#------------------------------------------------------------------------------
#$Date: 2021-07-17 08:38:58 +0300 (Sat, 17 Jul 2021) $
#$Revision: 267613 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/24/32/7243237.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_7243237
loop_
_publ_author_name
'Zhoujin, Yunping'
'Zhang, Mingtao'
'Parkin, Sean'
'Li, Tonglei'
'Yu, Faquan'
'Long, Sihui'
_publ_section_title
;
 A new solvate of clonixin and a comparison of the two clonixin solvates
;
_journal_issue                   40
_journal_name_full               'RSC Advances'
_journal_page_first              24836
_journal_page_last               24842
_journal_paper_doi               10.1039/D1RA03623H
_journal_volume                  11
_journal_year                    2021
_chemical_formula_moiety         'C13 H11 Cl N2 O2, C4 H9 N O'
_chemical_formula_sum            'C17 H20 Cl N3 O3'
_chemical_formula_weight         349.81
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_date             2017-03-08
_audit_creation_method
;
Olex2 1.2
(compiled 2017.03.02 svn.r3394 for OlexSys, GUI svn.r5324)
;
_audit_update_record
;
2021-04-25 deposited with the CCDC.	2021-07-02 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 100.548(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   15.4376(4)
_cell_length_b                   5.92226(13)
_cell_length_c                   19.0732(6)
_cell_measurement_reflns_used    4210
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      66.9240
_cell_measurement_theta_min      4.6980
_cell_volume                     1714.31(8)
_computing_cell_refinement       'CrysAlisPro 1.171.39.6a (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.39.6a (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.39.6a (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.4674
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 0.975
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     26.00 103.00   1.00    1.00    --   42.20  38.00 -60.00   77
  2  ω     26.00 114.00   1.00    1.00    --   42.20  38.00-150.00   88
  3  ω     16.00  64.00   1.00    2.99    --   92.50 -77.00 150.00   48
  4  ω     81.00 107.00   1.00    2.99    --   92.50 -61.00 -60.00   26
  5  ω     93.00 165.00   1.00    2.99    --   92.50  45.00  90.00   72
  6  ω     12.00  48.00   1.00    2.99    --   92.50 -95.00  30.00   36
  7  ω     19.00  96.00   1.00    2.99    --   92.50 -45.00 150.00   77
  8  ω    121.00 157.00   1.00    2.99    --   92.50  15.00 -30.00   36
  9  ω     10.00  53.00   1.00    2.99    --   92.50 -95.00   0.00   43
 10  ω     59.00  84.00   1.00    2.99    --   92.50 -95.00   0.00   25
 11  ω     93.00 127.00   1.00    2.99    --   92.50  61.00  30.00   34
 12  ω     46.00  72.00   1.00    2.99    --   92.50 -61.00 -60.00   26
 13  ω     18.00  44.00   1.00    2.99    --   92.50 -30.00-180.00   26
 14  ω     41.00 103.00   1.00    2.99    --   92.50  15.00 -30.00   62
 15  ω     89.00 115.00   1.00    2.99    --   92.50 -90.00 123.15   26
 16  ω     81.00 107.00   1.00    2.99    --   92.50 125.00   0.00   26
 17  ω    130.00 156.00   1.00    2.99    --   92.50 125.00   0.00   26
 18  ω     73.00  99.00   1.00    2.99    --   92.50  45.00-150.00   26
 19  ω     39.00  72.00   1.00    2.99    --   92.50 -95.00 150.00   33
 20  ω     24.00  49.00   1.00    2.99    --   92.50-125.00-180.00   25
 21  ω     40.00  75.00   1.00    2.99    --   92.50 -90.00 123.15   35
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Atlas, Gemini ultra'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0904347000
_diffrn_orient_matrix_UB_12      -0.0916939000
_diffrn_orient_matrix_UB_13      0.0097124000
_diffrn_orient_matrix_UB_21      0.0347221000
_diffrn_orient_matrix_UB_22      -0.0278531000
_diffrn_orient_matrix_UB_23      0.0805398000
_diffrn_orient_matrix_UB_31      -0.0303038000
_diffrn_orient_matrix_UB_32      0.2418509000
_diffrn_orient_matrix_UB_33      0.0129925000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0232
_diffrn_reflns_av_unetI/netI     0.0182
_diffrn_reflns_Laue_measured_fraction_full 0.975
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            9510
_diffrn_reflns_point_group_measured_fraction_full 0.975
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         66.856
_diffrn_reflns_theta_min         4.717
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance Ultra (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    2.150
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.79290
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.39.6a (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_density_diffrn    1.355
_exptl_crystal_F_000             736
_refine_diff_density_max         0.282
_refine_diff_density_min         -0.198
_refine_diff_density_rms         0.040
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.035
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     222
_refine_ls_number_reflns         3017
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.035
_refine_ls_R_factor_all          0.0492
_refine_ls_R_factor_gt           0.0405
_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)+(0.0610P)²+0.4319P]
 where P=(Fo²+2Fc²)/3
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1073
_refine_ls_wR_factor_ref         0.1155
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2517
_reflns_number_total             3017
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d1ra03623h2.cif
_cod_data_source_block           17228-e
_cod_database_code               7243237
_shelxl_version_number           2013-2
_chemical_oxdiff_formula         'C1 H1 O1 N1 Cl1'
_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.
;
_reflns_odcompleteness_completeness 98.90
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_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, All O(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 N7(H7), C4(H4), C12(H12), C11(H11), C2(H2), C13(H13), C3(H3)
2.b Idealised Me refined as rotating group:
 C24(H24A,H24B,H24C), C18(H18A,H18B,H18C), C22(H22A,H22B,H22C), C23(H23A,H23B,
 H23C)
2.c Idealised tetrahedral OH refined as rotating group:
 O16(H16)
;
_olex2_date_sample_data_collection 2017-03-08
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.299
_oxdiff_exptl_absorpt_empirical_full_min 0.812
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-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
Cl17 Cl 0.12763(4) 1.33253(10) 0.49578(3) 0.0736(2) Uani 1 1 d . . . . .
N21 N 0.93382(10) 0.3509(3) 0.66318(9) 0.0538(4) Uani 1 1 d . . . . .
O16 O 0.29890(10) 0.1582(3) 0.74643(9) 0.0760(5) Uani 1 1 d . . . . .
H16 H 0.2502 0.1427 0.7571 0.114 Uiso 1 1 calc GR . . . .
N7 N 0.32255(9) 0.6781(3) 0.60322(8) 0.0496(4) Uani 1 1 d . . . . .
H7 H 0.2771 0.6539 0.6223 0.060 Uiso 1 1 calc R . . . .
C1 C 0.31353(11) 0.8622(3) 0.55667(9) 0.0439(4) Uani 1 1 d . . . . .
C14 C 0.29658(12) 0.3249(3) 0.70100(10) 0.0493(4) Uani 1 1 d . . . . .
O19 O 0.84997(9) 0.5861(3) 0.71250(8) 0.0691(4) Uani 1 1 d . . . . .
C10 C 0.37875(11) 0.3527(3) 0.67239(9) 0.0437(4) Uani 1 1 d . . . . .
O15 O 0.23155(9) 0.4430(3) 0.68448(8) 0.0635(4) Uani 1 1 d . . . . .
C4 C 0.28713(14) 1.2385(4) 0.46752(11) 0.0629(5) Uani 1 1 d . . . . .
H4 H 0.2782 1.3646 0.4380 0.075 Uiso 1 1 calc R . . . .
C5 C 0.22407(13) 1.1704(3) 0.50565(10) 0.0529(5) Uani 1 1 d . . . . .
N8 N 0.46512(10) 0.5534(3) 0.59905(9) 0.0540(4) Uani 1 1 d . . . . .
C12 C 0.52389(13) 0.2254(4) 0.66435(12) 0.0614(5) Uani 1 1 d . . . . .
H12 H 0.5704 0.1244 0.6763 0.074 Uiso 1 1 calc R . . . .
C24 C 0.78370(14) 0.2378(4) 0.66501(13) 0.0650(5) Uani 1 1 d . . . . .
H24A H 0.7682 0.2186 0.6143 0.097 Uiso 1 1 calc GR . . . .
H24B H 0.7337 0.2943 0.6830 0.097 Uiso 1 1 calc GR . . . .
H24C H 0.8014 0.0951 0.6869 0.097 Uiso 1 1 calc GR . . . .
C18 C 0.16230(13) 0.9145(4) 0.59008(12) 0.0629(5) Uani 1 1 d . . . . .
H18A H 0.1487 0.7577 0.5812 0.094 Uiso 1 1 calc GR . . . .
H18B H 0.1105 1.0036 0.5742 0.094 Uiso 1 1 calc GR . . . .
H18C H 0.1823 0.9375 0.6403 0.094 Uiso 1 1 calc GR . . . .
C11 C 0.44746(12) 0.2022(3) 0.69135(10) 0.0529(4) Uani 1 1 d . . . . .
H11 H 0.4421 0.0844 0.7225 0.063 Uiso 1 1 calc R . . . .
C20 C 0.85835(12) 0.4025(3) 0.68185(10) 0.0515(4) Uani 1 1 d . . . . .
C22 C 0.94682(18) 0.1450(4) 0.62440(16) 0.0842(8) Uani 1 1 d . . . . .
H22A H 0.8987 0.0433 0.6256 0.126 Uiso 1 1 calc GR . . . .
H22B H 1.0010 0.0744 0.6463 0.126 Uiso 1 1 calc GR . . . .
H22C H 0.9493 0.1819 0.5758 0.126 Uiso 1 1 calc GR . . . .
C9 C 0.38996(11) 0.5291(3) 0.62426(9) 0.0426(4) Uani 1 1 d . . . . .
C6 C 0.23341(11) 0.9843(3) 0.55034(9) 0.0463(4) Uani 1 1 d . . . . .
C2 C 0.37687(12) 0.9287(4) 0.51781(10) 0.0535(5) Uani 1 1 d . . . . .
H2 H 0.4288 0.8465 0.5213 0.064 Uiso 1 1 calc R . . . .
C23 C 1.00799(12) 0.5074(4) 0.67696(12) 0.0656(6) Uani 1 1 d . . . . .
H23A H 1.0208 0.5611 0.6325 0.098 Uiso 1 1 calc GR . . . .
H23B H 1.0587 0.4311 0.7030 0.098 Uiso 1 1 calc GR . . . .
H23C H 0.9933 0.6328 0.7044 0.098 Uiso 1 1 calc GR . . . .
C13 C 0.52886(13) 0.4029(4) 0.61922(12) 0.0615(5) Uani 1 1 d . . . . .
H13 H 0.5806 0.4196 0.6013 0.074 Uiso 1 1 calc R . . . .
C3 C 0.36330(14) 1.1158(4) 0.47411(12) 0.0641(6) Uani 1 1 d . . . . .
H3 H 0.4066 1.1592 0.4487 0.077 Uiso 1 1 calc R . . . .
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.3639 0.7018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 '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
_geom_angle_publ_flag
C20 N21 C22 122.85(19) . . ?
C20 N21 C23 120.57(17) . . ?
C23 N21 C22 116.48(18) . . ?
C9 N7 C1 132.24(15) . . ?
N7 C1 C6 115.85(15) . . ?
C2 C1 N7 124.26(16) . . ?
C2 C1 C6 119.89(17) . . ?
O16 C14 C10 113.99(16) . . ?
O15 C14 O16 121.73(16) . . ?
O15 C14 C10 124.29(16) . . ?
C11 C10 C14 120.04(16) . . ?
C11 C10 C9 117.67(16) . . ?
C9 C10 C14 122.28(15) . . ?
C3 C4 C5 118.32(19) . . ?
C4 C5 Cl17 116.85(15) . . ?
C4 C5 C6 123.62(18) . . ?
C6 C5 Cl17 119.53(15) . . ?
C13 N8 C9 117.80(16) . . ?
C13 C12 C11 117.50(18) . . ?
C12 C11 C10 120.43(18) . . ?
N21 C20 C24 118.38(18) . . ?
O19 C20 N21 120.02(18) . . ?
O19 C20 C24 121.60(17) . . ?
N7 C9 C10 119.18(15) . . ?
N8 C9 N7 119.14(15) . . ?
N8 C9 C10 121.69(16) . . ?
C1 C6 C18 121.53(16) . . ?
C5 C6 C1 116.69(17) . . ?
C5 C6 C18 121.78(17) . . ?
C3 C2 C1 120.45(18) . . ?
N8 C13 C12 124.89(18) . . ?
C4 C3 C2 121.01(19) . . ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Cl17 C5 1.7524(19) . ?
N21 C20 1.315(2) . ?
N21 C22 1.459(3) . ?
N21 C23 1.459(3) . ?
O16 C14 1.310(2) . ?
N7 C1 1.397(2) . ?
N7 C9 1.368(2) . ?
C1 C6 1.419(2) . ?
C1 C2 1.388(2) . ?
C14 C10 1.479(2) . ?
C14 O15 1.217(2) . ?
O19 C20 1.252(2) . ?
C10 C11 1.382(3) . ?
C10 C9 1.422(2) . ?
C4 C5 1.378(3) . ?
C4 C3 1.368(3) . ?
C5 C6 1.385(3) . ?
N8 C9 1.342(2) . ?
N8 C13 1.331(3) . ?
C12 C11 1.378(3) . ?
C12 C13 1.370(3) . ?
C24 C20 1.499(3) . ?
C18 C6 1.502(3) . ?
C2 C3 1.379(3) . ?
