#------------------------------------------------------------------------------
#$Date: 2019-11-17 05:34:54 +0200 (Sun, 17 Nov 2019) $
#$Revision: 228162 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/12/26/7122624.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_7122624
loop_
_publ_author_name
'An, Peng'
'Wu, Hsuan-Yi'
'Lewandowski, Tracey M.'
'Lin, Qing'
_publ_section_title
;
 Hydrophilic azaspiroalkenes as robust bioorthogonal reporters.
;
_journal_issue                   99
_journal_name_full
'Chemical communications (Cambridge, England)'
_journal_page_first              14005
_journal_page_last               14008
_journal_paper_doi               10.1039/c8cc07432a
_journal_volume                  54
_journal_year                    2018
_chemical_formula_moiety         'C9 H9 N3 O'
_chemical_formula_sum            'C9 H9 N3 O'
_chemical_formula_weight         175.19
_space_group_crystal_system      orthorhombic
_space_group_IT_number           62
_space_group_name_Hall           '-P 2ac 2n'
_space_group_name_H-M_alt        'P n m a'
_symmetry_space_group_name_Hall  '-P 2ac 2n'
_symmetry_space_group_name_H-M   'P n m a'
_atom_sites_solution_hydrogens   geom
_audit_creation_date             2016-07-14
_audit_creation_method
;
Olex2 1.2
(compiled 2016.02.19 svn.r3266 for OlexSys, GUI svn.r5155)
;
_audit_update_record
;
2018-08-29 deposited with the CCDC.
2018-11-20 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   6.1464(11)
_cell_length_b                   6.8359(12)
_cell_length_c                   19.339(3)
_cell_measurement_reflns_used    2462
_cell_measurement_temperature    90
_cell_measurement_theta_max      30.514
_cell_measurement_theta_min      3.478
_cell_volume                     812.6(2)
_computing_cell_refinement       'SAINT v8.34A (Bruker, 2013)'
_computing_data_reduction        'SAINT v8.34A (Bruker, 2013)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'olex2.solve (Bourhis et al., 2015)'
_diffrn_ambient_temperature      90.0
_diffrn_detector_area_resol_mean 7.9
_diffrn_detector_type            'CCD area detector'
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device       'three-circle diffractometer'
_diffrn_measurement_device_type  'Bruker SMART APEX2 area detector'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0609
_diffrn_reflns_av_unetI/netI     0.0305
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_number            12301
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        26.000
_diffrn_reflns_theta_max         30.573
_diffrn_reflns_theta_min         2.106
_exptl_absorpt_coefficient_mu    0.099
_exptl_absorpt_correction_T_max  0.7461
_exptl_absorpt_correction_T_min  0.6384
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2014/2 (Bruker,2014/2) was used for absorption correction.
wR2(int) was 0.1345 before and 0.0547 after correction.
The Ratio of minimum to maximum transmission is 0.8556.
The λ/2 correction factor is 0.00150.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.432
_exptl_crystal_description       plate
_exptl_crystal_F_000             368
_exptl_crystal_size_max          0.16
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.01
_refine_diff_density_max         0.439
_refine_diff_density_min         -0.310
_refine_diff_density_rms         0.060
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.123
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     76
_refine_ls_number_reflns         1339
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.123
_refine_ls_R_factor_all          0.0673
_refine_ls_R_factor_gt           0.0502
_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)+(0.0508P)²+0.3470P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1098
_refine_ls_wR_factor_ref         0.1154
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1070
_reflns_number_total             1339
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            c8cc07432a2.cif
_cod_data_source_block           jmc_071603_0m
_cod_depositor_comments          'Adding full bibliography for 7122624.cif.'
_cod_database_code               7122624
_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 C(H,H) groups
2. Others
 Fixed Sof: H5A(0.5) H5B(0.5) H6B(0.5) H6A(0.5)
3.a Secondary CH2 refined with riding coordinates:
 C5(H5A,H5B), C6(H6B,H6A)
3.b Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C3(H3), C8(H8)
;
_shelx_shelxl_version_number     2014/7
_olex2_submission_special_instructions 'No special instructions were received'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'x+1/2, -y+1/2, -z+1/2'
'-x, y+1/2, -z'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'-x-1/2, y-1/2, z-1/2'
'x, -y-1/2, 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_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
O1 O 0.75337(19) 0.7500 0.48931(7) 0.0143(3) Uani 1 2 d S T P
N1 N 0.4134(2) 0.7500 0.31146(8) 0.0113(3) Uani 1 2 d S T P
N2 N 0.4388(2) 0.7500 0.42623(7) 0.0086(3) Uani 1 2 d S T P
N3 N 0.4379(2) 0.7500 0.54814(7) 0.0110(3) Uani 1 2 d S T P
C1 C 0.2068(3) 0.7500 0.34057(9) 0.0112(4) Uani 1 2 d S T P
H1 H 0.0752 0.7500 0.3148 0.013 Uiso 1 2 calc RS T P
C2 C 0.2174(3) 0.7500 0.41056(9) 0.0106(4) Uani 1 2 d S T P
H2 H 0.0992 0.7500 0.4422 0.013 Uiso 1 2 calc RS T P
C3 C 0.5463(3) 0.7500 0.36410(9) 0.0105(4) Uani 1 2 d S T P
H3 H 0.7003 0.7500 0.3599 0.013 Uiso 1 2 calc RS T P
C4 C 0.5541(3) 0.7500 0.49069(9) 0.0082(3) Uani 1 2 d S T P
C5 C 0.5279(3) 0.7500 0.61901(8) 0.0089(3) Uani 1 2 d S T P
H5A H 0.6105 0.8696 0.6310 0.011 Uiso 0.5 1 calc R . .
H5B H 0.6105 0.6304 0.6310 0.011 Uiso 0.5 1 calc R . .
C6 C 0.2062(3) 0.7500 0.56958(9) 0.0105(3) Uani 1 2 d S T P
H6B H 0.1254 0.6304 0.5564 0.013 Uiso 0.5 1 calc R . .
H6A H 0.1254 0.8696 0.5564 0.013 Uiso 0.5 1 calc R . .
C7 C 0.2901(3) 0.7500 0.64481(9) 0.0093(3) Uani 1 2 d S T P
C8 C 0.1918(2) 0.8445(2) 0.70646(6) 0.0127(3) Uani 1 1 d . . .
H8 H 0.1547 0.9623 0.7297 0.015 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 0.0033 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'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 '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
C3 N1 C1 104.83(15) . .
C2 N2 C4 132.18(15) . .
C3 N2 C2 106.25(14) . .
C3 N2 C4 121.56(14) . .
C4 N3 C5 125.29(14) . .
C4 N3 C6 138.97(15) . .
C5 N3 C6 95.74(12) . .
N1 C1 H1 124.4 . .
C2 C1 N1 111.13(16) . .
C2 C1 H1 124.4 . .
N2 C2 H2 127.3 . .
C1 C2 N2 105.32(15) . .
C1 C2 H2 127.3 . .
N1 C3 N2 112.46(16) . .
N1 C3 H3 123.8 . .
N2 C3 H3 123.8 . .
O1 C4 N2 118.38(15) . .
O1 C4 N3 123.98(16) . .
N3 C4 N2 117.64(14) . .
N3 C5 H5A 114.2 . .
N3 C5 H5B 114.2 . .
N3 C5 C7 86.88(12) . .
H5A C5 H5B 111.3 . .
C7 C5 H5A 114.2 . .
C7 C5 H5B 114.2 . .
N3 C6 H6B 114.2 . .
N3 C6 H6A 114.2 . .
N3 C6 C7 86.71(12) . .
H6B C6 H6A 111.4 . .
C7 C6 H6B 114.2 . .
C7 C6 H6A 114.2 . .
C6 C7 C5 90.67(13) . .
C8 C7 C5 130.13(12) 8_575 .
C8 C7 C5 130.13(12) . .
C8 C7 C6 128.38(12) 8_575 .
C8 C7 C6 128.38(12) . .
C8 C7 C8 51.61(12) . 8_575
C7 C8 H8 147.9 . .
C8 C8 C7 64.20(6) 8_575 .
C8 C8 H8 147.9 8_575 .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
O1 C4 1.225(2) .
N1 C1 1.389(2) .
N1 C3 1.305(2) .
N2 C2 1.394(2) .
N2 C3 1.371(2) .
N2 C4 1.434(2) .
N3 C4 1.321(2) .
N3 C5 1.478(2) .
N3 C6 1.483(2) .
C1 H1 0.9500 .
C1 C2 1.355(2) .
C2 H2 0.9500 .
C3 H3 0.9500 .
C5 H5A 0.9900 .
C5 H5B 0.9900 .
C5 C7 1.544(2) .
C6 H6B 0.9900 .
C6 H6A 0.9900 .
C6 C7 1.544(2) .
C7 C8 1.4847(19) 8_575
C7 C8 1.4847(19) .
C8 C8 1.293(3) 8_575
C8 H8 0.9500 .
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_4
N1 C1 C2 N2 0.000(0) .
N3 C5 C7 C6 0.000(1) .
N3 C5 C7 C8 -145.30(11) .
N3 C5 C7 C8 145.30(11) 8_575
N3 C6 C7 C5 0.000(1) .
N3 C6 C7 C8 -146.27(10) 8_575
N3 C6 C7 C8 146.27(10) .
C1 N1 C3 N2 0.000(0) .
C2 N2 C3 N1 0.000(0) .
C2 N2 C4 O1 180.000(1) .
C2 N2 C4 N3 0.000(1) .
C3 N1 C1 C2 0.000(1) .
C3 N2 C2 C1 0.000(0) .
C3 N2 C4 O1 0.000(1) .
C3 N2 C4 N3 180.000(1) .
C4 N2 C2 C1 180.000(1) .
C4 N2 C3 N1 180.000(0) .
C4 N3 C5 C7 180.000(1) .
C4 N3 C6 C7 180.000(1) .
C5 N3 C4 O1 0.000(1) .
C5 N3 C4 N2 180.000(1) .
C5 N3 C6 C7 0.000(1) .
C5 C7 C8 C8 -114.05(13) 8_575
C6 N3 C4 O1 180.000(1) .
C6 N3 C4 N2 0.000(1) .
C6 N3 C5 C7 0.000(1) .
C6 C7 C8 C8 112.52(12) 8_575
