 0.0390(19) 1.0000 Uiso D . . . . .
H112 H 0.472(5) 0.2544(9) 0.756(9) 0.0410(19) 1.0000 Uiso D . . . . .
H11 H 0.976(5) 0.2538(8) 0.371(9) 0.0391(19) 1.0000 Uiso D . . . . .
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 0.036(3) 0.031(3) 0.031(3) 0.007(2) -0.004(2) 0.000(3)
C2 0.023(3) 0.034(3) 0.029(3) -0.006(2) -0.002(2) -0.002(3)
C3 0.020(3) 0.033(3) 0.031(3) -0.002(2) -0.002(2) -0.002(3)
C4 0.028(3) 0.030(3) 0.021(3) 0.000(2) 0.003(2) 0.000(3)
C5 0.025(3) 0.030(3) 0.026(3) -0.004(2) 0.004(2) 0.001(3)
C6 0.033(4) 0.038(4) 0.028(3) 0.002(3) 0.002(3) 0.002(3)
C7 0.043(4) 0.039(4) 0.036(4) 0.001(3) -0.003(3) 0.007(3)
C8 0.090(7) 0.043(5) 0.060(5) 0.000(4) 0.011(5) 0.019(5)
N11 0.027(3) 0.032(3) 0.043(3) -0.003(2) 0.004(3) -0.001(3)
C12 0.026(3) 0.030(3) 0.030(3) -0.003(2) -0.006(3) 0.000(3)
C13 0.032(3) 0.032(3) 0.020(3) -0.003(2) -0.003(2) 0.005(3)
C14 0.032(3) 0.037(4) 0.023(3) 0.004(2) 0.004(3) 0.001(3)
C15 0.027(3) 0.037(4) 0.027(3) 0.003(2) 0.001(3) -0.002(3)
C16 0.038(4) 0.034(3) 0.022(3) 0.000(2) -0.002(3) 0.000(3)
C17 0.049(4) 0.031(3) 0.031(4) 0.000(3) -0.002(3) 0.002(3)
C18 0.078(6) 0.032(4) 0.065(5) -0.003(3) 0.005(5) 0.013(4)

_refine_ls_extinction_method     None
_oxford_refine_ls_scale          0.2016(5)

loop_
_oxford_twin_element_scale_factors
0.773(6)
0.227(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
N1 . C2 . 1.468(8) yes
N1 . H12 . 0.863(19) no
N1 . H11 . 0.866(19) no
C2 . C3 . 1.523(8) yes
C2 . H22 . 0.970(19) no
C2 . H21 . 0.973(19) no
C3 . C4 . 1.520(8) yes
C3 . H32 . 0.972(19) no
C3 . H31 . 0.971(19) no
C4 . C5 . 1.523(8) yes
C4 . H42 . 0.972(19) no
C4 . H41 . 0.982(19) no
C5 . C6 . 1.513(8) yes
C5 . H52 . 0.977(19) no
C5 . H51 . 0.970(19) no
C6 . C7 . 1.525(10) yes
C6 . H62 . 0.978(19) no
C6 . H61 . 0.975(19) no
C7 . C8 . 1.519(9) yes
C7 . H72 . 0.970(19) no
C7 . H71 . 0.964(19) no
C8 . H83 . 0.957(19) no
C8 . H82 . 0.962(19) no
C8 . H81 . 0.965(19) no
N11 . C12 . 1.460(7) yes
N11 . H111 . 0.867(19) no
N11 . H112 . 0.860(19) no
C12 . C13 . 1.519(8) yes
C12 . H121 . 0.971(19) no
C12 . H122 . 0.975(19) no
C13 . C14 . 1.527(8) yes
C13 . H131 . 0.976(19) no
C13 . H132 . 0.971(19) no
C14 . C15 . 1.527(8) yes
C14 . H141 . 0.973(19) no
C14 . H142 . 0.971(19) no
C15 . C16 . 1.518(8) yes
C15 . H151 . 0.975(19) no
C15 . H152 . 0.974(19) no
C16 . C17 . 1.502(9) yes
C16 . H161 . 0.969(19) no
C16 . H162 . 0.972(19) no
C17 . C18 . 1.512(9) yes
C17 . H171 . 0.972(19) no
C17 . H172 . 0.966(19) no
C18 . H183 . 0.960(19) no
C18 . H181 . 0.962(19) no
C18 . H182 . 0.968(19) 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 . H12 . 117.8(18) no
C2 . N1 . H11 . 118.0(18) no
H12 . N1 . H11 . 98(5) no
N1 . C2 . C3 . 116.0(5) yes
N1 . C2 . H22 . 106.8(15) no
C3 . C2 . H22 . 107.0(15) no
N1 . C2 . H21 . 108.5(15) no
C3 . C2 . H21 . 108.7(15) no
H22 . C2 . H21 . 109.7(17) no
C2 . C3 . C4 . 114.3(5) yes
C2 . C3 . H32 . 107.8(15) no
C4 . C3 . H32 . 107.9(15) no
C2 . C3 . H31 . 108.8(15) no
C4 . C3 . H31 . 109.1(15) no
H32 . C3 . H31 . 108.9(17) no
C3 . C4 . C5 . 113.5(5) yes
C3 . C4 . H42 . 108.3(15) no
C5 . C4 . H42 . 107.4(15) no
C3 . C4 . H41 . 109.1(15) no
C5 . C4 . H41 . 108.8(15) no
H42 . C4 . H41 . 109.7(17) no
C4 . C5 . C6 . 114.7(5) yes
C4 . C5 . H52 . 108.3(15) no
C6 . C5 . H52 . 108.1(15) no
C4 . C5 . H51 . 108.1(15) no
C6 . C5 . H51 . 108.9(15) no
H52 . C5 . H51 . 108.6(17) no
C5 . C6 . C7 . 113.4(5) yes
C5 . C6 . H62 . 108.1(16) no
C7 . C6 . H62 . 108.4(16) no
C5 . C6 . H61 . 108.7(16) no
C7 . C6 . H61 . 108.5(16) no
H62 . C6 . H61 . 109.8(17) no
C6 . C7 . C8 . 114.3(6) yes
C6 . C7 . H72 . 108.5(16) no
C8 . C7 . H72 . 108.3(16) no
C6 . C7 . H71 . 108.2(16) no
C8 . C7 . H71 . 108.6(16) no
H72 . C7 . H71 . 108.8(17) no
C7 . C8 . H83 . 109.8(17) no
C7 . C8 . H82 . 108.9(17) no
H83 . C8 . H82 . 109.3(17) no
C7 . C8 . H81 . 109.6(17) no
H83 . C8 . H81 . 110.2(17) no
H82 . C8 . H81 . 109.0(17) no
C12 . N11 . H111 . 117.6(18) no
C12 . N11 . H112 . 117.8(18) no
H111 . N11 . H112 . 95(6) no
N11 . C12 . C13 . 114.9(5) yes
N11 . C12 . H121 . 107.1(15) no
C13 . C12 . H121 . 108.0(15) no
N11 . C12 . H122 . 108.1(15) no
C13 . C12 . H122 . 109.1(15) no
H121 . C12 . H122 . 109.5(17) no
C12 . C13 . C14 . 113.2(5) yes
C12 . C13 . H131 . 108.2(15) no
C14 . C13 . H131 . 108.7(15) no
C12 . C13 . H132 . 109.0(16) no
C14 . C13 . H132 . 108.3(15) no
H131 . C13 . H132 . 109.4(17) no
C13 . C14 . C15 . 113.0(5) yes
C13 . C14 . H141 . 109.3(16) no
C15 . C14 . H141 . 109.2(15) no
C13 . C14 . H142 . 108.1(15) no
C15 . C14 . H142 . 108.8(16) no
H141 . C14 . H142 . 108.3(17) no
C14 . C15 . C16 . 114.7(5) yes
C14 . C15 . H151 . 107.6(16) no
C16 . C15 . H151 . 108.3(15) no
C14 . C15 . H152 . 108.5(15) no
C16 . C15 . H152 . 109.0(15) no
H151 . C15 . H152 . 108.7(17) no
C15 . C16 . C17 . 113.8(5) yes
C15 . C16 . H161 . 108.2(16) no
C17 . C16 . H161 . 109.1(15) no
C15 . C16 . H162 . 108.0(16) no
C17 . C16 . H162 . 108.9(16) no
H161 . C16 . H162 . 108.8(17) no
C16 . C17 . C18 . 113.6(6) yes
C16 . C17 . H171 . 107.9(16) no
C18 . C17 . H171 . 108.1(16) no
C16 . C17 . H172 . 109.1(16) no
C18 . C17 . H172 . 109.7(16) no
H171 . C17 . H172 . 108.3(17) no
C17 . C18 . H183 . 110.2(17) no
C17 . C18 . H181 . 109.1(17) no
H183 . C18 . H181 . 109.1(17) no
C17 . C18 . H182 . 110.0(17) no
H183 . C18 . H182 . 109.4(17) no
H181 . C18 . H182 . 109.0(17) no


_iucr_refine_instruction_details_constraints 
;
#
# Punched on 07/02/13 at 11:02:19
#
#LIST     12                                                                    
BLOCK 
CONT SCALE 
CONT N    (    1 ,X'S,U'S)  UNTIL C    (   18 ) 
CONT H    (   22 ,X'S,U[ISO])  UNTIL H    (   11 ) 
SUMFIX ELEMENT SCALES 
END                                                                             
;


_iucr_refine_instruction_details_restraints 
;
#
# Punched on 07/02/13 at 11:02:19
#
#LIST     16                                                                    
NO 
REM   HREST   START (DO NOT REMOVE THIS LINE) 
REM NO H   NO #H U MULT DIST 
REM C-H 
REM >4           1.5    .96 DISORDER 
REM 1      1     1.2    .93 C C-H (ACETYLENE) 
REM 1      2     1.2    .93 C-C(H)-C 
REM 1      3     1.2    .98 (C)3-C-H 
REM 2      1     1.2    .93 C=C-H(2) 
REM 2      2     1.2    .97 (C)2-C-(H)2 
REM 3      1     1.5    .96 C-C-(H)3 
REM N-H 
REM >4           1.5    .89 DISORDER 
REM 1      1     1.2    .86 N-N/H 
REM 1      2     1.2    .86 (C)2-N-H 
REM 1      3     1.2    .89 (C)3-N-H 
REM 2      1     1.2    .86 C-N-(H)2 
REM 2      2     1.2    .89 (C)2-N-(H)2 
REM 3      1     1.2    .89 C-H-(H)3 
REM O-H 
REM 1      1     1.5    .82 O-H 
REM 
REM DIST      ESD = 0.02 
REM VIB       ESD = 0.002 
REM ANGLE     ESD = 2.0 
REM            H2-N-R 
DIST 0.86, 0.02 = 
CONT N ( 1) TO H(12) 
CONT N ( 1) TO H(11) 
REST 0.039, 0.002 = H(12,U[ISO]) 
REST 0.039, 0.002 = H(11,U[ISO]) 
ANGLE 120.0, 2.0 = 
CONT C(2) TO N ( 1) TO H(12) 
CONT C(2) TO N ( 1) TO H(11) 
REM            2 H ON SP 3 
DIST 0.97, 0.02 = 
CONT C ( 2) TO H(22) 
CONT C ( 2) TO H(21) 
REST 0.034, 0.002 = H(22,U[ISO]) 
REST 0.034, 0.002 = H(21,U[ISO]) 
ANGLE 0.0, 2.0 = MEAN 
CONT H(22) TO C ( 2) TO N(1) 
CONT H(22) TO C ( 2) TO C(3) 
CONT H(21) TO C ( 2) TO N(1) 
CONT H(21) TO C ( 2) TO C(3) 
ANGLE 109.54, 2.0 = 
CONT H(22) TO C ( 2) TO H(21) 
REM            2 H ON SP 3 
DIST 0.97, 0.02 = 
CONT C ( 3) TO H(32) 
CONT C ( 3) TO H(31) 
REST 0.033, 0.002 = H(32,U[ISO]) 
REST 0.033, 0.002 = H(31,U[ISO]) 
ANGLE 0.0, 2.0 = MEAN 
CONT H(32) TO C ( 3) TO C(2) 
CONT H(32) TO C ( 3) TO C(4) 
CONT H(31) TO C ( 3) TO C(2) 
CONT H(31) TO C ( 3) TO C(4) 
ANGLE 109.54, 2.0 = 
CONT H(32) TO C ( 3) TO H(31) 
REM            2 H ON SP 3 
DIST 0.97, 0.02 = 
CONT C ( 4) TO H(42) 
CONT C ( 4) TO H(41) 
REST 0.031, 0.002 = H(42,U[ISO]) 
REST 0.031, 0.002 = H(41,U[ISO]) 
ANGLE 0.0, 2.0 = MEAN 
CONT H(42) TO C ( 4) TO C(3) 
CONT H(42) TO C ( 4) TO C(5) 
CONT H(41) TO C ( 4) TO C(3) 
CONT H(41) TO C ( 4) TO C(5) 
ANGLE 109.54, 2.0 = 
CONT H(42) TO C ( 4) TO H(41) 
REM            2 H ON SP 3 
DIST 0.97, 0.02 = 
CONT C ( 5) TO H(52) 
CONT C ( 5) TO H(51) 
REST 0.033, 0.002 = H(52,U[ISO]) 
REST 0.033, 0.002 = H(51,U[ISO]) 
ANGLE 0.0, 2.0 = MEAN 
CONT H(52) TO C ( 5) TO C(4) 
CONT H(52) TO C ( 5) TO C(6) 
CONT H(51) TO C ( 5) TO C(4) 
CONT H(51) TO C ( 5) TO C(6) 
ANGLE 109.54, 2.0 = 
CONT H(52) TO C ( 5) TO H(51) 
REM            2 H ON SP 3 
DIST 0.97, 0.02 = 
CONT C ( 6) TO H(62) 
CONT C ( 6) TO H(61) 
REST 0.040, 0.002 = H(62,U[ISO]) 
REST 0.040, 0.002 = H(61,U[ISO]) 
ANGLE 0.0, 2.0 = MEAN 
CONT H(62) TO C ( 6) TO C(5) 
CONT H(62) TO C ( 6) TO C(7) 
CONT H(61) TO C ( 6) TO C(5) 
CONT H(61) TO C ( 6) TO C(7) 
ANGLE 109.54, 2.0 = 
CONT H(62) TO C ( 6) TO H(61) 
REM            2 H ON SP 3 
DIST 0.97, 0.02 = 
CONT C ( 7) TO H(72) 
CONT C ( 7) TO H(71) 
REST 0.047, 0.002 = H(72,U[ISO]) 
REST 0.047, 0.002 = H(71,U[ISO]) 
ANGLE 0.0, 2.0 = MEAN 
CONT H(72) TO C ( 7) TO C(6) 
CONT H(72) TO C ( 7) TO C(8) 
CONT H(71) TO C ( 7) TO C(6) 
CONT H(71) TO C ( 7) TO C(8) 
ANGLE 109.54, 2.0 = 
CONT H(72) TO C ( 7) TO H(71) 
REM            3 H ON SP 3 
DIST 0.96, 0.02 = 
CONT C ( 8) TO H(83) 
CONT C ( 8) TO H(82) 
CONT C ( 8) TO H(81) 
REST 0.096, 0.002 = H(83,U[ISO]) 
REST 0.096, 0.002 = H(82,U[ISO]) 
REST 0.096, 0.002 = H(81,U[ISO]) 
ANGLE 109.54, 2.0 = 
CONT C(7) TO C ( 8) TO H(83) 
CONT C(7) TO C ( 8) TO H(82) 
CONT C(7) TO C ( 8) TO H(81) 
ANGLE 0.0, 2.0 = MEAN H(83) TO C ( 8) TO H(82) 
CONT H(83) TO C ( 8) TO H(81) 
CONT H(82) TO C ( 8) TO H(81) 
REM            H2-N-R 
DIST 0.86, 0.02 = 
CONT N ( 11) TO H(111) 
CONT N ( 11) TO H(112) 
REST 0.041, 0.002 = H(111,U[ISO]) 
REST 0.041, 0.002 = H(112,U[ISO]) 
ANGLE 120.0, 2.0 = 
CONT C(12) TO N ( 11) TO H(111) 
CONT C(12) TO N ( 11) TO H(112) 
REM            2 H ON SP 3 
DIST 0.97, 0.02 = 
CONT C ( 12) TO H(121) 
CONT C ( 12) TO H(122) 
REST 0.035, 0.002 = H(121,U[ISO]) 
REST 0.035, 0.002 = H(122,U[ISO]) 
ANGLE 0.0, 2.0 = MEAN 
CONT H(121) TO C ( 12) TO N(11) 
CONT H(121) TO C ( 12) TO C(13) 
CONT H(122) TO C ( 12) TO N(11) 
CONT H(122) TO C ( 12) TO C(13) 
ANGLE 109.54, 2.0 = 
CONT H(121) TO C ( 12) TO H(122) 
REM            2 H ON SP 3 
DIST 0.97, 0.02 = 
CONT C ( 13) TO H(131) 
CONT C ( 13) TO H(132) 
REST 0.034, 0.002 = H(131,U[ISO]) 
REST 0.034, 0.002 = H(132,U[ISO]) 
ANGLE 0.0, 2.0 = MEAN 
CONT H(131) TO C ( 13) TO C(12) 
CONT H(131) TO C ( 13) TO C(14) 
CONT H(132) TO C ( 13) TO C(12) 
CONT H(132) TO C ( 13) TO C(14) 
ANGLE 109.54, 2.0 = 
CONT H(131) TO C ( 13) TO H(132) 
REM            2 H ON SP 3 
DIST 0.97, 0.02 = 
CONT C ( 14) TO H(141) 
CONT C ( 14) TO H(142) 
REST 0.037, 0.002 = H(141,U[ISO]) 
REST 0.037, 0.002 = H(142,U[ISO]) 
ANGLE 0.0, 2.0 = MEAN 
CONT H(141) TO C ( 14) TO C(13) 
CONT H(141) TO C ( 14) TO C(15) 
CONT H(142) TO C ( 14) TO C(13) 
CONT H(142) TO C ( 14) TO C(15) 
ANGLE 109.54, 2.0 = 
CONT H(141) TO C ( 14) TO H(142) 
REM            2 H ON SP 3 
DIST 0.97, 0.02 = 
CONT C ( 15) TO H(151) 
CONT C ( 15) TO H(152) 
REST 0.037, 0.002 = H(151,U[ISO]) 
REST 0.037, 0.002 = H(152,U[ISO]) 
ANGLE 0.0, 2.0 = MEAN 
CONT H(151) TO C ( 15) TO C(14) 
CONT H(151) TO C ( 15) TO C(16) 
CONT H(152) TO C ( 15) TO C(14) 
CONT H(152) TO C ( 15) TO C(16) 
ANGLE 109.54, 2.0 = 
CONT H(151) TO C ( 15) TO H(152) 
REM            2 H ON SP 3 
DIST 0.97, 0.02 = 
CONT C ( 16) TO H(161) 
CONT C ( 16) TO H(162) 
REST 0.037, 0.002 = H(161,U[ISO]) 
REST 0.037, 0.002 = H(162,U[ISO]) 
ANGLE 0.0, 2.0 = MEAN 
CONT H(161) TO C ( 16) TO C(15) 
CONT H(161) TO C ( 16) TO C(17) 
CONT H(162) TO C ( 16) TO C(15) 
CONT H(162) TO C ( 16) TO C(17) 
ANGLE 109.54, 2.0 = 
CONT H(161) TO C ( 16) TO H(162) 
REM            2 H ON SP 3 
DIST 0.97, 0.02 = 
CONT C ( 17) TO H(171) 
CONT C ( 17) TO H(172) 
REST 0.044, 0.002 = H(171,U[ISO]) 
REST 0.044, 0.002 = H(172,U[ISO]) 
ANGLE 0.0, 2.0 = MEAN 
CONT H(171) TO C ( 17) TO C(16) 
CONT H(171) TO C ( 17) TO C(18) 
CONT H(172) TO C ( 17) TO C(16) 
CONT H(172) TO C ( 17) TO C(18) 
ANGLE 109.54, 2.0 = 
CONT H(171) TO C ( 17) TO H(172) 
REM            3 H ON SP 3 
DIST 0.96, 0.02 = 
CONT C ( 18) TO H(183) 
CONT C ( 18) TO H(181) 
CONT C ( 18) TO H(182) 
REST 0.088, 0.002 = H(183,U[ISO]) 
REST 0.088, 0.002 = H(181,U[ISO]) 
REST 0.088, 0.002 = H(182,U[ISO]) 
ANGLE 109.54, 2.0 = 
CONT C(17) TO C ( 18) TO H(183) 
CONT C(17) TO C ( 18) TO H(181) 
CONT C(17) TO C ( 18) TO H(182) 
ANGLE 0.0, 2.0 = MEAN H(183) TO C ( 18) TO H(181) 
CONT H(183) TO C ( 18) TO H(182) 
CONT H(181) TO C ( 18) TO H(182) 
REM   HREST   END (DO NOT REMOVE THIS LINE) 
END                                                                             
;
_database_code_depnum_ccdc_archive 'CCDC 978658'
#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_octylamine
_audit_creation_date             11-02-18
_audit_creation_method           CRYSTALS_ver_14.11

_oxford_structure_analysis_title 'Octylamine in Pca2(1)'
_chemical_name_systematic        octylamine
_chemical_melting_point          268

#end of refcif 
_cell_length_a                   7.0309(5)
_cell_length_b                   22.3077(15)
_cell_length_c                   5.5826(4)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     875.59(11)

_symmetry_cell_setting           Orthorhombic
_symmetry_space_group_name_H-M   'P c a 21 '
_symmetry_space_group_name_Hall  'P 2c -2ac'
loop_
_symmetry_equiv_pos_as_xyz
x,y,z
-x+1/2,y,z+1/2
x+1/2,-y,z
-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 0.0033 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            4

# Given Formula = C8 H19 N1 
# Dc =      0.98 Fooo =    296.00 Mu =      0.56 M =    129.25
# Found Formula = C8 H19 N1 
# Dc =      0.98 FOOO =    296.00 Mu =      0.56 M =    129.25

_chemical_formula_sum            'C8 H19 N1'
_chemical_formula_moiety         'C8 H19 N1'
_chemical_compound_source        Aldrich
_chemical_formula_weight         129.25


_cell_measurement_reflns_used    4823
_cell_measurement_theta_min      3
_cell_measurement_theta_max      27
_cell_measurement_temperature    150

_exptl_crystal_description       cylinder
_exptl_crystal_colour            colourless
_exptl_crystal_size_min          0.230
_exptl_crystal_size_mid          0.230
_exptl_crystal_size_max          2.000

_exptl_crystal_density_diffrn    0.980
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
# Non-dispersive F(000): 
_exptl_crystal_F_000             296
_exptl_absorpt_coefficient_mu    0.056

# Sheldrick geometric approximatio 0.99 0.99 
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   Twinabs
_exptl_absorpt_correction_T_min  0.65
_exptl_absorpt_correction_T_max  0.99
_diffrn_measurement_device_type  'Bruker Kappa Apex2'
_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       'Apex2 (Bruker AXS, 2006)'
_computing_cell_refinement       'Apex2 (Bruker AXS, 2006)'
_computing_data_reduction        'Apex2 (Bruker AXS, 2006)'
_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            16559
_reflns_number_total             998
_diffrn_reflns_av_R_equivalents  0.075
# Number of reflections without Friedels Law is 0 
# Number of reflections with Friedels Law is 998 
# Theoretical number of reflections is about 1808 


_diffrn_reflns_theta_min         1.826
_diffrn_reflns_theta_max         26.464
_diffrn_measured_fraction_theta_max 0.993

_diffrn_reflns_theta_full        25.935
_diffrn_measured_fraction_theta_full 0.997


_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_k_max       27
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_limit_l_max       6
_reflns_limit_h_min              0
_reflns_limit_h_max              8
_reflns_limit_k_min              0
_reflns_limit_k_max              27
_reflns_limit_l_min              0
_reflns_limit_l_max              6

_oxford_diffrn_Wilson_B_factor   2.48
_oxford_diffrn_Wilson_scale      18.11

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

_refine_diff_density_min         -0.17
_refine_diff_density_max         0.17


# 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>-10.0\s(I)
_refine_ls_number_reflns         998
_refine_ls_number_restraints     82
_refine_ls_number_parameters     158
_oxford_refine_ls_R_factor_ref   0.0550
_refine_ls_wR_factor_ref         0.1084
_refine_ls_goodness_of_fit_ref   1.0043
_refine_ls_shift/su_max          0.0001564
_refine_ls_shift/su_mean         0.0000091


# The values computed from all data 
_oxford_reflns_number_all        998
_refine_ls_R_factor_all          0.0550
_refine_ls_wR_factor_all         0.1084

# The values computed with a 2 sigma cutoff - a la SHELX 
_reflns_threshold_expression     I>2.0σ(I)
_reflns_number_gt                980
_refine_ls_R_factor_gt           0.0536
_refine_ls_wR_factor_gt          0.1062

# 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    'restrained refall'

_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: 
 2.46 3.20 0.798 
;

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

# Replace last . with number of unfound hydrogen atomsattached 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 0.5538(3) 0.02850(7) 0.2336(5) 0.0298 1.0000 Uani D . . . . .
C2 C 0.4686(3) 0.08814(7) 0.2478(5) 0.0260 1.0000 Uani D . . . . .
C3 C 0.5475(3) 0.12860(8) 0.4428(5) 0.0225 1.0000 Uani D . . . . .
C4 C 0.4593(3) 0.19095(8) 0.4462(5) 0.0235 1.0000 Uani D . . . . .
C5 C 0.5412(3) 0.23130(8) 0.6411(5) 0.0232 1.0000 Uani D . . . . .
C6 C 0.4569(3) 0.29407(8) 0.6439(5) 0.0247 1.0000 Uani D . . . . .
C7 C 0.5399(3) 0.33427(8) 0.8375(5) 0.0246 1.0000 Uani D . . . . .
C8 C 0.4540(3) 0.39711(8) 0.8405(5) 0.0307 1.0000 Uani D . . . . .
C9 C 0.5389(4) 0.43732(9) 1.0339(6) 0.0369 1.0000 Uani D . . . . .
H22 H 0.487(3) 0.1075(8) 0.091(3) 0.0352(19) 1.0000 Uiso D . . . . .
H21 H 0.331(2) 0.0840(7) 0.274(4) 0.0335(19) 1.0000 Uiso D . . . . .
H32 H 0.684(2) 0.1317(7) 0.422(4) 0.0311(19) 1.0000 Uiso D . . . . .
H31 H 0.525(3) 0.1096(8) 0.598(3) 0.0307(19) 1.0000 Uiso D . . . . .
H42 H 0.482(3) 0.2110(8) 0.292(3) 0.0318(19) 1.0000 Uiso D . . . . .
H41 H 0.321(2) 0.1871(7) 0.470(4) 0.0319(19) 1.0000 Uiso D . . . . .
H52 H 0.678(2) 0.2335(7) 0.617(3) 0.0316(19) 1.0000 Uiso D . . . . .
H51 H 0.515(3) 0.2127(8) 0.797(3) 0.0303(19) 1.0000 Uiso D . . . . .
H61 H 0.485(3) 0.3129(8) 0.488(3) 0.0324(19) 1.0000 Uiso D . . . . .
H62 H 0.318(2) 0.2905(7) 0.665(4) 0.0321(19) 1.0000 Uiso D . . . . .
H71 H 0.678(2) 0.3371(7) 0.811(4) 0.0335(19) 1.0000 Uiso D . . . . .
H72 H 0.517(3) 0.3156(8) 0.993(3) 0.0341(19) 1.0000 Uiso D . . . . .
H81 H 0.477(3) 0.4149(8) 0.683(3) 0.0408(19) 1.0000 Uiso D . . . . .
H82 H 0.318(2) 0.3932(8) 0.869(3) 0.0412(19) 1.0000 Uiso D . . . . .
H92 H 0.482(3) 0.4762(7) 1.034(5) 0.0614(19) 1.0000 Uiso D . . . . .
H93 H 0.674(2) 0.4410(9) 1.007(4) 0.0618(19) 1.0000 Uiso D . . . . .
H91 H 0.518(3) 0.4200(10) 1.193(3) 0.0617(19) 1.0000 Uiso D . . . . .
H12 H 0.675(2) 0.0287(8) 0.210(7) 0.0396(19) 1.0000 Uiso D . . . . .
H11 H 0.545(4) 0.0084(9) 0.369(3) 0.0403(19) 1.0000 Uiso D . . . . .
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 0.0414(10) 0.0233(7) 0.0246(9) -0.0021(8) -0.0008(11) 0.0014(8)
C2 0.0292(10) 0.0271(9) 0.0217(10) -0.0017(9) -0.0023(13) -0.0008(8)
C3 0.0256(10) 0.0229(8) 0.0191(8) -0.0009(8) -0.0023(11) 0.0006(8)
C4 0.0210(10) 0.0260(9) 0.0235(9) -0.0004(9) -0.0003(11) -0.0013(8)
C5 0.0243(10) 0.0250(9) 0.0202(9) -0.0011(7) -0.0019(11) 0.0007(9)
C6 0.0235(10) 0.0257(9) 0.0249(11) -0.0011(8) -0.0011(11) -0.0012(8)
C7 0.0283(11) 0.0247(8) 0.0209(9) -0.0008(9) 0.0002(11) -0.0001(8)
C8 0.0325(11) 0.0261(9) 0.0336(12) -0.0012(10) -0.0020(12) 0.0006(9)
C9 0.0460(12) 0.0292(9) 0.0356(11) -0.0061(10) -0.0022(15) 0.0010(10)

_refine_ls_extinction_method     None
_oxford_refine_ls_scale          0.2246(4)
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 . 1.461(2) yes
N1 . H12 . 0.864(15) no
N1 . H11 . 0.880(17) no
C2 . C3 . 1.519(3) yes
C2 . H22 . 0.984(16) no
C2 . H21 . 0.980(14) no
C3 . C4 . 1.523(2) yes
C3 . H32 . 0.968(14) no
C3 . H31 . 0.976(16) no
C4 . C5 . 1.525(2) yes
C4 . H42 . 0.985(17) no
C4 . H41 . 0.984(14) no
C5 . C6 . 1.521(2) yes
C5 . H52 . 0.974(14) no
C5 . H51 . 0.982(17) no
C6 . C7 . 1.521(3) yes
C6 . H61 . 0.984(16) no
C6 . H62 . 0.988(14) no
C7 . C8 . 1.526(3) yes
C7 . H71 . 0.981(14) no
C7 . H72 . 0.976(16) no
C8 . C9 . 1.525(3) yes
C8 . H81 . 0.978(17) no
C8 . H82 . 0.973(14) no
C9 . H92 . 0.954(16) no
C9 . H93 . 0.962(15) no
C9 . H91 . 0.977(18) 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 . H12 . 114.1(12) no
C2 . N1 . H11 . 112.8(13) no
H12 . N1 . H11 . 102(3) no
N1 . C2 . C3 . 115.47(17) yes
N1 . C2 . H22 . 107.3(11) no
C3 . C2 . H22 . 109.1(11) no
N1 . C2 . H21 . 109.0(9) no
C3 . C2 . H21 . 107.9(11) no
H22 . C2 . H21 . 107.8(14) no
C2 . C3 . C4 . 113.75(16) yes
C2 . C3 . H32 . 108.6(11) no
C4 . C3 . H32 . 109.9(10) no
C2 . C3 . H31 . 108.4(11) no
C4 . C3 . H31 . 108.6(11) no
H32 . C3 . H31 . 107.3(13) no
C3 . C4 . C5 . 113.22(15) yes
C3 . C4 . H42 . 109.7(11) no
C5 . C4 . H42 . 107.2(11) no
C3 . C4 . H41 . 108.8(9) no
C5 . C4 . H41 . 109.2(11) no
H42 . C4 . H41 . 108.6(13) no
C4 . C5 . C6 . 113.82(15) yes
C4 . C5 . H52 . 107.7(11) no
C6 . C5 . H52 . 109.9(10) no
C4 . C5 . H51 . 108.2(11) no
C6 . C5 . H51 . 107.8(11) no
H52 . C5 . H51 . 109.3(14) no
C5 . C6 . C7 . 113.63(16) yes
C5 . C6 . H61 . 107.8(12) no
C7 . C6 . H61 . 107.3(11) no
C5 . C6 . H62 . 108.3(9) no
C7 . C6 . H62 . 109.9(11) no
H61 . C6 . H62 . 109.9(14) no
C6 . C7 . C8 . 113.42(17) yes
C6 . C7 . H71 . 108.0(12) no
C8 . C7 . H71 . 109.4(10) no
C6 . C7 . H72 . 108.4(11) no
C8 . C7 . H72 . 108.4(11) no
H71 . C7 . H72 . 109.1(14) no
C7 . C8 . C9 . 113.14(19) yes
C7 . C8 . H81 . 107.3(12) no
C9 . C8 . H81 . 109.6(11) no
C7 . C8 . H82 . 107.9(10) no
C9 . C8 . H82 . 108.8(11) no
H81 . C8 . H82 . 110.0(14) no
C8 . C9 . H92 . 111.9(14) no
C8 . C9 . H93 . 109.0(13) no
H92 . C9 . H93 . 109.5(14) no
C8 . C9 . H91 . 110.5(13) no
H92 . C9 . H91 . 107.1(15) no
H93 . C9 . H91 . 108.8(15) no


_iucr_refine_instruction_details_constraints 
;
#
# Punched on 18/02/11 at 16:10:33
#
#LIST     12                                                                    
BLOCK 
CONT SCALE 
CONT N    (    1 ,X'S,U'S)  UNTIL C    (    9 ) 
CONT H    (   22 ,X'S,U[ISO])  UNTIL H    (   11 ) 
END                                                                             
;


_iucr_refine_instruction_details_restraints 
;
#
# Punched on 18/02/11 at 16:10:33
#
#LIST     16                                                                    
NO 
REM   HREST   START (DO NOT REMOVE THIS LINE) 
REM NO H   NO #H U MULT DIST 
REM C-H 
REM >4           1.5    .96 DISORDER 
REM 1      1     1.2    .93 C C-H (ACETYLENE) 
REM 1      2     1.2    .93 C-C(H)-C 
REM 1      3     1.2    .98 (C)3-C-H 
REM 2      1     1.2    .93 C=C-H(2) 
REM 2      2     1.2    .97 (C)2-C-(H)2 
REM 3      1     1.5    .96 C-C-(H)3 
REM N-H 
REM >4           1.5    .89 DISORDER 
REM 1      1     1.2    .86 N-N/H 
REM 1      2     1.2    .86 (C)2-N-H 
REM 1      3     1.2    .89 (C)3-N-H 
REM 2      1     1.2    .86 C-N-(H)2 
REM 2      2     1.2    .89 (C)2-N-(H)2 
REM 3      1     1.2    .89 C-H-(H)3 
REM O-H 
REM 1      1     1.5    .82 O-H 
REM 
REM DIST      ESD = 0.02 
REM VIB       ESD = 0.002 
REM ANGLE     ESD = 2.0 
REM            H2-N-R 
DIST 0.86, 0.02 = 
CONT N ( 1) TO H(12) 
CONT N ( 1) TO H(11) 
REST 0.040, 0.002 = H(12,U[ISO]) 
REST 0.040, 0.002 = H(11,U[ISO]) 
ANGLE 120.0, 2.0 = 
CONT C(2) TO N ( 1) TO H(12) 
CONT C(2) TO N ( 1) TO H(11) 
REM            2 H ON SP 3 
DIST 0.97, 0.02 = 
CONT C ( 2) TO H(22) 
CONT C ( 2) TO H(21) 
REST 0.035, 0.002 = H(22,U[ISO]) 
REST 0.035, 0.002 = H(21,U[ISO]) 
ANGLE 0.0, 2.0 = MEAN 
CONT H(22) TO C ( 2) TO N(1) 
CONT H(22) TO C ( 2) TO C(3) 
CONT H(21) TO C ( 2) TO N(1) 
CONT H(21) TO C ( 2) TO C(3) 
ANGLE 109.54, 2.0 = 
CONT H(22) TO C ( 2) TO H(21) 
REM            2 H ON SP 3 
DIST 0.97, 0.02 = 
CONT C ( 3) TO H(32) 
CONT C ( 3) TO H(31) 
REST 0.032, 0.002 = H(32,U[ISO]) 
REST 0.032, 0.002 = H(31,U[ISO]) 
ANGLE 0.0, 2.0 = MEAN 
CONT H(32) TO C ( 3) TO C(2) 
CONT H(32) TO C ( 3) TO C(4) 
CONT H(31) TO C ( 3) TO C(2) 
CONT H(31) TO C ( 3) TO C(4) 
ANGLE 109.54, 2.0 = 
CONT H(32) TO C ( 3) TO H(31) 
REM            2 H ON SP 3 
DIST 0.97, 0.02 = 
CONT C ( 4) TO H(42) 
CONT C ( 4) TO H(41) 
REST 0.033, 0.002 = H(42,U[ISO]) 
REST 0.033, 0.002 = H(41,U[ISO]) 
ANGLE 0.0, 2.0 = MEAN 
CONT H(42) TO C ( 4) TO C(3) 
CONT H(42) TO C ( 4) TO C(5) 
CONT H(41) TO C ( 4) TO C(3) 
CONT H(41) TO C ( 4) TO C(5) 
ANGLE 109.54, 2.0 = 
CONT H(42) TO C ( 4) TO H(41) 
REM            2 H ON SP 3 
DIST 0.97, 0.02 = 
CONT C ( 5) TO H(52) 
CONT C ( 5) TO H(51) 
REST 0.032, 0.002 = H(52,U[ISO]) 
REST 0.032, 0.002 = H(51,U[ISO]) 
ANGLE 0.0, 2.0 = MEAN 
CONT H(52) TO C ( 5) TO C(4) 
CONT H(52) TO C ( 5) TO C(6) 
CONT H(51) TO C ( 5) TO C(4) 
CONT H(51) TO C ( 5) TO C(6) 
ANGLE 109.54, 2.0 = 
CONT H(52) TO C ( 5) TO H(51) 
REM            2 H ON SP 3 
DIST 0.97, 0.02 = 
CONT C ( 6) TO H(61) 
CONT C ( 6) TO H(62) 
REST 0.034, 0.002 = H(61,U[ISO]) 
REST 0.034, 0.002 = H(62,U[ISO]) 
ANGLE 0.0, 2.0 = MEAN 
CONT H(61) TO C ( 6) TO C(5) 
CONT H(61) TO C ( 6) TO C(7) 
CONT H(62) TO C ( 6) TO C(5) 
CONT H(62) TO C ( 6) TO C(7) 
ANGLE 109.54, 2.0 = 
CONT H(61) TO C ( 6) TO H(62) 
REM            2 H ON SP 3 
DIST 0.97, 0.02 = 
CONT C ( 7) TO H(71) 
CONT C ( 7) TO H(72) 
REST 0.034, 0.002 = H(71,U[ISO]) 
REST 0.034, 0.002 = H(72,U[ISO]) 
ANGLE 0.0, 2.0 = MEAN 
CONT H(71) TO C ( 7) TO C(6) 
CONT H(71) TO C ( 7) TO C(8) 
CONT H(72) TO C ( 7) TO C(6) 
CONT H(72) TO C ( 7) TO C(8) 
ANGLE 109.54, 2.0 = 
CONT H(71) TO C ( 7) TO H(72) 
REM            2 H ON SP 3 
DIST 0.97, 0.02 = 
CONT C ( 8) TO H(81) 
CONT C ( 8) TO H(82) 
REST 0.041, 0.002 = H(81,U[ISO]) 
REST 0.041, 0.002 = H(82,U[ISO]) 
ANGLE 0.0, 2.0 = MEAN 
CONT H(81) TO C ( 8) TO C(7) 
CONT H(81) TO C ( 8) TO C(9) 
CONT H(82) TO C ( 8) TO C(7) 
CONT H(82) TO C ( 8) TO C(9) 
ANGLE 109.54, 2.0 = 
CONT H(81) TO C ( 8) TO H(82) 
REM            3 H ON SP 3 
DIST 0.96, 0.02 = 
CONT C ( 9) TO H(92) 
CONT C ( 9) TO H(93) 
CONT C ( 9) TO H(91) 
REST 0.062, 0.002 = H(92,U[ISO]) 
REST 0.062, 0.002 = H(93,U[ISO]) 
REST 0.062, 0.002 = H(91,U[ISO]) 
ANGLE 109.54, 2.0 = 
CONT C(8) TO C ( 9) TO H(92) 
CONT C(8) TO C ( 9) TO H(93) 
CONT C(8) TO C ( 9) TO H(91) 
ANGLE 0.0, 2.0 = MEAN H(92) TO C ( 9) TO H(93) 
CONT H(92) TO C ( 9) TO H(91) 
CONT H(93) TO C ( 9) TO H(91) 
REM   HREST   END (DO NOT REMOVE THIS LINE) 
END                                                                             
;
_database_code_depnum_ccdc_archive 'CCDC 978659'
#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_nonylamine

_audit_creation_date             11-02-22
_audit_creation_method           CRYSTALS_ver_14.11

_oxford_structure_analysis_title 'Nonylamine in P2(1)/c'
_chemical_name_systematic        nonylamine
_chemical_melting_point          272

#end of refcif 
_cell_length_a                   5.5458(2)
_cell_length_b                   50.6527(17)
_cell_length_c                   7.0521(2)
_cell_angle_alpha                90
_cell_angle_beta                 90.040(2)
_cell_angle_gamma                90
_cell_volume                     1981.00(11)

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   'P 1 21/c 1 '
_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'


_cell_formula_units_Z            8

# Given Formula = C9 H21 N1 
# Dc =      0.96 Fooo =    656.00 Mu =      0.55 M =    286.54
# Found Formula = C9 H21 N1 
# Dc =      0.96 FOOO =    656.00 Mu =      0.55 M =    286.54

_chemical_formula_sum            'C9 H21 N1'
_chemical_formula_moiety         'C9 H21 N1'
_chemical_compound_source        Aldrich
_chemical_formula_weight         143.27


_cell_measurement_reflns_used    3031
_cell_measurement_theta_min      2
_cell_measurement_theta_max      25
_cell_measurement_temperature    150

_exptl_crystal_description       cylinder
_exptl_crystal_colour            colourless
_exptl_crystal_size_min          0.400
_exptl_crystal_size_mid          0.400
_exptl_crystal_size_max          2.000

_exptl_crystal_density_diffrn    0.961
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
# Non-dispersive F(000): 
_exptl_crystal_F_000             656
_exptl_absorpt_coefficient_mu    0.055

# Sheldrick geometric approximatio 0.98 0.98 
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Siemens, 1996)'
_exptl_absorpt_correction_T_min  0.86
_exptl_absorpt_correction_T_max  0.98
_diffrn_measurement_device_type  'Bruker Kappa Apex2'
_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       'Apex2 (Bruker AXS, 2006)'
_computing_cell_refinement       'Apex2 (Bruker AXS, 2006)'
_computing_data_reduction        'Apex2 (Bruker AXS, 2006)'
_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            3641
_reflns_number_total             3641
_diffrn_reflns_av_R_equivalents  0.078
# Number of reflections without Friedels Law is 0 
# Number of reflections with Friedels Law is 3641 
# Theoretical number of reflections is about 5185 


_diffrn_reflns_theta_min         1.608
_diffrn_reflns_theta_max         25.346
_diffrn_measured_fraction_theta_max 1.000

_diffrn_reflns_theta_full        25.346
_diffrn_measured_fraction_theta_full 1.000


_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_k_max       60
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_limit_l_max       8
_reflns_limit_h_min              -6
_reflns_limit_h_max              6
_reflns_limit_k_min              0
_reflns_limit_k_max              60
_reflns_limit_l_min              0
_reflns_limit_l_max              8

_oxford_diffrn_Wilson_B_factor   2.33
_oxford_diffrn_Wilson_scale      36.67

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

_refine_diff_density_min         -0.13
_refine_diff_density_max         0.09


# 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>-10.0\s(I)
_refine_ls_number_reflns         2585
_refine_ls_number_restraints     180
_refine_ls_number_parameters     350
_oxford_refine_ls_R_factor_ref   0.0924
_refine_ls_wR_factor_ref         0.1425
_refine_ls_goodness_of_fit_ref   0.8769
_refine_ls_shift/su_max          0.0005328
_refine_ls_shift/su_mean         0.0000529


# The values computed from all data 
_oxford_reflns_number_all        2585
_refine_ls_R_factor_all          0.0924
_refine_ls_wR_factor_all         0.1425

# The values computed with a 2 sigma cutoff - a la SHELX 
_reflns_threshold_expression     I>2.0σ(I)
_reflns_number_gt                1162
_refine_ls_R_factor_gt           0.0369
_refine_ls_wR_factor_gt          0.0946

# 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    'restrained refall'

_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: 
 5.61 8.33 3.76 0.866 
;

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

# Replace last . with number of unfound hydrogen atomsattached 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 0.8269(5) 0.73701(6) 0.3765(4) 0.0300 1.0000 Uani D . . . . .
C2 C 0.8112(6) 0.71093(7) 0.2909(5) 0.0275 1.0000 Uani D . . . . .
C3 C 0.6157(6) 0.69306(7) 0.3694(5) 0.0244 1.0000 Uani D . . . . .
C4 C 0.6085(7) 0.66563(7) 0.2821(5) 0.0261 1.0000 Uani D . . . . .
C5 C 0.4113(7) 0.64800(7) 0.3628(5) 0.0271 1.0000 Uani D . . . . .
C6 C 0.4041(6) 0.62035(7) 0.2813(5) 0.0268 1.0000 Uani D . . . . .
C7 C 0.2062(7) 0.60305(7) 0.3645(5) 0.0263 1.0000 Uani D . . . . .
C8 C 0.2002(7) 0.57512(7) 0.2870(5) 0.0300 1.0000 Uani D . . . . .
C9 C 0.0049(8) 0.55811(7) 0.3747(5) 0.0356 1.0000 Uani D . . . . .
C10 C 0.0046(10) 0.52989(8) 0.3012(6) 0.0560 1.0000 Uani D . . . . .
N11 N 0.3279(6) 0.76276(6) 0.2680(4) 0.0311 1.0000 Uani D . . . . .
C12 C 0.3123(6) 0.78881(7) 0.3546(5) 0.0282 1.0000 Uani D . . . . .
C13 C 0.1143(6) 0.80665(7) 0.2762(5) 0.0258 1.0000 Uani D . . . . .
C14 C 0.1073(6) 0.83413(7) 0.3646(5) 0.0248 1.0000 Uani D . . . . .
C15 C -0.0878(6) 0.85178(7) 0.2840(4) 0.0223 1.0000 Uani D . . . . .
C16 C -0.0944(7) 0.87918(7) 0.3677(5) 0.0256 1.0000 Uani D . . . . .
C17 C -0.2909(7) 0.89660(7) 0.2842(5) 0.0262 1.0000 Uani D . . . . .
C18 C -0.2988(7) 0.92444(7) 0.3656(5) 0.0274 1.0000 Uani D . . . . .
C19 C -0.4958(8) 0.94168(7) 0.2798(5) 0.0361 1.0000 Uani D . . . . .
C20 C -0.5002(10) 0.96940(8) 0.3566(6) 0.0567 1.0000 Uani D . . . . .
H22 H 0.785(4) 0.7130(4) 0.155(3) 0.0328(19) 1.0000 Uiso D . . . . .
H21 H 0.968(3) 0.7023(4) 0.308(3) 0.0325(19) 1.0000 Uiso D . . . . .
H32 H 0.463(3) 0.7016(4) 0.347(3) 0.0289(19) 1.0000 Uiso D . . . . .
H31 H 0.640(4) 0.6911(4) 0.506(2) 0.0287(19) 1.0000 Uiso D . . . . .
H42 H 0.586(4) 0.6672(4) 0.146(2) 0.0284(19) 1.0000 Uiso D . . . . .
H41 H 0.764(3) 0.6569(4) 0.305(3) 0.0291(19) 1.0000 Uiso D . . . . .
H52 H 0.257(3) 0.6562(4) 0.340(3) 0.0294(19) 1.0000 Uiso D . . . . .
H51 H 0.433(4) 0.6467(4) 0.499(3) 0.0297(19) 1.0000 Uiso D . . . . .
H62 H 0.383(4) 0.6212(4) 0.145(3) 0.0295(19) 1.0000 Uiso D . . . . .
H61 H 0.557(3) 0.6123(4) 0.309(3) 0.0296(19) 1.0000 Uiso D . . . . .
H72 H 0.051(3) 0.6114(4) 0.342(3) 0.0295(19) 1.0000 Uiso D . . . . .
H71 H 0.231(4) 0.6020(4) 0.501(2) 0.0288(19) 1.0000 Uiso D . . . . .
H82 H 0.177(4) 0.5759(4) 0.150(3) 0.0330(19) 1.0000 Uiso D . . . . .
H81 H 0.354(3) 0.5667(4) 0.311(3) 0.0331(19) 1.0000 Uiso D . . . . .
H92 H -0.151(4) 0.5660(4) 0.345(3) 0.0440(19) 1.0000 Uiso D . . . . .
H91 H 0.025(5) 0.5580(4) 0.512(3) 0.0437(19) 1.0000 Uiso D . . . . .
H103 H -0.127(5) 0.5204(5) 0.360(4) 0.0795(19) 1.0000 Uiso D . . . . .
H102 H -0.016(6) 0.5299(5) 0.165(3) 0.0798(19) 1.0000 Uiso D . . . . .
H101 H 0.154(4) 0.5214(5) 0.333(4) 0.0799(19) 1.0000 Uiso D . . . . .
H122 H 0.469(3) 0.7975(4) 0.336(3) 0.0288(19) 1.0000 Uiso D . . . . .
H121 H 0.287(4) 0.7869(4) 0.489(3) 0.0290(19) 1.0000 Uiso D . . . . .
H132 H 0.140(4) 0.8086(4) 0.140(2) 0.0286(19) 1.0000 Uiso D . . . . .
H131 H -0.040(3) 0.7984(4) 0.295(3) 0.0289(19) 1.0000 Uiso D . . . . .
H142 H 0.263(3) 0.8426(4) 0.349(3) 0.0257(19) 1.0000 Uiso D . . . . .
H141 H 0.080(4) 0.8321(4) 0.500(2) 0.0256(19) 1.0000 Uiso D . . . . .
H152 H -0.062(4) 0.8530(4) 0.147(2) 0.0266(19) 1.0000 Uiso D . . . . .
H151 H -0.244(3) 0.8436(4) 0.305(3) 0.0271(19) 1.0000 Uiso D . . . . .
H162 H 0.061(3) 0.8879(4) 0.347(3) 0.0297(19) 1.0000 Uiso D . . . . .
H161 H -0.122(4) 0.8781(4) 0.504(3) 0.0295(19) 1.0000 Uiso D . . . . .
H172 H -0.270(4) 0.8977(4) 0.147(2) 0.0283(19) 1.0000 Uiso D . . . . .
H171 H -0.446(3) 0.8882(4) 0.307(3) 0.0291(19) 1.0000 Uiso D . . . . .
H182 H -0.143(3) 0.9328(4) 0.343(3) 0.0319(19) 1.0000 Uiso D . . . . .
H181 H -0.326(4) 0.9231(4) 0.501(3) 0.0318(19) 1.0000 Uiso D . . . . .
H192 H -0.472(4) 0.9425(4) 0.144(3) 0.0414(19) 1.0000 Uiso D . . . . .
H191 H -0.650(4) 0.9335(4) 0.307(3) 0.0421(19) 1.0000 Uiso D . . . . .
H203 H -0.629(5) 0.9796(5) 0.301(4) 0.0848(19) 1.0000 Uiso D . . . . .
H202 H -0.350(4) 0.9782(5) 0.328(5) 0.0847(19) 1.0000 Uiso D . . . . .
H201 H -0.518(7) 0.9691(5) 0.493(3) 0.0846(19) 1.0000 Uiso D . . . . .
H112 H 0.348(6) 0.7632(5) 0.144(3) 0.0363(19) 1.0000 Uiso D . . . . .
H111 H 0.198(4) 0.7536(5) 0.273(5) 0.0364(19) 1.0000 Uiso D . . . . .
H11 H 0.858(6) 0.7371(5) 0.498(3) 0.0343(19) 1.0000 Uiso D . . . . .
H12 H 0.697(4) 0.7465(5) 0.364(4) 0.0346(19) 1.0000 Uiso D . . . . .
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 0.0271(19) 0.0254(17) 0.0376(18) -0.0013(14) 0.0008(14) -0.0012(14)
C2 0.020(2) 0.030(2) 0.032(2) 0.0038(16) 0.0023(14) 0.0029(16)
C3 0.018(2) 0.028(2) 0.027(2) 0.0020(15) -0.0036(14) 0.0031(16)
C4 0.025(2) 0.027(2) 0.026(2) 0.0008(15) 0.0009(15) 0.0004(16)
C5 0.029(2) 0.029(2) 0.023(2) 0.0018(15) 0.0012(15) 0.0000(16)
C6 0.024(2) 0.031(2) 0.025(2) -0.0007(15) -0.0052(15) 0.0019(16)
C7 0.023(2) 0.029(2) 0.0265(19) 0.0002(15) 0.0008(15) -0.0029(17)
C8 0.032(2) 0.030(2) 0.028(2) -0.0014(15) -0.0002(16) 0.0004(18)
C9 0.039(2) 0.031(2) 0.037(2) 0.0027(16) -0.0026(17) -0.0068(19)
C10 0.067(3) 0.037(3) 0.064(3) 0.001(2) 0.004(2) -0.017(2)
N11 0.0304(19) 0.0246(17) 0.0383(18) -0.0008(14) -0.0009(14) -0.0019(14)
C12 0.026(2) 0.030(2) 0.028(2) 0.0003(16) 0.0010(15) -0.0011(17)
C13 0.022(2) 0.030(2) 0.025(2) 0.0009(15) 0.0005(14) 0.0001(16)
C14 0.021(2) 0.031(2) 0.023(2) 0.0028(15) 0.0011(14) -0.0016(16)
C15 0.019(2) 0.023(2) 0.0246(19) -0.0001(14) 0.0025(14) 0.0003(15)
C16 0.029(2) 0.024(2) 0.024(2) 0.0004(15) -0.0005(15) -0.0005(16)
C17 0.030(2) 0.0237(19) 0.0249(19) -0.0031(14) 0.0002(15) -0.0011(16)
C18 0.028(2) 0.028(2) 0.0259(19) 0.0007(14) 0.0021(15) 0.0013(17)
C19 0.040(2) 0.031(2) 0.038(2) 0.0018(16) 0.0004(18) 0.0076(19)
C20 0.071(3) 0.031(3) 0.068(3) 0.002(2) -0.004(3) 0.011(2)

_refine_ls_extinction_method     None
_oxford_refine_ls_scale          0.16727(17)

loop_
_oxford_twin_element_scale_factors
0.795(2)
0.205(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
N1 . C2 . 1.455(4) yes
N1 . H11 . 0.874(17) no
N1 . H12 . 0.871(17) no
C2 . C3 . 1.517(5) yes
C2 . H22 . 0.972(17) no
C2 . H21 . 0.983(17) no
C3 . C4 . 1.520(4) yes
C3 . H32 . 0.962(17) no
C3 . H31 . 0.979(17) no
C4 . C5 . 1.523(5) yes
C4 . H42 . 0.971(17) no
C4 . H41 . 0.981(17) no
C5 . C6 . 1.515(5) yes
C5 . H52 . 0.965(17) no
C5 . H51 . 0.971(17) no
C6 . C7 . 1.522(5) yes
C6 . H62 . 0.969(17) no
C6 . H61 . 0.963(17) no
C7 . C8 . 1.517(5) yes
C7 . H72 . 0.972(17) no
C7 . H71 . 0.977(17) no
C8 . C9 . 1.516(5) yes
C8 . H82 . 0.974(17) no
C8 . H81 . 0.969(17) no
C9 . C10 . 1.520(5) yes
C9 . H92 . 0.975(18) no
C9 . H91 . 0.974(17) no
C10 . H103 . 0.965(18) no
C10 . H102 . 0.969(18) no
C10 . H101 . 0.960(18) no
N11 . C12 . 1.457(4) yes
N11 . H112 . 0.881(17) no
N11 . H111 . 0.858(17) no
C12 . C13 . 1.526(5) yes
C12 . H122 . 0.983(17) no
C12 . H121 . 0.966(17) no
C13 . C14 . 1.526(5) yes
C13 . H132 . 0.976(17) no
C13 . H131 . 0.961(17) no
C14 . C15 . 1.514(5) yes
C14 . H142 . 0.971(17) no
C14 . H141 . 0.976(17) no
C15 . C16 . 1.508(4) yes
C15 . H152 . 0.977(16) no
C15 . H151 . 0.973(17) no
C16 . C17 . 1.521(5) yes
C16 . H162 . 0.978(17) no
C16 . H161 . 0.976(17) no
C17 . C18 . 1.524(5) yes
C17 . H172 . 0.974(17) no
C17 . H171 . 0.974(17) no
C18 . C19 . 1.523(5) yes
C18 . H182 . 0.973(17) no
C18 . H181 . 0.971(17) no
C19 . C20 . 1.505(5) yes
C19 . H192 . 0.968(17) no
C19 . H191 . 0.970(17) no
C20 . H203 . 0.962(18) no
C20 . H202 . 0.967(18) no
C20 . H201 . 0.968(18) 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 . H11 . 115.1(15) no
C2 . N1 . H12 . 114.3(15) no
H11 . N1 . H12 . 105(3) no
N1 . C2 . C3 . 115.7(3) yes
N1 . C2 . H22 . 108.6(13) no
C3 . C2 . H22 . 108.5(13) no
N1 . C2 . H21 . 107.5(12) no
C3 . C2 . H21 . 108.8(13) no
H22 . C2 . H21 . 107.5(15) no
C2 . C3 . C4 . 114.6(3) yes
C2 . C3 . H32 . 107.6(13) no
C4 . C3 . H32 . 108.7(12) no
C2 . C3 . H31 . 108.8(13) no
C4 . C3 . H31 . 108.1(12) no
H32 . C3 . H31 . 109.0(15) no
C3 . C4 . C5 . 113.8(3) yes
C3 . C4 . H42 . 109.3(12) no
C5 . C4 . H42 . 109.1(13) no
C3 . C4 . H41 . 109.0(12) no
C5 . C4 . H41 . 107.7(13) no
H42 . C4 . H41 . 107.9(15) no
C4 . C5 . C6 . 114.8(3) yes
C4 . C5 . H52 . 108.8(12) no
C6 . C5 . H52 . 108.3(13) no
C4 . C5 . H51 . 108.6(13) no
C6 . C5 . H51 . 108.4(13) no
H52 . C5 . H51 . 107.6(15) no
C5 . C6 . C7 . 113.9(3) yes
C5 . C6 . H62 . 109.7(13) no
C7 . C6 . H62 . 108.9(13) no
C5 . C6 . H61 . 106.9(13) no
C7 . C6 . H61 . 108.4(13) no
H62 . C6 . H61 . 109.1(15) no
C6 . C7 . C8 . 114.4(3) yes
C6 . C7 . H72 . 109.1(12) no
C8 . C7 . H72 . 109.0(12) no
C6 . C7 . H71 . 108.2(13) no
C8 . C7 . H71 . 108.0(13) no
H72 . C7 . H71 . 108.1(15) no
C7 . C8 . C9 . 113.5(3) yes
C7 . C8 . H82 . 108.8(13) no
C9 . C8 . H82 . 109.5(13) no
C7 . C8 . H81 . 109.2(13) no
C9 . C8 . H81 . 107.9(13) no
H82 . C8 . H81 . 107.8(15) no
C8 . C9 . C10 . 113.3(3) yes
C8 . C9 . H92 . 108.3(13) no
C10 . C9 . H92 . 108.1(13) no
C8 . C9 . H91 . 109.0(13) no
C10 . C9 . H91 . 109.6(13) no
H92 . C9 . H91 . 108.5(15) no
C9 . C10 . H103 . 108.8(15) no
C9 . C10 . H102 . 109.7(15) no
H103 . C10 . H102 . 109.5(16) no
C9 . C10 . H101 . 109.8(15) no
H103 . C10 . H101 . 109.2(16) no
H102 . C10 . H101 . 109.8(16) no
C12 . N11 . H112 . 113.6(15) no
C12 . N11 . H111 . 114.9(15) no
H112 . N11 . H111 . 99(3) no
N11 . C12 . C13 . 115.3(3) yes
N11 . C12 . H122 . 107.4(12) no
C13 . C12 . H122 . 108.9(12) no
N11 . C12 . H121 . 109.2(12) no
C13 . C12 . H121 . 108.2(12) no
H122 . C12 . H121 . 107.6(15) no
C12 . C13 . C14 . 114.3(3) yes
C12 . C13 . H132 . 108.2(12) no
C14 . C13 . H132 . 108.3(12) no
C12 . C13 . H131 . 109.3(13) no
C14 . C13 . H131 . 108.6(13) no
H132 . C13 . H131 . 108.1(15) no
C13 . C14 . C15 . 113.8(3) yes
C13 . C14 . H142 . 109.6(12) no
C15 . C14 . H142 . 109.3(12) no
C13 . C14 . H141 . 108.1(12) no
C15 . C14 . H141 . 108.5(12) no
H142 . C14 . H141 . 107.3(15) no
C14 . C15 . C16 . 114.4(3) yes
C14 . C15 . H152 . 107.7(12) no
C16 . C15 . H152 . 109.4(13) no
C14 . C15 . H151 . 109.3(12) no
C16 . C15 . H151 . 108.2(12) no
H152 . C15 . H151 . 107.6(15) no
C15 . C16 . C17 . 113.6(3) yes
C15 . C16 . H162 . 109.6(13) no
C17 . C16 . H162 . 108.2(13) no
C15 . C16 . H161 . 109.7(12) no
C17 . C16 . H161 . 107.5(13) no
H162 . C16 . H161 . 108.0(15) no
C16 . C17 . C18 . 114.3(3) yes
C16 . C17 . H172 . 109.3(13) no
C18 . C17 . H172 . 108.9(12) no
C16 . C17 . H171 . 108.5(12) no
C18 . C17 . H171 . 108.4(12) no
H172 . C17 . H171 . 107.2(15) no
C17 . C18 . C19 . 113.7(3) yes
C17 . C18 . H182 . 108.3(13) no
C19 . C18 . H182 . 108.6(13) no
C17 . C18 . H181 . 108.2(13) no
C19 . C18 . H181 . 108.6(13) no
H182 . C18 . H181 . 109.3(15) no
C18 . C19 . C20 . 113.8(3) yes
C18 . C19 . H192 . 108.7(13) no
C20 . C19 . H192 . 108.5(13) no
C18 . C19 . H191 . 107.8(13) no
C20 . C19 . H191 . 108.2(13) no
H192 . C19 . H191 . 109.8(15) no
C19 . C20 . H203 . 111.5(15) no
C19 . C20 . H202 . 109.8(15) no
H203 . C20 . H202 . 108.0(16) no
C19 . C20 . H201 . 110.3(15) no
H203 . C20 . H201 . 109.4(16) no
H202 . C20 . H201 . 107.7(16) no


_iucr_refine_instruction_details_constraints 
;
#
# Punched on 22/02/11 at 15:06:03
#
#LIST     12                                                                    
BLOCK 
CONT SCALE 
CONT N    (    1 ,X'S,U'S)  UNTIL C    (   20 ) 
CONT H    (   22 ,X'S,U[ISO])  UNTIL H    (   12 ) 
SUMFIX ELEMENT SCALES 
END                                                                             
;


_iucr_refine_instruction_details_restraints 
;
#
# Punched on 22/02/11 at 15:06:03
#
#LIST     16                                                                    
NO 
REM   HREST   START (DO NOT REMOVE THIS LINE) 
REM NO H   NO #H U MULT DIST 
REM C-H 
REM >4           1.5    .96 DISORDER 
REM 1      1     1.2    .93 C C-H (ACETYLENE) 
REM 1      2     1.2    .93 C-C(H)-C 
REM 1      3     1.2    .98 (C)3-C-H 
REM 2      1     1.2    .93 C=C-H(2) 
REM 2      2     1.2    .97 (C)2-C-(H)2 
REM 3      1     1.5    .96 C-C-(H)3 
REM N-H 
REM >4           1.5    .89 DISORDER 
REM 1      1     1.2    .86 N-N/H 
REM 1      2     1.2    .86 (C)2-N-H 
REM 1      3     1.2    .89 (C)3-N-H 
REM 2      1     1.2    .86 C-N-(H)2 
REM 2      2     1.2    .89 (C)2-N-(H)2 
REM 3      1     1.2    .89 C-H-(H)3 
REM O-H 
REM 1      1     1.5    .82 O-H 
REM 
REM DIST      ESD = 0.02 
REM VIB       ESD = 0.002 
REM ANGLE     ESD = 2.0 
REM            H2-N-R 
DIST 0.86, 0.02 = 
CONT N ( 1) TO H(11) 
CONT N ( 1) TO H(12) 
REST 0.034, 0.002 = H(11,U[ISO]) 
REST 0.034, 0.002 = H(12,U[ISO]) 
ANGLE 120.0, 2.0 = 
CONT C(2) TO N ( 1) TO H(11) 
CONT C(2) TO N ( 1) TO H(12) 
REM            2 H ON SP 3 
DIST 0.97, 0.02 = 
CONT C ( 2) TO H(22) 
CONT C ( 2) TO H(21) 
REST 0.033, 0.002 = H(22,U[ISO]) 
REST 0.033, 0.002 = H(21,U[ISO]) 
ANGLE 0.0, 2.0 = MEAN 
CONT H(22) TO C ( 2) TO N(1) 
CONT H(22) TO C ( 2) TO C(3) 
CONT H(21) TO C ( 2) TO N(1) 
CONT H(21) TO C ( 2) TO C(3) 
ANGLE 109.54, 2.0 = 
CONT H(22) TO C ( 2) TO H(21) 
REM            2 H ON SP 3 
DIST 0.97, 0.02 = 
CONT C ( 3) TO H(32) 
CONT C ( 3) TO H(31) 
REST 0.029, 0.002 = H(32,U[ISO]) 
REST 0.029, 0.002 = H(31,U[ISO]) 
ANGLE 0.0, 2.0 = MEAN 
CONT H(32) TO C ( 3) TO C(2) 
CONT H(32) TO C ( 3) TO C(4) 
CONT H(31) TO C ( 3) TO C(2) 
CONT H(31) TO C ( 3) TO C(4) 
ANGLE 109.54, 2.0 = 
CONT H(32) TO C ( 3) TO H(31) 
REM            2 H ON SP 3 
DIST 0.97, 0.02 = 
CONT C ( 4) TO H(42) 
CONT C ( 4) TO H(41) 
REST 0.029, 0.002 = H(42,U[ISO]) 
REST 0.029, 0.002 = H(41,U[ISO]) 
ANGLE 0.0, 2.0 = MEAN 
CONT H(42) TO C ( 4) TO C(3) 
CONT H(42) TO C ( 4) TO C(5) 
CONT H(41) TO C ( 4) TO C(3) 
CONT H(41) TO C ( 4) TO C(5) 
ANGLE 109.54, 2.0 = 
CONT H(42) TO C ( 4) TO H(41) 
REM            2 H ON SP 3 
DIST 0.97, 0.02 = 
CONT C ( 5) TO H(52) 
CONT C ( 5) TO H(51) 
REST 0.030, 0.002 = H(52,U[ISO]) 
REST 0.030, 0.002 = H(51,U[ISO]) 
ANGLE 0.0, 2.0 = MEAN 
CONT H(52) TO C ( 5) TO C(4) 
CONT H(52) TO C ( 5) TO C(6) 
CONT H(51) TO C ( 5) TO C(4) 
CONT H(51) TO C ( 5) TO C(6) 
ANGLE 109.54, 2.0 = 
CONT H(52) TO C ( 5) TO H(51) 
REM            2 H ON SP 3 
DIST 0.97, 0.02 = 
CONT C ( 6) TO H(62) 
CONT C ( 6) TO H(61) 
REST 0.030, 0.002 = H(62,U[ISO]) 
REST 0.030, 0.002 = H(61,U[ISO]) 
ANGLE 0.0, 2.0 = MEAN 
CONT H(62) TO C ( 6) TO C(5) 
CONT H(62) TO C ( 6) TO C(7) 
CONT H(61) TO C ( 6) TO C(5) 
CONT H(61) TO C ( 6) TO C(7) 
ANGLE 109.54, 2.0 = 
CONT H(62) TO C ( 6) TO H(61) 
REM            2 H ON SP 3 
DIST 0.97, 0.02 = 
CONT C ( 7) TO H(72) 
CONT C ( 7) TO H(71) 
REST 0.029, 0.002 = H(72,U[ISO]) 
REST 0.029, 0.002 = H(71,U[ISO]) 
ANGLE 0.0, 2.0 = MEAN 
CONT H(72) TO C ( 7) TO C(6) 
CONT H(72) TO C ( 7) TO C(8) 
CONT H(71) TO C ( 7) TO C(6) 
CONT H(71) TO C ( 7) TO C(8) 
ANGLE 109.54, 2.0 = 
CONT H(72) TO C ( 7) TO H(71) 
REM            2 H ON SP 3 
DIST 0.97, 0.02 = 
CONT C ( 8) TO H(82) 
CONT C ( 8) TO H(81) 
REST 0.033, 0.002 = H(82,U[ISO]) 
REST 0.033, 0.002 = H(81,U[ISO]) 
ANGLE 0.0, 2.0 = MEAN 
CONT H(82) TO C ( 8) TO C(7) 
CONT H(82) TO C ( 8) TO C(9) 
CONT H(81) TO C ( 8) TO C(7) 
CONT H(81) TO C ( 8) TO C(9) 
ANGLE 109.54, 2.0 = 
CONT H(82) TO C ( 8) TO H(81) 
REM            2 H ON SP 3 
DIST 0.97, 0.02 = 
CONT C ( 9) TO H(92) 
CONT C ( 9) TO H(91) 
REST 0.044, 0.002 = H(92,U[ISO]) 
REST 0.044, 0.002 = H(91,U[ISO]) 
ANGLE 0.0, 2.0 = MEAN 
CONT H(92) TO C ( 9) TO C(8) 
CONT H(92) TO C ( 9) TO C(10) 
CONT H(91) TO C ( 9) TO C(8) 
CONT H(91) TO C ( 9) TO C(10) 
ANGLE 109.54, 2.0 = 
CONT H(92) TO C ( 9) TO H(91) 
REM            3 H ON SP 3 
DIST 0.96, 0.02 = 
CONT C ( 10) TO H(103) 
CONT C ( 10) TO H(102) 
CONT C ( 10) TO H(101) 
REST 0.080, 0.002 = H(103,U[ISO]) 
REST 0.080, 0.002 = H(102,U[ISO]) 
REST 0.080, 0.002 = H(101,U[ISO]) 
ANGLE 109.54, 2.0 = 
CONT C(9) TO C ( 10) TO H(103) 
CONT C(9) TO C ( 10) TO H(102) 
CONT C(9) TO C ( 10) TO H(101) 
ANGLE 0.0, 2.0 = MEAN H(103) TO C ( 10) TO H(102) 
CONT H(103) TO C ( 10) TO H(101) 
CONT H(102) TO C ( 10) TO H(101) 
REM            H2-N-R 
DIST 0.86, 0.02 = 
CONT N ( 11) TO H(112) 
CONT N ( 11) TO H(111) 
REST 0.036, 0.002 = H(112,U[ISO]) 
REST 0.036, 0.002 = H(111,U[ISO]) 
ANGLE 120.0, 2.0 = 
CONT C(12) TO N ( 11) TO H(112) 
CONT C(12) TO N ( 11) TO H(111) 
REM            2 H ON SP 3 
DIST 0.97, 0.02 = 
CONT C ( 12) TO H(122) 
CONT C ( 12) TO H(121) 
REST 0.029, 0.002 = H(122,U[ISO]) 
REST 0.029, 0.002 = H(121,U[ISO]) 
ANGLE 0.0, 2.0 = MEAN 
CONT H(122) TO C ( 12) TO N(11) 
CONT H(122) TO C ( 12) TO C(13) 
CONT H(121) TO C ( 12) TO N(11) 
CONT H(121) TO C ( 12) TO C(13) 
ANGLE 109.54, 2.0 = 
CONT H(122) TO C ( 12) TO H(121) 
REM            2 H ON SP 3 
DIST 0.97, 0.02 = 
CONT C ( 13) TO H(132) 
CONT C ( 13) TO H(131) 
REST 0.029, 0.002 = H(132,U[ISO]) 
REST 0.029, 0.002 = H(131,U[ISO]) 
ANGLE 0.0, 2.0 = MEAN 
CONT H(132) TO C ( 13) TO C(12) 
CONT H(132) TO C ( 13) TO C(14) 
CONT H(131) TO C ( 13) TO C(12) 
CONT H(131) TO C ( 13) TO C(14) 
ANGLE 109.54, 2.0 = 
CONT H(132) TO C ( 13) TO H(131) 
REM            2 H ON SP 3 
DIST 0.97, 0.02 = 
CONT C ( 14) TO H(142) 
CONT C ( 14) TO H(141) 
REST 0.026, 0.002 = H(142,U[ISO]) 
REST 0.026, 0.002 = H(141,U[ISO]) 
ANGLE 0.0, 2.0 = MEAN 
CONT H(142) TO C ( 14) TO C(13) 
CONT H(142) TO C ( 14) TO C(15) 
CONT H(141) TO C ( 14) TO C(13) 
CONT H(141) TO C ( 14) TO C(15) 
ANGLE 109.54, 2.0 = 
CONT H(142) TO C ( 14) TO H(141) 
REM            2 H ON SP 3 
DIST 0.97, 0.02 = 
CONT C ( 15) TO H(152) 
CONT C ( 15) TO H(151) 
REST 0.027, 0.002 = H(152,U[ISO]) 
REST 0.027, 0.002 = H(151,U[ISO]) 
ANGLE 0.0, 2.0 = MEAN 
CONT H(152) TO C ( 15) TO C(14) 
CONT H(152) TO C ( 15) TO C(16) 
CONT H(151) TO C ( 15) TO C(14) 
CONT H(151) TO C ( 15) TO C(16) 
ANGLE 109.54, 2.0 = 
CONT H(152) TO C ( 15) TO H(151) 
REM            2 H ON SP 3 
DIST 0.97, 0.02 = 
CONT C ( 16) TO H(162) 
CONT C ( 16) TO H(161) 
REST 0.030, 0.002 = H(162,U[ISO]) 
REST 0.030, 0.002 = H(161,U[ISO]) 
ANGLE 0.0, 2.0 = MEAN 
CONT H(162) TO C ( 16) TO C(15) 
CONT H(162) TO C ( 16) TO C(17) 
CONT H(161) TO C ( 16) TO C(15) 
CONT H(161) TO C ( 16) TO C(17) 
ANGLE 109.54, 2.0 = 
CONT H(162) TO C ( 16) TO H(161) 
REM            2 H ON SP 3 
DIST 0.97, 0.02 = 
CONT C ( 17) TO H(172) 
CONT C ( 17) TO H(171) 
REST 0.029, 0.002 = H(172,U[ISO]) 
REST 0.029, 0.002 = H(171,U[ISO]) 
ANGLE 0.0, 2.0 = MEAN 
CONT H(172) TO C ( 17) TO C(16) 
CONT H(172) TO C ( 17) TO C(18) 
CONT H(171) TO C ( 17) TO C(16) 
CONT H(171) TO C ( 17) TO C(18) 
ANGLE 109.54, 2.0 = 
CONT H(172) TO C ( 17) TO H(171) 
REM            2 H ON SP 3 
DIST 0.97, 0.02 = 
CONT C ( 18) TO H(182) 
CONT C ( 18) TO H(181) 
REST 0.032, 0.002 = H(182,U[ISO]) 
REST 0.032, 0.002 = H(181,U[ISO]) 
ANGLE 0.0, 2.0 = MEAN 
CONT H(182) TO C ( 18) TO C(17) 
CONT H(182) TO C ( 18) TO C(19) 
CONT H(181) TO C ( 18) TO C(17) 
CONT H(181) TO C ( 18) TO C(19) 
ANGLE 109.54, 2.0 = 
CONT H(182) TO C ( 18) TO H(181) 
REM            2 H ON SP 3 
DIST 0.97, 0.02 = 
CONT C ( 19) TO H(192) 
CONT C ( 19) TO H(191) 
REST 0.042, 0.002 = H(192,U[ISO]) 
REST 0.042, 0.002 = H(191,U[ISO]) 
ANGLE 0.0, 2.0 = MEAN 
CONT H(192) TO C ( 19) TO C(18) 
CONT H(192) TO C ( 19) TO C(20) 
CONT H(191) TO C ( 19) TO C(18) 
CONT H(191) TO C ( 19) TO C(20) 
ANGLE 109.54, 2.0 = 
CONT H(192) TO C ( 19) TO H(191) 
REM            3 H ON SP 3 
DIST 0.96, 0.02 = 
CONT C ( 20) TO H(203) 
CONT C ( 20) TO H(202) 
CONT C ( 20) TO H(201) 
REST 0.085, 0.002 = H(203,U[ISO]) 
REST 0.085, 0.002 = H(202,U[ISO]) 
REST 0.085, 0.002 = H(201,U[ISO]) 
ANGLE 109.54, 2.0 = 
CONT C(19) TO C ( 20) TO H(203) 
CONT C(19) TO C ( 20) TO H(202) 
CONT C(19) TO C ( 20) TO H(201) 
ANGLE 0.0, 2.0 = MEAN H(203) TO C ( 20) TO H(202) 
CONT H(203) TO C ( 20) TO H(201) 
CONT H(202) TO C ( 20) TO H(201) 
REM   HREST   END (DO NOT REMOVE THIS LINE) 
END                                                                             
;
_database_code_depnum_ccdc_archive 'CCDC 978660'
#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_decylamine
_audit_creation_date             11-02-18
_audit_creation_method           CRYSTALS_ver_14.11

_oxford_structure_analysis_title 'Decylamine in Pca2(1)'
_chemical_name_systematic        decylamine
_chemical_melting_point          284

#end of refcif 
_cell_length_a                   7.0660(4)
_cell_length_b                   26.8352(15)
_cell_length_c                   5.5730(3)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1056.74(10)

_symmetry_cell_setting           Orthorhombic
_symmetry_space_group_name_H-M   'P c a 21 '
_symmetry_space_group_name_Hall  'P 2c -2ac'
loop_
_symmetry_equiv_pos_as_xyz
x,y,z
-x+1/2,y,z+1/2
x+1/2,-y,z
-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 0.0033 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            4

# Given Formula = C10 H21 N1 
# Dc =      0.98 Fooo =    360.00 Mu =      0.56 M =    155.28
# Found Formula = C10 H23 N1 
# Dc =      0.99 FOOO =    360.00 Mu =      0.56 M =    157.30

_chemical_formula_sum            'C10 H23 N1'
_chemical_formula_moiety         'C10 H23 N1'
_chemical_compound_source        Aldrich
_chemical_formula_weight         157.30


_cell_measurement_reflns_used    3950
_cell_measurement_theta_min      3
_cell_measurement_theta_max      27
_cell_measurement_temperature    150

_exptl_crystal_description       cylinder
_exptl_crystal_colour            colourless
_exptl_crystal_size_min          0.250
_exptl_crystal_size_mid          0.250
_exptl_crystal_size_max          2.000

_exptl_crystal_density_diffrn    0.989
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
# Non-dispersive F(000): 
_exptl_crystal_F_000             360
_exptl_absorpt_coefficient_mu    0.056

# Sheldrick geometric approximatio 0.99 0.99 
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Siemens, 1996)'
_exptl_absorpt_correction_T_min  0.81
_exptl_absorpt_correction_T_max  0.99
_diffrn_measurement_device_type  'Bruker Kappa Apex2'
_diffrn_measurement_device       Area
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_measurement_method       'φ & ω scans'

# If a reference occurs more than once, delete the author 
# and date from subsequent references. 
_computing_data_collection       'Apex2 (Bruker AXS, 2006)'
_computing_cell_refinement       'Apex2 (Bruker AXS, 2006)'
_computing_data_reduction        'Apex2 (Bruker AXS, 2006)'
_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            9645
_reflns_number_total             1286
_diffrn_reflns_av_R_equivalents  0.048
# Number of reflections without Friedels Law is 0 
# Number of reflections with Friedels Law is 1286 
# Theoretical number of reflections is about 2335 


_diffrn_reflns_theta_min         1.518
_diffrn_reflns_theta_max         27.118
_diffrn_measured_fraction_theta_max 0.990

_diffrn_reflns_theta_full        26.033
_diffrn_measured_fraction_theta_full 0.995


_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -31
_diffrn_reflns_limit_k_max       34
_diffrn_reflns_limit_l_min       -7
_diffrn_reflns_limit_l_max       6
_reflns_limit_h_min              0
_reflns_limit_h_max              9
_reflns_limit_k_min              0
_reflns_limit_k_max              34
_reflns_limit_l_min              0
_reflns_limit_l_max              7

_oxford_diffrn_Wilson_B_factor   0.00
_oxford_diffrn_Wilson_scale      0.00

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

_refine_diff_density_min         -0.16
_refine_diff_density_max         0.30


# 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>-10.0\s(I)
_refine_ls_number_reflns         1281
_refine_ls_number_restraints     100
_refine_ls_number_parameters     192
_oxford_refine_ls_R_factor_ref   0.0592
_refine_ls_wR_factor_ref         0.1229
_refine_ls_goodness_of_fit_ref   0.9762
_refine_ls_shift/su_max          0.0002583
_refine_ls_shift/su_mean         0.0000195


# The values computed from all data 
_oxford_reflns_number_all        1281
_refine_ls_R_factor_all          0.0592
_refine_ls_wR_factor_all         0.1229

# The values computed with a 2 sigma cutoff - a la SHELX 
_reflns_threshold_expression     I>2.0σ(I)
_reflns_number_gt                1182
_refine_ls_R_factor_gt           0.0536
_refine_ls_wR_factor_gt          0.1187

# 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    'restrained refall'

_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: 
 2.90 4.25 1.98 0.539 -0.465E-01 
;

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

# Replace last . with number of unfound hydrogen atomsattached 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 0.5539(3) 0.47623(6) 1.1810(5) 0.0290 1.0000 Uani D . . . . .
C2 C 0.4689(3) 0.42661(6) 1.1656(5) 0.0250 1.0000 Uani D . . . . .
H22 H 0.484(3) 0.4098(7) 1.317(3) 0.0283(19) 1.0000 Uiso D . . . . .
H21 H 0.334(2) 0.4310(6) 1.140(4) 0.0274(19) 1.0000 Uiso D . . . . .
C3 C 0.5472(3) 0.39322(7) 0.9670(4) 0.0214 1.0000 Uani D . . . . .
H32 H 0.682(2) 0.3899(6) 0.989(4) 0.0251(19) 1.0000 Uiso D . . . . .
H31 H 0.524(2) 0.4094(6) 0.812(3) 0.0250(19) 1.0000 Uiso D . . . . .
C4 C 0.4591(3) 0.34132(7) 0.9619(5) 0.0221 1.0000 Uani D . . . . .
H41 H 0.323(2) 0.3438(6) 0.943(3) 0.0249(19) 1.0000 Uiso D . . . . .
H42 H 0.480(2) 0.3251(6) 1.116(3) 0.0259(19) 1.0000 Uiso D . . . . .
C5 C 0.5414(3) 0.30825(7) 0.7644(5) 0.0224 1.0000 Uani D . . . . .
H51 H 0.519(3) 0.3241(6) 0.614(3) 0.0247(19) 1.0000 Uiso D . . . . .
H52 H 0.676(2) 0.3058(6) 0.790(3) 0.0254(19) 1.0000 Uiso D . . . . .
C6 C 0.4580(3) 0.25592(7) 0.7586(5) 0.0230 1.0000 Uani D . . . . .
H61 H 0.322(2) 0.2583(6) 0.738(4) 0.0268(19) 1.0000 Uiso D . . . . .
H62 H 0.483(3) 0.2396(6) 0.914(3) 0.0256(19) 1.0000 Uiso D . . . . .
C7 C 0.5415(3) 0.22307(7) 0.5627(5) 0.0222 1.0000 Uani D . . . . .
H71 H 0.512(3) 0.2390(6) 0.412(3) 0.0249(19) 1.0000 Uiso D . . . . .
H72 H 0.677(2) 0.2211(6) 0.583(3) 0.0259(19) 1.0000 Uiso D . . . . .
C8 C 0.4579(3) 0.17069(7) 0.5571(5) 0.0234 1.0000 Uani D . . . . .
H81 H 0.320(2) 0.1725(6) 0.539(3) 0.0290(19) 1.0000 Uiso D . . . . .
H82 H 0.483(3) 0.1545(6) 0.707(3) 0.0278(19) 1.0000 Uiso D . . . . .
C9 C 0.5409(3) 0.13768(7) 0.3616(5) 0.0239 1.0000 Uani D . . . . .
H91 H 0.516(3) 0.1531(6) 0.203(3) 0.0283(19) 1.0000 Uiso D . . . . .
H92 H 0.678(2) 0.1356(6) 0.385(4) 0.0293(19) 1.0000 Uiso D . . . . .
C10 C 0.4547(3) 0.08541(7) 0.3567(5) 0.0291 1.0000 Uani D . . . . .
H101 H 0.319(2) 0.0877(7) 0.334(4) 0.0371(19) 1.0000 Uiso D . . . . .
H102 H 0.479(3) 0.0697(7) 0.511(3) 0.0350(19) 1.0000 Uiso D . . . . .
C11 C 0.5391(3) 0.05230(8) 0.1622(6) 0.0355 1.0000 Uani D . . . . .
H112 H 0.672(2) 0.0489(8) 0.185(4) 0.0545(19) 1.0000 Uiso D . . . . .
H113 H 0.487(3) 0.0194(6) 0.166(5) 0.0537(19) 1.0000 Uiso D . . . . .
H111 H 0.514(3) 0.0664(9) 0.001(3) 0.0536(19) 1.0000 Uiso D . . . . .
H11 H 0.542(4) 0.4930(7) 1.050(3) 0.0331(19) 1.0000 Uiso D . . . . .
H12 H 0.673(2) 0.4752(7) 1.200(6) 0.0338(19) 1.0000 Uiso D . . . . .


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 0.0389(9) 0.0215(7) 0.0266(10) -0.0024(9) -0.0018(13) -0.0004(7)
C2 0.0297(11) 0.0242(8) 0.0211(11) -0.0030(10) 0.0056(13) 0.0006(8)
C3 0.0254(11) 0.0211(8) 0.0179(10) -0.0020(8) 0.0037(11) -0.0003(8)
C4 0.0218(10) 0.0229(9) 0.0217(10) -0.0014(9) 0.0015(12) 0.0002(8)
C5 0.0229(10) 0.0229(9) 0.0215(10) -0.0019(8) 0.0023(11) 0.0007(8)
C6 0.0226(11) 0.0237(9) 0.0226(10) -0.0006(8) 0.0018(10) 0.0012(9)
C7 0.0241(10) 0.0220(8) 0.0205(10) -0.0006(9) 0.0029(11) 0.0003(9)
C8 0.0239(11) 0.0235(9) 0.0228(11) -0.0014(9) 0.0004(11) 0.0006(8)
C9 0.0251(11) 0.0241(8) 0.0225(11) -0.0026(10) -0.0023(11) 0.0007(8)
C10 0.0340(12) 0.0241(8) 0.0291(14) -0.0007(11) 0.0008(12) -0.0004(9)
C11 0.0461(13) 0.0284(9) 0.0319(13) -0.0091(11) 0.0027(17) 0.0005(9)

_refine_ls_extinction_method     None
_oxford_refine_ls_scale          0.1792(3)
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 . 1.463(2) yes
N1 . H12 . 0.847(15) no
N1 . H11 . 0.862(16) no
C2 . H22 . 0.962(16) no
C2 . H21 . 0.970(14) no
C2 . C3 . 1.527(3) yes
C3 . H32 . 0.964(14) no
C3 . H31 . 0.982(16) no
C3 . C4 . 1.526(3) yes
C4 . H41 . 0.967(14) no
C4 . C5 . 1.529(3) yes
C4 . H42 . 0.974(16) no
C5 . H51 . 0.955(16) no
C5 . H52 . 0.965(15) no
C5 . C6 . 1.523(2) yes
C6 . H61 . 0.967(14) no
C6 . H62 . 0.985(17) no
C6 . C7 . 1.523(3) yes
C7 . H71 . 0.962(17) no
C7 . H72 . 0.968(15) no
C7 . C8 . 1.525(3) yes
C8 . H81 . 0.981(15) no
C8 . H82 . 0.961(17) no
C8 . C9 . 1.522(3) yes
C9 . H91 . 0.993(17) no
C9 . H92 . 0.976(14) no
C9 . C10 . 1.530(3) yes
C10 . H101 . 0.966(15) no
C10 . H102 . 0.974(17) no
C10 . C11 . 1.523(4) yes
C11 . H112 . 0.950(16) no
C11 . H113 . 0.956(16) no
C11 . H111 . 0.990(18) 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 . H12 . 112.6(12) no
C2 . N1 . H11 . 112.6(14) no
H12 . N1 . H11 . 103(3) no
N1 . C2 . H22 . 109.1(11) no
N1 . C2 . H21 . 107.5(9) no
H22 . C2 . H21 . 107.2(13) no
N1 . C2 . C3 . 115.34(19) yes
H22 . C2 . C3 . 108.7(11) no
H21 . C2 . C3 . 108.7(12) no
C2 . C3 . H32 . 108.6(11) no
C2 . C3 . H31 . 108.5(11) no
H32 . C3 . H31 . 108.7(13) no
C2 . C3 . C4 . 113.67(17) yes
H32 . C3 . C4 . 108.8(10) no
H31 . C3 . C4 . 108.5(10) no
C3 . C4 . H41 . 110.1(10) no
C3 . C4 . C5 . 112.86(17) yes
H41 . C4 . C5 . 109.8(11) no
C3 . C4 . H42 . 109.3(11) no
H41 . C4 . H42 . 106.0(13) no
C5 . C4 . H42 . 108.6(11) no
C4 . C5 . H51 . 108.2(11) no
C4 . C5 . H52 . 107.8(11) no
H51 . C5 . H52 . 108.9(14) no
C4 . C5 . C6 . 113.79(16) yes
H51 . C5 . C6 . 109.2(11) no
H52 . C5 . C6 . 108.8(10) no
C5 . C6 . H61 . 109.0(10) no
C5 . C6 . H62 . 108.9(11) no
H61 . C6 . H62 . 108.0(14) no
C5 . C6 . C7 . 113.51(16) yes
H61 . C6 . C7 . 109.6(11) no
H62 . C6 . C7 . 107.6(11) no
C6 . C7 . H71 . 106.5(11) no
C6 . C7 . H72 . 109.3(11) no
H71 . C7 . H72 . 110.0(13) no
C6 . C7 . C8 . 113.45(16) yes
H71 . C7 . C8 . 107.9(11) no
H72 . C7 . C8 . 109.6(10) no
C7 . C8 . H81 . 110.0(10) no
C7 . C8 . H82 . 109.1(11) no
H81 . C8 . H82 . 107.1(13) no
C7 . C8 . C9 . 113.67(17) yes
H81 . C8 . C9 . 109.9(11) no
H82 . C8 . C9 . 106.8(11) no
C8 . C9 . H91 . 109.1(11) no
C8 . C9 . H92 . 108.5(11) no
H91 . C9 . H92 . 108.7(13) no
C8 . C9 . C10 . 113.13(17) yes
H91 . C9 . C10 . 107.1(11) no
H92 . C9 . C10 . 110.2(10) no
C9 . C10 . H101 . 109.8(11) no
C9 . C10 . H102 . 108.1(12) no
H101 . C10 . H102 . 108.6(14) no
C9 . C10 . C11 . 113.06(19) yes
H101 . C10 . C11 . 109.3(11) no
H102 . C10 . C11 . 107.9(12) no
C10 . C11 . H112 . 110.3(13) no
C10 . C11 . H113 . 111.9(13) no
H112 . C11 . H113 . 106.6(13) no
C10 . C11 . H111 . 110.6(13) no
H112 . C11 . H111 . 109.7(15) no
H113 . C11 . H111 . 107.7(15) no


_iucr_refine_instruction_details_constraints 
;
#
# Punched on 18/02/11 at 16:47:28
#
#LIST     12                                                                    
BLOCK 
CONT SCALE 
CONT N    (    1 ,X'S,U'S)  UNTIL C    (    2 ) 
CONT H    (   22 ,X'S,U[ISO])  UNTIL H    (   21 ) 
CONT C    (    3 ,X'S,U'S) 
CONT H    (   32 ,X'S,U[ISO])  UNTIL H    (   31 ) 
CONT C    (    4 ,X'S,U'S) 
CONT H    (   41 ,X'S,U[ISO]) 
CONT C    (    5 ,X'S,U'S) 
CONT H    (   51 ,X'S,U[ISO])  UNTIL H    (   52 ) 
CONT C    (    6 ,X'S,U'S) 
CONT H    (   61 ,X'S,U[ISO])  UNTIL H    (   62 ) 
CONT C    (    7 ,X'S,U'S) 
CONT H    (   71 ,X'S,U[ISO])  UNTIL H    (   72 ) 
CONT C    (    8 ,X'S,U'S) 
CONT H    (   81 ,X'S,U[ISO])  UNTIL H    (   82 ) 
CONT C    (    9 ,X'S,U'S) 
CONT H    (   91 ,X'S,U[ISO])  UNTIL H    (   92 ) 
CONT C    (   10 ,X'S,U'S) 
CONT H    (  101 ,X'S,U[ISO])  UNTIL H    (  102 ) 
CONT C    (   11 ,X'S,U'S) 
CONT H    (  112 ,X'S,U[ISO])  UNTIL H    (   42 ) 
END                                                                             
;


_iucr_refine_instruction_details_restraints 
;
#
# Punched on 18/02/11 at 16:47:28
#
#LIST     16                                                                    
NO 
REM   HREST   START (DO NOT REMOVE THIS LINE) 
REM NO H   NO #H U MULT DIST 
REM C-H 
REM >4           1.5    .96 DISORDER 
REM 1      1     1.2    .93 C C-H (ACETYLENE) 
REM 1      2     1.2    .93 C-C(H)-C 
REM 1      3     1.2    .98 (C)3-C-H 
REM 2      1     1.2    .93 C=C-H(2) 
REM 2      2     1.2    .97 (C)2-C-(H)2 
REM 3      1     1.5    .96 C-C-(H)3 
REM N-H 
REM >4           1.5    .89 DISORDER 
REM 1      1     1.2    .86 N-N/H 
REM 1      2     1.2    .86 (C)2-N-H 
REM 1      3     1.2    .89 (C)3-N-H 
REM 2      1     1.2    .86 C-N-(H)2 
REM 2      2     1.2    .89 (C)2-N-(H)2 
REM 3      1     1.2    .89 C-H-(H)3 
REM O-H 
REM 1      1     1.5    .82 O-H 
REM 
REM DIST      ESD = 0.02 
REM VIB       ESD = 0.002 
REM ANGLE     ESD = 2.0 
REM            H2-N-R 
DIST 0.86, 0.02 = 
CONT N ( 1) TO H(12) 
CONT N ( 1) TO H(11) 
REST 0.033, 0.002 = H(12,U[ISO]) 
REST 0.033, 0.002 = H(11,U[ISO]) 
ANGLE 120.0, 2.0 = 
CONT C(2) TO N ( 1) TO H(12) 
CONT C(2) TO N ( 1) TO H(11) 
REM            2 H ON SP 3 
DIST 0.97, 0.02 = 
CONT C ( 2) TO H(22) 
CONT C ( 2) TO H(21) 
REST 0.028, 0.002 = H(22,U[ISO]) 
REST 0.028, 0.002 = H(21,U[ISO]) 
ANGLE 0.0, 2.0 = MEAN 
CONT H(22) TO C ( 2) TO N(1) 
CONT H(22) TO C ( 2) TO C(3) 
CONT H(21) TO C ( 2) TO N(1) 
CONT H(21) TO C ( 2) TO C(3) 
ANGLE 109.54, 2.0 = 
CONT H(22) TO C ( 2) TO H(21) 
REM            2 H ON SP 3 
DIST 0.97, 0.02 = 
CONT C ( 3) TO H(32) 
CONT C ( 3) TO H(31) 
REST 0.025, 0.002 = H(32,U[ISO]) 
REST 0.025, 0.002 = H(31,U[ISO]) 
ANGLE 0.0, 2.0 = MEAN 
CONT H(32) TO C ( 3) TO C(2) 
CONT H(32) TO C ( 3) TO C(4) 
CONT H(31) TO C ( 3) TO C(2) 
CONT H(31) TO C ( 3) TO C(4) 
ANGLE 109.54, 2.0 = 
CONT H(32) TO C ( 3) TO H(31) 
REM            2 H ON SP 3 
DIST 0.97, 0.02 = 
CONT C ( 4) TO H(41) 
CONT C ( 4) TO H(42) 
REST 0.025, 0.002 = H(41,U[ISO]) 
REST 0.025, 0.002 = H(42,U[ISO]) 
ANGLE 0.0, 2.0 = MEAN 
CONT H(41) TO C ( 4) TO C(3) 
CONT H(41) TO C ( 4) TO C(5) 
CONT H(42) TO C ( 4) TO C(3) 
CONT H(42) TO C ( 4) TO C(5) 
ANGLE 109.54, 2.0 = 
CONT H(41) TO C ( 4) TO H(42) 
REM            2 H ON SP 3 
DIST 0.97, 0.02 = 
CONT C ( 5) TO H(51) 
CONT C ( 5) TO H(52) 
REST 0.025, 0.002 = H(51,U[ISO]) 
REST 0.025, 0.002 = H(52,U[ISO]) 
ANGLE 0.0, 2.0 = MEAN 
CONT H(51) TO C ( 5) TO C(4) 
CONT H(51) TO C ( 5) TO C(6) 
CONT H(52) TO C ( 5) TO C(4) 
CONT H(52) TO C ( 5) TO C(6) 
ANGLE 109.54, 2.0 = 
CONT H(51) TO C ( 5) TO H(52) 
REM            2 H ON SP 3 
DIST 0.97, 0.02 = 
CONT C ( 6) TO H(61) 
CONT C ( 6) TO H(62) 
REST 0.027, 0.002 = H(61,U[ISO]) 
REST 0.027, 0.002 = H(62,U[ISO]) 
ANGLE 0.0, 2.0 = MEAN 
CONT H(61) TO C ( 6) TO C(5) 
CONT H(61) TO C ( 6) TO C(7) 
CONT H(62) TO C ( 6) TO C(5) 
CONT H(62) TO C ( 6) TO C(7) 
ANGLE 109.54, 2.0 = 
CONT H(61) TO C ( 6) TO H(62) 
REM            2 H ON SP 3 
DIST 0.97, 0.02 = 
CONT C ( 7) TO H(71) 
CONT C ( 7) TO H(72) 
REST 0.026, 0.002 = H(71,U[ISO]) 
REST 0.026, 0.002 = H(72,U[ISO]) 
ANGLE 0.0, 2.0 = MEAN 
CONT H(71) TO C ( 7) TO C(6) 
CONT H(71) TO C ( 7) TO C(8) 
CONT H(72) TO C ( 7) TO C(6) 
CONT H(72) TO C ( 7) TO C(8) 
ANGLE 109.54, 2.0 = 
CONT H(71) TO C ( 7) TO H(72) 
REM            2 H ON SP 3 
DIST 0.97, 0.02 = 
CONT C ( 8) TO H(81) 
CONT C ( 8) TO H(82) 
REST 0.029, 0.002 = H(81,U[ISO]) 
REST 0.029, 0.002 = H(82,U[ISO]) 
ANGLE 0.0, 2.0 = MEAN 
CONT H(81) TO C ( 8) TO C(7) 
CONT H(81) TO C ( 8) TO C(9) 
CONT H(82) TO C ( 8) TO C(7) 
CONT H(82) TO C ( 8) TO C(9) 
ANGLE 109.54, 2.0 = 
CONT H(81) TO C ( 8) TO H(82) 
REM            2 H ON SP 3 
DIST 0.97, 0.02 = 
CONT C ( 9) TO H(91) 
CONT C ( 9) TO H(92) 
REST 0.029, 0.002 = H(91,U[ISO]) 
REST 0.029, 0.002 = H(92,U[ISO]) 
ANGLE 0.0, 2.0 = MEAN 
CONT H(91) TO C ( 9) TO C(8) 
CONT H(91) TO C ( 9) TO C(10) 
CONT H(92) TO C ( 9) TO C(8) 
CONT H(92) TO C ( 9) TO C(10) 
ANGLE 109.54, 2.0 = 
CONT H(91) TO C ( 9) TO H(92) 
REM            2 H ON SP 3 
DIST 0.97, 0.02 = 
CONT C ( 10) TO H(101) 
CONT C ( 10) TO H(102) 
REST 0.035, 0.002 = H(101,U[ISO]) 
REST 0.035, 0.002 = H(102,U[ISO]) 
ANGLE 0.0, 2.0 = MEAN 
CONT H(101) TO C ( 10) TO C(9) 
CONT H(101) TO C ( 10) TO C(11) 
CONT H(102) TO C ( 10) TO C(9) 
CONT H(102) TO C ( 10) TO C(11) 
ANGLE 109.54, 2.0 = 
CONT H(101) TO C ( 10) TO H(102) 
REM            3 H ON SP 3 
DIST 0.96, 0.02 = 
CONT C ( 11) TO H(112) 
CONT C ( 11) TO H(113) 
CONT C ( 11) TO H(111) 
REST 0.054, 0.002 = H(112,U[ISO]) 
REST 0.054, 0.002 = H(113,U[ISO]) 
REST 0.054, 0.002 = H(111,U[ISO]) 
ANGLE 109.54, 2.0 = 
CONT C(10) TO C ( 11) TO H(112) 
CONT C(10) TO C ( 11) TO H(113) 
CONT C(10) TO C ( 11) TO H(111) 
ANGLE 0.0, 2.0 = MEAN H(112) TO C ( 11) TO H(113) 
CONT H(112) TO C ( 11) TO H(111) 
CONT H(113) TO C ( 11) TO H(111) 
REM   HREST   END (DO NOT REMOVE THIS LINE) 
END                                                                             
;
_database_code_depnum_ccdc_archive 'CCDC 978661'
