#------------------------------------------------------------------------------
#$Date: 2020-11-06 14:34:03 +0200 (Fri, 06 Nov 2020) $
#$Revision: 258882 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/24/12/7241225.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_7241225
loop_
_publ_author_name
'Zhu, Lixiang'
'Ren, Xiaoyu'
'Du, Juan'
'Wu, Jia-Hong'
'Tan, Jian-Ping'
'Che, Jixing'
'Pan, Jianke'
'Wang, Tianli'
_publ_section_title
;
 A transition-metal-free multicomponent reaction towards constructing
 chiral 2H-1,4-benzoxazine scaffolds
;
_journal_issue                   21
_journal_name_full               'Green Chemistry'
_journal_page_first              7506
_journal_page_last               7512
_journal_paper_doi               10.1039/D0GC02134B
_journal_volume                  22
_journal_year                    2020
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C23 H19 N O2'
_chemical_formula_sum            'C23 H19 N O2'
_chemical_formula_weight         341.39
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_date             2019-09-11
_audit_creation_method
;
Olex2 1.2
(compiled 2016.02.19 svn.r3266 for OlexSys, GUI svn.r5155)
;
_audit_update_record
;
2020-05-18 deposited with the CCDC.	2020-09-03 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   8.4921(2)
_cell_length_b                   13.5753(4)
_cell_length_c                   15.0981(5)
_cell_measurement_reflns_used    3849
_cell_measurement_temperature    295.88(16)
_cell_measurement_theta_max      71.5490
_cell_measurement_theta_min      4.3440
_cell_volume                     1740.55(9)
_computing_cell_refinement       'CrysAlisPro 1.171.39.46e (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.39.46e (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.46e (Rigaku OD, 2018)'
_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    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_environment      air
_diffrn_ambient_temperature      295.88(16)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 15.9595
_diffrn_detector_type            EosS2
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω   -103.00 -19.00   1.00    1.00    --  -36.04 -57.00 -60.00   84
  2  ω    -89.00  -2.00   1.00    1.00    --  -36.04 125.00-180.00   87
  3  ω   -105.00  33.00   1.00    1.00    --  -36.04   0.00-180.00  138
  4  ω    100.00 176.00   1.00    1.00    --  106.21 111.00   0.00   76
  5  ω     38.00 124.00   1.00    1.00    --  106.21 -45.00   0.00   86
  6  ω     37.00 109.00   1.00    1.00    --  106.21 -94.00 -60.00   72
  7  ω     38.00 124.00   1.00    1.00    --  106.21 -45.00 -90.00   86
  8  ω     88.00 173.00   1.00    1.00    --  106.21  61.00 -30.00   85
  9  ω     85.00 176.00   1.00    1.00    --  106.21  30.00-120.00   91
 10  ω     39.00 133.00   1.00    1.00    --  106.21 -77.00  60.00   94
 11  ω   -103.00 -52.00   1.00    1.00    --  -36.04 -57.00 120.00   51
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'New Gemini, Dual, Cu at home/near, EosS2'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.1690366000
_diffrn_orient_matrix_UB_12      0.0152348000
_diffrn_orient_matrix_UB_13      -0.0345410000
_diffrn_orient_matrix_UB_21      -0.0656309000
_diffrn_orient_matrix_UB_22      -0.0271465000
_diffrn_orient_matrix_UB_23      0.0919853000
_diffrn_orient_matrix_UB_31      0.0070353000
_diffrn_orient_matrix_UB_32      0.1090494000
_diffrn_orient_matrix_UB_33      0.0276597000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0416
_diffrn_reflns_av_unetI/netI     0.0432
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            7797
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.982
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         71.397
_diffrn_reflns_theta_min         4.380
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.658
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.63155
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.39.46e (Rigaku Oxford Diffraction, 2018)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.303
_exptl_crystal_description       block
_exptl_crystal_F_000             720
_exptl_crystal_size_max          0.6
_exptl_crystal_size_mid          0.6
_exptl_crystal_size_min          0.3
_refine_diff_density_max         0.391
_refine_diff_density_min         -0.400
_refine_diff_density_rms         0.130
_refine_ls_abs_structure_details
;
 Flack x determined using 1216 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.0(2)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.116
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     235
_refine_ls_number_reflns         3330
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.116
_refine_ls_R_factor_all          0.0690
_refine_ls_R_factor_gt           0.0666
_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)+(0.1149P)²+0.0107P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1623
_refine_ls_wR_factor_ref         0.1667
_reflns_Friedel_coverage         0.718
_reflns_Friedel_fraction_full    0.999
_reflns_Friedel_fraction_max     0.966
_reflns_number_gt                3132
_reflns_number_total             3330
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d0gc02134b2.cif
_cod_data_source_block           wtl-zlx-2
_cod_depositor_comments
'Adding full bibliography for 7241224--7241225.cif.'
_cod_original_cell_volume        1740.54(9)
_cod_database_code               7241225
_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 99.89
_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 C(H,H) groups, All N(H) groups
2.a Ternary CH refined with riding coordinates:
 C00B(H00B)
2.b Secondary CH2 refined with riding coordinates:
 C00H(H00D,H00E), C00N(H00F,H00H)
2.c Aromatic/amide H refined with riding coordinates:
 N003(H003), C005(H005), C006(H006), C009(H009), C00A(H00A), C00C(H00C),
 C00G(H00G), C00J(H00J), C00K(H00K), C00L(H00L), C00M(H00M), C00O(H00O),
 C00P(H00P), C00Q(H00Q)
;
_shelx_shelxl_version_number     2014/7
_olex2_date_sample_data_collection 2019-09-11
_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
- Detector area scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.456
_oxdiff_exptl_absorpt_empirical_full_min 0.602
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -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
_atom_site_disorder_assembly
_atom_site_disorder_group
O001 O 0.5622(3) 0.18822(17) 0.31179(15) 0.0490(6) Uani 1 1 d . . . . .
O002 O 0.4197(3) 0.37666(18) 0.22682(18) 0.0564(7) Uani 1 1 d . . . . .
N003 N 0.8077(3) 0.29886(19) 0.38238(16) 0.0420(6) Uani 1 1 d . . . . .
H003 H 0.9039 0.3170 0.3893 0.050 Uiso 1 1 calc R . . . .
C004 C 0.7951(3) 0.4251(2) 0.26741(17) 0.0331(6) Uani 1 1 d . . . . .
C005 C 0.5628(4) 0.0850(2) 0.4363(2) 0.0388(6) Uani 1 1 d . . . . .
H005 H 0.4864 0.0465 0.4089 0.047 Uiso 1 1 calc R . . . .
C006 C 0.7219(3) 0.5112(2) 0.2422(2) 0.0388(6) Uani 1 1 d . . . . .
H006 H 0.6167 0.5212 0.2567 0.047 Uiso 1 1 calc R . . . .
C007 C 0.6249(3) 0.16557(19) 0.39289(18) 0.0319(6) Uani 1 1 d . . . . .
C008 C 0.7431(3) 0.2222(2) 0.43174(18) 0.0334(6) Uani 1 1 d . . . . .
C009 C 0.7939(4) 0.1973(2) 0.5159(2) 0.0418(7) Uani 1 1 d . . . . .
H009 H 0.8726 0.2344 0.5428 0.050 Uiso 1 1 calc R . . . .
C00A C 0.7292(4) 0.1179(2) 0.5608(2) 0.0474(8) Uani 1 1 d . . . . .
H00A H 0.7632 0.1029 0.6178 0.057 Uiso 1 1 calc R . . . .
C00B C 0.7039(3) 0.3472(2) 0.31801(17) 0.0341(6) Uani 1 1 d . . . . .
H00B H 0.6178 0.3794 0.3501 0.041 Uiso 1 1 calc R . . . .
C00C C 0.6149(4) 0.0615(2) 0.5211(2) 0.0464(8) Uani 1 1 d . . . . .
H00C H 0.5724 0.0078 0.5508 0.056 Uiso 1 1 calc R . . . .
C00D C 0.5178(4) 0.1529(2) 0.10904(19) 0.0414(7) Uani 1 1 d . . . . .
C00E C 0.4274(4) 0.2324(2) 0.13858(18) 0.0373(6) Uani 1 1 d . . . . .
C00F C 0.4858(3) 0.3009(2) 0.20760(18) 0.0345(6) Uani 1 1 d . . . . .
C00G C 0.8035(4) 0.5835(2) 0.1953(2) 0.0489(8) Uani 1 1 d . . . . .
H00G H 0.7525 0.6411 0.1781 0.059 Uiso 1 1 calc R . . . .
C00H C 0.7505(4) 0.2212(2) 0.1944(2) 0.0424(7) Uani 1 1 d . . . . .
H00D H 0.8431 0.1997 0.2266 0.051 Uiso 1 1 calc R . . . .
H00E H 0.7831 0.2710 0.1521 0.051 Uiso 1 1 calc R . . . .
C00I C 0.6338(3) 0.26557(19) 0.25848(17) 0.0321(6) Uani 1 1 d . . . . .
C00J C 0.9557(3) 0.4128(2) 0.2473(2) 0.0428(7) Uani 1 1 d . . . . .
H00J H 1.0083 0.3563 0.2658 0.051 Uiso 1 1 calc R . . . .
C00K C 0.9599(4) 0.5693(3) 0.1744(2) 0.0504(8) Uani 1 1 d . . . . .
H00K H 1.0143 0.6173 0.1429 0.060 Uiso 1 1 calc R . . . .
C00L C 1.0358(4) 0.4845(3) 0.2000(2) 0.0516(8) Uani 1 1 d . . . . .
H00L H 1.1412 0.4752 0.1856 0.062 Uiso 1 1 calc R . . . .
C00M C 0.2745(4) 0.2464(3) 0.1056(2) 0.0524(8) Uani 1 1 d . . . . .
H00M H 0.2143 0.2993 0.1252 0.063 Uiso 1 1 calc R . . . .
C00N C 0.6795(4) 0.1336(3) 0.1447(3) 0.0517(8) Uani 1 1 d . . . . .
H00F H 0.7484 0.1163 0.0958 0.062 Uiso 1 1 calc R . . . .
H00H H 0.6749 0.0775 0.1844 0.062 Uiso 1 1 calc R . . . .
C00O C 0.4524(5) 0.0909(3) 0.0449(2) 0.0574(9) Uani 1 1 d . . . . .
H00O H 0.5120 0.0385 0.0237 0.069 Uiso 1 1 calc R . . . .
C00P C 0.2136(5) 0.1813(3) 0.0439(3) 0.0667(11) Uani 1 1 d . . . . .
H00P H 0.1111 0.1893 0.0235 0.080 Uiso 1 1 calc R . . . .
C00Q C 0.3045(6) 0.1046(3) 0.0127(3) 0.0691(12) Uani 1 1 d . . . . .
H00Q H 0.2648 0.0623 -0.0304 0.083 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'
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
C007 O001 C00I 119.6(2) . . ?
C008 N003 H003 121.5 . . ?
C008 N003 C00B 116.9(2) . . ?
C00B N003 H003 121.5 . . ?
C006 C004 C00B 120.0(2) . . ?
C006 C004 C00J 118.6(3) . . ?
C00J C004 C00B 121.4(3) . . ?
C007 C005 H005 120.1 . . ?
C007 C005 C00C 119.8(3) . . ?
C00C C005 H005 120.1 . . ?
C004 C006 H006 119.6 . . ?
C004 C006 C00G 120.9(3) . . ?
C00G C006 H006 119.6 . . ?
O001 C007 C005 117.0(2) . . ?
O001 C007 C008 122.2(3) . . ?
C005 C007 C008 120.9(3) . . ?
N003 C008 C007 118.1(2) . . ?
C009 C008 N003 123.4(3) . . ?
C009 C008 C007 118.5(3) . . ?
C008 C009 H009 119.5 . . ?
C008 C009 C00A 121.0(3) . . ?
C00A C009 H009 119.5 . . ?
C009 C00A H00A 120.0 . . ?
C00C C00A C009 120.0(3) . . ?
C00C C00A H00A 120.0 . . ?
N003 C00B C004 109.8(2) . . ?
N003 C00B H00B 108.6 . . ?
N003 C00B C00I 107.2(2) . . ?
C004 C00B H00B 108.6 . . ?
C004 C00B C00I 113.8(2) . . ?
C00I C00B H00B 108.6 . . ?
C005 C00C H00C 120.0 . . ?
C00A C00C C005 119.9(3) . . ?
C00A C00C H00C 120.0 . . ?
C00E C00D C00N 121.6(3) . . ?
C00E C00D C00O 117.9(3) . . ?
C00O C00D C00N 120.5(3) . . ?
C00D C00E C00F 121.7(3) . . ?
C00D C00E C00M 120.0(3) . . ?
C00M C00E C00F 118.3(3) . . ?
O002 C00F C00E 123.2(3) . . ?
O002 C00F C00I 121.5(3) . . ?
C00E C00F C00I 115.2(2) . . ?
C006 C00G H00G 120.1 . . ?
C00K C00G C006 119.7(3) . . ?
C00K C00G H00G 120.1 . . ?
H00D C00H H00E 108.0 . . ?
C00I C00H H00D 109.3 . . ?
C00I C00H H00E 109.3 . . ?
C00I C00H C00N 111.4(3) . . ?
C00N C00H H00D 109.3 . . ?
C00N C00H H00E 109.3 . . ?
O001 C00I C00B 110.9(2) . . ?
O001 C00I C00F 99.1(2) . . ?
O001 C00I C00H 109.9(2) . . ?
C00B C00I C00F 112.3(2) . . ?
C00H C00I C00B 113.9(2) . . ?
C00H C00I C00F 109.8(2) . . ?
C004 C00J H00J 119.9 . . ?
C00L C00J C004 120.3(3) . . ?
C00L C00J H00J 119.9 . . ?
C00G C00K H00K 119.8 . . ?
C00L C00K C00G 120.3(3) . . ?
C00L C00K H00K 119.8 . . ?
C00J C00L H00L 119.9 . . ?
C00K C00L C00J 120.2(3) . . ?
C00K C00L H00L 119.9 . . ?
C00E C00M H00M 120.1 . . ?
C00P C00M C00E 119.8(4) . . ?
C00P C00M H00M 120.1 . . ?
C00D C00N C00H 113.7(3) . . ?
C00D C00N H00F 108.8 . . ?
C00D C00N H00H 108.8 . . ?
C00H C00N H00F 108.8 . . ?
C00H C00N H00H 108.8 . . ?
H00F C00N H00H 107.7 . . ?
C00D C00O H00O 118.9 . . ?
C00Q C00O C00D 122.2(4) . . ?
C00Q C00O H00O 118.9 . . ?
C00M C00P H00P 119.9 . . ?
C00M C00P C00Q 120.2(4) . . ?
C00Q C00P H00P 119.9 . . ?
C00O C00Q C00P 119.8(4) . . ?
C00O C00Q H00Q 120.1 . . ?
C00P C00Q H00Q 120.1 . . ?
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
O001 C007 1.370(3) . ?
O001 C00I 1.456(3) . ?
O002 C00F 1.208(4) . ?
N003 H003 0.8600 . ?
N003 C008 1.392(4) . ?
N003 C00B 1.467(4) . ?
C004 C006 1.378(4) . ?
C004 C00B 1.517(4) . ?
C004 C00J 1.407(4) . ?
C005 H005 0.9300 . ?
C005 C007 1.380(4) . ?
C005 C00C 1.391(4) . ?
C006 H006 0.9300 . ?
C006 C00G 1.395(5) . ?
C007 C008 1.394(4) . ?
C008 C009 1.384(4) . ?
C009 H009 0.9300 . ?
C009 C00A 1.386(5) . ?
C00A H00A 0.9300 . ?
C00A C00C 1.374(5) . ?
C00B H00B 0.9800 . ?
C00B C00I 1.546(4) . ?
C00C H00C 0.9300 . ?
C00D C00E 1.397(4) . ?
C00D C00N 1.498(5) . ?
C00D C00O 1.398(4) . ?
C00E C00F 1.482(4) . ?
C00E C00M 1.403(4) . ?
C00F C00I 1.549(4) . ?
C00G H00G 0.9300 . ?
C00G C00K 1.379(5) . ?
C00H H00D 0.9700 . ?
C00H H00E 0.9700 . ?
C00H C00I 1.510(4) . ?
C00H C00N 1.531(5) . ?
C00J H00J 0.9300 . ?
C00J C00L 1.385(5) . ?
C00K H00K 0.9300 . ?
C00K C00L 1.375(5) . ?
C00L H00L 0.9300 . ?
C00M H00M 0.9300 . ?
C00M C00P 1.384(5) . ?
C00N H00F 0.9700 . ?
C00N H00H 0.9700 . ?
C00O H00O 0.9300 . ?
C00O C00Q 1.359(6) . ?
C00P H00P 0.9300 . ?
C00P C00Q 1.380(7) . ?
C00Q H00Q 0.9300 . ?
