#------------------------------------------------------------------------------
#$Date: 2016-03-26 16:25:43 +0200 (Sat, 26 Mar 2016) $
#$Revision: 180338 $
#$URL: svn://www.crystallography.net/cod/cif/7/20/07/7200715.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_7200715
loop_
_publ_author_name
'Khan, Mujeeb'
'Enkelmann, Volker'
'Brunklaus, Gunther'
_publ_section_title
;
 Probing atomic level structural transformation in O--H⋯N
 heterosynthon crystal
;
_journal_issue                   6
_journal_name_full               CrystEngComm
_journal_page_first              1001
_journal_paper_doi               10.1039/b820732a
_journal_volume                  11
_journal_year                    2009
_chemical_formula_moiety         'C18 H16 N2 O2'
_chemical_formula_sum            'C18 H16 N2 O2'
_chemical_formula_weight         292.34
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_date             09-01-15
_audit_creation_method           CRYSTALS_ver_12.84
_cell_angle_alpha                94.4493(12)
_cell_angle_beta                 104.8507(13)
_cell_angle_gamma                111.4950(13)
_cell_formula_units_Z            2
_cell_length_a                   7.7682(4)
_cell_length_b                   9.7938(5)
_cell_length_c                   11.0478(5)
_cell_measurement_reflns_used    0
_cell_measurement_temperature    120
_cell_measurement_theta_max      0
_cell_measurement_theta_min      0
_cell_volume                     742.07(6)
_computing_cell_refinement       'DENZO/SCALEPACK (Otwinowski & Minor, 1997)'
_computing_data_collection       'COLLECT (Nonius, 1997-2001).'
_computing_data_reduction        'DENZO/SCALEPACK (Otwinowski & Minor, 1997)'
_computing_molecular_graphics    'CAMERON (Watkin et al., 1996)'
_computing_publication_material  'CRYSTALS (Betteridge et al., 2003)'
_computing_structure_refinement  'CRYSTALS (Betteridge et al., 2003)'
_computing_structure_solution    'SHELXS 86 (Sheldrick, 1986)'
_diffrn_ambient_temperature      120
_diffrn_measured_fraction_theta_full 0.823
_diffrn_measured_fraction_theta_max 0.784
_diffrn_measurement_device_type  'Nonius KappaCCD'
_diffrn_measurement_method       'φ & ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.067
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number            13514
_diffrn_reflns_theta_full        25.017
_diffrn_reflns_theta_max         27.491
_diffrn_reflns_theta_min         4.101
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.087
_exptl_absorpt_correction_T_max  0.99
_exptl_absorpt_correction_T_min  0.88
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SORTAV (Blessing)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.308
_exptl_crystal_description       prism
_exptl_crystal_F_000             308
_exptl_crystal_size_max          0.33
_exptl_crystal_size_mid          0.19
_exptl_crystal_size_min          0.07
_refine_diff_density_max         0.29
_refine_diff_density_min         -0.34
_refine_ls_extinction_method     None
_refine_ls_goodness_of_fit_ref   0.8852
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     217
_refine_ls_number_reflns         2100
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0542
_refine_ls_R_factor_gt           0.0528
_refine_ls_shift/su_max          0.003586
_refine_ls_structure_factor_coef F
_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:
1.48 1.45 0.459
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_all         0.0574
_refine_ls_wR_factor_gt          0.0561
_refine_ls_wR_factor_ref         0.0561
_reflns_limit_h_max              9
_reflns_limit_h_min              -10
_reflns_limit_k_max              12
_reflns_limit_k_min              -12
_reflns_limit_l_max              14
_reflns_limit_l_min              0
_reflns_number_gt                2100
_reflns_number_total             3357
_reflns_threshold_expression     I>1.5σ(I)
_oxford_diffrn_Wilson_B_factor   0.00
_oxford_diffrn_Wilson_scale      0.00
_oxford_refine_ls_scale          2.194(5)
_oxford_structure_analysis_title 'Khanx1 irrad 120K 02-07'
_cod_data_source_file            b820732a.txt
_cod_data_source_block           CRYSTALS_cif2
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Triclinic' changed to 'triclinic'
according to '/home/saulius/struct/CIF-dictionaries/cif_core.dic'
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_enum 1527 2010-12-29 10:47:43Z saulius 
;
_cod_original_sg_symbol_H-M      'P -1 '
_cod_database_code               7200715
loop_
_symmetry_equiv_pos_as_xyz
x,y,z
-x,-y,-z
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
C1 C 0.3540(3) 0.8051(2) 0.6615(2) 0.0423 1.0000 Uani . . . . . .
C2 C 0.3730(4) 0.8507(2) 0.7893(2) 0.0514 1.0000 Uani . . . . . .
C3 C 0.5508(4) 0.8891(2) 0.8796(2) 0.0534 1.0000 Uani . . . . . .
C4 C 0.7115(3) 0.8871(2) 0.84933(17) 0.0437 1.0000 Uani . . . . . .
C5 C 0.6920(3) 0.84366(16) 0.72038(15) 0.0321 1.0000 Uani . . . . . .
C6 C 0.5132(3) 0.80245(16) 0.62765(15) 0.0314 1.0000 Uani . . . . . .
C11 C 0.8711(3) 0.4897(2) -0.2886(2) 0.0589 1.0000 Uani . . . . . .
C12 C 0.8369(4) 0.5361(2) -0.1799(2) 0.0673 1.0000 Uani . . . . . .
C13 C 0.7474(4) 0.4318(2) -0.11204(19) 0.0629 1.0000 Uani . . . . . .
C14 C 0.7028(3) 0.2820(2) -0.15942(19) 0.0534 1.0000 Uani . . . . . .
C15 C 0.7389(3) 0.2448(2) -0.2699(2) 0.0488 1.0000 Uani . . . . . .
C16 C 0.7433(5) 0.4759(3) 0.0013(3) 0.0419 0.5841 Uani . . . . . .
C17 C 0.7825(5) 0.6152(3) 0.0571(3) 0.0357 0.5841 Uani . . . . . .
C18 C 0.7389(3) 0.65930(19) 0.18656(16) 0.0464 1.0000 Uani . . . . . .
C19 C 0.8085(3) 0.81026(19) 0.23620(16) 0.0393 1.0000 Uani . . . . . .
C20 C 0.8201(3) 0.8562(2) 0.35904(18) 0.0427 1.0000 Uani . . . . . .
C21 C 0.6998(3) 0.6133(2) 0.3874(2) 0.0519 1.0000 Uani . . . . . .
C22 C 0.6816(3) 0.5591(2) 0.26549(18) 0.0420 1.0000 Uani . . . . . .
C26 C 0.6062(7) 0.4473(5) 0.0008(4) 0.0324 0.4159 Uani . . . . . .
C27 C 0.6257(6) 0.6051(4) 0.0538(3) 0.0301 0.4159 Uani . . . . . .
N11 N 0.8210(2) 0.34544(18) -0.33639(17) 0.0505 1.0000 Uani . . . . . .
N12 N 0.7675(3) 0.76087(19) 0.43584(16) 0.0516 1.0000 Uani . . . . . .
H21 H 0.2659 0.8550 0.8134 0.0531 1.0000 Uiso R . . . . .
H31 H 0.5622 0.9198 0.9661 0.0571 1.0000 Uiso R . . . . .
H41 H 0.8323 0.9134 0.9134 0.0515 1.0000 Uiso R . . . . .
H61 H 0.4999 0.7732 0.5406 0.0355 1.0000 Uiso R . . . . .
H111 H 0.9304 0.5627 -0.3336 0.0711 1.0000 Uiso R . . . . .
H121 H 0.8827 0.6403 -0.1487 0.0802 1.0000 Uiso R . . . . .
H141 H 0.6479 0.2066 -0.1149 0.0526 1.0000 Uiso R . . . . .
H151 H 0.7065 0.1425 -0.3008 0.0604 1.0000 Uiso R . . . . .
H161 H 0.7131 0.4012 0.0516 0.0306 0.5841 Uiso R . . . . .
H171 H 0.8424 0.6938 0.0169 0.0306 0.5841 Uiso R . . . . .
H191 H 0.8447 0.8815 0.1839 0.0476 1.0000 Uiso R . . . . .
H201 H 0.8662 0.9600 0.3918 0.0437 1.0000 Uiso R . . . . .
H211 H 0.6609 0.5445 0.4411 0.0592 1.0000 Uiso R . . . . .
H221 H 0.6293 0.4545 0.2344 0.0509 1.0000 Uiso R . . . . .
H261 H 0.6429 0.4043 0.0720 0.0306 0.4159 Uiso R . . . . .
H271 H 0.6870 0.6718 0.0050 0.0306 0.4159 Uiso R . . . . .
O1 O 0.1753(2) 0.76398(17) 0.57356(16) 0.0572 1.0000 Uani . . . . . .
O2 O 0.85341(17) 0.84151(14) 0.69283(11) 0.0380 1.0000 Uani . . . . . .
H1 H 0.1755 0.7259 0.4918 0.0600 1.0000 Uiso R . . . . .
H2 H 0.8245 0.8133 0.6033 0.0450 1.0000 Uiso R . . . . .
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'
O 0.0106 0.0060 3.0485 13.2771 2.2868 5.7011 1.5463 0.3239 0.8670 32.9089
0.2508 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
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'
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 . C1 . C6 . 120.1(2) yes
C2 . C1 . O1 . 117.69(18) yes
C6 . C1 . O1 . 122.19(18) yes
C1 . C2 . C3 . 118.51(18) yes
C1 . C2 . H21 . 120.9 no
C3 . C2 . H21 . 120.6 no
C2 . C3 . C4 . 122.84(18) yes
C2 . C3 . H31 . 117.9 no
C4 . C3 . H31 . 119.3 no
C3 . C4 . C5 . 118.3(2) yes
C3 . C4 . H41 . 121.3 no
C5 . C4 . H41 . 120.5 no
C4 . C5 . C6 . 119.89(17) yes
C4 . C5 . O2 . 117.17(16) yes
C6 . C5 . O2 . 122.94(14) yes
C5 . C6 . C1 . 120.36(16) yes
C5 . C6 . H61 . 120.0 no
C1 . C6 . H61 . 119.7 no
C12 . C11 . N11 . 123.3(2) yes
C12 . C11 . H111 . 118.7 no
N11 . C11 . H111 . 118.0 no
C11 . C12 . C13 . 120.4(2) yes
C11 . C12 . H121 . 118.9 no
C13 . C12 . H121 . 120.6 no
C12 . C13 . C14 . 116.1(2) yes
C12 . C13 . C16 . 120.3(2) yes
C14 . C13 . C16 . 122.2(2) yes
C13 . C14 . C15 . 119.86(19) yes
C13 . C14 . H141 . 119.9 no
C15 . C14 . H141 . 120.2 no
C14 . C15 . N11 . 123.73(18) yes
C14 . C15 . H151 . 118.5 no
N11 . C15 . H151 . 117.7 no
C13 . C16 . C17 . 127.8(3) yes
C13 . C16 . C26 . 109.8(4) yes
C17 . C16 . C26 . 88.4(3) yes
C13 . C16 . H161 . 116.2 no
C17 . C16 . H161 . 115.9 no
C26 . C16 . H161 . 71.2 no
C13 . C16 . H261 . 130.8 no
C17 . C16 . H261 . 97.6 no
C26 . C16 . H261 . 46.3 no
H161 . C16 . H261 . 28.3 no
C16 . C17 . C18 . 125.5(2) yes
C16 . C17 . C26 . 37.11(19) yes
C18 . C17 . C26 . 100.2(2) yes
C16 . C17 . C27 . 100.8(3) yes
C18 . C17 . C27 . 59.9(2) yes
C26 . C17 . C27 . 63.9(3) yes
C16 . C17 . H171 . 116.5 no
C18 . C17 . H171 . 118.0 no
C26 . C17 . H171 . 132.6 no
C27 . C17 . H171 . 111.1 no
C16 . C17 . H271 . 116.2 no
C18 . C17 . H271 . 89.0 no
C26 . C17 . H271 . 92.2 no
C27 . C17 . H271 . 48.2 no
H171 . C17 . H271 . 63.4 no
C17 . C18 . C19 . 116.73(17) yes
C17 . C18 . C22 . 123.58(18) yes
C19 . C18 . C22 . 117.69(17) yes
C17 . C18 . C27 . 44.8(2) yes
C19 . C18 . C27 . 118.9(2) yes
C22 . C18 . C27 . 114.0(2) yes
C18 . C19 . C20 . 120.01(16) yes
C18 . C19 . H191 . 119.8 no
C20 . C19 . H191 . 120.2 no
C19 . C20 . N12 . 122.66(17) yes
C19 . C20 . H201 . 119.3 no
N12 . C20 . H201 . 118.0 no
C22 . C21 . N12 . 123.30(17) yes
C22 . C21 . H211 . 118.7 no
N12 . C21 . H211 . 118.0 no
C18 . C22 . C21 . 118.99(17) yes
C18 . C22 . H221 . 120.4 no
C21 . C22 . H221 . 120.6 no
C27 2_665 C26 . C17 . 131.0(3) yes
C27 2_665 C26 . C16 . 159.4(4) yes
C17 . C26 . C16 . 54.5(3) yes
C27 2_665 C26 . C27 . 89.6(3) yes
C17 . C26 . C27 . 43.0(2) yes
C16 . C26 . C27 . 97.2(4) yes
C27 2_665 C26 . H161 . 138.1 no
C17 . C26 . H161 . 87.2 no
C16 . C26 . H161 . 52.5 no
C27 . C26 . H161 . 120.2 no
C27 2_665 C26 . H261 . 112.2 no
C17 . C26 . H261 . 96.4 no
C16 . C26 . H261 . 84.3 no
C27 . C26 . H261 . 107.2 no
H161 . C26 . H261 . 35.0 no
C26 . C27 . C26 2_665 90.4(3) yes
C26 . C27 . C18 . 113.7(3) yes
C26 2_665 C27 . C18 . 124.9(3) yes
C26 . C27 . C17 . 73.1(3) yes
C26 2_665 C27 . C17 . 158.5(4) yes
C18 . C27 . C17 . 75.3(3) yes
C26 . C27 . H271 . 107.6 no
C26 2_665 C27 . H271 . 109.6 no
C18 . C27 . H271 . 108.6 no
C17 . C27 . H271 . 64.4 no
C15 . N11 . C11 . 116.6(2) yes
C21 . N12 . C20 . 117.34(16) yes
C26 . H161 . C16 . 56.3 no
C26 . H161 . H261 . 56.9 no
C16 . H161 . H261 . 108.0 no
H161 . H261 . C26 . 88.0 no
H161 . H261 . C16 . 43.8 no
C26 . H261 . C16 . 49.3 no
C17 . H271 . C27 . 67.4 no
C1 . O1 . H1 . 110.7 no
C5 . O2 . H2 . 109.9 no
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
C1 . C2 . 1.400(3) yes
C1 . C6 . 1.389(2) yes
C1 . O1 . 1.368(2) yes
C2 . C3 . 1.378(3) yes
C2 . H21 . 0.950 no
C3 . C4 . 1.379(3) yes
C3 . H31 . 0.950 no
C4 . C5 . 1.408(2) yes
C4 . H41 . 0.950 no
C5 . C6 . 1.392(2) yes
C5 . O2 . 1.370(2) yes
C6 . H61 . 0.950 no
C11 . C12 . 1.373(3) yes
C11 . N11 . 1.343(3) yes
C11 . H111 . 0.950 no
C12 . C13 . 1.399(3) yes
C12 . H121 . 0.950 no
C13 . C14 . 1.400(3) yes
C13 . C16 . 1.305(4) yes
C14 . C15 . 1.372(3) yes
C14 . H141 . 0.950 no
C15 . N11 . 1.345(3) yes
C15 . H151 . 0.950 no
C16 . C17 . 1.343(4) yes
C16 . C26 . 0.996(5) yes
C16 . H161 . 0.950 no
C16 . H261 . 1.307 no
C17 . C18 . 1.614(4) yes
C17 . C26 . 1.650(5) yes
C17 . C27 . 1.176(5) yes
C17 . H171 . 0.950 no
C17 . H271 . 1.149 no
C18 . C19 . 1.384(2) yes
C18 . C22 . 1.390(2) yes
C18 . C27 . 1.443(4) yes
C19 . C20 . 1.366(2) yes
C19 . H191 . 0.950 no
C20 . N12 . 1.334(2) yes
C20 . H201 . 0.950 no
C21 . C22 . 1.361(3) yes
C21 . N12 . 1.353(3) yes
C21 . H211 . 0.950 no
C22 . H221 . 0.950 no
C26 . C27 2_665 1.609(6) yes
C26 . C27 . 1.548(5) yes
C26 . H161 . 1.133 no
C26 . H261 . 0.950 no
C27 . H271 . 0.950 no
H161 . H261 . 0.651 no
O1 . H1 . 0.950 no
O2 . H2 . 0.950 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
O1 . H1 . N11 2_665 179 0.95 1.81 2.764(2) yes
O2 . H2 . N12 . 179 0.95 1.77 2.725(2) yes
