#------------------------------------------------------------------------------
#$Date: 2016-03-26 16:25:43 +0200 (Sat, 26 Mar 2016) $
#$Revision: 180338 $
#$URL: svn://www.crystallography.net/cod/cif/7/20/07/7200714.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_7200714
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                93.0700(12)
_cell_angle_beta                 106.7800(13)
_cell_angle_gamma                113.5611(13)
_cell_formula_units_Z            2
_cell_length_a                   7.9360(4)
_cell_length_b                   9.8340(5)
_cell_length_c                   10.9160(5)
_cell_measurement_reflns_used    0
_cell_measurement_temperature    120
_cell_measurement_theta_max      0
_cell_measurement_theta_min      0
_cell_volume                     733.66(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 0.990
_diffrn_measured_fraction_theta_max 0.969
_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  0.045
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            12245
_diffrn_reflns_theta_full        25.225
_diffrn_reflns_theta_max         28.995
_diffrn_reflns_theta_min         4.079
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.088
_exptl_absorpt_correction_T_max  0.99
_exptl_absorpt_correction_T_min  0.90
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SORTAV (Blessing)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.323
_exptl_crystal_description       prism
_exptl_crystal_F_000             308
_exptl_crystal_size_max          0.39
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.13
_refine_diff_density_max         0.44
_refine_diff_density_min         -0.30
_refine_ls_extinction_method     None
_refine_ls_goodness_of_fit_ref   1.1864
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     194
_refine_ls_number_reflns         2050
_refine_ls_number_restraints     5
_refine_ls_R_factor_all          0.1338
_refine_ls_R_factor_gt           0.0672
_refine_ls_shift/su_max          0.016796
_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:
2.73 -8.79 0.158
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_all         0.0346
_refine_ls_wR_factor_gt          0.0214
_refine_ls_wR_factor_ref         0.0214
_reflns_limit_h_max              10
_reflns_limit_h_min              -10
_reflns_limit_k_max              13
_reflns_limit_k_min              -13
_reflns_limit_l_max              14
_reflns_limit_l_min              0
_reflns_number_gt                2050
_reflns_number_total             3779
_reflns_threshold_expression     I>2.0σ(I)
_oxford_diffrn_Wilson_B_factor   0.00
_oxford_diffrn_Wilson_scale      0.00
_oxford_refine_ls_scale          5.095(8)
_oxford_structure_analysis_title 'Khan_x1 teilumgesetzt 120K 06-07'
_cod_data_source_file            b820732a.txt
_cod_data_source_block           CRYSTALS_cif
_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               7200714
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
N11 N 0.2459(3) 0.75539(19) 0.43254(17) 0.0374 1.0000 Uani . . . . . .
N12 N 0.3265(2) 0.34793(18) -0.33493(17) 0.0337 1.0000 Uani . . . . . .
C1 C -0.1477(3) 0.8088(2) 0.6601(2) 0.0299 1.0000 Uani . . . . . .
C3 C 0.1870(3) 0.84577(17) 0.72265(18) 0.0262 1.0000 Uani . . . . . .
C13 C 0.2506(3) 0.6605(2) 0.18718(19) 0.0314 1.0000 Uani D . . . . .
C18 C 0.2626(3) 0.4386(2) -0.1103(2) 0.0367 1.0000 Uani D . . . . .
O1 O -0.32645(19) 0.76858(15) 0.56868(15) 0.0383 1.0000 Uani . . . . . .
O2 O 0.34193(19) 0.84276(14) 0.69449(13) 0.0319 1.0000 Uani . . . . . .
C2 C 0.0074(3) 0.80620(19) 0.62682(18) 0.0267 1.0000 Uani . . . . . .
C4 C 0.2116(3) 0.8898(2) 0.85243(18) 0.0318 1.0000 Uani . . . . . .
C5 C 0.0564(3) 0.8931(2) 0.8835(2) 0.0340 1.0000 Uani . . . . . .
C6 C -0.1237(3) 0.8530(2) 0.7894(2) 0.0337 1.0000 Uani . . . . . .
C11 C 0.1825(3) 0.6085(2) 0.3825(2) 0.0368 1.0000 Uani . . . . . .
C12 C 0.1817(3) 0.5575(2) 0.26393(18) 0.0302 1.0000 Uani . . . . . .
C14 C 0.3139(3) 0.81262(19) 0.23772(18) 0.0303 1.0000 Uani . . . . . .
C15 C 0.3086(3) 0.8550(2) 0.3578(2) 0.0334 1.0000 Uani . . . . . .
C19 C 0.2094(3) 0.2876(2) -0.1564(2) 0.0361 1.0000 Uani . . . . . .
C20 C 0.2426(3) 0.2469(2) -0.2667(2) 0.0350 1.0000 Uani . . . . . .
C21 C 0.3789(3) 0.4929(2) -0.2911(2) 0.0385 1.0000 Uani . . . . . .
C22 C 0.3497(3) 0.5419(2) -0.18218(19) 0.0397 1.0000 Uani . . . . . .
C16 C 0.2813(3) 0.6190(2) 0.0637(2) 0.0279 0.8529 Uani . . . . . .
C17 C 0.2352(3) 0.4806(2) 0.0073(2) 0.0279 0.8529 Uani . . . . . .
C26 C 0.1235(17) 0.6025(13) 0.0505(12) 0.0279 0.1471 Uani D . . . . .
C27 C 0.1066(18) 0.4480(13) -0.0045(12) 0.0279 0.1471 Uani D . . . . .
H21 H -0.0095 0.7768 0.5381 0.0342 1.0000 Uiso R . . . . .
H41 H 0.3338 0.9170 0.9187 0.0392 1.0000 Uiso R . . . . .
H51 H 0.0739 0.9240 0.9720 0.0425 1.0000 Uiso R . . . . .
H61 H -0.2291 0.8557 0.8125 0.0417 1.0000 Uiso R . . . . .
H111 H 0.1367 0.5363 0.4338 0.0458 1.0000 Uiso R . . . . .
H121 H 0.1336 0.4522 0.2331 0.0395 1.0000 Uiso R . . . . .
H141 H 0.3604 0.8866 0.1880 0.0410 1.0000 Uiso R . . . . .
H151 H 0.3515 0.9593 0.3896 0.0432 1.0000 Uiso R . . . . .
H191 H 0.1497 0.2122 -0.1118 0.0450 1.0000 Uiso R . . . . .
H201 H 0.2065 0.1432 -0.2958 0.0446 1.0000 Uiso R . . . . .
H211 H 0.4389 0.5651 -0.3379 0.0468 1.0000 Uiso R . . . . .
H221 H 0.3899 0.6467 -0.1550 0.0482 1.0000 Uiso R . . . . .
H161 H 0.3385 0.6985 0.0217 0.0367 0.8529 Uiso R . . . . .
H171 H 0.1790 0.4018 0.0503 0.0367 0.8529 Uiso R . . . . .
H261 H 0.1725 0.6751 0.0003 0.0367 0.1471 Uiso R . . . . .
H271 H 0.1430 0.4050 0.0688 0.0367 0.1471 Uiso R . . . . .
H1 H -0.3264 0.7283 0.4876 0.0497 1.0000 Uiso R . . . . .
H2 H 0.3086 0.8124 0.6033 0.0437 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
C11 . N11 . C15 . 116.60(18) yes
C20 . N12 . C21 . 117.17(19) yes
O1 . C1 . C2 . 121.77(19) yes
O1 . C1 . C6 . 117.97(18) yes
C2 . C1 . C6 . 120.27(19) yes
O2 . C3 . C2 . 122.21(19) yes
O2 . C3 . C4 . 118.16(17) yes
C2 . C3 . C4 . 119.6(2) yes
C12 . C13 . C14 . 116.61(19) yes
C12 . C13 . C16 . 123.86(17) yes
C14 . C13 . C16 . 119.12(18) yes
C12 . C13 . C26 . 110.1(5) yes
C14 . C13 . C26 . 117.8(5) yes
C16 . C13 . C26 . 46.0(5) yes
C19 . C18 . C22 . 116.0(2) yes
C19 . C18 . C17 . 119.9(2) yes
C22 . C18 . C17 . 124.09(18) yes
C1 . O1 . H1 . 108.6 no
C3 . O2 . H2 . 110.6 no
C1 . C2 . C3 . 120.31(19) yes
C1 . C2 . H21 . 119.9 no
C3 . C2 . H21 . 119.8 no
C3 . C4 . C5 . 119.25(19) yes
C3 . C4 . H41 . 120.3 no
C5 . C4 . H41 . 120.5 no
C4 . C5 . C6 . 121.9(2) yes
C4 . C5 . H51 . 119.1 no
C6 . C5 . H51 . 119.1 no
C1 . C6 . C5 . 118.7(2) yes
C1 . C6 . H61 . 120.5 no
C5 . C6 . H61 . 120.8 no
N11 . C11 . C12 . 124.09(18) yes
N11 . C11 . H111 . 117.7 no
C12 . C11 . H111 . 118.2 no
C13 . C12 . C11 . 119.56(17) yes
C13 . C12 . H121 . 120.0 no
C11 . C12 . H121 . 120.4 no
C13 . C14 . C15 . 120.35(18) yes
C13 . C14 . H141 . 119.4 no
C15 . C14 . H141 . 120.3 no
C14 . C15 . N11 . 122.76(18) yes
C14 . C15 . H151 . 118.7 no
N11 . C15 . H151 . 118.6 no
C18 . C19 . C20 . 120.21(19) yes
C18 . C19 . H191 . 120.0 no
C20 . C19 . H191 . 119.8 no
C19 . C20 . N12 . 123.03(18) yes
C19 . C20 . H201 . 118.8 no
N12 . C20 . H201 . 118.2 no
N12 . C21 . C22 . 123.1(2) yes
N12 . C21 . H211 . 118.0 no
C22 . C21 . H211 . 119.0 no
C18 . C22 . C21 . 120.53(19) yes
C18 . C22 . H221 . 119.8 no
C21 . C22 . H221 . 119.7 no
C13 . C16 . C17 . 125.71(19) yes
C13 . C16 . C26 . 65.4(6) yes
C17 . C16 . C26 . 97.1(6) yes
C13 . C16 . C27 . 105.6(5) yes
C17 . C16 . C27 . 33.2(4) yes
C26 . C16 . C27 . 64.0(7) yes
C13 . C16 . H161 . 117.7 no
C17 . C16 . H161 . 116.6 no
C26 . C16 . H161 . 108.6 no
C27 . C16 . H161 . 127.9 no
C13 . C16 . H261 . 91.2 no
C17 . C16 . H261 . 113.1 no
C26 . C16 . H261 . 45.8 no
C27 . C16 . H261 . 89.8 no
H161 . C16 . H261 . 63.0 no
C18 . C17 . C16 . 126.6(2) yes
C18 . C17 . C27 . 110.8(8) yes
C16 . C17 . C27 . 93.5(8) yes
C18 . C17 . H171 . 117.3 no
C16 . C17 . H171 . 116.1 no
C27 . C17 . H171 . 62.7 no
C18 . C17 . H271 . 130.7 no
C16 . C17 . H271 . 101.9 no
C27 . C17 . H271 . 51.4 no
H171 . C17 . H271 . 17.1 no
C27 2_565 C26 . C13 . 122.8(9) yes
C27 2_565 C26 . C16 . 167.2(11) yes
C13 . C26 . C16 . 68.6(6) yes
C27 2_565 C26 . C27 . 95.3(10) yes
C13 . C26 . C27 . 113.0(9) yes
C16 . C26 . C27 . 73.5(8) yes
C27 2_565 C26 . H261 . 106.0 no
C13 . C26 . H261 . 108.5 no
C16 . C26 . H261 . 73.0 no
C27 . C26 . H261 . 110.3 no
C26 . C27 . C26 2_565 84.7(10) yes
C26 . C27 . C16 . 42.5(5) yes
C26 2_565 C27 . C16 . 126.9(9) yes
C26 . C27 . C17 . 95.6(10) yes
C26 2_565 C27 . C17 . 169.9(12) yes
C16 . C27 . C17 . 53.2(6) yes
C26 . C27 . H171 . 119.6 no
C26 2_565 C27 . H171 . 127.5 no
C16 . C27 . H171 . 92.0 no
C17 . C27 . H171 . 61.0 no
C26 . C27 . H271 . 106.2 no
C26 2_565 C27 . H271 . 109.1 no
C16 . C27 . H271 . 94.1 no
C17 . C27 . H271 . 80.6 no
H171 . C27 . H271 . 24.3 no
C27 . H171 . C17 . 56.3 no
C27 . H171 . H271 . 75.7 no
C17 . H171 . H271 . 119.2 no
C26 . H261 . C16 . 61.1 no
C17 . H271 . C27 . 48.0 no
C17 . H271 . H171 . 43.7 no
C27 . H271 . H171 . 80.0 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
N11 . C11 . 1.347(3) yes
N11 . C15 . 1.343(2) yes
N12 . C20 . 1.350(2) yes
N12 . C21 . 1.331(2) yes
C1 . O1 . 1.363(2) yes
C1 . C2 . 1.389(3) yes
C1 . C6 . 1.390(3) yes
C3 . O2 . 1.362(2) yes
C3 . C2 . 1.389(2) yes
C3 . C4 . 1.393(3) yes
C13 . C12 . 1.393(2) yes
C13 . C14 . 1.394(3) yes
C13 . C16 . 1.501(3) yes
C13 . C26 . 1.466(12) yes
C18 . C19 . 1.390(3) yes
C18 . C22 . 1.401(3) yes
C18 . C17 . 1.429(3) yes
O1 . H1 . 0.950 no
O2 . H2 . 0.950 no
C2 . H21 . 0.950 no
C4 . C5 . 1.380(3) yes
C4 . H41 . 0.950 no
C5 . C6 . 1.382(3) yes
C5 . H51 . 0.950 no
C6 . H61 . 0.950 no
C11 . C12 . 1.360(3) yes
C11 . H111 . 0.950 no
C12 . H121 . 0.950 no
C14 . C15 . 1.372(3) yes
C14 . H141 . 0.950 no
C15 . H151 . 0.950 no
C19 . C20 . 1.377(3) yes
C19 . H191 . 0.950 no
C20 . H201 . 0.950 no
C21 . C22 . 1.373(3) yes
C21 . H211 . 0.950 no
C22 . H221 . 0.950 no
C16 . C17 . 1.322(3) yes
C16 . C26 . 1.160(12) yes
C16 . C27 . 1.647(12) yes
C16 . H161 . 0.950 no
C16 . H261 . 1.267 no
C17 . C27 . 0.904(12) yes
C17 . H171 . 0.950 no
C17 . H271 . 1.200 no
C26 . C27 2_565 1.598(16) yes
C26 . C27 . 1.543(17) yes
C26 . H261 . 0.950 no
C27 . H171 . 0.966 no
C27 . H271 . 0.950 no
H171 . H271 . 0.404 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 . N12 2_565 180 0.95 1.79 2.740(2) yes
O2 . H2 . N11 . 180 0.95 1.78 2.730(2) yes
