#------------------------------------------------------------------------------
#$Date: 2016-08-05 09:31:16 +0300 (Fri, 05 Aug 2016) $
#$Revision: 185007 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/10/76/2107632.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/. The original data for this entry
# were provided by IUCr Journals, http://journals.iucr.org/.
#
# The file may be used within the scientific community so long as
# proper attribution is given to the journal article from which the
# data were obtained.
#
data_2107632
loop_
_publ_author_name
'Chodkiewicz, Michał Leszek'
'Makal, Anna'
'Gajda, Roman'
'Vidovic, Dragoslav'
'Woźniak, Krzysztof'
_publ_section_title
;
 An insight into real and average structure from diffuse X-ray scattering
 -- a case study
;
_journal_coeditor_code           WF5124SUP1
_journal_issue                   4
_journal_name_full               'Acta Crystallographica Section B'
_journal_page_first              571
_journal_page_last               583
_journal_paper_doi               10.1107/S2052520616005552
_journal_volume                  72
_journal_year                    2016
_chemical_formula_moiety         'Cl, 2(C10.5 H13.5 N)'
_chemical_formula_sum            'C21 H27 Cl N2'
_chemical_formula_weight         342.89
_chemical_name_systematic
;
 ?
;
_space_group_crystal_system      tetragonal
_space_group_IT_number           87
_space_group_name_Hall           '-I 4'
_space_group_name_H-M_alt        'I 4/m'
_symmetry_space_group_name_Hall  '-I 4'
_symmetry_space_group_name_H-M   'I 4/m'
_atom_sites_solution_hydrogens   mixed
_audit_creation_date             2015-03-22
_audit_creation_method
;
Olex2 1.2
(compiled 2015.01.26 svn.r3151 for OlexSys, GUI svn.r4998)
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   20.2750(8)
_cell_length_b                   20.2750(8)
_cell_length_c                   5.0989(2)
_cell_measurement_temperature    296.2(2)
_cell_volume                     2096.03(14)
_computing_cell_refinement       'APEX2 v2012.4-3 (Bruker AXS)'
_computing_data_collection       'APEX2 v2012.4-3 (Bruker AXS)'
_computing_data_reduction        'SAINT V8.18C (Bruker AXS Inc., 2011)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      296.2(2)
_diffrn_detector                 'Bruker APEX2 area detector'
_diffrn_detector_area_resol_mean 7.9
_diffrn_detector_type            'CCD area detector'
_diffrn_measured_fraction_theta_full 0.638
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Bruker kappa APEX2 area detector'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_radiation_collimation    'focusing mirrors'
_diffrn_radiation_monochromator  'mirror optics'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0369
_diffrn_reflns_av_unetI/netI     0.0157
_diffrn_reflns_Laue_measured_fraction_full 0.638
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_l_max       5
_diffrn_reflns_limit_l_min       -5
_diffrn_reflns_number            8122
_diffrn_reflns_point_group_measured_fraction_full 0.638
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        26.000
_diffrn_reflns_theta_max         22.011
_diffrn_reflns_theta_min         1.420
_diffrn_source                   'rotating anode X-ray tube'
_diffrn_source_type              'Bruker TXS'
_exptl_absorpt_coefficient_mu    0.186
_exptl_absorpt_correction_T_max  0.976
_exptl_absorpt_correction_T_min  0.956
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS V2008/1 (Bruker AXS Inc.)'
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.087
_exptl_crystal_description       block
_exptl_crystal_F_000             736
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.13
_refine_diff_density_max         0.120
_refine_diff_density_min         -0.216
_refine_diff_density_rms         0.034
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.155
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     89
_refine_ls_number_reflns         737
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.155
_refine_ls_R_factor_all          0.0514
_refine_ls_R_factor_gt           0.0411
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0786P)²+1.3169P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1239
_refine_ls_wR_factor_ref         0.1561
_reflns_Friedel_coverage         0.000
_reflns_number_gt                615
_reflns_number_total             737
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            wf5124sup1.cif
_cod_data_source_block           DP_RT_initial
_cod_depositor_comments
'Adding full bibliography for 2107632--2107635.cif.'
_cod_original_cell_volume        2096.03(18)
_cod_database_code               2107632
_cod_database_fobs_code          2107632
_shelxl_version_number           2013-4
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Restrained distances
 H1-N1
 0.86 with sigma of 0.02
3. Others
 Fixed Sof: Cl1(0.25) H1(0.5) H7A(0.5) H7C(0.5) H8A(0.5) H8B(0.5) H8C(0.5)
 C9(0.5) C10(0.25) H10(0.25) C11(0.5) H11A(0.5) H11B(0.5) H11C(0.5)
4.a Me refined with riding coordinates:
 C7(H7A,H7B,H7C), C8(H8A,H8B,H8C)
4.b Aromatic/amide H refined with riding coordinates:
 C3(H3), C4(H4), C5(H5), C10(H10)
4.c Idealised Me refined as rotating group:
 C11(H11A,H11B,H11C)
;
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, z'
'-y, x, z'
'y, -x, z'
'x+1/2, y+1/2, z+1/2'
'-x+1/2, -y+1/2, z+1/2'
'-y+1/2, x+1/2, z+1/2'
'y+1/2, -x+1/2, z+1/2'
'-x, -y, -z'
'x, y, -z'
'y, -x, -z'
'-y, x, -z'
'-x+1/2, -y+1/2, -z+1/2'
'x+1/2, y+1/2, -z+1/2'
'y+1/2, -x+1/2, -z+1/2'
'-y+1/2, x+1/2, -z+1/2'
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Cl1 Cl 0.58070(10) 0.62014(9) 0.5000 0.0736(7) Uani 0.5 2 d S T P A 1
N1 N 0.55628(16) 0.69052(15) 0.0000 0.0667(9) Uani 1 2 d DS T P . .
H1 H 0.561(3) 0.672(3) 0.146(8) 0.080 Uiso 0.5 1 d DR . . . .
C1 C 0.55176(17) 0.76079(15) 0.0000 0.0606(10) Uani 1 2 d S T P D .
C2 C 0.49041(18) 0.79000(17) 0.0000 0.0725(11) Uani 1 2 d S T P . .
C3 C 0.4880(2) 0.8584(2) 0.0000 0.0852(12) Uani 1 2 d S T P D .
H3 H 0.4473 0.8795 0.0000 0.102 Uiso 1 2 calc RS T P . .
C4 C 0.5439(2) 0.8950(2) 0.0000 0.0893(13) Uani 1 2 d S T P . .
H4 H 0.5412 0.9408 0.0000 0.107 Uiso 1 2 calc RS T P D .
C5 C 0.6035(2) 0.86526(19) 0.0000 0.0919(13) Uani 1 2 d S T P D .
H5 H 0.6415 0.8910 0.0000 0.110 Uiso 1 2 calc RS T P . .
C6 C 0.60903(18) 0.79721(18) 0.0000 0.0738(11) Uani 1 2 d S T P . .
C7 C 0.4286(2) 0.7495(2) 0.0000 0.126(2) Uani 1 2 d S T P D .
H7A H 0.4276 0.7222 -0.1538 0.189 Uiso 0.5 1 calc R . . B -1
H7B H 0.3909 0.7782 0.0001 0.189 Uiso 0.5 1 calc RS T P B -1
H7C H 0.4277 0.7222 0.1537 0.189 Uiso 0.5 1 calc R . . B -1
C8 C 0.6750(2) 0.7637(2) 0.0000 0.1239(19) Uani 1 2 d S T P D .
H8A H 0.6789 0.7364 0.1530 0.186 Uiso 0.5 1 calc R . . C -1
H8B H 0.7093 0.7964 0.0015 0.186 Uiso 0.5 1 calc R . . C -1
H8C H 0.6792 0.7370 -0.1545 0.186 Uiso 0.5 1 calc R . . C -1
C9 C 0.5585(2) 0.6545(2) -0.2568(8) 0.0470(11) Uani 0.5 1 d . . . D 2
C10 C 0.5573(3) 0.6844(3) -0.5000 0.0456(15) Uani 0.5 2 d S T P D 2
H10 H 0.5556 0.7302 -0.5000 0.055 Uiso 0.5 2 calc RS T P D 2
C11 C 0.5623(2) 0.58243(19) -0.2073(8) 0.0582(12) Uani 0.5 1 d . . . D 2
H11A H 0.5644 0.5746 -0.0218 0.087 Uiso 0.5 1 calc GR . . D 2
H11B H 0.6010 0.5649 -0.2898 0.087 Uiso 0.5 1 calc GR . . D 2
H11C H 0.5238 0.5613 -0.2781 0.087 Uiso 0.5 1 calc GR . . D 2
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
C1 N1 H1 117(5) . .
C1 N1 C9 119.19(17) . 10
C1 N1 C9 119.19(17) . .
C9 N1 H1 5(5) 10 .
C9 N1 H1 124(5) . .
C9 N1 C9 121.6(3) 10 .
C2 C1 N1 119.1(3) . .
C6 C1 N1 118.8(3) . .
C6 C1 C2 122.1(3) . .
C1 C2 C3 117.5(4) . .
C1 C2 C7 121.3(3) . .
C3 C2 C7 121.2(4) . .
C2 C3 H3 119.4 . .
C4 C3 C2 121.1(4) . .
C4 C3 H3 119.4 . .
C3 C4 H4 119.8 . .
C5 C4 C3 120.3(4) . .
C5 C4 H4 119.8 . .
C4 C5 H5 119.5 . .
C4 C5 C6 121.1(4) . .
C6 C5 H5 119.5 . .
C1 C6 C5 117.8(3) . .
C1 C6 C8 120.6(3) . .
C5 C6 C8 121.5(4) . .
C2 C7 H7A 109.5 . .
C2 C7 H7B 109.5 . .
C2 C7 H7C 109.5 . .
H7A C7 H7B 109.5 . .
H7A C7 H7C 109.5 . .
H7B C7 H7C 109.5 . .
C6 C8 H8A 109.5 . .
C6 C8 H8B 109.5 . .
C6 C8 H8C 109.5 . .
H8A C8 H8B 109.5 . .
H8A C8 H8C 109.5 . .
H8B C8 H8C 109.5 . .
C10 C9 N1 124.8(3) . .
C10 C9 C11 125.8(4) . .
C11 C9 N1 109.4(3) . .
C9 C10 C9 128.0(5) 10_554 .
C9 C10 H10 116.0 10_554 .
C9 C10 H10 116.0 . .
C9 C11 H11A 109.5 . .
C9 C11 H11B 109.5 . .
C9 C11 H11C 109.5 . .
H11A C11 H11B 109.5 . .
H11A C11 H11C 109.5 . .
H11B C11 H11C 109.5 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
N1 H1 0.84(2) .
N1 C1 1.428(4) .
N1 C9 1.500(4) 10
N1 C9 1.500(4) .
C1 C2 1.377(5) .
C1 C6 1.376(5) .
C2 C3 1.388(5) .
C2 C7 1.498(6) .
C3 H3 0.9300 .
C3 C4 1.354(6) .
C4 H4 0.9300 .
C4 C5 1.351(6) .
C5 H5 0.9300 .
C5 C6 1.384(5) .
C6 C8 1.501(6) .
C7 H7A 0.9600 .
C7 H7B 0.9600 .
C7 H7C 0.9600 .
C8 H8A 0.9600 .
C8 H8B 0.9600 .
C8 H8C 0.9600 .
C9 C10 1.380(5) .
C9 C11 1.485(6) .
C10 C9 1.380(5) 10_554
C10 H10 0.9300 .
C11 H11A 0.9600 .
C11 H11B 0.9600 .
C11 H11C 0.9600 .
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
N1 H1 Cl1 0.84(2) 2.13(2) 2.9633(19) 174(7)
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_4
N1 C1 C2 C3 180.0 . .
N1 C1 C2 C7 0.0 . .
N1 C1 C6 C5 180.0 . .
N1 C1 C6 C8 0.0 . .
N1 C9 C10 C9 -179.2(4) . 10_554
C1 N1 C9 C10 1.0(6) . .
C1 N1 C9 C11 -179.3(4) . .
C1 C2 C3 C4 0.0 . .
C2 C1 C6 C5 0.0 . .
C2 C1 C6 C8 180.0 . .
C2 C3 C4 C5 0.0 . .
C3 C4 C5 C6 0.0 . .
C4 C5 C6 C1 0.0 . .
C4 C5 C6 C8 180.0 . .
C6 C1 C2 C3 0.0 . .
C6 C1 C2 C7 180.0 . .
C7 C2 C3 C4 180.0 . .
C9 N1 C1 C2 89.9(3) . .
C9 N1 C1 C2 -89.9(3) 10 .
C9 N1 C1 C6 -90.1(3) . .
C9 N1 C1 C6 90.1(3) 10 .
C9 N1 C9 C10 -179.3(3) 10 .
C9 N1 C9 C11 0.4(6) 10 .
C11 C9 C10 C9 1.1(10) . 10_554
